(49,'Hydrocortisone','hydrocortisone','Hydrocortisone is a glucocorticoid used to treat corticosteroid-responsive dermatoses, endocrine disorders, immune conditions, and allergic disorders.','Ala-cort, Ala-scalp, Alcortin, Alkindi, Anusol HC, Aquanil HC, Casporyn HC, Cipro, Cipro HC, Colocort, Cortaid, Cortane-B, Cortef, Cortenema, Cortisporin, Cortizone-10, Dermacort, Dermarest Eczema, Dermazene, Home Papkit, Hydroskin, Monistat Itch Relief, Neosporin Eczema, Preparation H Hydrocortisone, Procto-med, Procto-pak, Proctocort, Proctol, Proctosedyl, Proctosol, Proctozone HC, Scalpicin Itch Relief, Texacort, Vanoxide-HC, Xerese','Hydrocortisone','<p>Hydrocortisone, or cortisol, is a glucocorticoid secreted by the adrenal cortex.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Jung C, Greco S, Nguyen HH, Ho JT, Lewis JG, Torpy DJ, Inder WJ: Plasma, salivary and urinary cortisol levels following physiological and stress doses of hydrocortisone in normal volunteers. BMC Endocr Disord. 2014 Nov 26;14:91. doi: 10.1186/1472-6823-14-91. (PubMed ID 25425285)\" href=\"#reference-A188387\">7</a></sup> Hydrocortisone is used to treat immune, inflammatory, and neoplastic conditions.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Vosol Hydrocortisone and Glacial Acetic Acid Otic Drops\" href=\"#reference-L10529\">14</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Casporyn Neomycin Sulfate, Polymixin B Sulfate, and Hydrocortisone Otic Drops\" href=\"#reference-L10532\">15</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Cortef Hydrocortisone Oral Tablets\" href=\"#reference-L10535\">16</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Cortenema Hydrocortisone Rectal Enema\" href=\"#reference-L10538\">17</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Bacitracin, Neomycin, Polymyxin B, and Hydrocortisone Topical Ointment\" href=\"#reference-L7772\">18</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Xerese (Acyclovir and Hydrocortisone) Topical Cream\" href=\"#reference-L7321\">19</a></sup> It was discovered in the 1930s by Edward Kendall and named Compound F, or 17-hydroxycorticosterone.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Simoni R, Hill R, Vaughan M: The Isolation of Thyroxine and Cortisone: the Work of Edward C. Kendall Journal of Biological Chemistry. 2002 May 24;277(21):e10.\" href=\"#reference-A188420\">9</a></sup></p><p>Hydrocortisone was granted FDA approval on 5 August 1952.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Hydrocortone Hydrocortisone Oral Tablets (Discontinued)\" href=\"#reference-L10574\">20</a></sup></p>','C21H30O5','DB00741','Approved, Vet approved','Small Molecule','Average: 362.4599 Monoisotopic: 362.20932407 ',' , S01CB — Corticosteroids/antiinfectives/mydriatics in combination , S01C — ANTIINFLAMMATORY AGENTS AND ANTIINFECTIVES IN COMBINATION , S01 — OPHTHALMOLOGICALS , S — SENSORY ORGANS , A01AC — Corticosteroids for local oral treatment , A01A — STOMATOLOGICAL PREPARATIONS , A01 — STOMATOLOGICAL PREPARATIONS , A — ALIMENTARY TRACT AND METABOLISM , S01BA — Corticosteroids, plain , S01B — ANTIINFLAMMATORY AGENTS , S01 — OPHTHALMOLOGICALS , S — SENSORY ORGANS , S01CA — Corticosteroids and antiinfectives in combination , S01C — ANTIINFLAMMATORY AGENTS AND ANTIINFECTIVES IN COMBINATION , S01 — OPHTHALMOLOGICALS , S — SENSORY ORGANS , D07AA — Corticosteroids, weak (group I) , D07A — CORTICOSTEROIDS, PLAIN , D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS , D — DERMATOLOGICALS , S01BB — Corticosteroids and mydriatics in combination , S01B — ANTIINFLAMMATORY AGENTS , S01 — OPHTHALMOLOGICALS , S — SENSORY ORGANS , D07XA — Corticosteroids, weak, other combinations , D07X — CORTICOSTEROIDS, OTHER COMBINATIONS , D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS , D — DERMATOLOGICALS , D07BA — Corticosteroids, weak, combinations with antiseptics , D07B — CORTICOSTEROIDS, COMBINATIONS WITH ANTISEPTICS , D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS , D — DERMATOLOGICALS , S02CA — Corticosteroids and antiinfectives in combination , S02C — CORTICOSTEROIDS AND ANTIINFECTIVES IN COMBINATION , S02 — OTOLOGICALS , S — SENSORY ORGANS , A07EA — Corticosteroids acting locally , A07E — INTESTINAL ANTIINFLAMMATORY AGENTS , A07 — ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS , A — ALIMENTARY TRACT AND METABOLISM , S02BA — Corticosteroids , S02B — CORTICOSTEROIDS , S02 — OTOLOGICALS , S — SENSORY ORGANS , R01AD — Corticosteroids , R01A — DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE , R01 — NASAL PREPARATIONS , R — RESPIRATORY SYSTEM , H02AB — Glucocorticoids , H02A — CORTICOSTEROIDS FOR SYSTEMIC USE, PLAIN , H02 — CORTICOSTEROIDS FOR SYSTEMIC USE , H — SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS , D07CA — Corticosteroids, weak, combinations with antibiotics , D07C — CORTICOSTEROIDS, COMBINATIONS WITH ANTIBIOTICS , D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS , D — DERMATOLOGICALS , S03CA — Corticosteroids and antiinfectives in combination , S03C — CORTICOSTEROIDS AND ANTIINFECTIVES IN COMBINATION , S03 — OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS , S — SENSORY ORGANS , C05AA — Corticosteroids , C05A — AGENTS FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE , C05 — VASOPROTECTIVES , C — CARDIOVASCULAR SYSTEM','<p>Oral hydrocortisone at a dose of 0.2-0.3mg/kg/day reached a mean C<sub>max</sub> of 32.69nmol/L with a mean AUC of 90.63h*nmol/L<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Werumeus Buning J, Touw DJ, Brummelman P, Dullaart RPF, van den Berg G, van der Klauw MM, Kamp J, Wolffenbuttel BHR, van Beek AP: Pharmacokinetics of oral hydrocortisone - Results and implications from a randomized controlled trial. Metabolism. 2017 Jun;71:7-16. doi: 10.1016/j.metabol.2017.02.005. Epub 2017 Feb 13. (PubMed ID 28521880)\" href=\"#reference-A188354\">1</a></sup> A 0.4-0.6mg/kg/day dose reached a mean C<sub>max</sub> of 70.81nmol/L with a mean AUC of 199.11h*nmol/L.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Werumeus Buning J, Touw DJ, Brummelman P, Dullaart RPF, van den Berg G, van der Klauw MM, Kamp J, Wolffenbuttel BHR, van Beek AP: Pharmacokinetics of oral hydrocortisone - Results and implications from a randomized controlled trial. Metabolism. 2017 Jun;71:7-16. doi: 10.1016/j.metabol.2017.02.005. Epub 2017 Feb 13. (PubMed ID 28521880)\" href=\"#reference-A188354\">1</a></sup> However, the pharmacokinetics of hydrocortisone can vary by 10 times from patient to patient.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Werumeus Buning J, Touw DJ, Brummelman P, Dullaart RPF, van den Berg G, van der Klauw MM, Kamp J, Wolffenbuttel BHR, van Beek AP: Pharmacokinetics of oral hydrocortisone - Results and implications from a randomized controlled trial. Metabolism. 2017 Jun;71:7-16. doi: 10.1016/j.metabol.2017.02.005. Epub 2017 Feb 13. (PubMed ID 28521880)\" href=\"#reference-A188354\">1</a></sup></p><p>Topical hydrocortisone cream is 4-19% bioavailable[8546995] with a T<sub>max</sub> of 24h.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Aalto-Korte K, Turpeinen M: Pharmacokinetics of topical hydrocortisone at plasma level after applications once or twice daily in patients with widespread dermatitis. Br J Dermatol. 1995 Aug;133(2):259-63. doi: 10.1111/j.1365-2133.1995.tb02625.x. (PubMed ID 7547394)\" href=\"#reference-A188372\">2</a></sup></p><p>Hydrocortisone retention enemas are have a bioavailability of 0.810 for slow absorbers and 0.502 in rapid absorbers.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lima JJ, Jusko WJ: Bioavailability of hydrocortisone retention enemas in relation to absorption kinetics. Clin Pharmacol Ther. 1980 Aug;28(2):262-9. doi: 10.1038/clpt.1980.159. (PubMed ID 7398193)\" href=\"#reference-A188378\">4</a></sup> Slow absorbers take up hydrocortisone at a rate of 0.361±0.255/h while fast absorbers take up hydrocortisone at a rate of 1.05±0.255/h.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lima JJ, Jusko WJ: Bioavailability of hydrocortisone retention enemas in relation to absorption kinetics. Clin Pharmacol Ther. 1980 Aug;28(2):262-9. doi: 10.1038/clpt.1980.159. (PubMed ID 7398193)\" href=\"#reference-A188378\">4</a></sup></p><p>A 20mg IV dose of hydrocortisone has an AUC of 1163±277ng*h/mL.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Derendorf H, Mollmann H, Barth J, Mollmann C, Tunn S, Krieg M: Pharmacokinetics and oral bioavailability of hydrocortisone. J Clin Pharmacol. 1991 May;31(5):473-6. doi: 10.1002/j.1552-4604.1991.tb01906.x. (PubMed ID 2050835)\" href=\"#reference-A188381\">6</a></sup></p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroids with a structure based on a hydroxylated prostane moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001468\" rel=\"noopener\" target=\"_blank\">Gluco/mineralocorticoids, progestogins and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003058\" rel=\"noopener\" target=\"_blank\">20-oxosteroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"3-oxo steroids containing a double bond between positions  3 and 4.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002974\" rel=\"noopener\" target=\"_blank\">3-oxo delta-4-steroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroids carrying a hydroxyl group at the 17-position of the steroid backbone.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003236\" rel=\"noopener\" target=\"_blank\">17-hydroxysteroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Hydroxysteroids carrying a beta-hydroxyl group at the 11-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003227\" rel=\"noopener\" target=\"_blank\">11-beta-hydroxysteroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroids containing a double bond between positions 4 and 5.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002978\" rel=\"noopener\" target=\"_blank\">Delta-4-steroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004325\" rel=\"noopener\" target=\"_blank\">Cyclohexenones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carboxylic acid, and an amine group attached to the alpha carbon atom, relative to the C=O group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002912\" rel=\"noopener\" target=\"_blank\">Alpha-hydroxy ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001292\" rel=\"noopener\" target=\"_blank\">Cyclic alcohols and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000286\" rel=\"noopener\" target=\"_blank\">Primary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 4 more</a>','Not Available','Not Available','13775','50-23-7','17650','CHEMBL389621','5551','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Fatty acids and their derivatives, and substances related biosynthetically or functionally to these compounds.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000012\" rel=\"noopener\" target=\"_blank\">Lipids and lipid-like molecules</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000258\" rel=\"noopener\" target=\"_blank\">Steroids and steroid derivatives</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an steroid backbone, with at least one hydrogen substituted by a hydroxyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001295\" rel=\"noopener\" target=\"_blank\">Hydroxysteroids</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Steroids carrying a hydroxyl group at the 21-position of the steroid backbone.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003095\" rel=\"noopener\" target=\"_blank\">21-hydroxysteroids</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroids with a structure based on a hydroxylated prostane moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001468\" rel=\"noopener\" target=\"_blank\">Gluco/mineralocorticoids, progestogins and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003058\" rel=\"noopener\" target=\"_blank\">20-oxosteroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"3-oxo steroids containing a double bond between positions  3 and 4.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002974\" rel=\"noopener\" target=\"_blank\">3-oxo delta-4-steroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroids carrying a hydroxyl group at the 17-position of the steroid backbone.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003236\" rel=\"noopener\" target=\"_blank\">17-hydroxysteroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Hydroxysteroids carrying a beta-hydroxyl group at the 11-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003227\" rel=\"noopener\" target=\"_blank\">11-beta-hydroxysteroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroids containing a double bond between positions 4 and 5.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002978\" rel=\"noopener\" target=\"_blank\">Delta-4-steroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004325\" rel=\"noopener\" target=\"_blank\">Cyclohexenones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carboxylic acid, and an amine group attached to the alpha carbon atom, relative to the C=O group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002912\" rel=\"noopener\" target=\"_blank\">Alpha-hydroxy ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001292\" rel=\"noopener\" target=\"_blank\">Cyclic alcohols and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000286\" rel=\"noopener\" target=\"_blank\">Primary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 4 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">11-beta-hydroxysteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">11-hydroxysteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">17-hydroxysteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">20-oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">21-hydroxysteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">3-oxo-delta-4-steroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">3-oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aliphatic homopolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alpha-hydroxy ketone</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclic alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclic ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclohexenone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Delta-4-steroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pregnane-skeleton</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Progestogin-skeleton</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 16 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aliphatic homopolycyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">3-oxo steroid, 11beta-hydroxy steroid, 17alpha-hydroxy steroid, glucocorticoid, 20-oxo steroid, 21-hydroxy steroid, C21-steroid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17650\" rel=\"noopener\" target=\"_blank\">CHEBI:17650</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Pregnane and derivatives [Fig], Glucocorticoids, C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C00735\" rel=\"noopener\" target=\"_blank\">C00735</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMST02030001\" rel=\"noopener\" target=\"_blank\">LMST02030001</a>) </span></span></dd></dl>','Steroids and steroid derivatives','<p>Total hydrocortisone by the oral route has a mean clearance of 12.85L/h, while the free fraction has a mean clearance of 235.78L/h.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Werumeus Buning J, Touw DJ, Brummelman P, Dullaart RPF, van den Berg G, van der Klauw MM, Kamp J, Wolffenbuttel BHR, van Beek AP: Pharmacokinetics of oral hydrocortisone - Results and implications from a randomized controlled trial. Metabolism. 2017 Jun;71:7-16. doi: 10.1016/j.metabol.2017.02.005. Epub 2017 Feb 13. (PubMed ID 28521880)\" href=\"#reference-A188354\">1</a></sup> A 20mg IV dose of hydrocortisone has a clearance of 18.2±4.2L/h.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Derendorf H, Mollmann H, Barth J, Mollmann C, Tunn S, Krieg M: Pharmacokinetics and oral bioavailability of hydrocortisone. J Clin Pharmacol. 1991 May;31(5):473-6. doi: 10.1002/j.1552-4604.1991.tb01906.x. (PubMed ID 2050835)\" href=\"#reference-A188381\">6</a></sup></p>','This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.','21-hydroxysteroids','<li>Avoid alcohol.</li>','Drugs.com Drug Page',' , 11-Hydroxycorticosteroids , 17-Hydroxycorticosteroids , Adrenal Cortex Hormones , Adrenals , Agents for Treatment of Hemorrhoids and Anal Fissures for Topical Use , Alimentary Tract and Metabolism , Anti-Inflammatory Agents , Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents , Corticosteroid Hormone Receptor Agonists , Corticosteroids , Corticosteroids Acting Locally , Corticosteroids for Local Oral Treatment , Corticosteroids for Systemic Use , Corticosteroids for Systemic Use, Plain , Corticosteroids, Dermatological Preparations , Corticosteroids, Weak (Group I) , Cytochrome P-450 CYP2A6 Inducers , Cytochrome P-450 CYP2B6 Inducers , Cytochrome P-450 CYP2B6 Inducers (strength unknown) , Cytochrome P-450 CYP2C19 Inducers , Cytochrome P-450 CYP2C19 Inducers (strength unknown) , Cytochrome P-450 CYP2C8 Inducers , Cytochrome P-450 CYP2C8 Inducers (strength unknown) , Cytochrome P-450 CYP2C9 Inducers , Cytochrome P-450 CYP2C9 Inducers (strength unknown) , Cytochrome P-450 CYP3A Inducers , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Inducers , Cytochrome P-450 CYP3A4 Inducers (strength unknown) , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A5 Substrates , Cytochrome P-450 CYP3A7 Substrates , Cytochrome P-450 Enzyme Inducers , Cytochrome P-450 Substrates , Dermatologicals , Fused-Ring Compounds , Hormones , Hormones, Hormone Substitutes, and Hormone Antagonists , Hydrocortisone and derivatives , Hydroxycorticosteroids , Hyperglycemia-Associated Agents , Immunosuppressive Agents , Intestinal Antiinflammatory Agents , Nasal Preparations , OAT3/SLC22A8 Substrates , Ophthalmological and Otological Preparations , Ophthalmologicals , Otologicals , P-glycoprotein inducers , P-glycoprotein substrates , Pregnanes , Pregnenediones , Pregnenes , Sensory Organs , Steroids , Stomatological Preparations , Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins , Vasoprotectives','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>220 °C</td><td>PhysProp</td></tr><tr><td>water solubility</td><td>320 mg/L (at 25 °C)</td><td>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</td></tr><tr><td>logP</td><td>1.61</td><td>HANSCH,C ET AL. (1995)</td></tr><tr><td>logS</td><td>-2.97</td><td>ADME Research, USCD</td></tr><tr><td>Caco2 permeability</td><td>-4.66</td><td>ADME Research, USCD</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">3-oxo steroid, 11beta-hydroxy steroid, 17alpha-hydroxy steroid, glucocorticoid, 20-oxo steroid, 21-hydroxy steroid, C21-steroid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17650\" rel=\"noopener\" target=\"_blank\">CHEBI:17650</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Pregnane and derivatives [Fig], Glucocorticoids, C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C00735\" rel=\"noopener\" target=\"_blank\">C00735</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMST02030001\" rel=\"noopener\" target=\"_blank\">LMST02030001</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0000063\" rel=\"noopener\" target=\"_blank\">HMDB0000063</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D00088\" rel=\"noopener\" target=\"_blank\">D00088</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C00735\" rel=\"noopener\" target=\"_blank\">C00735</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5754\" rel=\"noopener\" target=\"_blank\">5754</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505089\" rel=\"noopener\" target=\"_blank\">46505089</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.5551.html\" rel=\"noopener\" target=\"_blank\">5551</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=13775\" rel=\"noopener\" target=\"_blank\">13775</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=5492\" rel=\"noopener\" target=\"_blank\">5492</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=17650\" rel=\"noopener\" target=\"_blank\">17650</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL389621\" rel=\"noopener\" target=\"_blank\">CHEMBL389621</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000013540519\" rel=\"noopener\" target=\"_blank\">ZINC000013540519</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000718\" rel=\"noopener\" target=\"_blank\">DAP000718</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA449905\" rel=\"noopener\" target=\"_blank\">PA449905</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"guide-to-pharmacology\">Guide to Pharmacology</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=2868\" rel=\"noopener\" target=\"_blank\">GtP Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/HCY\" rel=\"noopener\" target=\"_blank\">HCY</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic/hydrocortisone.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/cdi/hydrocortisone.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdrhealth\">PDRhealth</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/hyd1199.shtml\" rel=\"noopener\" target=\"_blank\">PDRhealth Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Hydrocortisone\" rel=\"noopener\" target=\"_blank\">Hydrocortisone</a></dd></dl>','<li>Avoid alcohol.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A188354\">Werumeus Buning J, Touw DJ, Brummelman P, Dullaart RPF, van den Berg G, van der Klauw MM, Kamp J, Wolffenbuttel BHR, van Beek AP: Pharmacokinetics of oral hydrocortisone - Results and implications from a randomized controlled trial. Metabolism. 2017 Jun;71:7-16. doi: 10.1016/j.metabol.2017.02.005. Epub 2017 Feb 13. [<a href=\"/articles/A188354\" target=\"_blank\">Article</a>] </li><li id=\"reference-A188372\">Aalto-Korte K, Turpeinen M: Pharmacokinetics of topical hydrocortisone at plasma level after applications once or twice daily in patients with widespread dermatitis. Br J Dermatol. 1995 Aug;133(2):259-63. doi: 10.1111/j.1365-2133.1995.tb02625.x. [<a href=\"/articles/A188372\" target=\"_blank\">Article</a>] </li><li id=\"reference-A188375\">Aalto-Korte K, Turpeinen M: Quantifying systemic absorption of topical hydrocortisone in erythroderma. Br J Dermatol. 1995 Sep;133(3):403-8. doi: 10.1111/j.1365-2133.1995.tb02668.x. [<a href=\"/articles/A188375\" target=\"_blank\">Article</a>] </li><li id=\"reference-A188378\">Lima JJ, Jusko WJ: Bioavailability of hydrocortisone retention enemas in relation to absorption kinetics. Clin Pharmacol Ther. 1980 Aug;28(2):262-9. doi: 10.1038/clpt.1980.159. [<a href=\"/articles/A188378\" target=\"_blank\">Article</a>] </li><li id=\"reference-A184223\">FLORINI JR, BUYSKE DA: Plasma protein binding of triamcinolone-H3 and hydrocortisone-4-C14. J Biol Chem. 1961 Jan;236:247-51. [<a href=\"/articles/A184223\" target=\"_blank\">Article</a>] </li><li id=\"reference-A188381\">Derendorf H, Mollmann H, Barth J, Mollmann C, Tunn S, Krieg M: Pharmacokinetics and oral bioavailability of hydrocortisone. J Clin Pharmacol. 1991 May;31(5):473-6. doi: 10.1002/j.1552-4604.1991.tb01906.x. [<a href=\"/articles/A188381\" target=\"_blank\">Article</a>] </li><li id=\"reference-A188387\">Jung C, Greco S, Nguyen HH, Ho JT, Lewis JG, Torpy DJ, Inder WJ: Plasma, salivary and urinary cortisol levels following physiological and stress doses of hydrocortisone in normal volunteers. BMC Endocr Disord. 2014 Nov 26;14:91. doi: 10.1186/1472-6823-14-91. [<a href=\"/articles/A188387\" target=\"_blank\">Article</a>] </li><li id=\"reference-A188405\">Ciriaco M, Ventrice P, Russo G, Scicchitano M, Mazzitello G, Scicchitano F, Russo E: Corticosteroid-related central nervous system side effects. J Pharmacol Pharmacother. 2013 Dec;4(Suppl 1):S94-8. doi: 10.4103/0976-500X.120975. [<a href=\"/articles/A188405\" target=\"_blank\">Article</a>] </li><li id=\"reference-A188420\">Simoni R, Hill R, Vaughan M: The Isolation of Thyroxine and Cortisone: the Work of Edward C. Kendall Journal of Biological Chemistry. 2002 May 24;277(21):e10. [<a href=\"/articles/A188420\" target=\"_blank\">Article</a>] </li><li id=\"reference-A187463\">Yasir M, Sonthalia S: Corticosteroid Adverse Effects . [<a href=\"/articles/A187463\" target=\"_blank\">Article</a>] </li><li id=\"reference-A187439\">Gardill BR, Vogl MR, Lin HY, Hammond GL, Muller YA: Corticosteroid-binding globulin: structure-function implications from species differences. PLoS One. 2012;7(12):e52759. doi: 10.1371/journal.pone.0052759. Epub 2012 Dec 26. [<a href=\"/articles/A187439\" target=\"_blank\">Article</a>] </li><li id=\"reference-A187436\">Czock D, Keller F, Rasche FM, Haussler U: Pharmacokinetics and pharmacodynamics of systemically administered glucocorticoids. Clin Pharmacokinet. 2005;44(1):61-98. doi: 10.2165/00003088-200544010-00003. [<a href=\"/articles/A187436\" target=\"_blank\">Article</a>] </li><li id=\"reference-A188321\">Sarkar U, Rivera-Burgos D, Large EM, Hughes DJ, Ravindra KC, Dyer RL, Ebrahimkhani MR, Wishnok JS, Griffith LG, Tannenbaum SR: Metabolite profiling and pharmacokinetic evaluation of hydrocortisone in a perfused three-dimensional human liver bioreactor. Drug Metab Dispos. 2015 Jul;43(7):1091-9. doi: 10.1124/dmd.115.063495. Epub 2015 Apr 29. [<a href=\"/articles/A188321\" target=\"_blank\">Article</a>] </li><li id=\"reference-L10529\">FDA Approved Drug Products: Vosol Hydrocortisone and Glacial Acetic Acid Otic Drops [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/1997/012770s024lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L10532\">FDA Approved Drug Products: Casporyn Neomycin Sulfate, Polymixin B Sulfate, and Hydrocortisone Otic Drops [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/060613s013lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L10535\">FDA Approved Drug Products: Cortef Hydrocortisone Oral Tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/008697s036lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L10538\">FDA Approved Drug Products: Cortenema Hydrocortisone Rectal Enema [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/016199s035lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7772\">FDA Approved Drug Products: Bacitracin, Neomycin, Polymyxin B, and Hydrocortisone Topical Ointment [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/50168slr078_cotisporin_lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7321\">FDA Approved Drug Products: Xerese (Acyclovir and Hydrocortisone) Topical Cream [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022436s004lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L10574\">FDA Approved Drug Products: Hydrocortone Hydrocortisone Oral Tablets (Discontinued) [<a href=\"https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&amp;ApplNo=008506\" target=\"_blank\">Link</a>] </li><li id=\"reference-L16533\">FDA Approved Drug Products: ALKINDI SPRINKLE (hydrocortisone) oral granules [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213876s000lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>Total hydrocortisone via the oral route has a half life of 2.15h while the free fraction has a half life of 1.39h.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Werumeus Buning J, Touw DJ, Brummelman P, Dullaart RPF, van den Berg G, van der Klauw MM, Kamp J, Wolffenbuttel BHR, van Beek AP: Pharmacokinetics of oral hydrocortisone - Results and implications from a randomized controlled trial. Metabolism. 2017 Jun;71:7-16. doi: 10.1016/j.metabol.2017.02.005. Epub 2017 Feb 13. (PubMed ID 28521880)\" href=\"#reference-A188354\">1</a></sup> A 20mg IV dose of hydrocortisone has a terminal half life of 1.9±0.4h.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Derendorf H, Mollmann H, Barth J, Mollmann C, Tunn S, Krieg M: Pharmacokinetics and oral bioavailability of hydrocortisone. J Clin Pharmacol. 1991 May;31(5):473-6. doi: 10.1002/j.1552-4604.1991.tb01906.x. (PubMed ID 2050835)\" href=\"#reference-A188381\">6</a></sup></p>','HMDB0000063','(1R,3aS,3bS,9aR,9bS,10S,11aS)-1,10-dihydroxy-1-(2-hydroxyacetyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one','InChI=1S/C21H30O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-16,18,22,24,26H,3-8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1','JYGXADMDTFJGBT-VWUMJDOOSA-N','<p>Otic solutions are indicated for infections of the external auditory canal caused by susceptible organisms and with inflammation.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Vosol Hydrocortisone and Glacial Acetic Acid Otic Drops\" href=\"#reference-L10529\">14</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Casporyn Neomycin Sulfate, Polymixin B Sulfate, and Hydrocortisone Otic Drops\" href=\"#reference-L10532\">15</a></sup> Hydrocortisone tablets are indicated for certain endocrine, rheumatic, collagen, allergic, ophthalmic, respiratory, hematologic, neoplastic, edematous, gastrointestinal, and other conditions.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Cortef Hydrocortisone Oral Tablets\" href=\"#reference-L10535\">16</a></sup> A hydrocortisone enema is indicated for ulcerative colitis,<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Cortenema Hydrocortisone Rectal Enema\" href=\"#reference-L10538\">17</a></sup> a topical ointment with antibiotics is indicated for corticosteroid responsive dermatoses with infections,<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Bacitracin, Neomycin, Polymyxin B, and Hydrocortisone Topical Ointment\" href=\"#reference-L7772\">18</a></sup> and a topical cream with <a href=\"https://go.drugbank.com/drugs/DB00787\">acyclovir</a> is indicated to treat cold sores.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Xerese (Acyclovir and Hydrocortisone) Topical Cream\" href=\"#reference-L7321\">19</a></sup> Oral granules of hydrocortisone are used as a replacement therapy for Adrenocortical Insufficiency (AI) in children under 17 years of age.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: ALKINDI SPRINKLE (hydrocortisone) oral granules\" href=\"#reference-L16533\">21</a></sup></p>','C00735','D00088','Organic compounds','<p>Hydrocortisone is metabolised to 6-beta hydrocortisol via CYP3A, 5-beta tetrahydrocortisol via 3-oxo-5-beta-steroid 4-dehydrogenase, 5-alpha tetrahydrocortisol via 3-oxo-5-alpha-steroid 4-dehydrogenase 2, cortisone via Corticosteroid 11-beta-dehydrogenase isozyme 1 and Corticosteroid 11-beta-dehydrogenase isozyme 2, and glucuronide products.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sarkar U, Rivera-Burgos D, Large EM, Hughes DJ, Ravindra KC, Dyer RL, Ebrahimkhani MR, Wishnok JS, Griffith LG, Tannenbaum SR: Metabolite profiling and pharmacokinetic evaluation of hydrocortisone in a perfused three-dimensional human liver bioreactor. Drug Metab Dispos. 2015 Jul;43(7):1091-9. doi: 10.1124/dmd.115.063495. Epub 2015 Apr 29. (PubMed ID 25926431)\" href=\"#reference-A188321\">13</a></sup> Cortisone is further metabolized to tetrahydrocortisone and dihydrocortisol.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sarkar U, Rivera-Burgos D, Large EM, Hughes DJ, Ravindra KC, Dyer RL, Ebrahimkhani MR, Wishnok JS, Griffith LG, Tannenbaum SR: Metabolite profiling and pharmacokinetic evaluation of hydrocortisone in a perfused three-dimensional human liver bioreactor. Drug Metab Dispos. 2015 Jul;43(7):1091-9. doi: 10.1124/dmd.115.063495. Epub 2015 Apr 29. (PubMed ID 25926431)\" href=\"#reference-A188321\">13</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aliphatic homopolycyclic compounds','HCY','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000372?highlight[compounds][]=DB00741&amp;highlight[proteins][]=DB00741\">Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000577?highlight[compounds][]=DB00741&amp;highlight[proteins][]=DB00741\">Corticosterone Methyl Oxidase I Deficiency (CMO I)</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000718?highlight[compounds][]=DB00741&amp;highlight[proteins][]=DB00741\">3-beta-Hydroxysteroid Dehydrogenase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000310?highlight[compounds][]=DB00741&amp;highlight[proteins][]=DB00741\">Corticotropin Activation of Cortisol Production</a></td><td>Signaling</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000371?highlight[compounds][]=DB00741&amp;highlight[proteins][]=DB00741\">Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000575?highlight[compounds][]=DB00741&amp;highlight[proteins][]=DB00741\">11-beta-Hydroxylase Deficiency (CYP11B1)</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000717?highlight[compounds][]=DB00741&amp;highlight[proteins][]=DB00741\">Apparent Mineralocorticoid Excess Syndrome</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000130?highlight[compounds][]=DB00741&amp;highlight[proteins][]=DB00741\">Steroidogenesis</a></td><td>Metabolic</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000373?highlight[compounds][]=DB00741&amp;highlight[proteins][]=DB00741\">Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia Due to 21-Hydroxylase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000566?highlight[compounds][]=DB00741&amp;highlight[proteins][]=DB00741\">17-alpha-Hydroxylase Deficiency (CYP17)</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000576?highlight[compounds][]=DB00741&amp;highlight[proteins][]=DB00741\">21-Hydroxylase Deficiency (CYP21)</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000578?highlight[compounds][]=DB00741&amp;highlight[proteins][]=DB00741\">Corticosterone Methyl Oxidase II Deficiency (CMO II)</a></td><td>Disease</td></tr></tbody>','PA449905','<p>Corticosteroids are generally bound to corticosteroid binding globulin<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Gardill BR, Vogl MR, Lin HY, Hammond GL, Muller YA: Corticosteroid-binding globulin: structure-function implications from species differences. PLoS One. 2012;7(12):e52759. doi: 10.1371/journal.pone.0052759. Epub 2012 Dec 26. (PubMed ID 23300763)\" href=\"#reference-A187439\">11</a></sup> and serum albumin<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Czock D, Keller F, Rasche FM, Haussler U: Pharmacokinetics and pharmacodynamics of systemically administered glucocorticoids. Clin Pharmacokinet. 2005;44(1):61-98. doi: 10.2165/00003088-200544010-00003. (PubMed ID 15634032)\" href=\"#reference-A187436\">12</a></sup> in plasma. Hydrocortisone is 90.1% bound to proteins in plasma, with 56.2% bound to albumin.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FLORINI JR, BUYSKE DA: Plasma protein binding of triamcinolone-H3 and hydrocortisone-4-C14. J Biol Chem. 1961 Jan;236:247-51. (PubMed ID 13700365)\" href=\"#reference-A184223\">5</a></sup></p>','5754','46505089','<p>Corticosteroids are eliminated predominantly in the urine.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Czock D, Keller F, Rasche FM, Haussler U: Pharmacokinetics and pharmacodynamics of systemically administered glucocorticoids. Clin Pharmacokinet. 2005;44(1):61-98. doi: 10.2165/00003088-200544010-00003. (PubMed ID 15634032)\" href=\"#reference-A187436\">12</a></sup> However, data regarding the exact proportion is not readily available.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Jung C, Greco S, Nguyen HH, Ho JT, Lewis JG, Torpy DJ, Inder WJ: Plasma, salivary and urinary cortisol levels following physiological and stress doses of hydrocortisone in normal volunteers. BMC Endocr Disord. 2014 Nov 26;14:91. doi: 10.1186/1472-6823-14-91. (PubMed ID 25425285)\" href=\"#reference-A188387\">7</a></sup></p>','RxList Drug Page','5492','[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C','Solid','Hydroxysteroids','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">11-beta-hydroxysteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">11-hydroxysteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">17-hydroxysteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">20-oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">21-hydroxysteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">3-oxo-delta-4-steroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">3-oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aliphatic homopolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alpha-hydroxy ketone</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclic alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclic ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclohexenone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Delta-4-steroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pregnane-skeleton</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Progestogin-skeleton</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 16 more</a>','Lipids and lipid-like molecules','<span class=\"citations\"><p>Manfred Baumgarth, Dieter Orth, Jurgen Harting, Hans Schaefer, Achim Zesch, \"Hydrocortisone orthoesters, pharmaceutical formulations thereof and processes for the preparation thereof.\" U.S. Patent US4264584, issued March, 1974.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=4264584&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US4264584</a>','DAP000718','<p>Data regarding acute overdoses of glucocorticoids are rare.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Vosol Hydrocortisone and Glacial Acetic Acid Otic Drops\" href=\"#reference-L10529\">14</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Casporyn Neomycin Sulfate, Polymixin B Sulfate, and Hydrocortisone Otic Drops\" href=\"#reference-L10532\">15</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Cortef Hydrocortisone Oral Tablets\" href=\"#reference-L10535\">16</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Cortenema Hydrocortisone Rectal Enema\" href=\"#reference-L10538\">17</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Bacitracin, Neomycin, Polymyxin B, and Hydrocortisone Topical Ointment\" href=\"#reference-L7772\">18</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Xerese (Acyclovir and Hydrocortisone) Topical Cream\" href=\"#reference-L7321\">19</a></sup> Chronic high doses of glucocorticoids can lead to the development of cataract, glaucoma, hypertension, water retention, hyperlipidemia, peptic ulcer, pancreatitis, myopathy, osteoporosis, mood changes, psychosis, dermal atrophy, allergy, acne, hypertrichosis, immune suppression, decreased resistance to infection, moon face, hyperglycemia, hypocalcemia, hypophosphatemia, metabolic acidosis, growth suppression, and secondary adrenal insufficiency.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Ciriaco M, Ventrice P, Russo G, Scicchitano M, Mazzitello G, Scicchitano F, Russo E: Corticosteroid-related central nervous system side effects. J Pharmacol Pharmacother. 2013 Dec;4(Suppl 1):S94-8. doi: 10.4103/0976-500X.120975. (PubMed ID 24347992)\" href=\"#reference-A188405\">8</a></sup> Overdose may be treated by adjusting the dose or stopping the corticosteroid as well as initiating symptomatic and supportive treatment.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Ciriaco M, Ventrice P, Russo G, Scicchitano M, Mazzitello G, Scicchitano F, Russo E: Corticosteroid-related central nervous system side effects. J Pharmacol Pharmacother. 2013 Dec;4(Suppl 1):S94-8. doi: 10.4103/0976-500X.120975. (PubMed ID 24347992)\" href=\"#reference-A188405\">8</a></sup></p>','WI4X0X7BPJ','<p>Total hydrocortisone has a volume of distribution of 39.82L, while the free fraction has a volume of distribution of 474.38L.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Werumeus Buning J, Touw DJ, Brummelman P, Dullaart RPF, van den Berg G, van der Klauw MM, Kamp J, Wolffenbuttel BHR, van Beek AP: Pharmacokinetics of oral hydrocortisone - Results and implications from a randomized controlled trial. Metabolism. 2017 Jun;71:7-16. doi: 10.1016/j.metabol.2017.02.005. Epub 2017 Feb 13. (PubMed ID 28521880)\" href=\"#reference-A188354\">1</a></sup></p>','Hydrocortisone','ZINC000013540519'),(50,'Tetracycline','tetracycline','Tetracycline is an antibiotic used to treat a wide variety of susceptible infections.','Achromycin, Pylera, Sumycin','Tetracycline','<p>Tetracycline is a broad spectrum polyketide antibiotic produced by the Streptomyces genus of Actinobacteria. It exerts a bacteriostatic effect on bacteria by binding reversible to the bacterial 30S ribosomal subunit and blocking incoming aminoacyl tRNA from binding to the ribosome acceptor site. It also binds to some extent to the bacterial 50S ribosomal subunit and may alter the cytoplasmic membrane causing intracellular components to leak from bacterial cells.</p>','C22H24N2O8','DB00759','Approved, Vet approved','Small Molecule','Average: 444.4346 Monoisotopic: 444.153265754 ',' , S02AA — Antiinfectives , S02A — ANTIINFECTIVES , S02 — OTOLOGICALS , S — SENSORY ORGANS , A02BD — Combinations for eradication of Helicobacter pylori , A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) , A02 — DRUGS FOR ACID RELATED DISORDERS , A — ALIMENTARY TRACT AND METABOLISM , A01AB — Antiinfectives and antiseptics for local oral treatment , A01A — STOMATOLOGICAL PREPARATIONS , A01 — STOMATOLOGICAL PREPARATIONS , A — ALIMENTARY TRACT AND METABOLISM , J01AA — Tetracyclines , J01A — TETRACYCLINES , J01 — ANTIBACTERIALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , S01AA — Antibiotics , S01A — ANTIINFECTIVES , S01 — OPHTHALMOLOGICALS , S — SENSORY ORGANS , J01AA — Tetracyclines , J01A — TETRACYCLINES , J01 — ANTIBACTERIALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , J01RA — Combinations of antibacterials , J01R — COMBINATIONS OF ANTIBACTERIALS , J01 — ANTIBACTERIALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , S03AA — Antiinfectives , S03A — ANTIINFECTIVES , S03 — OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS , S — SENSORY ORGANS , D06AA — Tetracycline and derivatives , D06A — ANTIBIOTICS FOR TOPICAL USE , D06 — ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE , D — DERMATOLOGICALS , A02BD — Combinations for eradication of Helicobacter pylori , A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) , A02 — DRUGS FOR ACID RELATED DISORDERS , A — ALIMENTARY TRACT AND METABOLISM','<p>Bioavailability is less than 40% when administered via intramuscular injection, 100% intravenously, and 60-80% orally (fasting adults). Food and/or milk reduce GI absorption of oral preparations of tetracycline by 50% or more.</p>','','Enteric bacteria and other eubacteria\nBorrelia burgdorferi\nChlamydia trachomatis\nMycoplasma pneumoniae\nRickettsia rickettsii\nVibrio cholerae\nEscherichia coli\nShigella\nCoxiella','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a naphthacene moiety, which is a polyaromatic hydrocarbon made of four linearly fused benzene rings.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000022\" rel=\"noopener\" target=\"_blank\">Naphthacenes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carboxylic acid group (or a derivative thereof) attached to an anthracene ring system.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001911\" rel=\"noopener\" target=\"_blank\">Anthracenecarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000048\" rel=\"noopener\" target=\"_blank\">Tetralins</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R\', where R = aryl group and R\'=organyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003670\" rel=\"noopener\" target=\"_blank\">Aryl ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Phenols that a unsubstituted at the 2-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004646\" rel=\"noopener\" target=\"_blank\">1-hydroxy-2-unsubstituted benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Phenols that are unsubstituted at the 4-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004647\" rel=\"noopener\" target=\"_blank\">1-hydroxy-4-unsubstituted benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003899\" rel=\"noopener\" target=\"_blank\">Aralkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004325\" rel=\"noopener\" target=\"_blank\">Cyclohexenones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003889\" rel=\"noopener\" target=\"_blank\">Vinylogous acids</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, a carboxylic acid group (or a derivative thereof), and a side-chain that is specific to each amino acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000347\" rel=\"noopener\" target=\"_blank\">Amino acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds comprising primary carboxylic acid amide functional group, with the general structure RC(=O)NH2.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001662\" rel=\"noopener\" target=\"_blank\">Primary carboxylic acid amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing the enol functional group, with the structure HO(R)C=CR\'. Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000132\" rel=\"noopener\" target=\"_blank\">Enols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing more than one hydroxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002286\" rel=\"noopener\" target=\"_blank\">Polyols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 8 more</a>','Not Available','Not Available','50237605','60-54-8','27902','CHEMBL1440','10257122','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds that are synthesized either from the amino acid phenylalanine (phenylpropanoids) or the decarboxylative condensation of malonyl-CoA (polyketides). Phenylpropanoids are aromatic compounds based on the phenylpropane skeleton. Polyketides usually consist of alternating carbonyl and methylene groups (beta-polyketones), biogenetically derived from repeated condensation of acetyl coenzyme A (via malonyl coenzyme A), and usually the compounds derived from them by further condensations.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000261\" rel=\"noopener\" target=\"_blank\">Phenylpropanoids and polyketides</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000181\" rel=\"noopener\" target=\"_blank\">Tetracyclines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"not-available\">Not Available</span></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000181\" rel=\"noopener\" target=\"_blank\">Tetracyclines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a naphthacene moiety, which is a polyaromatic hydrocarbon made of four linearly fused benzene rings.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000022\" rel=\"noopener\" target=\"_blank\">Naphthacenes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carboxylic acid group (or a derivative thereof) attached to an anthracene ring system.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001911\" rel=\"noopener\" target=\"_blank\">Anthracenecarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000048\" rel=\"noopener\" target=\"_blank\">Tetralins</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R\', where R = aryl group and R\'=organyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003670\" rel=\"noopener\" target=\"_blank\">Aryl ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Phenols that a unsubstituted at the 2-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004646\" rel=\"noopener\" target=\"_blank\">1-hydroxy-2-unsubstituted benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Phenols that are unsubstituted at the 4-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004647\" rel=\"noopener\" target=\"_blank\">1-hydroxy-4-unsubstituted benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003899\" rel=\"noopener\" target=\"_blank\">Aralkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004325\" rel=\"noopener\" target=\"_blank\">Cyclohexenones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003889\" rel=\"noopener\" target=\"_blank\">Vinylogous acids</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, a carboxylic acid group (or a derivative thereof), and a side-chain that is specific to each amino acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000347\" rel=\"noopener\" target=\"_blank\">Amino acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds comprising primary carboxylic acid amide functional group, with the general structure RC(=O)NH2.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001662\" rel=\"noopener\" target=\"_blank\">Primary carboxylic acid amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing the enol functional group, with the structure HO(R)C=CR\'. Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000132\" rel=\"noopener\" target=\"_blank\">Enols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing more than one hydroxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002286\" rel=\"noopener\" target=\"_blank\">Polyols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 8 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1-hydroxy-2-unsubstituted benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">1-hydroxy-4-unsubstituted benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amino acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anthracene carboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aralkylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic homopolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxamide group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclohexenone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Enol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Naphthacene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Polyol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary carboxylic acid amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetracene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetracycline</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetralin</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous acid</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 23 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic homopolycyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">tetracyclines (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:27902\" rel=\"noopener\" target=\"_blank\">CHEBI:27902</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">tetracyclines, Linear tetracyclines (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C06570\" rel=\"noopener\" target=\"_blank\">C06570</a>) </span></span></dd></dl>','Tetracyclines','<p><span class=\"not-available\">Not Available</span></p>','This compound belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.','Tetracyclines','<li>Avoid milk and dairy products.</li>\n<li>Take on an empty stomach. Take at least 1 hour before or 2 hours after meals.</li>\n<li>Take with a full glass of water.</li>','Drugs.com Drug Page',' , Agents that produce neuromuscular block (indirect) , Alimentary Tract and Metabolism , Anti-Bacterial Agents , Anti-Infective Agents , Antibacterials for Systemic Use , Antibiotics for Topical Use , Antiinfectives and Antiseptics for Local Oral Treatment , Antiinfectives for Systemic Use , Cytochrome P-450 CYP3A Inhibitors , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Inhibitors , Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Dermatologicals , Drugs causing inadvertant photosensitivity , Drugs for Acid Related Disorders , Drugs for Peptic Ulcer and Gastro-Oesophageal Reflux Disease (Gord) , Drugs that are Mainly Renally Excreted , Enzyme Inhibitors , Naphthacenes , OAT1/SLC22A6 inhibitors , OAT3/SLC22A8 Inhibitors , OAT3/SLC22A8 Substrates , Ophthalmological and Otological Preparations , Ophthalmologicals , Organic Anion Transporting Polypeptide 2B1 Inhibitors , Otologicals , Photosensitizing Agents , Protein Synthesis Inhibitors , Sensory Organs , Stomatological Preparations , Tetracyclines','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>172.5 dec °C</td><td>PhysProp</td></tr><tr><td>water solubility</td><td>231 mg/L (at 25 °C)</td><td>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</td></tr><tr><td>logP</td><td>-1.30</td><td>HANSCH,C ET AL. (1995)</td></tr><tr><td>logS</td><td>-3.12</td><td>ADME Research, USCD</td></tr><tr><td>pKa</td><td>3.3 (at 25 °C)</td><td>SERJEANT,EP &amp; DEMPSEY,B (1979)</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">tetracyclines (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:27902\" rel=\"noopener\" target=\"_blank\">CHEBI:27902</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">tetracyclines, Linear tetracyclines (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C06570\" rel=\"noopener\" target=\"_blank\">C06570</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0014897\" rel=\"noopener\" target=\"_blank\">HMDB0014897</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D00201\" rel=\"noopener\" target=\"_blank\">D00201</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C06570\" rel=\"noopener\" target=\"_blank\">C06570</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=54675776\" rel=\"noopener\" target=\"_blank\">54675776</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506693\" rel=\"noopener\" target=\"_blank\">46506693</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.10257122.html\" rel=\"noopener\" target=\"_blank\">10257122</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50237605\" rel=\"noopener\" target=\"_blank\">50237605</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=10395\" rel=\"noopener\" target=\"_blank\">10395</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=27902\" rel=\"noopener\" target=\"_blank\">27902</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL1440\" rel=\"noopener\" target=\"_blank\">CHEMBL1440</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000084441937\" rel=\"noopener\" target=\"_blank\">ZINC000084441937</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP001527\" rel=\"noopener\" target=\"_blank\">DAP001527</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA451640\" rel=\"noopener\" target=\"_blank\">PA451640</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/TAC\" rel=\"noopener\" target=\"_blank\">TAC</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic2/tetcycl2.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/tetracycline.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Tetracycline\" rel=\"noopener\" target=\"_blank\">Tetracycline</a></dd></dl>','<li>Avoid milk and dairy products.</li>\n<li>Take on an empty stomach. Take at least 1 hour before or 2 hours after meals.</li>\n<li>Take with a full glass of water.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A1165\">Griffin MO, Fricovsky E, Ceballos G, Villarreal F: Tetracyclines: a pleitropic family of compounds with promising therapeutic properties. Review of the literature. Am J Physiol Cell Physiol. 2010 Sep;299(3):C539-48. doi: 10.1152/ajpcell.00047.2010. Epub 2010 Jun 30. [<a href=\"/articles/A1165\" target=\"_blank\">Article</a>] </li></ol>','<p>6-12 hours</p>','HMDB0014897','(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide','InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1','OFVLGDICTFRJMM-WESIUVDSSA-N','<p>Used to treat bacterial infections such as Rocky Mountain spotted fever, typhus fever, tick fevers, Q fever, rickettsialpox and Brill-Zinsser disease. May be used to treat infections caused by Chlamydiae spp., B. burgdorferi (Lyme disease), and upper respiratory infections caused by typical (S. pneumoniae, H. influenzae, and M. catarrhalis) and atypical organisms (C. pneumoniae, M. pneumoniae, L. pneumophila). May also be used to treat acne. Tetracycline may be an alternative drug for people who are allergic to penicillin.</p>','C06570','D00201','Organic compounds','<p>Not metabolized</p>','Aromatic homopolycyclic compounds','TAC','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000294?highlight[compounds][]=DB00759&amp;highlight[proteins][]=DB00759\">Tetracycline Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA451640','<p>20 - 67% protein bound</p>','54675776','46506693','<p>They are concentrated by the liver in the bile and excreted in the urine and feces at high concentrations in a biologically active form.</p>','RxList Drug Page','10395','[H][C@@]12C[C@@]3([H])C(=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C)C(=O)C1=C(O)C=CC=C1[C@@]3(C)O','Solid','Not Available','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1-hydroxy-2-unsubstituted benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">1-hydroxy-4-unsubstituted benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amino acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anthracene carboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aralkylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic homopolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxamide group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclohexenone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Enol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Naphthacene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Polyol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary carboxylic acid amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetracene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetracycline</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetralin</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous acid</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 23 more</a>','Phenylpropanoids and polyketides','<span class=\"citations\"><p>Thomas F. McNamara, Nungavaram S. Ramamurthy, Lorne M. Golub, \"Non-antibacterial tetracycline compositions possessing anti-collagenolytic properties and methods of preparing and using same.\" U.S. Patent US4704383, issued May, 1963.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=4704383&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US4704383</a>','DAP001527','<p>LD<sub>50</sub>=808mg/kg (orally in mice)</p>','F8VB5M810T','<p><span class=\"not-available\">Not Available</span></p>','Tetracycline','ZINC000084441937'),(51,'Etoposide','etoposide','Etoposide is a podophyllotoxin derivative used to treat testicular and small cell lung tumors.','Etopophos, Toposar, Vepesid','Etoposide','<p>A semisynthetic derivative of podophyllotoxin that exhibits antitumor activity. Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent entry into the mitotic phase of cell division, and lead to cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle.</p>','C29H32O13','DB00773','Approved','Small Molecule','Average: 588.5566 Monoisotopic: 588.18429111 ',' , L01CB — Podophyllotoxin derivatives , L01C — PLANT ALKALOIDS AND OTHER NATURAL PRODUCTS , L01 — ANTINEOPLASTIC AGENTS , L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS','<p>Absorbed well, time to peak plasma concentration is 1-1.5 hrs. Mean bioavailability is 50% (range of 25% - 75%). Cmax and AUC values for orally administered etoposide capsules display intra- and inter-subject variability. There is no evidence of first-pass effect for etoposide. </p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Lignans with a structure based on the 1-phenyltetralin skeleton.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003425\" rel=\"noopener\" target=\"_blank\">Aryltetralin lignans</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic heterocyclic compounds containing a 1,3-dioxole ring linearly fused to the a naphthofuran.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004792\" rel=\"noopener\" target=\"_blank\">Furanonaphthodioxoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000048\" rel=\"noopener\" target=\"_blank\">Tetralins</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic compounds containing a pyranodioxin moiety, which consists of a pyran ring fused to a dioxin ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002011\" rel=\"noopener\" target=\"_blank\">Pyranodioxins</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004111\" rel=\"noopener\" target=\"_blank\">Dimethoxybenzenes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a methoxy group attached to the benzene ring of a phenol moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000190\" rel=\"noopener\" target=\"_blank\">Methoxyphenols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000296\" rel=\"noopener\" target=\"_blank\">Benzodioxoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a methoxybenzene or a derivative thereof.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000138\" rel=\"noopener\" target=\"_blank\">Anisoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds contaning a phenoxy group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004742\" rel=\"noopener\" target=\"_blank\">Phenoxy compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R\' , where R is an alkyl group and R\' is an aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000128\" rel=\"noopener\" target=\"_blank\">Alkyl aryl ethers</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing 1,3-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 3.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001314\" rel=\"noopener\" target=\"_blank\">1,3-dioxanes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002012\" rel=\"noopener\" target=\"_blank\">Oxanes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001540\" rel=\"noopener\" target=\"_blank\">Monosaccharides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001245\" rel=\"noopener\" target=\"_blank\">Gamma butyrolactones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002648\" rel=\"noopener\" target=\"_blank\">Tetrahydrofurans</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001238\" rel=\"noopener\" target=\"_blank\">Carboxylic acid esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polyols containing an alcohol group at two adjacent positions.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002467\" rel=\"noopener\" target=\"_blank\">1,2-diols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds having the structure R2C(OR\')2 ( R\' not Hydrogen) and thus diethers of geminal diols. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H ). Mixed acetals have different R\' groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001656\" rel=\"noopener\" target=\"_blank\">Acetals</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 14 more</a>','Not Available','Not Available','50127140','33419-42-0','4911','CHEMBL44657','33510','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5\', C8-C8\'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001392\" rel=\"noopener\" target=\"_blank\">Lignans, neolignans and related compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001510\" rel=\"noopener\" target=\"_blank\">Lignan lactones</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000047\" rel=\"noopener\" target=\"_blank\">Podophyllotoxins</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000047\" rel=\"noopener\" target=\"_blank\">Podophyllotoxins</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Lignans with a structure based on the 1-phenyltetralin skeleton.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003425\" rel=\"noopener\" target=\"_blank\">Aryltetralin lignans</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic heterocyclic compounds containing a 1,3-dioxole ring linearly fused to the a naphthofuran.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004792\" rel=\"noopener\" target=\"_blank\">Furanonaphthodioxoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000048\" rel=\"noopener\" target=\"_blank\">Tetralins</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic compounds containing a pyranodioxin moiety, which consists of a pyran ring fused to a dioxin ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002011\" rel=\"noopener\" target=\"_blank\">Pyranodioxins</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004111\" rel=\"noopener\" target=\"_blank\">Dimethoxybenzenes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a methoxy group attached to the benzene ring of a phenol moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000190\" rel=\"noopener\" target=\"_blank\">Methoxyphenols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000296\" rel=\"noopener\" target=\"_blank\">Benzodioxoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a methoxybenzene or a derivative thereof.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000138\" rel=\"noopener\" target=\"_blank\">Anisoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds contaning a phenoxy group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004742\" rel=\"noopener\" target=\"_blank\">Phenoxy compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R\' , where R is an alkyl group and R\' is an aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000128\" rel=\"noopener\" target=\"_blank\">Alkyl aryl ethers</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing 1,3-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 3.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001314\" rel=\"noopener\" target=\"_blank\">1,3-dioxanes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002012\" rel=\"noopener\" target=\"_blank\">Oxanes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001540\" rel=\"noopener\" target=\"_blank\">Monosaccharides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001245\" rel=\"noopener\" target=\"_blank\">Gamma butyrolactones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002648\" rel=\"noopener\" target=\"_blank\">Tetrahydrofurans</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001238\" rel=\"noopener\" target=\"_blank\">Carboxylic acid esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polyols containing an alcohol group at two adjacent positions.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002467\" rel=\"noopener\" target=\"_blank\">1,2-diols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds having the structure R2C(OR\')2 ( R\' not Hydrogen) and thus diethers of geminal diols. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H ). Mixed acetals have different R\' groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001656\" rel=\"noopener\" target=\"_blank\">Acetals</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 14 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1,2-diol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">1-aryltetralin lignan</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Acetal</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anisole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzodioxole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dimethoxybenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Gamma butyrolactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Lactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Linear furanonaphthodioxole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">M-dimethoxybenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Meta-dioxane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Methoxybenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Methoxyphenol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocyclic benzene moiety</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monosaccharide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Naphthofuran</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenol ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenoxy compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Podophyllotoxin</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyranodioxin</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetrahydrofuran</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetralin</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 30 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic heteropolycyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">organic heterotetracyclic compound, beta-D-glucoside, furonaphthodioxole (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4911\" rel=\"noopener\" target=\"_blank\">CHEBI:4911</a>) </span></span></dd></dl>','Lignan lactones','','This compound belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).','Podophyllotoxins','<li>Avoid grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum concentration of etoposide.</li>\n<li>Exercise caution with St. John\'s Wort. This herb induces CYP3A4 metabolism, which may reduce serum levels of etoposide.</li>','Drugs.com Drug Page',' , Antineoplastic Agents , Antineoplastic Agents, Phytogenic , Antineoplastic and Immunomodulating Agents , BCRP/ABCG2 Substrates , Carbohydrates , Cardiotoxic antineoplastic agents , Cytochrome P-450 CYP1A2 Substrates , Cytochrome P-450 CYP1A2 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2E1 Substrates , Cytochrome P-450 CYP2E1 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP3A Inducers , Cytochrome P-450 CYP3A Inhibitors , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Inducers , Cytochrome P-450 CYP3A4 Inducers (strength unknown) , Cytochrome P-450 CYP3A4 Inhibitors , Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP3A5 Substrates , Cytochrome P-450 CYP3A5 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 Enzyme Inducers , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Enzyme Inhibitors , Glucosides , Glycosides , Immunosuppressive Agents , Myelosuppressive Agents , Naphthalenes , Narrow Therapeutic Index Drugs , P-glycoprotein inhibitors , P-glycoprotein substrates , P-glycoprotein substrates with a Narrow Therapeutic Index , Podophyllotoxin , Podophyllotoxin Derivatives , Tetrahydronaphthalenes , Topoisomerase II Inhibitors , Topoisomerase Inhibitors , UGT1A1 Substrates , UGT1A1 Substrates with a Narrow Therapeutic Index','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>236-251 °C</td><td>PhysProp</td></tr><tr><td>water solubility</td><td>Sparingly soluble </td><td>FDA label </td></tr><tr><td>logP</td><td>0.60</td><td>HANSCH,C ET AL. (1995)</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">organic heterotetracyclic compound, beta-D-glucoside, furonaphthodioxole (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4911\" rel=\"noopener\" target=\"_blank\">CHEBI:4911</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0014911\" rel=\"noopener\" target=\"_blank\">HMDB0014911</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D00125\" rel=\"noopener\" target=\"_blank\">D00125</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C01576\" rel=\"noopener\" target=\"_blank\">C01576</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=36462\" rel=\"noopener\" target=\"_blank\">36462</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505434\" rel=\"noopener\" target=\"_blank\">46505434</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.33510.html\" rel=\"noopener\" target=\"_blank\">33510</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50127140\" rel=\"noopener\" target=\"_blank\">50127140</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=4179\" rel=\"noopener\" target=\"_blank\">4179</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=4911\" rel=\"noopener\" target=\"_blank\">4911</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL44657\" rel=\"noopener\" target=\"_blank\">CHEMBL44657</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000003938684\" rel=\"noopener\" target=\"_blank\">ZINC000003938684</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000786\" rel=\"noopener\" target=\"_blank\">DAP000786</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA449552\" rel=\"noopener\" target=\"_blank\">PA449552</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/EVP\" rel=\"noopener\" target=\"_blank\">EVP</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic2/etopophos.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/cdi/etoposide.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Etoposide\" rel=\"noopener\" target=\"_blank\">Etoposide</a></dd></dl>','<li>Avoid grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum concentration of etoposide.</li>\n<li>Exercise caution with St. John\'s Wort. This herb induces CYP3A4 metabolism, which may reduce serum levels of etoposide.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A1178\">Zhou Z, Zwelling LA, Ganapathi R, Kleinerman ES: Enhanced etoposide sensitivity following adenovirus-mediated human topoisomerase IIalpha gene transfer is independent of topoisomerase IIbeta. Br J Cancer. 2001 Sep 1;85(5):747-51. [<a href=\"/articles/A1178\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1179\">Azarova AM, Lyu YL, Lin CP, Tsai YC, Lau JY, Wang JC, Liu LF: Roles of DNA topoisomerase II isozymes in chemotherapy and secondary malignancies. Proc Natl Acad Sci U S A. 2007 Jun 26;104(26):11014-9. Epub 2007 Jun 19. [<a href=\"/articles/A1179\" target=\"_blank\">Article</a>] </li></ol>','<p>4-11 hours</p>','HMDB0014911','(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one','InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1','VJJPUSNTGOMMGY-MRVIYFEKSA-N','<p>For use in combination with other chemotherapeutic agents in the treatment of refractory testicular tumors and as first line treatment in patients with small cell lung cancer. Also used to treat other malignancies such as lymphoma, non-lymphocytic leukemia, and glioblastoma multiforme.</p>','C01576','D00125','Organic compounds','<p>Primarily hepatic (through O-demethylation via the CYP450 3A4 isoenzyme pathway) with 40% excreted unchanged in the urine. Etoposide also undergoes glutathione and glucuronide conjugation which are catalyzed by GSTT1/GSTP1 and UGT1A1, respectively. Prostaglandin synthases are also responsible for the conversion of etoposide to O-demethylated metabolites (quinone). </p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteropolycyclic compounds','EVP','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000601?highlight[compounds][]=DB00773&amp;highlight[proteins][]=DB00773\">Etoposide Metabolism Pathway</a></td><td>Drug metabolism</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000442?highlight[compounds][]=DB00773&amp;highlight[proteins][]=DB00773\">Etoposide Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA449552','<p>97% protein bound. </p>','36462','46505434','<p>Etoposide is cleared by both renal and nonrenal processes, i.e., metabolism and biliary excretion. Glucuronide and/or sulfate conjugates of etoposide are also excreted in human urine. Biliary excretion of unchanged drug and/or metabolites is an important route of etoposide elimination as fecal recovery of radioactivity is 44% of the intravenous dose. 56% of the dose was in the urine, 45% of which was excreted as etoposide. </p>','RxList Drug Page','4179','[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@H]2O[C@@H]1O[C@]2([H])CO[C@@H](C)O[C@@]2([H])[C@H](O)[C@H]1O','Solid','Podophyllotoxins','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1,2-diol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">1-aryltetralin lignan</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Acetal</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anisole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzodioxole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dimethoxybenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Gamma butyrolactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Lactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Linear furanonaphthodioxole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">M-dimethoxybenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Meta-dioxane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Methoxybenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Methoxyphenol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocyclic benzene moiety</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monosaccharide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Naphthofuran</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenol ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenoxy compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Podophyllotoxin</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyranodioxin</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetrahydrofuran</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetralin</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 30 more</a>','Lignans, neolignans and related compounds','<a href=\"https://www.google.com/?tbm=pts#q=3524844&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US3524844</a>','DAP000786','<p>Side effects include alopecia, constipation, diarrhea, nausea and vomiting and secondary malignancies (leukemia).</p>','6PLQ3CP4P3','<p>The disposition of etoposide is a biphasic process with a distribution half-life of 1.5 hours. It does not cross into cerebrospinal fluid well.\nVolume of distribution, steady state = 18 - 29 L. </p>','Etoposide','ZINC000003938684'),(52,'Naproxen','naproxen','Naproxen is an NSAID used to treat rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, polyarticular juvenile idiopathic arthritis, tendinitis, bursitis, acute gout, primary dysmenorrhea, and mild to moderate pain.','Aleve, Aleve PM, Aleve-D, Anaprox, EC-Naprosyn, Naprelan, Naprosyn, Sallus, Sudafed Sinus & Pain, Treximet, Vimovo','Naproxen','<p>Naproxen is classified as a nonsteroidal anti-inflammatory dug (NSAID) and was initially approved for prescription use in 1976 and then for over-the-counter (OTC) use in 1994.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Brutzkus JC, Varacallo M: Naproxen . (PubMed ID 30247840)\" href=\"#reference-A178975\">3</a></sup> It can effectively manage acute pain as well as pain related to rheumatic diseases, and has a well studied adverse effect profile.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Todd PA, Clissold SP: Naproxen. A reappraisal of its pharmacology, and therapeutic use in rheumatic diseases and pain states. Drugs. 1990 Jul;40(1):91-137. doi: 10.2165/00003495-199040010-00006. (PubMed ID 2202585)\" href=\"#reference-A179098\">5</a></sup> Given its overall tolerability and effectiveness, naproxen can be considered a first line treatment for a variety of clinical situations requiring analgesia.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Todd PA, Clissold SP: Naproxen. A reappraisal of its pharmacology, and therapeutic use in rheumatic diseases and pain states. Drugs. 1990 Jul;40(1):91-137. doi: 10.2165/00003495-199040010-00006. (PubMed ID 2202585)\" href=\"#reference-A179098\">5</a></sup> Naproxen is available in both immediate and delayed release formulations, in combination with sumatriptan to treat migraines, and in combination with esomeprazole to lower the risk of developing gastric ulcers.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprelan FDA Label\" href=\"#reference-L6582\">12</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprosyn FDA Label\" href=\"#reference-L6583\">13</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Treximet FDA Label\" href=\"#reference-L7309\">15</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Vimovo FDA Label\" href=\"#reference-L7312\">16</a></sup></p>','C14H14O3','DB00788','Approved, Vet approved','Small Molecule','Average: 230.2592 Monoisotopic: 230.094294314 ',' , G02CC — Antiinflammatory products for vaginal administration , G02C — OTHER GYNECOLOGICALS , G02 — OTHER GYNECOLOGICALS , G — GENITO URINARY SYSTEM AND SEX HORMONES , M02AA — Antiinflammatory preparations, non-steroids for topical use , M02A — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN , M02 — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN , M — MUSCULO-SKELETAL SYSTEM , M01AE — Propionic acid derivatives , M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS , M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS , M — MUSCULO-SKELETAL SYSTEM , M01AE — Propionic acid derivatives , M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS , M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS , M — MUSCULO-SKELETAL SYSTEM , M01AE — Propionic acid derivatives , M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS , M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS , M — MUSCULO-SKELETAL SYSTEM','<p>Naproxen is available as a free acid and sodium salt.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Todd PA, Clissold SP: Naproxen. A reappraisal of its pharmacology, and therapeutic use in rheumatic diseases and pain states. Drugs. 1990 Jul;40(1):91-137. doi: 10.2165/00003495-199040010-00006. (PubMed ID 2202585)\" href=\"#reference-A179098\">5</a></sup> At comparable doses, (naproxen 500 mg = naproxen sodium 550 mg) they differ slightly in their rates of absorption, but otherwise they are therapeutically and pharmacologically equivalent.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Todd PA, Clissold SP: Naproxen. A reappraisal of its pharmacology, and therapeutic use in rheumatic diseases and pain states. Drugs. 1990 Jul;40(1):91-137. doi: 10.2165/00003495-199040010-00006. (PubMed ID 2202585)\" href=\"#reference-A179098\">5</a></sup> Naproxen sodium achieves a peak plasma concentration after 1 hour, while peak plasma concentration is observed after 2 hours with naproxen (free acid).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Todd PA, Clissold SP: Naproxen. A reappraisal of its pharmacology, and therapeutic use in rheumatic diseases and pain states. Drugs. 1990 Jul;40(1):91-137. doi: 10.2165/00003495-199040010-00006. (PubMed ID 2202585)\" href=\"#reference-A179098\">5</a></sup> There are no differences between the 2 forms in the post-absorption phase pharmacokinetics.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Todd PA, Clissold SP: Naproxen. A reappraisal of its pharmacology, and therapeutic use in rheumatic diseases and pain states. Drugs. 1990 Jul;40(1):91-137. doi: 10.2165/00003495-199040010-00006. (PubMed ID 2202585)\" href=\"#reference-A179098\">5</a></sup> The difference in initial absorption should be considered when treating acute pain, since naproxen sodium may offer a quicker onset of action.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Todd PA, Clissold SP: Naproxen. A reappraisal of its pharmacology, and therapeutic use in rheumatic diseases and pain states. Drugs. 1990 Jul;40(1):91-137. doi: 10.2165/00003495-199040010-00006. (PubMed ID 2202585)\" href=\"#reference-A179098\">5</a></sup></p><p>The mean Cmax for the various formulations (immediate release, enteric coated, controlled release etc.) of naproxen are comparable and range from 94 mcg/mL to 97.4 mcg/mL.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprelan FDA Label\" href=\"#reference-L6582\">12</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprosyn FDA Label\" href=\"#reference-L6583\">13</a></sup> In one pharmacokinetic study, the mean Tmax of naproxen 500 mg (immediate release) given every 12 hours over 5 days was 3 hours, compared to a mean Tmax of 5 hours for Naprelan 1000 mg (controlled release) given every 24 hours over 5 days.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprelan FDA Label\" href=\"#reference-L6582\">12</a></sup> In this same study, the AUC<sub>0-24hr</sub> was 1446mcgxhr/mL for naproxen immediate release and 1448 mcgxhr/mL for the controlled release formulation.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprelan FDA Label\" href=\"#reference-L6582\">12</a></sup> A separate study comparing the pharmacokinetics of Naprosyn tablets and EC-Naprosyn observed the following values: Tmax and AUC<sub>0-12hrs</sub> of EC-Naprosyn were 4 hours and 845 mcgxhr/mL respectively, and Tmax and AUC<sub>0-12hrs</sub> values of Naprosyn were 1.9 hours and 767 mcgxhr/mL respectively.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprosyn FDA Label\" href=\"#reference-L6583\">13</a></sup> </p><p>When given in combination with sumatriptan the Cmax of naproxen is roughly 36% lower compared to naproxen sodium 550 mg tablets, and the median Tmax is 5 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Treximet FDA Label\" href=\"#reference-L7309\">15</a></sup></p><p>Based on the AUC and Cmax of naproxen, Vimovo (naproxen/esomeprazole combination product) and enteric-coated naproxen may be considered bioequivalent.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Vimovo FDA Label\" href=\"#reference-L7312\">16</a></sup></p><p>Overall, naproxen is rapidly and completely absorbed when administered orally and rectally.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Davies NM, Anderson KE: Clinical pharmacokinetics of naproxen. Clin Pharmacokinet. 1997 Apr;32(4):268-93. doi: 10.2165/00003088-199732040-00002. (PubMed ID 9113437)\" href=\"#reference-A179110\">6</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Todd PA, Clissold SP: Naproxen. A reappraisal of its pharmacology, and therapeutic use in rheumatic diseases and pain states. Drugs. 1990 Jul;40(1):91-137. doi: 10.2165/00003495-199040010-00006. (PubMed ID 2202585)\" href=\"#reference-A179098\">5</a></sup> Food may contribute to a delay in the absorption of orally administered naproxen, but will not affect the extent of absorption.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Todd PA, Clissold SP: Naproxen. A reappraisal of its pharmacology, and therapeutic use in rheumatic diseases and pain states. Drugs. 1990 Jul;40(1):91-137. doi: 10.2165/00003495-199040010-00006. (PubMed ID 2202585)\" href=\"#reference-A179098\">5</a></sup></p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a methoxybenzene or a derivative thereof.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000138\" rel=\"noopener\" target=\"_blank\">Anisoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R\' , where R is an alkyl group and R\' is an aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000128\" rel=\"noopener\" target=\"_blank\">Alkyl aryl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a carboxylic acid group with the formula -C(=O)OH.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001205\" rel=\"noopener\" target=\"_blank\">Carboxylic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span></span></span>','Not Available','Not Available','50339185','22204-53-1','7476','CHEMBL154','137720','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing one or more benzene rings.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002448\" rel=\"noopener\" target=\"_blank\">Benzenoids</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a naphthalene moiety, which consists of two fused benzene rings.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000023\" rel=\"noopener\" target=\"_blank\">Naphthalenes</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"not-available\">Not Available</span></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a naphthalene moiety, which consists of two fused benzene rings.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000023\" rel=\"noopener\" target=\"_blank\">Naphthalenes</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a methoxybenzene or a derivative thereof.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000138\" rel=\"noopener\" target=\"_blank\">Anisoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R\' , where R is an alkyl group and R\' is an aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000128\" rel=\"noopener\" target=\"_blank\">Alkyl aryl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a carboxylic acid group with the formula -C(=O)OH.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001205\" rel=\"noopener\" target=\"_blank\">Carboxylic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anisole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic homopolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Naphthalene</span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic homopolycyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">monocarboxylic acid, methoxynaphthalene (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7476\" rel=\"noopener\" target=\"_blank\">CHEBI:7476</a>) </span></span></dd></dl>','Naphthalenes','<p>Naproxen is cleared at a rate of 0.13 mL/min/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprelan FDA Label\" href=\"#reference-L6582\">12</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprosyn FDA Label\" href=\"#reference-L6583\">13</a></sup></p>','This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.','Naphthalenes','<li>Take with food. Food reduces GI irritation.</li>','Drugs.com Drug Page',' , Agents causing hyperkalemia , Agents that produce hypertension , Analgesics , Analgesics, Non-Narcotic , Anti-Inflammatory Agents , Anti-Inflammatory Agents, Non-Steroidal , Anti-Inflammatory Agents, Non-Steroidal (Non-Selective) , Antigout Preparations , Antiinflammatory and Antirheumatic Products , Antiinflammatory and Antirheumatic Products, Non-Steroids , Antiinflammatory Preparations, Non-Steroids for Topical Use , Antiinflammatory Products for Vaginal Administration , Antirheumatic Agents , BSEP/ABCB11 Substrates , Central Nervous System Agents , Cyclooxygenase Inhibitors , Cytochrome P-450 CYP1A2 Substrates , Cytochrome P-450 CYP2C8 Substrates , Cytochrome P-450 CYP2C9 Substrates , Cytochrome P-450 Substrates , Drugs causing inadvertant photosensitivity , Enzyme Inhibitors , Genito Urinary System and Sex Hormones , Musculo-Skeletal System , Naphthaleneacetic Acids , Naphthalenes , Nephrotoxic agents , Non COX-2 selective NSAIDS , OAT1/SLC22A6 inhibitors , Other Nonsteroidal Anti-inflammatory Agents , P-glycoprotein inhibitors , Peripheral Nervous System Agents , Photosensitizing Agents , Propionates , Sensory System Agents , Topical Products for Joint and Muscular Pain , UGT1A1 Substrates , UGT1A3 substrates , UGT1A6 substrate , UGT1A9 Substrates , UGT2B7 substrates','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>152°C</td><td>MSDS Label</td></tr><tr><td>water solubility</td><td>15.9 mg/L (at 25 °C)</td><td>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</td></tr><tr><td>logP</td><td>3.18</td><td>HANSCH,C ET AL. (1995)</td></tr><tr><td>logS</td><td>-4.16</td><td>ADME Research, USCD</td></tr><tr><td>Caco2 permeability</td><td>-4.83</td><td>ADME Research, USCD</td></tr><tr><td>pKa</td><td>4.15</td><td>SANGSTER (1994)</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">monocarboxylic acid, methoxynaphthalene (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7476\" rel=\"noopener\" target=\"_blank\">CHEBI:7476</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0001923\" rel=\"noopener\" target=\"_blank\">HMDB0001923</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D00118\" rel=\"noopener\" target=\"_blank\">D00118</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C01517\" rel=\"noopener\" target=\"_blank\">C01517</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=156391\" rel=\"noopener\" target=\"_blank\">156391</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505508\" rel=\"noopener\" target=\"_blank\">46505508</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.137720.html\" rel=\"noopener\" target=\"_blank\">137720</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50339185\" rel=\"noopener\" target=\"_blank\">50339185</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=7258\" rel=\"noopener\" target=\"_blank\">7258</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=7476\" rel=\"noopener\" target=\"_blank\">7476</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL154\" rel=\"noopener\" target=\"_blank\">CHEMBL154</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000000105216\" rel=\"noopener\" target=\"_blank\">ZINC000000105216</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000968\" rel=\"noopener\" target=\"_blank\">DAP000968</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA450595\" rel=\"noopener\" target=\"_blank\">PA450595</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/NPS\" rel=\"noopener\" target=\"_blank\">NPS</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic/naproxsod.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/naproxen.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdrhealth\">PDRhealth</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ana1021.shtml\" rel=\"noopener\" target=\"_blank\">PDRhealth Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Naproxen\" rel=\"noopener\" target=\"_blank\">Naproxen</a></dd></dl>','<li>Take with food. Food reduces GI irritation.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A912\">Kearney PM, Baigent C, Godwin J, Halls H, Emberson JR, Patrono C: Do selective cyclo-oxygenase-2 inhibitors and traditional non-steroidal anti-inflammatory drugs increase the risk of atherothrombosis? Meta-analysis of randomised trials. BMJ. 2006 Jun 3;332(7553):1302-8. [<a href=\"/articles/A912\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1195\">Zhang J, Ding EL, Song Y: Adverse effects of cyclooxygenase 2 inhibitors on renal and arrhythmia events: meta-analysis of randomized trials. JAMA. 2006 Oct 4;296(13):1619-32. Epub 2006 Sep 12. [<a href=\"/articles/A1195\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178975\">Brutzkus JC, Varacallo M: Naproxen . [<a href=\"/articles/A178975\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178990\">Wongrakpanich S, Wongrakpanich A, Melhado K, Rangaswami J: A Comprehensive Review of Non-Steroidal Anti-Inflammatory Drug Use in The Elderly. Aging Dis. 2018 Feb 1;9(1):143-150. doi: 10.14336/AD.2017.0306. eCollection 2018 Feb. [<a href=\"/articles/A178990\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179098\">Todd PA, Clissold SP: Naproxen. A reappraisal of its pharmacology, and therapeutic use in rheumatic diseases and pain states. Drugs. 1990 Jul;40(1):91-137. doi: 10.2165/00003495-199040010-00006. [<a href=\"/articles/A179098\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179110\">Davies NM, Anderson KE: Clinical pharmacokinetics of naproxen. Clin Pharmacokinet. 1997 Apr;32(4):268-93. doi: 10.2165/00003088-199732040-00002. [<a href=\"/articles/A179110\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179197\">Falany CN, Strom P, Swedmark S: Sulphation of o-desmethylnaproxen and related compounds by human cytosolic sulfotransferases. Br J Clin Pharmacol. 2005 Dec;60(6):632-40. doi: 10.1111/j.1365-2125.2005.02506.x. [<a href=\"/articles/A179197\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179191\">Bowalgaha K, Elliot DJ, Mackenzie PI, Knights KM, Swedmark S, Miners JO: S-Naproxen and desmethylnaproxen glucuronidation by human liver microsomes and recombinant human UDP-glucuronosyltransferases (UGT): role of UGT2B7 in the elimination of naproxen. Br J Clin Pharmacol. 2005 Oct;60(4):423-33. doi: 10.1111/j.1365-2125.2005.02446.x. [<a href=\"/articles/A179191\" target=\"_blank\">Article</a>] </li><li id=\"reference-A38985\">Tracy TS, Marra C, Wrighton SA, Gonzalez FJ, Korzekwa KR: Involvement of multiple cytochrome P450 isoforms in naproxen O-demethylation. Eur J Clin Pharmacol. 1997;52(4):293-8. [<a href=\"/articles/A38985\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179224\">Ruschitzka F, Borer JS, Krum H, Flammer AJ, Yeomans ND, Libby P, Luscher TF, Solomon DH, Husni ME, Graham DY, Davey DA, Wisniewski LM, Menon V, Fayyad R, Beckerman B, Iorga D, Lincoff AM, Nissen SE: Differential blood pressure effects of ibuprofen, naproxen, and celecoxib in patients with arthritis: the PRECISION-ABPM (Prospective Randomized Evaluation of Celecoxib Integrated Safety Versus Ibuprofen or Naproxen Ambulatory Blood Pressure Measurement) Trial. Eur Heart J. 2017 Nov 21;38(44):3282-3292. doi: 10.1093/eurheartj/ehx508. [<a href=\"/articles/A179224\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179227\">Mellemkjaer L, Blot WJ, Sorensen HT, Thomassen L, McLaughlin JK, Nielsen GL, Olsen JH: Upper gastrointestinal bleeding among users of NSAIDs: a population-based cohort study in Denmark. Br J Clin Pharmacol. 2002 Feb;53(2):173-81. doi: 10.1046/j.0306-5251.2001.01220.x. [<a href=\"/articles/A179227\" target=\"_blank\">Article</a>] </li><li id=\"reference-L6582\">Naprelan FDA Label [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020353s034lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L6583\">Naprosyn FDA Label [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017581s113,018164s063,020067s020lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L6595\">Over-the-counter Medications in Pregnancy [<a href=\"https://www.aafp.org/afp/2003/0615/p2517.html\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7309\">Treximet FDA Label [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021926s013lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7312\">Vimovo FDA Label [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022511s023lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>The elimination half-life of naproxen is reported to be 12-17 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Brutzkus JC, Varacallo M: Naproxen . (PubMed ID 30247840)\" href=\"#reference-A178975\">3</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprosyn FDA Label\" href=\"#reference-L6583\">13</a></sup></p>','HMDB0001923','(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid','InChI=1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m0/s1','CMWTZPSULFXXJA-VIFPVBQESA-N','<p>Naproxen is indicated for the management of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, polyarticular juvenile idiopathic arthritis, tendinitis, bursitis, acute gout, primary dysmenorrhea, and for the relief of mild to moderate pain.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprelan FDA Label\" href=\"#reference-L6582\">12</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprosyn FDA Label\" href=\"#reference-L6583\">13</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Brutzkus JC, Varacallo M: Naproxen . (PubMed ID 30247840)\" href=\"#reference-A178975\">3</a></sup> Further, it is first-line therapy for osteoarthritis, acute gouty arthritis, dysmenorrhea, and musculoskeletal inflammation and pain.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Brutzkus JC, Varacallo M: Naproxen . (PubMed ID 30247840)\" href=\"#reference-A178975\">3</a></sup></p>','C01517','D00118','Organic compounds','<p>Naproxen is heavily metabolized in the liver and undergoes both Phase I and Phase II metabolism.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprelan FDA Label\" href=\"#reference-L6582\">12</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprosyn FDA Label\" href=\"#reference-L6583\">13</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Falany CN, Strom P, Swedmark S: Sulphation of o-desmethylnaproxen and related compounds by human cytosolic sulfotransferases. Br J Clin Pharmacol. 2005 Dec;60(6):632-40. doi: 10.1111/j.1365-2125.2005.02506.x. (PubMed ID 16305588)\" href=\"#reference-A179197\">7</a></sup> The first step involves demethylation of naproxen via CYP 1A2, 2C8, and 2C9<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Bowalgaha K, Elliot DJ, Mackenzie PI, Knights KM, Swedmark S, Miners JO: S-Naproxen and desmethylnaproxen glucuronidation by human liver microsomes and recombinant human UDP-glucuronosyltransferases (UGT): role of UGT2B7 in the elimination of naproxen. Br J Clin Pharmacol. 2005 Oct;60(4):423-33. doi: 10.1111/j.1365-2125.2005.02446.x. (PubMed ID 16187975)\" href=\"#reference-A179191\">8</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Tracy TS, Marra C, Wrighton SA, Gonzalez FJ, Korzekwa KR: Involvement of multiple cytochrome P450 isoforms in naproxen O-demethylation. Eur J Clin Pharmacol. 1997;52(4):293-8. (PubMed ID 9248768)\" href=\"#reference-A38985\">9</a></sup>. Both naproxen and desmethylnaproxen proceed to Phase II metabolism; however, desmethylnaproxen can form both acyl and phenolic glucoronide products, while naproxen only produces the acyl glucuronide.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Bowalgaha K, Elliot DJ, Mackenzie PI, Knights KM, Swedmark S, Miners JO: S-Naproxen and desmethylnaproxen glucuronidation by human liver microsomes and recombinant human UDP-glucuronosyltransferases (UGT): role of UGT2B7 in the elimination of naproxen. Br J Clin Pharmacol. 2005 Oct;60(4):423-33. doi: 10.1111/j.1365-2125.2005.02446.x. (PubMed ID 16187975)\" href=\"#reference-A179191\">8</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Falany CN, Strom P, Swedmark S: Sulphation of o-desmethylnaproxen and related compounds by human cytosolic sulfotransferases. Br J Clin Pharmacol. 2005 Dec;60(6):632-40. doi: 10.1111/j.1365-2125.2005.02506.x. (PubMed ID 16305588)\" href=\"#reference-A179197\">7</a></sup> The acyl glucuronidation process involves UGT 1A1, 1A3, 1A6, 1A7, 1A9, 1A10 and 2B7, while phenolic glucuronidation is catalyzed by UGT 1A1, 1A7,1A9, and 1A10.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Bowalgaha K, Elliot DJ, Mackenzie PI, Knights KM, Swedmark S, Miners JO: S-Naproxen and desmethylnaproxen glucuronidation by human liver microsomes and recombinant human UDP-glucuronosyltransferases (UGT): role of UGT2B7 in the elimination of naproxen. Br J Clin Pharmacol. 2005 Oct;60(4):423-33. doi: 10.1111/j.1365-2125.2005.02446.x. (PubMed ID 16187975)\" href=\"#reference-A179191\">8</a></sup> Desmethylnaproxen also undergoes sulphation which is mediated by SULT 1A1, 1B1 and 1E1.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Falany CN, Strom P, Swedmark S: Sulphation of o-desmethylnaproxen and related compounds by human cytosolic sulfotransferases. Br J Clin Pharmacol. 2005 Dec;60(6):632-40. doi: 10.1111/j.1365-2125.2005.02506.x. (PubMed ID 16305588)\" href=\"#reference-A179197\">7</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic homopolycyclic compounds','NPS','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000120?highlight[compounds][]=DB00788&amp;highlight[proteins][]=DB00788\">Naproxen Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA450595','<p>Naproxen is highly protein bound with &gt;99% of the drug bound to albumin at therapeutic levels.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprelan FDA Label\" href=\"#reference-L6582\">12</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprosyn FDA Label\" href=\"#reference-L6583\">13</a></sup></p>','156391','46505508','<p>After oral administration, about 95% of naproxen and it\'s metabolites can be recovered in the urine with 66-92% recovered as conjugated metabolite and less than 1% recovered as naproxen or desmethylnaproxen.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Falany CN, Strom P, Swedmark S: Sulphation of o-desmethylnaproxen and related compounds by human cytosolic sulfotransferases. Br J Clin Pharmacol. 2005 Dec;60(6):632-40. doi: 10.1111/j.1365-2125.2005.02506.x. (PubMed ID 16305588)\" href=\"#reference-A179197\">7</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprelan FDA Label\" href=\"#reference-L6582\">12</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprosyn FDA Label\" href=\"#reference-L6583\">13</a></sup> Less than 5% of naproxen is excreted in the feces.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprelan FDA Label\" href=\"#reference-L6582\">12</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprosyn FDA Label\" href=\"#reference-L6583\">13</a></sup></p>','RxList Drug Page','7258','COC1=CC2=C(C=C1)C=C(C=C2)[C@H](C)C(O)=O','Solid','Not Available','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anisole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic homopolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Naphthalene</span></span></span>','Benzenoids','<a href=\"https://www.google.com/?tbm=pts#q=4009197&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US4009197</a>','DAP000968','<p>Although the over-the-counter (OTC) availability of naproxen provides convenience to patients, it also increases the likelihood of overdose.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Brutzkus JC, Varacallo M: Naproxen . (PubMed ID 30247840)\" href=\"#reference-A178975\">3</a></sup> Thankfully, the extent of overdose is typically mild with adverse effects normally limited to drowsiness, lethargy, epigastric pain, nausea and vomiting.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Brutzkus JC, Varacallo M: Naproxen . (PubMed ID 30247840)\" href=\"#reference-A178975\">3</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprelan FDA Label\" href=\"#reference-L6582\">12</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprosyn FDA Label\" href=\"#reference-L6583\">13</a></sup> Although there is no antidote for naproxen overdose, symptoms will typically subside with appropriate supportive care.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprelan FDA Label\" href=\"#reference-L6582\">12</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprosyn FDA Label\" href=\"#reference-L6583\">13</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Brutzkus JC, Varacallo M: Naproxen . (PubMed ID 30247840)\" href=\"#reference-A178975\">3</a></sup></p><p>Naproxen is classified as Category B during the first 2 trimesters of pregnancy, and as Category D during the third trimester.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Over-the-counter Medications in Pregnancy\" href=\"#reference-L6595\">14</a></sup> Naproxen is contraindicated in the 3rd trimester since it increases the risk of premature closure of the fetal ductus arteriosus and should be avoided in pregnant women starting at 30 weeks gestation.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprelan FDA Label\" href=\"#reference-L6582\">12</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprosyn FDA Label\" href=\"#reference-L6583\">13</a></sup></p>','57Y76R9ATQ','<p>Naproxen has a volume of distribution of 0.16 L/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprelan FDA Label\" href=\"#reference-L6582\">12</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Naprosyn FDA Label\" href=\"#reference-L6583\">13</a></sup></p>','Naproxen','ZINC000000105216'),(53,'Meloxicam','meloxicam','Meloxicam is an NSAID used to treat osteoarthritis in adults, rheumatoid arthritis in adults, and juvenile rheumatoid arthritis in pediatrics.','Anjeso, Mobic, Qmiiz, Vivlodex','Meloxicam','<p>Meloxicam is a nonsteroidal anti-inflammatory drug (NSAID) used to relieve various types of pain, including pain caused by musculoskeletal conditions, osteoarthritis, and rheumatoid arthritis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Bekker A, Kloepping C, Collingwood S: Meloxicam in the management of post-operative pain: Narrative review. J Anaesthesiol Clin Pharmacol. 2018 Oct-Dec;34(4):450-457. doi: 10.4103/joacp.JOACP_133_18. (PubMed ID 30774225)\" href=\"#reference-A190189\">1</a></sup> With a longer half-life than most other NSAIDS, it is a favorable option for those who require once-daily dosing. Meloxicam is available in oral, transdermal, and intravenous formulations. It is a preferential COX-2 inhibitor, purportedly reducing the risk of adverse gastrointestinal tract effects, however, this is a topic of controversy.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Katz JA: COX-2 inhibition: what we learned--a controversial update on safety data. Pain Med. 2013 Dec;14 Suppl 1:S29-34. doi: 10.1111/pme.12252. (PubMed ID 24373107)\" href=\"#reference-A190198\">4</a>,<a class=\"reference-popover-link\" data-content=\"Seddik H, Rabhi M: [Meloxicam-induced colitis revealed by acute abdominal pain]. Ann Pharm Fr. 2013 Mar;71(2):119-22. doi: 10.1016/j.pharma.2012.12.003. Epub 2013 Mar 8. (PubMed ID 23537413)\" href=\"#reference-A190201\">5</a></sup></p>','C14H13N3O4S2','DB00814','Approved, Vet approved','Small Molecule','Average: 351.401 Monoisotopic: 351.034747299 ',' , M01AC — Oxicams , M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS , M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS , M — MUSCULO-SKELETAL SYSTEM , M01AC — Oxicams , M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS , M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS , M — MUSCULO-SKELETAL SYSTEM','<p>The absolute bioavailability oral capsules after a dose was 89% in one pharmacokinetic study. Cmax was reached 5–6 hours after administration of a single dose given after the first meal of the day. The Cmax doubled when the drug was administered in the fasting state. Despite this, meloxicam can be taken without regard to food, unlike many other NSAIDS.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Bekker A, Kloepping C, Collingwood S: Meloxicam in the management of post-operative pain: Narrative review. J Anaesthesiol Clin Pharmacol. 2018 Oct-Dec;34(4):450-457. doi: 10.4103/joacp.JOACP_133_18. (PubMed ID 30774225)\" href=\"#reference-A190189\">1</a>,<a class=\"reference-popover-link\" data-content=\"FDA approved products: Mobic (meloxicam) oral tablets\" href=\"#reference-L11398\">10</a></sup></p><p>Meloxicam formulated for instillation with <a href=\"https://go.drugbank.com/drugs/DB00297\">bupivacaine</a> produced varied systemic measures following a single dose of varying strength. In patients undergoing bunionectomy, 1.8 mg of meloxicam produced a C<sub>max</sub> of 26 ± 14 ng/mL, a median T<sub>max</sub> of 18 h, and an AUC<sub>∞</sub> of 2079 ± 1631 ng*h/mL. For a 9 mg dose used in herniorrhaphy, the corresponding values were 225 ± 96 ng/mL, 54 h, and the AUC<sub>∞</sub> was not reported. Lastly, a 12 mg dose used in total knee arthroplasty produced values of 275 ± 134 ng/mL, 36 h, and 25,673 ± 17,666 ng*h/mL.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: ZYNRELEF (bupivacaine and meloxicam) extended-release solution for injection\" href=\"#reference-L34100\">13</a></sup></p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000060\" rel=\"noopener\" target=\"_blank\">Alpha amino acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds that contain a carboxamide group that is N-linked to a aryl group. They have the generic structure RC(=O)N(R\')H, R = organyl group and R\'= aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003282\" rel=\"noopener\" target=\"_blank\">N-arylamides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a thiazole ring substituted at positions 2 and 5 only.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002635\" rel=\"noopener\" target=\"_blank\">2,5-disubstituted thiazoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing the sulfonamide functional group, an amide of sulfonic acid with the general structure R1S(=O)2N(R2)R3 (R1=alkyl, aryl; R2,R3=H, alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001585\" rel=\"noopener\" target=\"_blank\">Organosulfonamides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing one or more benzene rings.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002448\" rel=\"noopener\" target=\"_blank\">Benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing 1,2-thiazine, a six-member ring with a nitrogen and a sulfur atoms in ring positions 1 and 2 respectively, as well as two double bonds.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001348\" rel=\"noopener\" target=\"_blank\">1,2-thiazines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003889\" rel=\"noopener\" target=\"_blank\">Vinylogous acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R\')H (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001663\" rel=\"noopener\" target=\"_blank\">Secondary carboxylic acid amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 4 more</a>','Not Available','Not Available','50056998','71125-38-7','6741','CHEMBL599','10442740','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a ring with least one carbon atom and one non-carbon atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000002\" rel=\"noopener\" target=\"_blank\">Organoheterocyclic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000309\" rel=\"noopener\" target=\"_blank\">Benzothiazines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"not-available\">Not Available</span></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000309\" rel=\"noopener\" target=\"_blank\">Benzothiazines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000060\" rel=\"noopener\" target=\"_blank\">Alpha amino acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds that contain a carboxamide group that is N-linked to a aryl group. They have the generic structure RC(=O)N(R\')H, R = organyl group and R\'= aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003282\" rel=\"noopener\" target=\"_blank\">N-arylamides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a thiazole ring substituted at positions 2 and 5 only.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002635\" rel=\"noopener\" target=\"_blank\">2,5-disubstituted thiazoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing the sulfonamide functional group, an amide of sulfonic acid with the general structure R1S(=O)2N(R2)R3 (R1=alkyl, aryl; R2,R3=H, alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001585\" rel=\"noopener\" target=\"_blank\">Organosulfonamides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing one or more benzene rings.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002448\" rel=\"noopener\" target=\"_blank\">Benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing 1,2-thiazine, a six-member ring with a nitrogen and a sulfur atoms in ring positions 1 and 2 respectively, as well as two double bonds.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001348\" rel=\"noopener\" target=\"_blank\">1,2-thiazines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003889\" rel=\"noopener\" target=\"_blank\">Vinylogous acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R\')H (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001663\" rel=\"noopener\" target=\"_blank\">Secondary carboxylic acid amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 4 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">2,5-disubstituted 1,3-thiazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alpha-amino acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzothiazine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxamide group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Heteroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">N-arylamide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic sulfonic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organosulfonic acid amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organosulfonic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ortho-thiazine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary carboxylic acid amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Thiazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous acid</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 16 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic heteropolycyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">monocarboxylic acid amide, 1,3-thiazole, benzothiazine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6741\" rel=\"noopener\" target=\"_blank\">CHEBI:6741</a>) </span></span></dd></dl>','Benzothiazines','<p>After an oral dose, the total clearance of meloxicam is 0.42–0.48 L/h.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Bekker A, Kloepping C, Collingwood S: Meloxicam in the management of post-operative pain: Narrative review. J Anaesthesiol Clin Pharmacol. 2018 Oct-Dec;34(4):450-457. doi: 10.4103/joacp.JOACP_133_18. (PubMed ID 30774225)\" href=\"#reference-A190189\">1</a>,<a class=\"reference-popover-link\" data-content=\"Turck D, Roth W, Busch U: A review of the clinical pharmacokinetics of meloxicam. Br J Rheumatol. 1996 Apr;35 Suppl 1:13-6. doi: 10.1093/rheumatology/35.suppl_1.13. (PubMed ID 8630630)\" href=\"#reference-A190195\">3</a></sup> The FDA label indicates a plasma clearance from 7 to 9 mL/min. No dose changes are required in mild to moderate renal or hepatic impairment. The use of meloxicam in patients with severe renal or hepatic impairment has not been studied. FDA prescribing information advises against it.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA approved products: Mobic (meloxicam) oral tablets\" href=\"#reference-L11398\">10</a></sup></p>','This compound belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).','Benzothiazines','<li>Avoid alcohol. The risk of gastrointestinal bleeding may be increased.</li>\n<li>Take with or without food. The absorption is unaffected by food.</li>','Drugs.com Drug Page',' , Agents causing hyperkalemia , Agents that produce hypertension , Analgesics , Analgesics, Non-Narcotic , Anti-Inflammatory Agents , Anti-Inflammatory Agents, Non-Steroidal , Anti-Inflammatory Agents, Non-Steroidal (Non-Selective) , Antiinflammatory and Antirheumatic Products , Antiinflammatory and Antirheumatic Products, Non-Steroids , Antirheumatic Agents , COX-2 Inhibitors , Cyclooxygenase Inhibitors , Cytochrome P-450 CYP2C8 Substrates , Cytochrome P-450 CYP2C9 Substrates , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 Substrates , Musculo-Skeletal System , Nephrotoxic agents , Other Nonsteroidal Anti-inflammatory Agents , Oxicams , Peripheral Nervous System Agents , Selective Cyclooxygenase 2 Inhibitors (NSAIDs) , Sensory System Agents , Sulfur Compounds , Thiazines , Thiazoles','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>256</td><td>http://www.guildlink.com.au/gc/ws/by/pi.cfm?product=bypmobic10517</td></tr><tr><td>boiling point (°C)</td><td>581.3±60.0 </td><td>https://www.chemsrc.com/en/cas/71125-38-7_1083007.html</td></tr><tr><td>water solubility</td><td>22 mg/ml</td><td>https://www.chemicalbook.com/ChemicalProductProperty_US_CB2191355.aspx</td></tr><tr><td>logP</td><td>0.1</td><td>https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/20938s004lbl.pdf</td></tr><tr><td>Caco2 permeability</td><td>-4.71</td><td>ADME Research, USCD</td></tr><tr><td>pKa</td><td>4.08</td><td>https://www.chemicalbook.com/ChemicalProductProperty_US_CB2191355.aspx</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">monocarboxylic acid amide, 1,3-thiazole, benzothiazine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6741\" rel=\"noopener\" target=\"_blank\">CHEBI:6741</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0014952\" rel=\"noopener\" target=\"_blank\">HMDB0014952</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D00969\" rel=\"noopener\" target=\"_blank\">D00969</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C08169\" rel=\"noopener\" target=\"_blank\">C08169</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=54677470\" rel=\"noopener\" target=\"_blank\">54677470</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506624\" rel=\"noopener\" target=\"_blank\">46506624</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.10442740.html\" rel=\"noopener\" target=\"_blank\">10442740</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50056998\" rel=\"noopener\" target=\"_blank\">50056998</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=41493\" rel=\"noopener\" target=\"_blank\">41493</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=6741\" rel=\"noopener\" target=\"_blank\">6741</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL599\" rel=\"noopener\" target=\"_blank\">CHEMBL599</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000013129998\" rel=\"noopener\" target=\"_blank\">ZINC000013129998</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000971\" rel=\"noopener\" target=\"_blank\">DAP000971</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA450353\" rel=\"noopener\" target=\"_blank\">PA450353</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/MXM\" rel=\"noopener\" target=\"_blank\">MXM</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic/mobic.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/cdi/meloxicam.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Meloxicam\" rel=\"noopener\" target=\"_blank\">Meloxicam</a></dd></dl>','<li>Avoid alcohol. The risk of gastrointestinal bleeding may be increased.</li>\n<li>Take with or without food. The absorption is unaffected by food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A190189\">Bekker A, Kloepping C, Collingwood S: Meloxicam in the management of post-operative pain: Narrative review. J Anaesthesiol Clin Pharmacol. 2018 Oct-Dec;34(4):450-457. doi: 10.4103/joacp.JOACP_133_18. [<a href=\"/articles/A190189\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190192\">Moore RA, Derry S, McQuay HJ: Single dose oral meloxicam for acute postoperative pain in adults. Cochrane Database Syst Rev. 2009 Oct 7;(4):CD007552. doi: 10.1002/14651858.CD007552.pub2. [<a href=\"/articles/A190192\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190195\">Turck D, Roth W, Busch U: A review of the clinical pharmacokinetics of meloxicam. Br J Rheumatol. 1996 Apr;35 Suppl 1:13-6. doi: 10.1093/rheumatology/35.suppl_1.13. [<a href=\"/articles/A190195\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190198\">Katz JA: COX-2 inhibition: what we learned--a controversial update on safety data. Pain Med. 2013 Dec;14 Suppl 1:S29-34. doi: 10.1111/pme.12252. [<a href=\"/articles/A190198\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190201\">Seddik H, Rabhi M: [Meloxicam-induced colitis revealed by acute abdominal pain]. Ann Pharm Fr. 2013 Mar;71(2):119-22. doi: 10.1016/j.pharma.2012.12.003. Epub 2013 Mar 8. [<a href=\"/articles/A190201\" target=\"_blank\">Article</a>] </li><li id=\"reference-A14902\">Chesne C, Guyomard C, Guillouzo A, Schmid J, Ludwig E, Sauter T: Metabolism of Meloxicam in human liver involves cytochromes P4502C9 and 3A4. Xenobiotica. 1998 Jan;28(1):1-13. doi: 10.1080/004982598239704. [<a href=\"/articles/A14902\" target=\"_blank\">Article</a>] </li><li id=\"reference-A176366\">Ricciotti E, FitzGerald GA: Prostaglandins and inflammation. Arterioscler Thromb Vasc Biol. 2011 May;31(5):986-1000. doi: 10.1161/ATVBAHA.110.207449. [<a href=\"/articles/A176366\" target=\"_blank\">Article</a>] </li><li id=\"reference-A39443\">Prasad GS, Srisailam K, Sashidhar RB: Metabolic inhibition of meloxicam by specific CYP2C9 inhibitors in Cunninghamella blakesleeana NCIM 687: in silico and in vitro studies. Springerplus. 2016 Feb 24;5:166. doi: 10.1186/s40064-016-1794-4. eCollection 2016. [<a href=\"/articles/A39443\" target=\"_blank\">Article</a>] </li><li id=\"reference-T757\">Carl P. Weiner MD, MBA, FACOG, Clifford Mason PhD (2019). Drugs for Pregnant and Lactating Women (3rd ed.). Elsevier. </li><li id=\"reference-L11398\">FDA approved products: Mobic (meloxicam) oral tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020938s024s025,021530s014s015lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L11470\">Medsafe NZ: Mobictab (meloxicam) oral tablets [<a href=\"https://www.medsafe.govt.nz/profs/Datasheet/m/Mobictab.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L11473\">American College of Cardiology: Meloxicam [<a href=\"https://www.cardiosmart.org/Healthwise/d045/32/d04532\" target=\"_blank\">Link</a>] </li><li id=\"reference-L34100\">FDA Approved Drug Products: ZYNRELEF (bupivacaine and meloxicam) extended-release solution for injection [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/211988s005lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>The half-life of meloxicam is approximately 20 hours<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Turck D, Roth W, Busch U: A review of the clinical pharmacokinetics of meloxicam. Br J Rheumatol. 1996 Apr;35 Suppl 1:13-6. doi: 10.1093/rheumatology/35.suppl_1.13. (PubMed ID 8630630)\" href=\"#reference-A190195\">3</a></sup>, which is considerably longer than most other NSAIDS. It can therefore be dosed without the need for slow-release formulations.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Bekker A, Kloepping C, Collingwood S: Meloxicam in the management of post-operative pain: Narrative review. J Anaesthesiol Clin Pharmacol. 2018 Oct-Dec;34(4):450-457. doi: 10.4103/joacp.JOACP_133_18. (PubMed ID 30774225)\" href=\"#reference-A190189\">1</a></sup></p><p>Meloxicam applied together with <a href=\"https://go.drugbank.com/drugs/DB00297\">bupivacaine</a> for postsurgical analgesia had a median half-life of 33-42 hours, depending on dose and application site.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: ZYNRELEF (bupivacaine and meloxicam) extended-release solution for injection\" href=\"#reference-L34100\">13</a></sup></p>','HMDB0014952','4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1lambda6,2-benzothiazine-3-carboxamide','InChI=1S/C14H13N3O4S2/c1-8-7-15-14(22-8)16-13(19)11-12(18)9-5-3-4-6-10(9)23(20,21)17(11)2/h3-7,18H,1-2H3,(H,15,16,19)','ZRVUJXDFFKFLMG-UHFFFAOYSA-N','<p>Meloxicam is indicated for the symptomatic treatment of arthritis and osteoarthritis. In addition, it is indicated for the pauciarticular and polyarticular course of Juvenile Rheumatoid Arthritis (JRA) in patients aged 2 years old or above.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA approved products: Mobic (meloxicam) oral tablets\" href=\"#reference-L11398\">10</a></sup> Off-label uses include the treatment of dental or post-surgical pain. In addition to the above, meloxicam has also been studied in the treatment of neuropathic pain. <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Bekker A, Kloepping C, Collingwood S: Meloxicam in the management of post-operative pain: Narrative review. J Anaesthesiol Clin Pharmacol. 2018 Oct-Dec;34(4):450-457. doi: 10.4103/joacp.JOACP_133_18. (PubMed ID 30774225)\" href=\"#reference-A190189\">1</a></sup></p><p>Meloxicam, in combination with <a href=\"https://go.drugbank.com/drugs/DB00297\">bupivacaine</a>, is indicated for postsurgical analgesia in adult patients for up to 72 hours following foot and ankle, small-to-medium open abdominal, and lower extremity total joint arthroplasty surgical procedures.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: ZYNRELEF (bupivacaine and meloxicam) extended-release solution for injection\" href=\"#reference-L34100\">13</a></sup></p>','C08169','D00969','Organic compounds','<p>Meloxicam is almost completely metabolized. CYP2C9 is the main enzyme responsible for the metabolism of meloxicam<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Bekker A, Kloepping C, Collingwood S: Meloxicam in the management of post-operative pain: Narrative review. J Anaesthesiol Clin Pharmacol. 2018 Oct-Dec;34(4):450-457. doi: 10.4103/joacp.JOACP_133_18. (PubMed ID 30774225)\" href=\"#reference-A190189\">1</a>,<a class=\"reference-popover-link\" data-content=\"Chesne C, Guyomard C, Guillouzo A, Schmid J, Ludwig E, Sauter T: Metabolism of Meloxicam in human liver involves cytochromes P4502C9 and 3A4. Xenobiotica. 1998 Jan;28(1):1-13. doi: 10.1080/004982598239704. (PubMed ID 9493314)\" href=\"#reference-A14902\">6</a></sup> with minor contributions from CYP3A4.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA approved products: Mobic (meloxicam) oral tablets\" href=\"#reference-L11398\">10</a></sup> Meloxicam has 4 major metabolites with no activity determined. About 60% of the ingested dose is metabolized to 5\'-carboxy meloxicam from hepatic cytochrome enzyme oxidation of an intermediate metabolite, 5’-hydroxymethylmeloxicam.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Chesne C, Guyomard C, Guillouzo A, Schmid J, Ludwig E, Sauter T: Metabolism of Meloxicam in human liver involves cytochromes P4502C9 and 3A4. Xenobiotica. 1998 Jan;28(1):1-13. doi: 10.1080/004982598239704. (PubMed ID 9493314)\" href=\"#reference-A14902\">6</a>,<a class=\"reference-popover-link\" data-content=\"Prasad GS, Srisailam K, Sashidhar RB: Metabolic inhibition of meloxicam by specific CYP2C9 inhibitors in Cunninghamella blakesleeana NCIM 687: in silico and in vitro studies. Springerplus. 2016 Feb 24;5:166. doi: 10.1186/s40064-016-1794-4. eCollection 2016. (PubMed ID 27026863)\" href=\"#reference-A39443\">8</a></sup> Two other metabolites are likely produced via peroxidation.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Chesne C, Guyomard C, Guillouzo A, Schmid J, Ludwig E, Sauter T: Metabolism of Meloxicam in human liver involves cytochromes P4502C9 and 3A4. Xenobiotica. 1998 Jan;28(1):1-13. doi: 10.1080/004982598239704. (PubMed ID 9493314)\" href=\"#reference-A14902\">6</a>,<a class=\"reference-popover-link\" data-content=\"FDA approved products: Mobic (meloxicam) oral tablets\" href=\"#reference-L11398\">10</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteropolycyclic compounds','MXM','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000106?highlight[compounds][]=DB00814&amp;highlight[proteins][]=DB00814\">Meloxicam Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA450353','<p>Meloxicam is about 99.4% protein bound, primarily to albumin.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Bekker A, Kloepping C, Collingwood S: Meloxicam in the management of post-operative pain: Narrative review. J Anaesthesiol Clin Pharmacol. 2018 Oct-Dec;34(4):450-457. doi: 10.4103/joacp.JOACP_133_18. (PubMed ID 30774225)\" href=\"#reference-A190189\">1</a>,<a class=\"reference-popover-link\" data-content=\"Turck D, Roth W, Busch U: A review of the clinical pharmacokinetics of meloxicam. Br J Rheumatol. 1996 Apr;35 Suppl 1:13-6. doi: 10.1093/rheumatology/35.suppl_1.13. (PubMed ID 8630630)\" href=\"#reference-A190195\">3</a>,<a class=\"reference-popover-link\" data-content=\"FDA approved products: Mobic (meloxicam) oral tablets\" href=\"#reference-L11398\">10</a></sup></p>','54677470','46506624','<p>Meloxicam is mainly eliminated through metabolism. Its metabolites are cleared through renal and fecal elimination.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Turck D, Roth W, Busch U: A review of the clinical pharmacokinetics of meloxicam. Br J Rheumatol. 1996 Apr;35 Suppl 1:13-6. doi: 10.1093/rheumatology/35.suppl_1.13. (PubMed ID 8630630)\" href=\"#reference-A190195\">3</a></sup> Less than &lt;0.25% of a dose is eliminated in the urine as unchanged drug.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA approved products: Mobic (meloxicam) oral tablets\" href=\"#reference-L11398\">10</a></sup> About 1.6% of the parent drug is excreted in the feces.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Bekker A, Kloepping C, Collingwood S: Meloxicam in the management of post-operative pain: Narrative review. J Anaesthesiol Clin Pharmacol. 2018 Oct-Dec;34(4):450-457. doi: 10.4103/joacp.JOACP_133_18. (PubMed ID 30774225)\" href=\"#reference-A190189\">1</a></sup></p>','RxList Drug Page','41493','CN1C(C(=O)NC2=NC=C(C)S2)=C(O)C2=C(C=CC=C2)S1(=O)=O','Solid','Not Available','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">2,5-disubstituted 1,3-thiazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alpha-amino acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzothiazine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxamide group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Heteroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">N-arylamide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic sulfonic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organosulfonic acid amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organosulfonic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ortho-thiazine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary carboxylic acid amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Thiazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous acid</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 16 more</a>','Organoheterocyclic compounds','<span class=\"citations\"><p>Laura Coppi, \"Crystalline forms of meloxicam and processes for their preparation and interconversion.\" U.S. Patent US20030109701, issued June 12, 2003.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=20030109701&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US20030109701</a>','DAP000971','<p>The oral LD50 in rats is 98 mg/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Medsafe NZ: Mobictab (meloxicam) oral tablets\" href=\"#reference-L11470\">11</a></sup> Signs and symptoms of overdose with meloxicam may include shallow breathing, seizure, decreased urine output, gastrointestinal irritation, nausea, vomiting, gastrointestinal bleeding, and black tarry stools.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"American College of Cardiology: Meloxicam\" href=\"#reference-L11473\">12</a></sup> In the case of an overdose, offer supportive treatment and attempt to remove gastrointestinal contents. Cholestyramine has been shown to enhance the elimination of meloxicam.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Medsafe NZ: Mobictab (meloxicam) oral tablets\" href=\"#reference-L11470\">11</a></sup></p>','VG2QF83CGL','<p>The volume of distribution of meloxicam is 10-15L. Because of its high binding to albumin, it is likely to be distributed in highly perfused tissues, such as the liver and kidney.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Bekker A, Kloepping C, Collingwood S: Meloxicam in the management of post-operative pain: Narrative review. J Anaesthesiol Clin Pharmacol. 2018 Oct-Dec;34(4):450-457. doi: 10.4103/joacp.JOACP_133_18. (PubMed ID 30774225)\" href=\"#reference-A190189\">1</a></sup> Meloxicam concentrations in synovial fluid, measured after an oral dose, is estimated at 40% to 50% of the concentrations measured in the plasma.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA approved products: Mobic (meloxicam) oral tablets\" href=\"#reference-L11398\">10</a></sup> This drug is known to cross the placenta in humans.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Carl P. Weiner MD, MBA, FACOG, Clifford Mason PhD (2019). Drugs for Pregnant and Lactating Women (3rd ed.). Elsevier.\" href=\"#reference-T757\">9</a></sup></p>','Meloxicam','ZINC000013129998'),(54,'Cysteamine','cysteamine','Cysteamine is a cystine depleting agent used to treat the effects of cystinosis.','Cystagon, Cystaran, Procysbi','Cysteamine','<p>Cystinosis is a rare disease caused by mutations in the CTNS gene that encodes for cystinosin, a protein responsible for transporting cystine out of the cell lysosome. A defect in cystinosin function is followed by cystine accumulation throughout the body, especially the eyes and kidneys.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Elmonem MA, Veys KR, Soliman NA, van Dyck M, van den Heuvel LP, Levtchenko E: Cystinosis: a review. Orphanet J Rare Dis. 2016 Apr 22;11:47. doi: 10.1186/s13023-016-0426-y. (PubMed ID 27102039)\" href=\"#reference-A218721\">2</a></sup></p><p>Several preparations of cysteamine exist for the treatment of cystinosis manifestations, some in capsule form, and others in ophthalmic solution form.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Products: Cystadrops (cysteamine solution 0.37%) for ophthalmic use\" href=\"#reference-L15606\">10</a>,<a class=\"reference-popover-link\" data-content=\"FDA approved products: PROCYSBI (cysteamine bitartrate) delayed-release oral capsules\" href=\"#reference-L15616\">12</a></sup> In particular, cystine deposits on the eye can cause significant discomfort throughout the day and require frequent treatment with eye drops, typically every waking hour.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA approved products: CYSTARAN (cysteamine 0.44%) for ophthalmic use\" href=\"#reference-L15611\">11</a></sup></p><p>On August 25th 2020, the first ophthalmic solution for cystinosis requiring only 4 daily treatments was granted FDA approval.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Products: Cystadrops (cysteamine solution 0.37%) for ophthalmic use\" href=\"#reference-L15606\">10</a></sup> Cysteamine eye drops are a practical and effective option for those affected by ocular cystinosis. Marketed by Recordati Rare Diseases Inc., CYSTADROPS® reduce the burden of multiple frequent medications normally administered to those with cystinosis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"PRN News Wire: U.S. FDA Approves CYSTADROPS® (Cysteamine Ophthalmic Solution) 0.37%, A New Practical Treatment Option for the Ocular Manifestations of Cystinosis\" href=\"#reference-L15601\">9</a></sup></p>','C2H7NS','DB00847','Approved, Investigational','Small Molecule','Average: 77.149 Monoisotopic: 77.029919919 ',' , A16AA — Amino acids and derivatives , A16A — OTHER ALIMENTARY TRACT AND METABOLISM PRODUCTS , A16 — OTHER ALIMENTARY TRACT AND METABOLISM PRODUCTS , A — ALIMENTARY TRACT AND METABOLISM , S01XA — Other ophthalmologicals , S01X — OTHER OPHTHALMOLOGICALS , S01 — OPHTHALMOLOGICALS , S — SENSORY ORGANS','<p>Orally administered cysteamine is absorbed in the gastrointestinal tract and reaches its maximum plasma concentration in about 1.4 hours, with some variation according to the type of formulation (delayed versus immediate-release).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Devereux G, Steele S, Griffiths K, Devlin E, Fraser-Pitt D, Cotton S, Norrie J, Chrystyn H, O\'Neil D: An Open-Label Investigation of the Pharmacokinetics and Tolerability of Oral Cysteamine in Adults with Cystic Fibrosis. Clin Drug Investig. 2016 Aug;36(8):605-12. doi: 10.1007/s40261-016-0405-z. (PubMed ID 27153825)\" href=\"#reference-A218941\">6</a>,<a class=\"reference-popover-link\" data-content=\"Gangoiti JA, Fidler M, Cabrera BL, Schneider JA, Barshop BA, Dohil R: Pharmacokinetics of enteric-coated cysteamine bitartrate in healthy adults: a pilot study. Br J Clin Pharmacol. 2010 Sep;70(3):376-82. doi: 10.1111/j.1365-2125.2010.03721.x. (PubMed ID 20716238)\" href=\"#reference-A218936\">5</a>,<a class=\"reference-popover-link\" data-content=\"FDA approved products: PROCYSBI (cysteamine bitartrate) delayed-release oral capsules\" href=\"#reference-L15616\">12</a></sup> One pharmacokinetic study of adults with Cystic Fibrosis revealed a Cmax of 2.86 mg/L.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Devereux G, Steele S, Griffiths K, Devlin E, Fraser-Pitt D, Cotton S, Norrie J, Chrystyn H, O\'Neil D: An Open-Label Investigation of the Pharmacokinetics and Tolerability of Oral Cysteamine in Adults with Cystic Fibrosis. Clin Drug Investig. 2016 Aug;36(8):605-12. doi: 10.1007/s40261-016-0405-z. (PubMed ID 27153825)\" href=\"#reference-A218941\">6</a></sup>The maximum plasma concentration after administration of cysteamine eye drops is unknown, however, it is likely to be considerably lower than oral administration.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Products: Cystadrops (cysteamine solution 0.37%) for ophthalmic use\" href=\"#reference-L15606\">10</a></sup></p><p>According to prescribing information, the AUC 0-12 h for the delayed-release oral tablets is 99.26 ± 44.2 μmol*h/L with a Cmax of 27.70 ± 14.99 μmol/L.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA approved products: PROCYSBI (cysteamine bitartrate) delayed-release oral capsules\" href=\"#reference-L15616\">12</a></sup> </p><p>The AUC 0-12 for the immediate-release tablets is 192.00 ± 75.62 μmol*h/L with a Cmax of 37.72 ± 12.10 μmol/L.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA approved products: PROCYSBI (cysteamine bitartrate) delayed-release oral capsules\" href=\"#reference-L15616\">12</a></sup></p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an primary aliphatic amine group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000469\" rel=\"noopener\" target=\"_blank\">Monoalkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span>','Not Available','Not Available','7968','60-23-1','17141','CHEMBL602','5834','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbon-sulfur bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000004\" rel=\"noopener\" target=\"_blank\">Organosulfur compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a functional group with the structure RSH (R = organyl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002485\" rel=\"noopener\" target=\"_blank\">Thiols</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the thiol functional group linked to an alkyl chain.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001212\" rel=\"noopener\" target=\"_blank\">Alkylthiols</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the thiol functional group linked to an alkyl chain.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001212\" rel=\"noopener\" target=\"_blank\">Alkylthiols</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an primary aliphatic amine group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000469\" rel=\"noopener\" target=\"_blank\">Monoalkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Aliphatic acyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkylthiol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary amine</span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aliphatic acyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">thiol, amine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17141\" rel=\"noopener\" target=\"_blank\">CHEBI:17141</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Biogenic amines (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C01678\" rel=\"noopener\" target=\"_blank\">C01678</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">a thiol (<a href=\"http://metacyc.org/META/new-image?type=COMPOUND&amp;object=CPD-239\" rel=\"noopener\" target=\"_blank\">CPD-239</a>) </span></span></dd></dl>','Thiols','<p>The plasma clearance of cysteamine is about 1.2 - 1.4 L/min.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA approved products: PROCYSBI (cysteamine bitartrate) delayed-release oral capsules\" href=\"#reference-L15616\">12</a></sup> One reference mentions a clearance of 89.9 L/h in patients with Cystic Fibrosis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Devereux G, Steele S, Griffiths K, Devlin E, Fraser-Pitt D, Cotton S, Norrie J, Chrystyn H, O\'Neil D: An Open-Label Investigation of the Pharmacokinetics and Tolerability of Oral Cysteamine in Adults with Cystic Fibrosis. Clin Drug Investig. 2016 Aug;36(8):605-12. doi: 10.1007/s40261-016-0405-z. (PubMed ID 27153825)\" href=\"#reference-A218941\">6</a></sup></p>','This compound belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain.','Alkylthiols','<li>Take on an empty stomach. The delayed-release capsules should be taken at least 30 minutes before or 2 hours after a high-fat meal to ensure adequate exposure.</li>\n<li>Take with or without food. The immediate release preparation can be taken with or without food.</li>','Drugs.com Drug Page',' , Alimentary Tract and Metabolism , Amines , Amino Acids and Derivatives , Cystine Depleting Agents , Cystine Disulfide Reduction , EENT Drugs, Miscellaneous , Ethylamines , Mercaptoethylamines , Ophthalmics , Ophthalmologicals , Other Miscellaneous Therapeutic Agents , Sensory Organs , Sulfhydryl Compounds , Sulfur Compounds','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>67-71</td><td>https://www.chemicalbook.com/ChemicalProductProperty_US_CB9337215.aspx</td></tr><tr><td>boiling point (°C)</td><td>133.6±23.0 </td><td>http://www.chemspider.com/Chemical-Structure.5834.html</td></tr><tr><td>water solubility</td><td>Freely soluble in water.</td><td>https://www.chemicalbook.com/ChemicalProductProperty_US_CB9337215.aspx</td></tr><tr><td>logP</td><td>0.1</td><td>https://link.springer.com/article/10.1007/s40261-016-0405-z</td></tr><tr><td>pKa</td><td>10.4</td><td>https://link.springer.com/article/10.1007/s40261-016-0405-z</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">thiol, amine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17141\" rel=\"noopener\" target=\"_blank\">CHEBI:17141</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Biogenic amines (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C01678\" rel=\"noopener\" target=\"_blank\">C01678</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">a thiol (<a href=\"http://metacyc.org/META/new-image?type=COMPOUND&amp;object=CPD-239\" rel=\"noopener\" target=\"_blank\">CPD-239</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0002991\" rel=\"noopener\" target=\"_blank\">HMDB0002991</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D03634\" rel=\"noopener\" target=\"_blank\">D03634</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C01678\" rel=\"noopener\" target=\"_blank\">C01678</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6058\" rel=\"noopener\" target=\"_blank\">6058</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507730\" rel=\"noopener\" target=\"_blank\">46507730</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.5834.html\" rel=\"noopener\" target=\"_blank\">5834</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=7968\" rel=\"noopener\" target=\"_blank\">7968</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=3022\" rel=\"noopener\" target=\"_blank\">3022</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=17141\" rel=\"noopener\" target=\"_blank\">17141</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL602\" rel=\"noopener\" target=\"_blank\">CHEMBL602</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000008034121\" rel=\"noopener\" target=\"_blank\">ZINC000008034121</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP001297\" rel=\"noopener\" target=\"_blank\">DAP001297</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA449171\" rel=\"noopener\" target=\"_blank\">PA449171</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/DHL\" rel=\"noopener\" target=\"_blank\">DHL</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cystagon-drug.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/cdi/cysteamine.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Cysteamine\" rel=\"noopener\" target=\"_blank\">Cysteamine</a></dd></dl>','<li>Take on an empty stomach. The delayed-release capsules should be taken at least 30 minutes before or 2 hours after a high-fat meal to ensure adequate exposure.</li>\n<li>Take with or without food. The immediate release preparation can be taken with or without food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A1262\">Dohil R, Fidler M, Gangoiti JA, Kaskel F, Schneider JA, Barshop BA: Twice-daily cysteamine bitartrate therapy for children with cystinosis. J Pediatr. 2010 Jan;156(1):71-75.e1-3. doi: 10.1016/j.jpeds.2009.07.016. Epub . [<a href=\"/articles/A1262\" target=\"_blank\">Article</a>] </li><li id=\"reference-A218721\">Elmonem MA, Veys KR, Soliman NA, van Dyck M, van den Heuvel LP, Levtchenko E: Cystinosis: a review. Orphanet J Rare Dis. 2016 Apr 22;11:47. doi: 10.1186/s13023-016-0426-y. [<a href=\"/articles/A218721\" target=\"_blank\">Article</a>] </li><li id=\"reference-A218726\">Besouw M, Masereeuw R, van den Heuvel L, Levtchenko E: Cysteamine: an old drug with new potential. Drug Discov Today. 2013 Aug;18(15-16):785-92. doi: 10.1016/j.drudis.2013.02.003. Epub 2013 Feb 14. [<a href=\"/articles/A218726\" target=\"_blank\">Article</a>] </li><li id=\"reference-A218931\">Cherqui S: Cysteamine therapy: a treatment for cystinosis, not a cure. Kidney Int. 2012 Jan;81(2):127-9. doi: 10.1038/ki.2011.301. [<a href=\"/articles/A218931\" target=\"_blank\">Article</a>] </li><li id=\"reference-A218936\">Gangoiti JA, Fidler M, Cabrera BL, Schneider JA, Barshop BA, Dohil R: Pharmacokinetics of enteric-coated cysteamine bitartrate in healthy adults: a pilot study. Br J Clin Pharmacol. 2010 Sep;70(3):376-82. doi: 10.1111/j.1365-2125.2010.03721.x. [<a href=\"/articles/A218936\" target=\"_blank\">Article</a>] </li><li id=\"reference-A218941\">Devereux G, Steele S, Griffiths K, Devlin E, Fraser-Pitt D, Cotton S, Norrie J, Chrystyn H, O\'Neil D: An Open-Label Investigation of the Pharmacokinetics and Tolerability of Oral Cysteamine in Adults with Cystic Fibrosis. Clin Drug Investig. 2016 Aug;36(8):605-12. doi: 10.1007/s40261-016-0405-z. [<a href=\"/articles/A218941\" target=\"_blank\">Article</a>] </li><li id=\"reference-A218951\">Langman CB, Greenbaum LA, Sarwal M, Grimm P, Niaudet P, Deschenes G, Cornelissen E, Morin D, Cochat P, Matossian D, Gaillard S, Bagger MJ, Rioux P: A randomized controlled crossover trial with delayed-release cysteamine bitartrate in nephropathic cystinosis: effectiveness on white blood cell cystine levels and comparison of safety. Clin J Am Soc Nephrol. 2012 Jul;7(7):1112-20. doi: 10.2215/CJN.12321211. Epub 2012 May 3. [<a href=\"/articles/A218951\" target=\"_blank\">Article</a>] </li><li id=\"reference-A218946\">Dohil R, Cabrera BL, Gangoiti JA, Barshop BA, Rioux P: Pharmacokinetics of cysteamine bitartrate following intraduodenal delivery. Fundam Clin Pharmacol. 2014 Apr;28(2):136-43. doi: 10.1111/fcp.12009. Epub 2012 Oct 31. [<a href=\"/articles/A218946\" target=\"_blank\">Article</a>] </li><li id=\"reference-L15601\">PRN News Wire: U.S. FDA Approves CYSTADROPS® (Cysteamine Ophthalmic Solution) 0.37%, A New Practical Treatment Option for the Ocular Manifestations of Cystinosis [<a href=\"https://www.prnewswire.com/news-releases/us-fda-approves-cystadrops-cysteamine-ophthalmic-solution-0-37-a-new-practical-treatment-option-for-the-ocular-manifestations-of-cystinosis-301118026.html\" target=\"_blank\">Link</a>] </li><li id=\"reference-L15606\">FDA Approved Products: Cystadrops (cysteamine solution 0.37%) for ophthalmic use [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/211302s000lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L15611\">FDA approved products: CYSTARAN (cysteamine 0.44%) for ophthalmic use [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/200740s000lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L15616\">FDA approved products: PROCYSBI (cysteamine bitartrate) delayed-release oral capsules [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/203389s000lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L15646\">FDA Approved Products: CYSTAGON® (cysteamine bitartrate) oral capsules [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/020392s010lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>The half-life of cysteamine is about 3.7 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Devereux G, Steele S, Griffiths K, Devlin E, Fraser-Pitt D, Cotton S, Norrie J, Chrystyn H, O\'Neil D: An Open-Label Investigation of the Pharmacokinetics and Tolerability of Oral Cysteamine in Adults with Cystic Fibrosis. Clin Drug Investig. 2016 Aug;36(8):605-12. doi: 10.1007/s40261-016-0405-z. (PubMed ID 27153825)\" href=\"#reference-A218941\">6</a></sup></p>','HMDB0002991','2-aminoethane-1-thiol','InChI=1S/C2H7NS/c3-1-2-4/h4H,1-3H2','UFULAYFCSOUIOV-UHFFFAOYSA-N','<p>The bitartrate salt of cysteamine is used for the oral treatment of nephropathic cystinosis and cystinuria in children 6 years old and above, and adults.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA approved products: PROCYSBI (cysteamine bitartrate) delayed-release oral capsules\" href=\"#reference-L15616\">12</a></sup> The hydrochloride salt, used in eye drop preparations, is indicated for the treatment of corneal cystine crystal accumulation in patients with cystinosis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"PRN News Wire: U.S. FDA Approves CYSTADROPS® (Cysteamine Ophthalmic Solution) 0.37%, A New Practical Treatment Option for the Ocular Manifestations of Cystinosis\" href=\"#reference-L15601\">9</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Products: Cystadrops (cysteamine solution 0.37%) for ophthalmic use\" href=\"#reference-L15606\">10</a></sup></p>','C01678','D03634','Organic compounds','<p>There is limited information in the literature regarding the metabolism of cysteamine. This drug undergoes significant first-pass metabolism.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Dohil R, Cabrera BL, Gangoiti JA, Barshop BA, Rioux P: Pharmacokinetics of cysteamine bitartrate following intraduodenal delivery. Fundam Clin Pharmacol. 2014 Apr;28(2):136-43. doi: 10.1111/fcp.12009. Epub 2012 Oct 31. (PubMed ID 23113697)\" href=\"#reference-A218946\">8</a></sup></p>','Aliphatic acyclic compounds','DHL','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000021?highlight[compounds][]=DB00847&amp;highlight[proteins][]=DB00847\">Taurine and Hypotaurine Metabolism</a></td><td>Metabolic</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000027?highlight[compounds][]=DB00847&amp;highlight[proteins][]=DB00847\">Pantothenate and CoA Biosynthesis</a></td><td>Metabolic</td></tr></tbody>','PA449171','<p>Cysteamine is 52% plasma protein bound, and is mostly bound to albumin.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA approved products: PROCYSBI (cysteamine bitartrate) delayed-release oral capsules\" href=\"#reference-L15616\">12</a></sup></p>','6058','46507730','<p><span class=\"not-available\">Not Available</span></p>','RxList Drug Page','3022','NCCS','Solid','Alkylthiols','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Aliphatic acyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkylthiol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary amine</span></span></span>','Organosulfur compounds','<span class=\"citations\"><p>Tethuharu Okazaki, Takeo Komukai, Saburo Uchikuga, \"Process for preparing cysteamine-S-substituted compounds and derivatives thereof.\" U.S. Patent US4371472, issued September, 1969.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=4371472&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US4371472</a>','DAP001297','<p>Two cases of human overdoses with cysteamine are recorded in the literature, according to prescribing information. In one case, vomiting was immediate after the administration of cysteamine, and the patient did not experience other symptoms. A 200 to 250 mg/kg dose was accidentally ingested by a healthy 13-month-old child. Vomiting and dehydration followed. A full recovery was made after hospitalization and the replenishment of fluids.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Products: CYSTAGON® (cysteamine bitartrate) oral capsules\" href=\"#reference-L15646\">13</a></sup></p><p>There is no known antidote for an overdose with cysteamine. In the case of an overdose, provide supportive treatment, especially to the cardiovascular and respiratory systems. Hemodialysis may be useful in some cases due to the fact that cysteamine has poor plasma protein binding.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Products: CYSTAGON® (cysteamine bitartrate) oral capsules\" href=\"#reference-L15646\">13</a></sup></p>','5UX2SD1KE2','<p>Cysteamine has a volume of distribution of about 129 L, according to one pharmacokinetic study.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Devereux G, Steele S, Griffiths K, Devlin E, Fraser-Pitt D, Cotton S, Norrie J, Chrystyn H, O\'Neil D: An Open-Label Investigation of the Pharmacokinetics and Tolerability of Oral Cysteamine in Adults with Cystic Fibrosis. Clin Drug Investig. 2016 Aug;36(8):605-12. doi: 10.1007/s40261-016-0405-z. (PubMed ID 27153825)\" href=\"#reference-A218941\">6</a></sup> Prescribing information indicates a volume of distribution of 382 L for the delayed-release formulation and 198 L for the immediate-release preparation.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA approved products: PROCYSBI (cysteamine bitartrate) delayed-release oral capsules\" href=\"#reference-L15616\">12</a></sup>\nIt is known to cross the blood-brain barrier.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Dohil R, Cabrera BL, Gangoiti JA, Barshop BA, Rioux P: Pharmacokinetics of cysteamine bitartrate following intraduodenal delivery. Fundam Clin Pharmacol. 2014 Apr;28(2):136-43. doi: 10.1111/fcp.12009. Epub 2012 Oct 31. (PubMed ID 23113697)\" href=\"#reference-A218946\">8</a></sup></p>','Cysteamine','ZINC000008034121'),(55,'Prednisolone','prednisolone','Prednisolone is a glucocorticoid used to treat adrenocortical insufficiency, inflammatory conditions, and some cancers.','Millipred Dp 6 Day','Prednisolone','<p>Prednisolone is a glucocorticoid similar to <a href=\"https://go.drugbank.com/drugs/DB00741\">cortisol</a> used for its anti-inflammatory, immunosuppressive, anti-neoplastic, and vasoconstrictive effects.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Yasir M, Sonthalia S: Corticosteroid Adverse Effects . (PubMed ID 30285357)\" href=\"#reference-A187463\">4</a></sup></p><p>Prednisolone was granted FDA approval on 21 June 1955.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Delta-Cortef Prednisolone Oral Tablets (Discontinued)\" href=\"#reference-L9431\">6</a></sup></p>','C21H28O5','DB00860','Approved, Vet approved','Small Molecule','Average: 360.444 Monoisotopic: 360.193674006 ',' , D07AA — Corticosteroids, weak (group I) , D07A — CORTICOSTEROIDS, PLAIN , D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS , D — DERMATOLOGICALS , S01CA — Corticosteroids and antiinfectives in combination , S01C — ANTIINFLAMMATORY AGENTS AND ANTIINFECTIVES IN COMBINATION , S01 — OPHTHALMOLOGICALS , S — SENSORY ORGANS , D07XA — Corticosteroids, weak, other combinations , D07X — CORTICOSTEROIDS, OTHER COMBINATIONS , D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS , D — DERMATOLOGICALS , A01AC — Corticosteroids for local oral treatment , A01A — STOMATOLOGICAL PREPARATIONS , A01 — STOMATOLOGICAL PREPARATIONS , A — ALIMENTARY TRACT AND METABOLISM , R01AD — Corticosteroids , R01A — DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE , R01 — NASAL PREPARATIONS , R — RESPIRATORY SYSTEM , S01BB — Corticosteroids and mydriatics in combination , S01B — ANTIINFLAMMATORY AGENTS , S01 — OPHTHALMOLOGICALS , S — SENSORY ORGANS , R01AD — Corticosteroids , R01A — DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE , R01 — NASAL PREPARATIONS , R — RESPIRATORY SYSTEM , S01CB — Corticosteroids/antiinfectives/mydriatics in combination , S01C — ANTIINFLAMMATORY AGENTS AND ANTIINFECTIVES IN COMBINATION , S01 — OPHTHALMOLOGICALS , S — SENSORY ORGANS , V03AB — Antidotes , V03A — ALL OTHER THERAPEUTIC PRODUCTS , V03 — ALL OTHER THERAPEUTIC PRODUCTS , V — VARIOUS , S03BA — Corticosteroids , S03B — CORTICOSTEROIDS , S03 — OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS , S — SENSORY ORGANS , D07BA — Corticosteroids, weak, combinations with antiseptics , D07B — CORTICOSTEROIDS, COMBINATIONS WITH ANTISEPTICS , D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS , D — DERMATOLOGICALS , D07CA — Corticosteroids, weak, combinations with antibiotics , D07C — CORTICOSTEROIDS, COMBINATIONS WITH ANTIBIOTICS , D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS , D — DERMATOLOGICALS , S01BA — Corticosteroids, plain , S01B — ANTIINFLAMMATORY AGENTS , S01 — OPHTHALMOLOGICALS , S — SENSORY ORGANS , S02BA — Corticosteroids , S02B — CORTICOSTEROIDS , S02 — OTOLOGICALS , S — SENSORY ORGANS , A07EA — Corticosteroids acting locally , A07E — INTESTINAL ANTIINFLAMMATORY AGENTS , A07 — ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS , A — ALIMENTARY TRACT AND METABOLISM , H02AB — Glucocorticoids , H02A — CORTICOSTEROIDS FOR SYSTEMIC USE, PLAIN , H02 — CORTICOSTEROIDS FOR SYSTEMIC USE , H — SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS , S02CA — Corticosteroids and antiinfectives in combination , S02C — CORTICOSTEROIDS AND ANTIINFECTIVES IN COMBINATION , S02 — OTOLOGICALS , S — SENSORY ORGANS , C05AA — Corticosteroids , C05A — AGENTS FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE , C05 — VASOPROTECTIVES , C — CARDIOVASCULAR SYSTEM , S03CA — Corticosteroids and antiinfectives in combination , S03C — CORTICOSTEROIDS AND ANTIINFECTIVES IN COMBINATION , S03 — OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS , S — SENSORY ORGANS','<p>Oral prednisolone reaches a C<sub>max</sub> of 113-1343ng/mL with a T<sub>max</sub> of 1.0-2.6 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pickup ME: Clinical pharmacokinetics of prednisone and prednisolone. Clin Pharmacokinet. 1979 Mar-Apr;4(2):111-28. doi: 10.2165/00003088-197904020-00004. (PubMed ID 378499)\" href=\"#reference-A187394\">1</a></sup> Oral prednisolone is approximately 70% bioavailable.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Ferry JJ, Horvath AM, Bekersky I, Heath EC, Ryan CF, Colburn WA: Relative and absolute bioavailability of prednisone and prednisolone after separate oral and intravenous doses. J Clin Pharmacol. 1988 Jan;28(1):81-7. doi: 10.1002/j.1552-4604.1988.tb03105.x. (PubMed ID 3350994)\" href=\"#reference-A187400\">2</a></sup></p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroids with a structure based on a hydroxylated prostane moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001468\" rel=\"noopener\" target=\"_blank\">Gluco/mineralocorticoids, progestogins and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003058\" rel=\"noopener\" target=\"_blank\">20-oxosteroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"3-oxo steroids containing a double bond between positions 1 and 2, as well as positions 4 and 5.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002973\" rel=\"noopener\" target=\"_blank\">3-oxo delta-1,4-steroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroids carrying a hydroxyl group at the 17-position of the steroid backbone.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003236\" rel=\"noopener\" target=\"_blank\">17-hydroxysteroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Hydroxysteroids carrying a beta-hydroxyl group at the 11-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003227\" rel=\"noopener\" target=\"_blank\">11-beta-hydroxysteroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroids containing a double bond between positions 1 and 2, as well as positions 4 and 5.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002977\" rel=\"noopener\" target=\"_blank\">Delta-1,4-steroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carboxylic acid, and an amine group attached to the alpha carbon atom, relative to the C=O group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002912\" rel=\"noopener\" target=\"_blank\">Alpha-hydroxy ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a ketone that is conjugated to a cyclic moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003487\" rel=\"noopener\" target=\"_blank\">Cyclic ketones</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001292\" rel=\"noopener\" target=\"_blank\">Cyclic alcohols and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000286\" rel=\"noopener\" target=\"_blank\">Primary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 4 more</a>','Not Available','Not Available','19190','50-24-8','8378','CHEMBL131','5552','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Fatty acids and their derivatives, and substances related biosynthetically or functionally to these compounds.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000012\" rel=\"noopener\" target=\"_blank\">Lipids and lipid-like molecules</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000258\" rel=\"noopener\" target=\"_blank\">Steroids and steroid derivatives</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an steroid backbone, with at least one hydrogen substituted by a hydroxyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001295\" rel=\"noopener\" target=\"_blank\">Hydroxysteroids</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Steroids carrying a hydroxyl group at the 21-position of the steroid backbone.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003095\" rel=\"noopener\" target=\"_blank\">21-hydroxysteroids</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroids with a structure based on a hydroxylated prostane moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001468\" rel=\"noopener\" target=\"_blank\">Gluco/mineralocorticoids, progestogins and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003058\" rel=\"noopener\" target=\"_blank\">20-oxosteroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"3-oxo steroids containing a double bond between positions 1 and 2, as well as positions 4 and 5.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002973\" rel=\"noopener\" target=\"_blank\">3-oxo delta-1,4-steroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroids carrying a hydroxyl group at the 17-position of the steroid backbone.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003236\" rel=\"noopener\" target=\"_blank\">17-hydroxysteroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Hydroxysteroids carrying a beta-hydroxyl group at the 11-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003227\" rel=\"noopener\" target=\"_blank\">11-beta-hydroxysteroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroids containing a double bond between positions 1 and 2, as well as positions 4 and 5.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002977\" rel=\"noopener\" target=\"_blank\">Delta-1,4-steroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carboxylic acid, and an amine group attached to the alpha carbon atom, relative to the C=O group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002912\" rel=\"noopener\" target=\"_blank\">Alpha-hydroxy ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a ketone that is conjugated to a cyclic moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003487\" rel=\"noopener\" target=\"_blank\">Cyclic ketones</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001292\" rel=\"noopener\" target=\"_blank\">Cyclic alcohols and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000286\" rel=\"noopener\" target=\"_blank\">Primary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 4 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">11-beta-hydroxysteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">11-hydroxysteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">17-hydroxysteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">20-oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">21-hydroxysteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">3-oxo-delta-1,4-steroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">3-oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aliphatic homopolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alpha-hydroxy ketone</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclic alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclic ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Delta-1,4-steroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pregnane-skeleton</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Progestogin-skeleton</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 15 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aliphatic homopolycyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">11beta-hydroxy steroid, 17alpha-hydroxy steroid, glucocorticoid, 20-oxo steroid, 3-oxo-Delta(1),Delta(4)-steroid, 21-hydroxy steroid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8378\" rel=\"noopener\" target=\"_blank\">CHEBI:8378</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Pregnane and derivatives [Fig] (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C07369\" rel=\"noopener\" target=\"_blank\">C07369</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMST02030179\" rel=\"noopener\" target=\"_blank\">LMST02030179</a>) </span></span></dd></dl>','Steroids and steroid derivatives','<p>A 0.15mg/kg dose of prednisolone has a clearance of 0.09L/kg/h, while a 0.30mg/kg dose has a clearance of 0.12L/kg/h.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pickup ME: Clinical pharmacokinetics of prednisone and prednisolone. Clin Pharmacokinet. 1979 Mar-Apr;4(2):111-28. doi: 10.2165/00003088-197904020-00004. (PubMed ID 378499)\" href=\"#reference-A187394\">1</a></sup></p>','This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.','21-hydroxysteroids','<li>Avoid alcohol.</li>\n<li>Take with food. Food reduces irritation.</li>','Drugs.com Drug Page',' , Adrenal Cortex Hormones , Adrenals , Agents for Treatment of Hemorrhoids and Anal Fissures for Topical Use , Alimentary Tract and Metabolism , Anti-Inflammatory Agents , Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents , Antidotes , Antineoplastic Agents , Antineoplastic Agents, Hormonal , Corticosteroid Hormone Receptor Agonists , Corticosteroids , Corticosteroids Acting Locally , Corticosteroids for Local Oral Treatment , Corticosteroids for Systemic Use , Corticosteroids for Systemic Use, Plain , Corticosteroids, Dermatological Preparations , Corticosteroids, Weak (Group I) , Cytochrome P-450 CYP3A Inducers , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Inducers , Cytochrome P-450 CYP3A4 Inducers (strength unknown) , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 Enzyme Inducers , Cytochrome P-450 Substrates , Dermatologicals , Fused-Ring Compounds , Hormones , Hormones, Hormone Substitutes, and Hormone Antagonists , Hyperglycemia-Associated Agents , Immunosuppressive Agents , Intestinal Antiinflammatory Agents , Nasal Preparations , Ophthalmological and Otological Preparations , Ophthalmologicals , Otologicals , P-glycoprotein substrates , Prednisolone and Prodrugs , Pregnadienes , Pregnadienetriols , Pregnanes , Sensory Organs , Steroids , Stomatological Preparations , Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins , Vasoprotectives','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>235 °C</td><td>PhysProp</td></tr><tr><td>water solubility</td><td>223 mg/L (at 25 °C)</td><td>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</td></tr><tr><td>logP</td><td>1.62</td><td>HANSCH,C ET AL. (1995)</td></tr><tr><td>logS</td><td>-3.21</td><td>ADME Research, USCD</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">11beta-hydroxy steroid, 17alpha-hydroxy steroid, glucocorticoid, 20-oxo steroid, 3-oxo-Delta(1),Delta(4)-steroid, 21-hydroxy steroid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8378\" rel=\"noopener\" target=\"_blank\">CHEBI:8378</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Pregnane and derivatives [Fig] (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C07369\" rel=\"noopener\" target=\"_blank\">C07369</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMST02030179\" rel=\"noopener\" target=\"_blank\">LMST02030179</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0014998\" rel=\"noopener\" target=\"_blank\">HMDB0014998</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D00472\" rel=\"noopener\" target=\"_blank\">D00472</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C07369\" rel=\"noopener\" target=\"_blank\">C07369</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5755\" rel=\"noopener\" target=\"_blank\">5755</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46504847\" rel=\"noopener\" target=\"_blank\">46504847</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.5552.html\" rel=\"noopener\" target=\"_blank\">5552</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=19190\" rel=\"noopener\" target=\"_blank\">19190</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=8638\" rel=\"noopener\" target=\"_blank\">8638</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=8378\" rel=\"noopener\" target=\"_blank\">8378</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL131\" rel=\"noopener\" target=\"_blank\">CHEMBL131</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000003833821\" rel=\"noopener\" target=\"_blank\">ZINC000003833821</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000419\" rel=\"noopener\" target=\"_blank\">DAP000419</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA451096\" rel=\"noopener\" target=\"_blank\">PA451096</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"guide-to-pharmacology\">Guide to Pharmacology</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=2866\" rel=\"noopener\" target=\"_blank\">GtP Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/TUA\" rel=\"noopener\" target=\"_blank\">TUA</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic/prednisolone.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/cdi/prednisolone-acetate-drops.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Prednisolone\" rel=\"noopener\" target=\"_blank\">Prednisolone</a></dd></dl>','<li>Avoid alcohol.</li>\n<li>Take with food. Food reduces irritation.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A187394\">Pickup ME: Clinical pharmacokinetics of prednisone and prednisolone. Clin Pharmacokinet. 1979 Mar-Apr;4(2):111-28. doi: 10.2165/00003088-197904020-00004. [<a href=\"/articles/A187394\" target=\"_blank\">Article</a>] </li><li id=\"reference-A187400\">Ferry JJ, Horvath AM, Bekersky I, Heath EC, Ryan CF, Colburn WA: Relative and absolute bioavailability of prednisone and prednisolone after separate oral and intravenous doses. J Clin Pharmacol. 1988 Jan;28(1):81-7. doi: 10.1002/j.1552-4604.1988.tb03105.x. [<a href=\"/articles/A187400\" target=\"_blank\">Article</a>] </li><li id=\"reference-A187403\">Matabosch X, Pozo OJ, Perez-Mana C, Papaseit E, Segura J, Ventura R: Detection and characterization of prednisolone metabolites in human urine by LC-MS/MS. J Mass Spectrom. 2015 Mar;50(3):633-42. doi: 10.1002/jms.3571. [<a href=\"/articles/A187403\" target=\"_blank\">Article</a>] </li><li id=\"reference-A187463\">Yasir M, Sonthalia S: Corticosteroid Adverse Effects . [<a href=\"/articles/A187463\" target=\"_blank\">Article</a>] </li><li id=\"reference-A187511\">Robinson J, McKenzie C, MacLeod D: Paediatric dosing errors with oral prednisolone mixture. Aust Prescr. 2016 Oct;39(5):176. doi: 10.18773/austprescr.2016.062. Epub 2016 Oct 1. [<a href=\"/articles/A187511\" target=\"_blank\">Article</a>] </li><li id=\"reference-L9431\">FDA Approved Drug Products: Delta-Cortef Prednisolone Oral Tablets (Discontinued) [<a href=\"https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&amp;ApplNo=009987\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9542\">FDA Approved Drug Products: Prednisolone Oral Syrup [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/anda/99/40287_Prednisolone_Prntlbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9545\">Cayman Chemicals: Prednisolone MSDS [<a href=\"https://www.caymanchem.com/msdss/20866m.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9449\">FDA Approved Drug Products: Prednisolone Acetate Oral Suspension [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022067s007lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9452\">FDA Approved Drug Products: Prednisolone Acetate Ophthalmic Suspension [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/017100s045lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9440\">FDA Approved Drug Products: Orapred Prednisolone Sodium Phosphate Orally Disintegrating Tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021959s004lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9437\">FDA Approved Drug Products: Pediapred Prednisolons Sodium Phosphate Oral Solution [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019157s021lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>Prednisolone has a plasma half life of 2.1-3.5 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pickup ME: Clinical pharmacokinetics of prednisone and prednisolone. Clin Pharmacokinet. 1979 Mar-Apr;4(2):111-28. doi: 10.2165/00003088-197904020-00004. (PubMed ID 378499)\" href=\"#reference-A187394\">1</a></sup> This half life is shorter in children and longer in those with liver disease.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pickup ME: Clinical pharmacokinetics of prednisone and prednisolone. Clin Pharmacokinet. 1979 Mar-Apr;4(2):111-28. doi: 10.2165/00003088-197904020-00004. (PubMed ID 378499)\" href=\"#reference-A187394\">1</a></sup></p>','HMDB0014998','(1R,3aS,3bS,9aR,9bS,10S,11aS)-1,10-dihydroxy-1-(2-hydroxyacetyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one','InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,9,14-16,18,22,24,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1','OIGNJSKKLXVSLS-VWUMJDOOSA-N','<p>Prednisolone is indicated to treat endocrine, rheumatic, and hematologic disorders; collagen, dermatologic, ophthalmic, respiratory, and gastrointestinal diseases; allergic and edematous states; and other conditions like tuberculous meningitis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Prednisolone Oral Syrup\" href=\"#reference-L9542\">7</a></sup></p>','C07369','D00472','Organic compounds','<p>Prednisolone can be reversibly metabolized to <a href=\"https://go.drugbank.com/drugs/DB00635\">prednisone</a> which is then metabolized to 17α,21-dihydroxy-pregnan-1,4,6-trien-3,11,30-trione (M-XVII), 20α-dihydro-prednisone (M-V), 6βhydroxy-prednisone (M-XII), 6α-hydroxy-prednisone (M-XIII), or 20β-dihydro-prednisone (M-IV).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Matabosch X, Pozo OJ, Perez-Mana C, Papaseit E, Segura J, Ventura R: Detection and characterization of prednisolone metabolites in human urine by LC-MS/MS. J Mass Spectrom. 2015 Mar;50(3):633-42. doi: 10.1002/jms.3571. (PubMed ID 25800201)\" href=\"#reference-A187403\">3</a></sup> 20β-dihydro-prednisone is metabolized to 17α,20ξ,21-trihydroxy-5ξ-pregn-1-en-3,11-dione(M-XVIII).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Matabosch X, Pozo OJ, Perez-Mana C, Papaseit E, Segura J, Ventura R: Detection and characterization of prednisolone metabolites in human urine by LC-MS/MS. J Mass Spectrom. 2015 Mar;50(3):633-42. doi: 10.1002/jms.3571. (PubMed ID 25800201)\" href=\"#reference-A187403\">3</a></sup> Prednisolone is metabolized to Δ6-prednisolone (M-XI), 20α-dihydro-prednisolone (M-III), 20β-dihydro-prednisolone (M-II), 6αhydroxy-prednisolone (M-VII), or 6βhydroxy-prednisolone(M-VI).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Matabosch X, Pozo OJ, Perez-Mana C, Papaseit E, Segura J, Ventura R: Detection and characterization of prednisolone metabolites in human urine by LC-MS/MS. J Mass Spectrom. 2015 Mar;50(3):633-42. doi: 10.1002/jms.3571. (PubMed ID 25800201)\" href=\"#reference-A187403\">3</a></sup> 6αhydroxy-prednisolone is metabolized to 6α,11β,17α,20β,21-pentahydroxypregnan-1,4-diene-3-one (M-X).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Matabosch X, Pozo OJ, Perez-Mana C, Papaseit E, Segura J, Ventura R: Detection and characterization of prednisolone metabolites in human urine by LC-MS/MS. J Mass Spectrom. 2015 Mar;50(3):633-42. doi: 10.1002/jms.3571. (PubMed ID 25800201)\" href=\"#reference-A187403\">3</a></sup> 6βhydroxy-prednisolone is metabolized to 6β,11β,17α,20β,21-pentahydroxypregnan-1,4-diene-3-one (M-VIII), 6β,11β,17α,20α,21-pentahydroxypregnan-1,4-diene-3-one (M-IX), and 6β,11β,17α,21-tetrahydroxy-5ξ-pregn-1-en-3,20-dione (M-XIV).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Matabosch X, Pozo OJ, Perez-Mana C, Papaseit E, Segura J, Ventura R: Detection and characterization of prednisolone metabolites in human urine by LC-MS/MS. J Mass Spectrom. 2015 Mar;50(3):633-42. doi: 10.1002/jms.3571. (PubMed ID 25800201)\" href=\"#reference-A187403\">3</a></sup> MVIII is metabolized to 6β,11β,17α,20β,21-pentahydroxy-5ξ-pregn-1-en-3-one (M-XV) and then to MXIV, while MIX is metabolized to 6β,11β,17α,20α,21-pentahydroxy-5ξ-pregn-1-en-3-one (M-XVI) and then to MXIV.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Matabosch X, Pozo OJ, Perez-Mana C, Papaseit E, Segura J, Ventura R: Detection and characterization of prednisolone metabolites in human urine by LC-MS/MS. J Mass Spectrom. 2015 Mar;50(3):633-42. doi: 10.1002/jms.3571. (PubMed ID 25800201)\" href=\"#reference-A187403\">3</a></sup> These metabolites and their glucuronide conjugates are excreted predominantly in the urine.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Matabosch X, Pozo OJ, Perez-Mana C, Papaseit E, Segura J, Ventura R: Detection and characterization of prednisolone metabolites in human urine by LC-MS/MS. J Mass Spectrom. 2015 Mar;50(3):633-42. doi: 10.1002/jms.3571. (PubMed ID 25800201)\" href=\"#reference-A187403\">3</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aliphatic homopolycyclic compounds','TUA','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000440?highlight[compounds][]=DB00860&amp;highlight[proteins][]=DB00860\">Prednisone Action Pathway</a></td><td>Drug action</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000441?highlight[compounds][]=DB00860&amp;highlight[proteins][]=DB00860\">Prednisolone Action Pathway</a></td><td>Drug action</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000631?highlight[compounds][]=DB00860&amp;highlight[proteins][]=DB00860\">Prednisone Metabolism Pathway</a></td><td>Drug metabolism</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000632?highlight[compounds][]=DB00860&amp;highlight[proteins][]=DB00860\">Prednisolone Metabolism Pathway</a></td><td>Drug metabolism</td></tr></tbody>','PA451096','<p>Prednisolone\'s protein binding is highly variable, ranging from 65-91% in healthy patients.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pickup ME: Clinical pharmacokinetics of prednisone and prednisolone. Clin Pharmacokinet. 1979 Mar-Apr;4(2):111-28. doi: 10.2165/00003088-197904020-00004. (PubMed ID 378499)\" href=\"#reference-A187394\">1</a></sup></p>','5755','46504847','<p>Prednisolone is over 98% eliminated in urine.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pickup ME: Clinical pharmacokinetics of prednisone and prednisolone. Clin Pharmacokinet. 1979 Mar-Apr;4(2):111-28. doi: 10.2165/00003088-197904020-00004. (PubMed ID 378499)\" href=\"#reference-A187394\">1</a></sup></p>','RxList Drug Page','8638','[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C','Solid','Hydroxysteroids','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">11-beta-hydroxysteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">11-hydroxysteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">17-hydroxysteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">20-oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">21-hydroxysteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">3-oxo-delta-1,4-steroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">3-oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aliphatic homopolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alpha-hydroxy ketone</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclic alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclic ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Delta-1,4-steroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pregnane-skeleton</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Progestogin-skeleton</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 15 more</a>','Lipids and lipid-like molecules','<span class=\"citations\"><p>Gunther Bellmann, \"Process for producing a sterile prednisolone gel.\" U.S. Patent US5811417, issued September 22, 1998.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=5811417&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5811417</a>','DAP000419','<p>The intraperitoneal LD<sub>50</sub> in rats is 2g/kg and 65mg/kg in mice.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Cayman Chemicals: Prednisolone MSDS\" href=\"#reference-L9545\">8</a></sup> The subcutaneous LD<sub>50</sub> in rats is 147mg/kg and &gt;3500mg/kg in mice.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Cayman Chemicals: Prednisolone MSDS\" href=\"#reference-L9545\">8</a></sup> The oral LD<sub>50</sub> in mice is 1680mg/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Cayman Chemicals: Prednisolone MSDS\" href=\"#reference-L9545\">8</a></sup> In humans, the oral TDLO in men is 9mg/kg/2W and in women is 14mg/kg/13D.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Cayman Chemicals: Prednisolone MSDS\" href=\"#reference-L9545\">8</a></sup></p><p>Patients experiencing an overdose of prednisolone may present with gastrointestinal disturbances, insomnia, and restlessness.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Robinson J, McKenzie C, MacLeod D: Paediatric dosing errors with oral prednisolone mixture. Aust Prescr. 2016 Oct;39(5):176. doi: 10.18773/austprescr.2016.062. Epub 2016 Oct 1. (PubMed ID 27789930)\" href=\"#reference-A187511\">5</a></sup> Overdose of oral prednisolone may be treated by gastric lavage or inducing vomiting if the overdose was recent, as well as supportive and symptomatic therapy.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Prednisolone Acetate Oral Suspension\" href=\"#reference-L9449\">9</a></sup> Chronic overdosage may be treated by dose reduction or treating patients on alternate days.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Prednisolone Acetate Oral Suspension\" href=\"#reference-L9449\">9</a></sup> An overdose by the ophthalmic route is not expected to cause problems.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Prednisolone Acetate Oral Suspension\" href=\"#reference-L9449\">9</a></sup></p>','9PHQ9Y1OLM','<p>A 0.15mg/kg dose of prednisolone has a volume of distribution of 29.3L, while a 0.30mg/kg dose has a volume of distribution of 44.2L.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pickup ME: Clinical pharmacokinetics of prednisone and prednisolone. Clin Pharmacokinet. 1979 Mar-Apr;4(2):111-28. doi: 10.2165/00003088-197904020-00004. (PubMed ID 378499)\" href=\"#reference-A187394\">1</a></sup></p>','Prednisolone','ZINC000003833821'),(56,'Emtricitabine','emtricitabine','Emtricitabine is a nucleoside reverse transcriptase inhibitor used for the treatment and prophylaxis of HIV.','Atripla, Biktarvy, Complera, Descovy, Emtriva, Genvoya, Odefsey, Stribild, Truvada','Emtricitabine','<p>Emtricitabine is a nucleoside reverse transcriptase inhibitor (NRTI) indicated for the treatment of HIV infection in adults<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules\" href=\"#reference-L9019\">6</a></sup> or combined with <a href=\"https://go.drugbank.com/drugs/DB09299\">tenofovir alafenamide</a> for the prevention of HIV-1 infection in high risk adolescents and adults.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Press Announcements: FDA approves second drug to prevent HIV infection as part of ongoing efforts to end the HIV epidemic\" href=\"#reference-L9010\">5</a></sup> Emtricitabine is a cytidine analogue.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules\" href=\"#reference-L9019\">6</a></sup> The drug works by inhibiting HIV reverse transcriptase, preventing transcription of HIV RNA to DNA.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules\" href=\"#reference-L9019\">6</a></sup></p><p>Emtricitabine was granted FDA approval on 2 July 2003.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules\" href=\"#reference-L9019\">6</a></sup></p>','C8H10FN3O3S','DB00879','Approved, Investigational','Small Molecule','Average: 247.247 Monoisotopic: 247.042690096 ',' , J05AR — Antivirals for treatment of HIV infections, combinations , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , J05AR — Antivirals for treatment of HIV infections, combinations , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , J05AR — Antivirals for treatment of HIV infections, combinations , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , J05AF — Nucleoside and nucleotide reverse transcriptase inhibitors , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , J05AR — Antivirals for treatment of HIV infections, combinations , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , J05AR — Antivirals for treatment of HIV infections, combinations , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , J05AR — Antivirals for treatment of HIV infections, combinations , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , J05AR — Antivirals for treatment of HIV infections, combinations , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , J05AR — Antivirals for treatment of HIV infections, combinations , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , J05AR — Antivirals for treatment of HIV infections, combinations , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE','<p>Emtricitabine reaches a C<sub>max</sub> of 1.8±0.7µg/mL with a T<sub>max</sub> of 1-2 hours, and has an AUC of 10±3.1µg*hr/mL.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules\" href=\"#reference-L9019\">6</a></sup> The bioavailability of emtricitabine capsules is 93% and the bioavailability of the oral solution is 75%.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules\" href=\"#reference-L9019\">6</a></sup> Taking emtricitabine with food decreases the C<sub>max</sub> by 29%.[L9019</p>','','Human Immunodeficiency Virus','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000291\" rel=\"noopener\" target=\"_blank\">Pyrimidones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amino group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001262\" rel=\"noopener\" target=\"_blank\">Aminopyrimidines and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001893\" rel=\"noopener\" target=\"_blank\">Halopyrimidines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the acyl fluoride functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001031\" rel=\"noopener\" target=\"_blank\">Aryl fluorides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a hydrogenated pyrimidine ring (i.e. containing less than the maximum number of double bonds.).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002202\" rel=\"noopener\" target=\"_blank\">Hydropyrimidines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Cyclic organooxygen compounds containing the structure RC(=N)N where the central carbon atom and one of the linked nitrogen atoms are part of the same ring( R here is an organyl group). They can also be viewed as analogs of lactams where the oxygen atom is replaced by a nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003886\" rel=\"noopener\" target=\"_blank\">Imidolactams</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an oxathiolane moiety, which consists of a saturated aliphatic five-member ring with one oxygen atom, a sulfur atom, and three carbon atoms. Isomers  of oxaphospholane include meta-oxathiolane, and ortho-oxathiolane.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000106\" rel=\"noopener\" target=\"_blank\">Oxathiolanes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a monothioacetal functional group with the general structure R2C(OR\')(SR\').\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002131\" rel=\"noopener\" target=\"_blank\">Monothioacetals</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000286\" rel=\"noopener\" target=\"_blank\">Primary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Amines having the nitrogen atom linked to exactly one hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002450\" rel=\"noopener\" target=\"_blank\">Primary amines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a chemical bond between a carbon atom and a fluorine atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001517\" rel=\"noopener\" target=\"_blank\">Organofluorides</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 7 more</a>','Not Available','Not Available','50107843','143491-57-0','31536','CHEMBL885','54859','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as 3\'-thia pyrimidine nucleosides. These are nucleoside analogues with a structure that consists of a pyrimidine base, which is N-substituted at the 1-position with a 3\'-thia derivative (1,3-oxazolidine) of the ribose moiety that is characteristic of nucleosides.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a nucleobase linked to a ribose or deoxyribose sugar via a beta-glycosidic linkage. The ribose or deoxyribose moiety bears at least a phosphate group in case of nucleotides.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000289\" rel=\"noopener\" target=\"_blank\">Nucleosides, nucleotides, and analogues</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003737\" rel=\"noopener\" target=\"_blank\">Nucleoside and nucleotide analogues</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Nucleoside analogues with a structure that consists of a pyrimidine base, which is N-substituted at the 1-position with a 3\'-thia derivative  (1,3-oxazolidine) of the ribose moiety that is characteristic of nucleosides.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003746\" rel=\"noopener\" target=\"_blank\">3\'-thia pyrimidine nucleosides</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Nucleoside analogues with a structure that consists of a pyrimidine base, which is N-substituted at the 1-position with a 3\'-thia derivative  (1,3-oxazolidine) of the ribose moiety that is characteristic of nucleosides.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003746\" rel=\"noopener\" target=\"_blank\">3\'-thia pyrimidine nucleosides</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000291\" rel=\"noopener\" target=\"_blank\">Pyrimidones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amino group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001262\" rel=\"noopener\" target=\"_blank\">Aminopyrimidines and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001893\" rel=\"noopener\" target=\"_blank\">Halopyrimidines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the acyl fluoride functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001031\" rel=\"noopener\" target=\"_blank\">Aryl fluorides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a hydrogenated pyrimidine ring (i.e. containing less than the maximum number of double bonds.).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002202\" rel=\"noopener\" target=\"_blank\">Hydropyrimidines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Cyclic organooxygen compounds containing the structure RC(=N)N where the central carbon atom and one of the linked nitrogen atoms are part of the same ring( R here is an organyl group). They can also be viewed as analogs of lactams where the oxygen atom is replaced by a nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003886\" rel=\"noopener\" target=\"_blank\">Imidolactams</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an oxathiolane moiety, which consists of a saturated aliphatic five-member ring with one oxygen atom, a sulfur atom, and three carbon atoms. Isomers  of oxaphospholane include meta-oxathiolane, and ortho-oxathiolane.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000106\" rel=\"noopener\" target=\"_blank\">Oxathiolanes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a monothioacetal functional group with the general structure R2C(OR\')(SR\').\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002131\" rel=\"noopener\" target=\"_blank\">Monothioacetals</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000286\" rel=\"noopener\" target=\"_blank\">Primary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Amines having the nitrogen atom linked to exactly one hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002450\" rel=\"noopener\" target=\"_blank\">Primary amines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a chemical bond between a carbon atom and a fluorine atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001517\" rel=\"noopener\" target=\"_blank\">Organofluorides</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 7 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">3\'-thia pyrimidine nucleoside</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminopyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteromonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl fluoride</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl halide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Halopyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Heteroaromatic compound</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydropyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidolactam</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monothioacetal</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organofluoride</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organohalogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxathiolane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrimidone</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 19 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic heteromonocyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">organofluorine compound, pyrimidone, nucleoside analogue, monothioacetal (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31536\" rel=\"noopener\" target=\"_blank\">CHEBI:31536</a>) </span></span></dd></dl>','Nucleoside and nucleotide analogues','<p>Emtricitabine has an apparent elimination rate of 15.1L/h.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Valade E, Treluyer JM, Bouazza N, Ghosn J, Foissac F, Benaboud S, Fauchet F, Viard JP, Urien S, Hirt D: Population pharmacokinetics of emtricitabine in HIV-1-infected adult patients. Antimicrob Agents Chemother. 2014;58(4):2256-61. doi: 10.1128/AAC.02058-13. Epub 2014 Feb 3. (PubMed ID 24492366)\" href=\"#reference-A187673\">2</a></sup> This rate is closely linked to creatinine clearance.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Valade E, Treluyer JM, Bouazza N, Ghosn J, Foissac F, Benaboud S, Fauchet F, Viard JP, Urien S, Hirt D: Population pharmacokinetics of emtricitabine in HIV-1-infected adult patients. Antimicrob Agents Chemother. 2014;58(4):2256-61. doi: 10.1128/AAC.02058-13. Epub 2014 Feb 3. (PubMed ID 24492366)\" href=\"#reference-A187673\">2</a></sup></p>','This compound belongs to the class of organic compounds known as 3\'-thia pyrimidine nucleosides. These are nucleoside analogues with a structure that consists of a pyrimidine base, which is N-substituted at the 1-position with a 3\'-thia derivative (1,3-oxazolidine) of the ribose moiety that is characteristic of nucleosides.','3\'-thia pyrimidine nucleosides','<li>Take with or without food. The absorption is unaffected by food.</li>','Drugs.com Drug Page',' , Anti-HIV Agents , Anti-Infective Agents , Anti-Retroviral Agents , Antiinfectives for Systemic Use , Antiviral Agents , Antivirals for Systemic Use , Antivirals used in combination for the treatment of HIV infections , Carbohydrates , Deoxycytidine , Deoxyribonucleosides , Dideoxynucleosides , Direct Acting Antivirals , Enzyme Inhibitors , Glycosides , Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor , MATE 1 Substrates , MATE substrates , Nucleic Acid Synthesis Inhibitors , Nucleic Acids, Nucleotides, and Nucleosides , Nucleoside and Nucleotide Reverse Transcriptase Inhibitors , Nucleoside Reverse Transcriptase Inhibitors , Nucleosides , Pyrimidine Nucleosides , Pyrimidines , Reverse Transcriptase Inhibitors , Ribonucleosides','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>136-138</td><td>ChemSpider</td></tr><tr><td>boiling point (°C)</td><td>443.28</td><td>ChemSpider</td></tr><tr><td>water solubility</td><td>112 mg/mL</td><td>FDA Label</td></tr><tr><td>logP</td><td>-0.43</td><td>FDA Label</td></tr><tr><td>pKa</td><td>2.65</td><td>FDA Label</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">organofluorine compound, pyrimidone, nucleoside analogue, monothioacetal (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31536\" rel=\"noopener\" target=\"_blank\">CHEBI:31536</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0015017\" rel=\"noopener\" target=\"_blank\">HMDB0015017</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D01199\" rel=\"noopener\" target=\"_blank\">D01199</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C12599\" rel=\"noopener\" target=\"_blank\">C12599</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=60877\" rel=\"noopener\" target=\"_blank\">60877</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507606\" rel=\"noopener\" target=\"_blank\">46507606</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.54859.html\" rel=\"noopener\" target=\"_blank\">54859</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50107843\" rel=\"noopener\" target=\"_blank\">50107843</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=276237\" rel=\"noopener\" target=\"_blank\">276237</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=31536\" rel=\"noopener\" target=\"_blank\">31536</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL885\" rel=\"noopener\" target=\"_blank\">CHEMBL885</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000003629271\" rel=\"noopener\" target=\"_blank\">ZINC000003629271</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP001084\" rel=\"noopener\" target=\"_blank\">DAP001084</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA10069\" rel=\"noopener\" target=\"_blank\">PA10069</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/ETV\" rel=\"noopener\" target=\"_blank\">ETV</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic3/emtriva.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/cdi/emtricitabine.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Emtricitabine\" rel=\"noopener\" target=\"_blank\">Emtricitabine</a></dd></dl>','<li>Take with or without food. The absorption is unaffected by food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A187643\">Shockcor JP, Wurm RM, Frick LW, Sanderson PN, Farrant RD, Sweatman BC, Lindon JC: Hplc-nmr identification of the human urinary metabolites of (-)-cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl] cytosine, a nucleoside analogue active against human immunodeficiency virus (HIV). Xenobiotica. 1996 Feb;26(2):189-99. doi: 10.3109/00498259609046699. [<a href=\"/articles/A187643\" target=\"_blank\">Article</a>] </li><li id=\"reference-A187673\">Valade E, Treluyer JM, Bouazza N, Ghosn J, Foissac F, Benaboud S, Fauchet F, Viard JP, Urien S, Hirt D: Population pharmacokinetics of emtricitabine in HIV-1-infected adult patients. Antimicrob Agents Chemother. 2014;58(4):2256-61. doi: 10.1128/AAC.02058-13. Epub 2014 Feb 3. [<a href=\"/articles/A187673\" target=\"_blank\">Article</a>] </li><li id=\"reference-A187688\">Orkin C, Llibre JM, Gallien S, Antinori A, Behrens G, Carr A: Nucleoside reverse transcriptase inhibitor-reducing strategies in HIV treatment: assessing the evidence. HIV Med. 2018 Jan;19(1):18-32. doi: 10.1111/hiv.12534. Epub 2017 Jul 24. [<a href=\"/articles/A187688\" target=\"_blank\">Article</a>] </li><li id=\"reference-A19948\">Bocedi A, Notaril S, Narciso P, Bolli A, Fasano M, Ascenzi P: Binding of anti-HIV drugs to human serum albumin. IUBMB Life. 2004 Oct;56(10):609-14. [<a href=\"/articles/A19948\" target=\"_blank\">Article</a>] </li><li id=\"reference-L9010\">FDA Press Announcements: FDA approves second drug to prevent HIV infection as part of ongoing efforts to end the HIV epidemic [<a href=\"https://www.fda.gov/news-events/press-announcements/fda-approves-second-drug-prevent-hiv-infection-part-ongoing-efforts-end-hiv-epidemic\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9019\">FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/021500s029lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L4388\">FDA Approved Drug Products: Descovy (Emtricitabine and Tenofovir Alafenamide) Oral Tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/208215s012lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9818\">Cayman Chemicals: Emtricitabine MSDS [<a href=\"https://www.caymanchem.com/msdss/16879m.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9833\">FDA Approved Drug Products: Truvada (emtricitabine and tenofovir disoproxil fumarate) tablets for oral use [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021752s061lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9836\">FDA Approved Drug Products: Symtuza (Darunavir, Cobicistat, Emtricitabine, and Tenofovir Alafenamide) Oral Tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210455s004lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9587\">FDA Approved Drug Products: Stribild (elvitegravir, cobicistat, emtricitabine, tenofovir disoproxil fumarate) tablets for oral use [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/203100s036lblet.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9839\">FDA Approved Drug Products: Odefsey (Emtricitabine, Rilpivirine, and Tenofovir Alafenamide) [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208351s006lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9647\">FDA Approved Drug Products: Genvoya (Elvitegravir, Cobicistat, Emtricitabine, and Tenofovir Alafenamide) Oral Tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/207561s023lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9842\">FDA Approved Drug Products: Complera (emtricitabine, rilpivirine, tenofovir disoproxil fumarate) tablets for oral use [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/202123s031lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9845\">FDA Approved Drug Products: Biktarvy (Bictegravir, Emtricitabine, and Tenofovir Alafenamide) Oral Tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210251s006lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9848\">FDA Approved Drug Products: Atripla (efavirenz, emtricitabine, and tenofovir disoproxil fumarate) tablets for oral use [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021937s044lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>The half life of emtricitabine is approximately 10 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules\" href=\"#reference-L9019\">6</a></sup></p>','HMDB0015017','4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one','InChI=1S/C8H10FN3O3S/c9-4-1-12(8(14)11-7(4)10)5-3-16-6(2-13)15-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6+/m0/s1','XQSPYNMVSIKCOC-NTSWFWBYSA-N','<p>Emtricitabine is indicated in combination with other medications for the treatment of HIV-1 infections;<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules\" href=\"#reference-L9019\">6</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Symtuza (Darunavir, Cobicistat, Emtricitabine, and Tenofovir Alafenamide) Oral Tablets\" href=\"#reference-L9836\">10</a></sup> treatment of HIV-1 infections in pediatric patients 25-35kg, treatment of HIV-1 infections in adult patients ≥35kg, for pre exposure prophylaxis of HIV-1 in adolescent and adult patients excluding those who have receptive vaginal sex;<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Descovy (Emtricitabine and Tenofovir Alafenamide) Oral Tablets\" href=\"#reference-L4388\">7</a>,<a class=\"reference-popover-link\" data-content=\"FDA Press Announcements: FDA approves second drug to prevent HIV infection as part of ongoing efforts to end the HIV epidemic\" href=\"#reference-L9010\">5</a></sup> treatment of HIV-1 infections in pediatric and adult patients ≥17kg, pre exposure prophylaxis in adolescents and adults ≥35kg;<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Truvada (emtricitabine and tenofovir disoproxil fumarate) tablets for oral use\" href=\"#reference-L9833\">9</a></sup> treatment of HIV-1 in patients ≥12 years and ≥35kg;<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Stribild (elvitegravir, cobicistat, emtricitabine, tenofovir disoproxil fumarate) tablets for oral use\" href=\"#reference-L9587\">11</a></sup> treatment of HIV-1 in patients weighing ≥35kg;<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Odefsey (Emtricitabine, Rilpivirine, and Tenofovir Alafenamide)\" href=\"#reference-L9839\">12</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Complera (emtricitabine, rilpivirine, tenofovir disoproxil fumarate) tablets for oral use\" href=\"#reference-L9842\">14</a></sup> treatment of HIV-1 in patients weighing ≥25kg;<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Genvoya (Elvitegravir, Cobicistat, Emtricitabine, and Tenofovir Alafenamide) Oral Tablets\" href=\"#reference-L9647\">13</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Biktarvy (Bictegravir, Emtricitabine, and Tenofovir Alafenamide) Oral Tablets\" href=\"#reference-L9845\">15</a></sup> and treatment of HIV-1 in patients weighing ≥40kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Atripla (efavirenz, emtricitabine, and tenofovir disoproxil fumarate) tablets for oral use\" href=\"#reference-L9848\">16</a></sup></p>','C12599','D01199','Organic compounds','<p>Emtricitabine is approximately 86% unmetabolized.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules\" href=\"#reference-L9019\">6</a></sup> Approximately 9% of a dose is metabolized to 3\'-sulfoxide diastereomers, 4% to the 2\'-O-glucuronide, and a minor amount is converted to 5-fluorocytosine.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Shockcor JP, Wurm RM, Frick LW, Sanderson PN, Farrant RD, Sweatman BC, Lindon JC: Hplc-nmr identification of the human urinary metabolites of (-)-cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl] cytosine, a nucleoside analogue active against human immunodeficiency virus (HIV). Xenobiotica. 1996 Feb;26(2):189-99. doi: 10.3109/00498259609046699. (PubMed ID 8868002)\" href=\"#reference-A187643\">1</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules\" href=\"#reference-L9019\">6</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteromonocyclic compounds','ETV','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000741?highlight[compounds][]=DB00879&amp;highlight[proteins][]=DB00879\">Emtricitabine Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA10069','<p>Emtricitabine is &lt;4% bound to plasma proteins,<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules\" href=\"#reference-L9019\">6</a></sup> mainly serum albumin.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Bocedi A, Notaril S, Narciso P, Bolli A, Fasano M, Ascenzi P: Binding of anti-HIV drugs to human serum albumin. IUBMB Life. 2004 Oct;56(10):609-14. (PubMed ID 15814459)\" href=\"#reference-A19948\">4</a></sup></p>','60877','46507606','<p>Emtricitabine is 86% recovered in the urine and 14% recovered in feces.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules\" href=\"#reference-L9019\">6</a></sup> 13% of the dose is recovered in the urine as metabolites; 9% as 3\'-sulfoxide diastereomers and 4% as 2\'-O-glucuronide.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules\" href=\"#reference-L9019\">6</a></sup></p>','RxList Drug Page','276237','NC1=NC(=O)N(C=C1F)[C@@H]1CS[C@H](CO)O1','Solid','3\'-thia pyrimidine nucleosides','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">3\'-thia pyrimidine nucleoside</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminopyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteromonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl fluoride</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl halide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Halopyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Heteroaromatic compound</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydropyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidolactam</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monothioacetal</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organofluoride</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organohalogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxathiolane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrimidone</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 19 more</a>','Nucleosides, nucleotides, and analogues','<a href=\"https://www.google.com/?tbm=pts#q=5538975&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5538975</a>','DAP001084','<p>The LD<sub>50</sub> of emtricitabine is not readily available.[9019,L9818]</p><p>Symptoms of emtricitabine toxicity include hepatotoxicity with steatosis, as well as lactic acidosis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules\" href=\"#reference-L9019\">6</a></sup> Treat overdose with symptomatic and supportive measures, including hemodialysis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules\" href=\"#reference-L9019\">6</a></sup></p>','G70B4ETF4S','<p>The apparent central volume of distribution is 42.3L and the peripheral volume of distribution is 55.4L.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Valade E, Treluyer JM, Bouazza N, Ghosn J, Foissac F, Benaboud S, Fauchet F, Viard JP, Urien S, Hirt D: Population pharmacokinetics of emtricitabine in HIV-1-infected adult patients. Antimicrob Agents Chemother. 2014;58(4):2256-61. doi: 10.1128/AAC.02058-13. Epub 2014 Feb 3. (PubMed ID 24492366)\" href=\"#reference-A187673\">2</a></sup></p>','Emtricitabine','ZINC000003629271'),(57,'Risedronic acid','risedronic-acid','Risedronic acid is a bisphosphonate used to treat osteoporosis and Paget\'s disease.','Actonel, Atelvia','Risedronic acid','<p>Risedronic acid is a third generation bisphosphonate that is used for the treatment of some forms of osteoperosis and Paget\'s disease<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Russell RG, Watts NB, Ebetino FH, Rogers MJ: Mechanisms of action of bisphosphonates: similarities and differences and their potential influence on clinical efficacy. Osteoporos Int. 2008 Jun;19(6):733-59. doi: 10.1007/s00198-007-0540-8. (PubMed ID 18214569)\" href=\"#reference-A959\">1</a>,<a class=\"reference-popover-link\" data-content=\"Cremers S, Drake MT, Ebetino FH, Bilezikian JP, Russell RGG: Pharmacology of bisphosphonates. Br J Clin Pharmacol. 2019 Jun;85(6):1052-1062. doi: 10.1111/bcp.13867. Epub 2019 Feb 28. (PubMed ID 30650219)\" href=\"#reference-A203111\">2</a></sup>. It functions by preventing resorption of bone<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Russell RG, Watts NB, Ebetino FH, Rogers MJ: Mechanisms of action of bisphosphonates: similarities and differences and their potential influence on clinical efficacy. Osteoporos Int. 2008 Jun;19(6):733-59. doi: 10.1007/s00198-007-0540-8. (PubMed ID 18214569)\" href=\"#reference-A959\">1</a></sup>.</p>','C7H11NO7P2','DB00884','Approved, Investigational','Small Molecule','Average: 283.1123 Monoisotopic: 283.001074735 ',' , M05BB — Bisphosphonates, combinations , M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION , M05 — DRUGS FOR TREATMENT OF BONE DISEASES , M — MUSCULO-SKELETAL SYSTEM , M05BB — Bisphosphonates, combinations , M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION , M05 — DRUGS FOR TREATMENT OF BONE DISEASES , M — MUSCULO-SKELETAL SYSTEM , M05BB — Bisphosphonates, combinations , M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION , M05 — DRUGS FOR TREATMENT OF BONE DISEASES , M — MUSCULO-SKELETAL SYSTEM , M05BA — Bisphosphonates , M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION , M05 — DRUGS FOR TREATMENT OF BONE DISEASES , M — MUSCULO-SKELETAL SYSTEM','<p>Oral bioavailability is 0.63% and maximum absorption is approximately 1 hour after dosing<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. Administration half and hour before a meal reduces bioavailability by 55% compared to fasting and dosing 1 hour before a meal reduces bioavailability by 30%<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000089\" rel=\"noopener\" target=\"_blank\">Pyridines and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing phosphonic acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001302\" rel=\"noopener\" target=\"_blank\">Organic phosphonic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the phosphorus atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000400\" rel=\"noopener\" target=\"_blank\">Organophosphorus compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a bond between a carbon atom and an oxygen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000323\" rel=\"noopener\" target=\"_blank\">Organooxygen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000278\" rel=\"noopener\" target=\"_blank\">Organonitrogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span>','Not Available','Not Available','12576','105462-24-6','8869','CHEMBL923','5055','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as bisphosphonates. These are organic compounds containing two phosphonate groups linked together through a carbon atoms.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds an organic acid or a derivative thereof.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000264\" rel=\"noopener\" target=\"_blank\">Organic acids and derivatives</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing phosphonic acid or a derivative thereof.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000419\" rel=\"noopener\" target=\"_blank\">Organic phosphonic acids and derivatives</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing two phosphonate groups linked together through a carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000327\" rel=\"noopener\" target=\"_blank\">Bisphosphonates</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing two phosphonate groups linked together through a carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000327\" rel=\"noopener\" target=\"_blank\">Bisphosphonates</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000089\" rel=\"noopener\" target=\"_blank\">Pyridines and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing phosphonic acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001302\" rel=\"noopener\" target=\"_blank\">Organic phosphonic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the phosphorus atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000400\" rel=\"noopener\" target=\"_blank\">Organophosphorus compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a bond between a carbon atom and an oxygen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000323\" rel=\"noopener\" target=\"_blank\">Organooxygen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000278\" rel=\"noopener\" target=\"_blank\">Organonitrogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Aromatic heteromonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Bisphosphonate</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Heteroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic heteromonocyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">pyridines (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8869\" rel=\"noopener\" target=\"_blank\">CHEBI:8869</a>) </span></span></dd></dl>','Organic phosphonic acids and derivatives','<p>Mean renal clearance was 52mL/min and mean total clearance was 73mL/min<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','This compound belongs to the class of organic compounds known as bisphosphonates. These are organic compounds containing two phosphonate groups linked together through a carbon atoms.','Bisphosphonates','<li>Administer vitamin supplements. Patients may require supplemental vitamin D.</li>\n<li>Avoid multivalent ions. Calcium, antacids, and divalent ions may interfere with the absorption of this medication.</li>\n<li>Take on an empty stomach.</li>\n<li>Take with a full glass of water.</li>','Drugs.com Drug Page',' , Agents Causing Muscle Toxicity , Bisphosphonates , Bone Density Conservation Agents , Calcium-Regulating Hormones and Agents , Cardiovascular Agents , Drugs Affecting Bone Structure and Mineralization , Drugs for Treatment of Bone Diseases , Membrane Transport Modulators , Musculo-Skeletal System , Organophosphonates , Organophosphorus Compounds , Pyridines','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>252-262</td><td>https://www.greenstonellc.com/sites/default/files/pdfs/MSDS/RISEDRONATE%20SODIUM%20TABLETS%20MSDS_0.pdf</td></tr><tr><td>boiling point (°C)</td><td>692.3</td><td>https://www.greenstonellc.com/sites/default/files/pdfs/MSDS/RISEDRONATE%20SODIUM%20TABLETS%20MSDS_0.pdf</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">pyridines (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8869\" rel=\"noopener\" target=\"_blank\">CHEBI:8869</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0015022\" rel=\"noopener\" target=\"_blank\">HMDB0015022</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D08484\" rel=\"noopener\" target=\"_blank\">D08484</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C08233\" rel=\"noopener\" target=\"_blank\">C08233</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5245\" rel=\"noopener\" target=\"_blank\">5245</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507526\" rel=\"noopener\" target=\"_blank\">46507526</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.5055.html\" rel=\"noopener\" target=\"_blank\">5055</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=12576\" rel=\"noopener\" target=\"_blank\">12576</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=55685\" rel=\"noopener\" target=\"_blank\">55685</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=8869\" rel=\"noopener\" target=\"_blank\">8869</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL923\" rel=\"noopener\" target=\"_blank\">CHEMBL923</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000001531009\" rel=\"noopener\" target=\"_blank\">ZINC000001531009</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000658\" rel=\"noopener\" target=\"_blank\">DAP000658</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA451255\" rel=\"noopener\" target=\"_blank\">PA451255</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/RIS\" rel=\"noopener\" target=\"_blank\">RIS</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic/risedronate.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/cdi/risedronate-tablets.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdrhealth\">PDRhealth</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/act1580.shtml\" rel=\"noopener\" target=\"_blank\">PDRhealth Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Risedronic_acid\" rel=\"noopener\" target=\"_blank\">Risedronic_acid</a></dd></dl>','<li>Administer vitamin supplements. Patients may require supplemental vitamin D.</li>\n<li>Avoid multivalent ions. Calcium, antacids, and divalent ions may interfere with the absorption of this medication.</li>\n<li>Take on an empty stomach.</li>\n<li>Take with a full glass of water.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A959\">Russell RG, Watts NB, Ebetino FH, Rogers MJ: Mechanisms of action of bisphosphonates: similarities and differences and their potential influence on clinical efficacy. Osteoporos Int. 2008 Jun;19(6):733-59. doi: 10.1007/s00198-007-0540-8. [<a href=\"/articles/A959\" target=\"_blank\">Article</a>] </li><li id=\"reference-A203111\">Cremers S, Drake MT, Ebetino FH, Bilezikian JP, Russell RGG: Pharmacology of bisphosphonates. Br J Clin Pharmacol. 2019 Jun;85(6):1052-1062. doi: 10.1111/bcp.13867. Epub 2019 Feb 28. [<a href=\"/articles/A203111\" target=\"_blank\">Article</a>] </li><li id=\"reference-T536\">Thompson Micromedex (2004). Usp Vol I Drug Info Health Vol: Volume I (USP DI: v.1 Drug Information for the Health Care Professional) (24th ed., pp. 2475). Thompson PDR. [<a href=\"https://www.google.com/search?tbo=p&amp;tbm=bks&amp;q=1563634635\" rel=\"noopener\" target=\"_blank\">ISBN:1563634635</a>] </li><li id=\"reference-L5864\">Risedronate Sodium Tablet MSDS [<a href=\"https://www.greenstonellc.com/sites/default/files/pdfs/MSDS/RISEDRONATE%20SODIUM%20TABLETS%20MSDS_0.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9179\">FDA Approved Drugs: Risedronic Acid Oral Tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020835s048lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9644\">FDA Approved Drug Products: Risedronic Acid Extended Release Tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022560s007lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>The initial half life of risedronic acid is approximately 1.5 hours<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Thompson Micromedex (2004). Usp Vol I Drug Info Health Vol: Volume I (USP DI: v.1 Drug Information for the Health Care Professional) (24th ed.). Thompson PDR. (ISBN 1563634635)\" href=\"#reference-T536\">3</a></sup>, with a terminal half life of 561 hours<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','HMDB0015022','[1-hydroxy-1-phosphono-2-(pyridin-3-yl)ethyl]phosphonic acid','InChI=1S/C7H11NO7P2/c9-7(16(10,11)12,17(13,14)15)4-6-2-1-3-8-5-6/h1-3,5,9H,4H2,(H2,10,11,12)(H2,13,14,15)','IIDJRNMFWXDHID-UHFFFAOYSA-N','<p>Risedronic acid is indicated for the treatment of osteoperosis in men, treatment of Paget\'s disease, treatment and prevention of osteoperosis in postmenopausal women, and treatment and prevention of glucocorticoid-induced osteoperosis<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','C08233','D08484','Organic compounds','<p>Risedronic acid is not likely not metabolized before elimination<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. The P-C-P group of bisphosphonates is resistant to chemical and enzymatic hydrolysis preventing metabolism of the molecule<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Russell RG, Watts NB, Ebetino FH, Rogers MJ: Mechanisms of action of bisphosphonates: similarities and differences and their potential influence on clinical efficacy. Osteoporos Int. 2008 Jun;19(6):733-59. doi: 10.1007/s00198-007-0540-8. (PubMed ID 18214569)\" href=\"#reference-A959\">1</a></sup>.</p>','Aromatic heteromonocyclic compounds','RIS','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000112?highlight[compounds][]=DB00884&amp;highlight[proteins][]=DB00884\">Risedronate Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA451255','<p>~24%<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','5245','46507526','<p>Risedronate is excreted by the kidneys and the unabsorbed dose is eliminated in the feces<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','RxList Drug Page','55685','OC(CC1=CN=CC=C1)(P(O)(O)=O)P(O)(O)=O','Solid','Bisphosphonates','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Aromatic heteromonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Bisphosphonate</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Heteroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span></span></span>','Organic acids and derivatives','<span class=\"citations\"><p>Srinivasa Rao V.N Divvela, Lenin Racha, Sivakumaran Meenakshisunderam, Ramesh Dandala, \"Process for the preparation of risedronate sodium hemi-pentahydrate.\" U.S. Patent US20070173484, issued July 26, 2007.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=20070173484&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US20070173484</a>','DAP000658','<p>In clinical trials, over 10% of patients experienced back pain, arthralgia, abdominal pain, and dyspepsia<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. Less commonly, patients experience angioedema, generalized rash, bullous skin reactions, iritis, and uveitis<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p><p>Patients experiencing an overdose may experience a decrease in serum calcium and phosphorus<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. Patients can be given milk or antacids to bind the drug and reduce its absorption<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. In more severe cases, patients may require gastric lavage and intravenous calcium<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. A lethal dose in rats is equivalent to 320 to 620 times the human dose based on surface area<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','KM2Z91756Z','<p>13.8 L/kg<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','Risedronic_acid','ZINC000001531009'),(58,'Quinidine','quinidine','Quinidine is a medication used to restore normal sinus rhythm, treat atrial fibrillation and flutter, and treat ventricular arrhythmias.','Nuedexta','Quinidine','<p>An optical isomer of <a href=\"https://go.drugbank.com/drugs/DB00468\">quinine</a>, extracted from the bark of the Cinchona tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular action potential, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.</p>','C20H24N2O2','DB00908','Approved, Investigational','Small Molecule','Average: 324.4168 Monoisotopic: 324.183778022 ',' , C01BA — Antiarrhythmics, class Ia , C01B — ANTIARRHYTHMICS, CLASS I AND III , C01 — CARDIAC THERAPY , C — CARDIOVASCULAR SYSTEM , C01BA — Antiarrhythmics, class Ia , C01B — ANTIARRHYTHMICS, CLASS I AND III , C01 — CARDIAC THERAPY , C — CARDIOVASCULAR SYSTEM , C01BA — Antiarrhythmics, class Ia , C01B — ANTIARRHYTHMICS, CLASS I AND III , C01 — CARDIAC THERAPY , C — CARDIOVASCULAR SYSTEM','<p><span class=\"not-available\">Not Available</span></p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organoheterocyclic compounds containing a quinoline moiety substituted at the 4-position with a methanol.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004538\" rel=\"noopener\" target=\"_blank\">4-quinolinemethanols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a 1-azabicyclo[2.2.2]octane moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000252\" rel=\"noopener\" target=\"_blank\">Quinuclidines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a methoxybenzene or a derivative thereof.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000138\" rel=\"noopener\" target=\"_blank\">Anisoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003899\" rel=\"noopener\" target=\"_blank\">Aralkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R\' , where R is an alkyl group and R\' is an aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000128\" rel=\"noopener\" target=\"_blank\">Alkyl aryl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000089\" rel=\"noopener\" target=\"_blank\">Pyridines and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000195\" rel=\"noopener\" target=\"_blank\">Piperidines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001897\" rel=\"noopener\" target=\"_blank\">1,2-aminoalcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an alcohol group attached to an aromatic carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003073\" rel=\"noopener\" target=\"_blank\">Aromatic alcohols</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 5 more</a>','Not Available','Not Available','50121975','56-54-2','28593','CHEMBL1294','389880','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000279\" rel=\"noopener\" target=\"_blank\">Alkaloids and derivatives</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002246\" rel=\"noopener\" target=\"_blank\">Cinchona alkaloids</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"not-available\">Not Available</span></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002246\" rel=\"noopener\" target=\"_blank\">Cinchona alkaloids</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organoheterocyclic compounds containing a quinoline moiety substituted at the 4-position with a methanol.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004538\" rel=\"noopener\" target=\"_blank\">4-quinolinemethanols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a 1-azabicyclo[2.2.2]octane moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000252\" rel=\"noopener\" target=\"_blank\">Quinuclidines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a methoxybenzene or a derivative thereof.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000138\" rel=\"noopener\" target=\"_blank\">Anisoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003899\" rel=\"noopener\" target=\"_blank\">Aralkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R\' , where R is an alkyl group and R\' is an aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000128\" rel=\"noopener\" target=\"_blank\">Alkyl aryl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000089\" rel=\"noopener\" target=\"_blank\">Pyridines and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000195\" rel=\"noopener\" target=\"_blank\">Piperidines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001897\" rel=\"noopener\" target=\"_blank\">1,2-aminoalcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an alcohol group attached to an aromatic carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003073\" rel=\"noopener\" target=\"_blank\">Aromatic alcohols</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 5 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1,2-aminoalcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">4-quinolinemethanol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anisole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aralkylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cinchonan-skeleton</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Heteroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Piperidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyridine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Quinoline</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Quinuclidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary amine</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 18 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic heteropolycyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">cinchona alkaloid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28593\" rel=\"noopener\" target=\"_blank\">CHEBI:28593</a>) </span></span></dd></dl>','Cinchona alkaloids','','This compound belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety.','Cinchona alkaloids','<li>Exercise caution with grapefruit products. Grapefruit may delay the absorption of quinidine, and inhibit its metabolism through CYP3A4.</li>\n<li>Exercise caution with St. John\'s Wort.</li>\n<li>Take separate from antacids. Antacids may reduce the absorption of quinidine.</li>\n<li>Take with or without food. Taking quinidine with food may slow its absorption.</li>','Drugs.com Drug Page',' , Adrenergic Agents , Adrenergic alpha-1 Receptor Antagonists , Adrenergic alpha-Antagonists , Adrenergic Antagonists , Agents producing tachycardia , Agents that produce hypertension , Agents that produce neuromuscular block (indirect) , Agents that reduce seizure threshold , Alkaloids , Anti-Infective Agents , Antiarrhythmic agents , Antiarrhythmics, Class I , Antiarrhythmics, Class Ia , Anticholinergic Agents , Antimalarials , Antiparasitic Agents , Antiprotozoals , Biological Products , Biopolymers , BSEP/ABCB11 Inhibitors , Carbohydrates , Cardiac Therapy , Cardiovascular Agents , Cholinergic Agents , Cinchona Alkaloids , Complex Mixtures , Compounds used in a research, industrial, or household setting , Cytochrome P-450 CYP1A2 Inhibitors , Cytochrome P-450 CYP1A2 Inhibitors (strong) , Cytochrome P-450 CYP2B6 Inhibitors , Cytochrome P-450 CYP2B6 Inhibitors (strength unknown) , Cytochrome P-450 CYP2C8 Inducers , Cytochrome P-450 CYP2C8 Inducers (weak) , Cytochrome P-450 CYP2C8 Inhibitors , Cytochrome P-450 CYP2C8 Inhibitors (weak) , Cytochrome P-450 CYP2C9 Inhibitors , Cytochrome P-450 CYP2C9 Inhibitors (moderate) , Cytochrome P-450 CYP2C9 Substrates , Cytochrome P-450 CYP2C9 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2D6 Inhibitors , Cytochrome P-450 CYP2D6 Inhibitors (strong) , Cytochrome P-450 CYP2E1 Substrates , Cytochrome P-450 CYP2E1 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP3A Inhibitors , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Inhibitors , Cytochrome P-450 CYP3A4 Inhibitors (weak) , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP3A7 Substrates , Cytochrome P-450 CYP3A7 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 Enzyme Inducers , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Drugs causing inadvertant photosensitivity , Drugs that are Mainly Renally Excreted , Drugs that are Mainly Renally Excreted with a Narrow Therapeutic Index , Enzyme Inhibitors , Heterocyclic Compounds, Fused-Ring , Highest Risk QTc-Prolonging Agents , Macromolecular Substances , Membrane Transport Modulators , Muscarinic Antagonists , Narrow Therapeutic Index Drugs , Neurotransmitter Agents , OAT3/SLC22A8 Inhibitors , OATP1B1/SLCO1B1 Inhibitors , OCT1 inhibitors , OCT2 Inhibitors , P-glycoprotein inhibitors , P-glycoprotein substrates , P-glycoprotein substrates with a Narrow Therapeutic Index , Pharmaceutical Preparations , Photosensitizing Agents , Plant Extracts , Plant Preparations , Polymers , Polysaccharides , QTc Prolonging Agents , Quinolines , Quinuclidines , Sodium Channel Blockers , Voltage-Gated Sodium Channel Blockers','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>174 °C</td><td>PhysProp</td></tr><tr><td>water solubility</td><td>140 mg/L (at 25 °C)</td><td>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</td></tr><tr><td>logP</td><td>3.44</td><td>HANSCH,C ET AL. (1995)</td></tr><tr><td>logS</td><td>-3.37</td><td>ADME Research, USCD</td></tr><tr><td>Caco2 permeability</td><td>-4.69</td><td>ADME Research, USCD</td></tr><tr><td>pKa</td><td>8.56 (at 25 °C)</td><td>SANGSTER (1994)</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">cinchona alkaloid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28593\" rel=\"noopener\" target=\"_blank\">CHEBI:28593</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0015044\" rel=\"noopener\" target=\"_blank\">HMDB0015044</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D08458\" rel=\"noopener\" target=\"_blank\">D08458</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C06527\" rel=\"noopener\" target=\"_blank\">C06527</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=441074\" rel=\"noopener\" target=\"_blank\">441074</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505356\" rel=\"noopener\" target=\"_blank\">46505356</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.389880.html\" rel=\"noopener\" target=\"_blank\">389880</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50121975\" rel=\"noopener\" target=\"_blank\">50121975</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=9068\" rel=\"noopener\" target=\"_blank\">9068</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=28593\" rel=\"noopener\" target=\"_blank\">28593</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL1294\" rel=\"noopener\" target=\"_blank\">CHEMBL1294</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000003831405\" rel=\"noopener\" target=\"_blank\">ZINC000003831405</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000515\" rel=\"noopener\" target=\"_blank\">DAP000515</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA451209\" rel=\"noopener\" target=\"_blank\">PA451209</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"guide-to-pharmacology\">Guide to Pharmacology</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=2342\" rel=\"noopener\" target=\"_blank\">GtP Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/QDN\" rel=\"noopener\" target=\"_blank\">QDN</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic/quinidine.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/cdi/quinidine-gluconate-controlled-release-tablets.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Quinidine\" rel=\"noopener\" target=\"_blank\">Quinidine</a></dd></dl>','<li>Exercise caution with grapefruit products. Grapefruit may delay the absorption of quinidine, and inhibit its metabolism through CYP3A4.</li>\n<li>Exercise caution with St. John\'s Wort.</li>\n<li>Take separate from antacids. Antacids may reduce the absorption of quinidine.</li>\n<li>Take with or without food. Taking quinidine with food may slow its absorption.</li>','<span class=\"not-available\">Not Available</span>','<p>6-8 hours</p>','HMDB0015044','(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol','InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19+,20-/m0/s1','LOUPRKONTZGTKE-LHHVKLHASA-N','<p>For the treatment of ventricular pre-excitation and cardiac dysrhythmias</p>','C06527','D08458','Organic compounds','<p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteropolycyclic compounds','QDN','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000323?highlight[compounds][]=DB00908&amp;highlight[proteins][]=DB00908\">Quinidine Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA451209','<p>80-88%</p>','441074','46505356','<p>When the urine pH is less than 7, about 20% of administered quinidine appears unchanged in the urine, but this fraction drops to as little as 5% when the urine is more alkaline.</p>','RxList Drug Page','9068','[H][C@@]12CCN(C[C@@H]1C=C)[C@]([H])(C2)[C@@H](O)C1=C2C=C(OC)C=CC2=NC=C1','Solid','Not Available','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1,2-aminoalcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">4-quinolinemethanol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anisole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aralkylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cinchonan-skeleton</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Heteroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Piperidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyridine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Quinoline</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Quinuclidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary amine</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 18 more</a>','Alkaloids and derivatives','<span class=\"citations\"><p>Jean Paul REMON, Chris Vervaet, \"QUININE AND QUINIDINE SALTS, METHODS FOR MAKING THEM, AND PHARMACEUTICAL FORMULATIONS COMPRISING THEM.\" U.S. Patent US20090239900, issued September 24, 2009.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=20090239900&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US20090239900</a>','DAP000515','<p><span class=\"not-available\">Not Available</span></p>','ITX08688JL','','Quinidine','ZINC000003831405'),(59,'Repaglinide','repaglinide','Repaglinide is a antihyperglycemic used to improve glycemic control in diabetes.','Enyglid, Gluconorm, Prandin','Repaglinide','<p>Repaglinide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the meglitinide class of short-acting insulin secretagogues, which act by binding to β cells of the pancreas to stimulate insulin release. Repaglinide induces an early insulin response to meals decreasing postprandial blood glucose levels. It should only be taken with meals and meal-time doses should be skipped with any skipped meal. Approximately one month of therapy is required before a decrease in fasting blood glucose is seen. Meglitnides may have a neutral effect on weight or cause a slight increase in weight. The average weight gain caused by meglitinides appears to be lower than that caused by sulfonylureas and insulin and appears to occur only in those naïve to oral antidiabetic agents. Due to their mechanism of action, meglitinides may cause hypoglycemia although the risk is thought to be lower than that of sulfonylureas since their action is dependent on the presence of glucose. In addition to reducing postprandial and fasting blood glucose, meglitnides have been shown to decrease glycosylated hemoglobin (HbA1c) levels, which are reflective of the last 8-10 weeks of glucose control. Meglitinides appear to be more effective at lowering postprandial blood glucose than metformin, sulfonylureas and thiazolidinediones. Repaglinide is extensively metabolized in the liver and excreted in bile. Repaglinide metabolites do not possess appreciable hypoglycemic activity. Approximately 90% of a single orally administered dose is eliminated in feces and 8% in urine.</p>','C27H36N2O4','DB00912','Approved, Investigational','Small Molecule','Average: 452.5857 Monoisotopic: 452.26750765 ',' , A10BD — Combinations of oral blood glucose lowering drugs , A10B — BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS , A10 — DRUGS USED IN DIABETES , A — ALIMENTARY TRACT AND METABOLISM , A10BX — Other blood glucose lowering drugs, excl. insulins , A10B — BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS , A10 — DRUGS USED IN DIABETES , A — ALIMENTARY TRACT AND METABOLISM','<p>Rapidly and completely absorbed following oral administration. Peak plasma concentrations are observed within 1 hour (range 0.5-1.4 hours). The absolute bioavailability is approximately 56%. Maximal biological effect is observed within 3-3.5 hours and plasma insulin levels remain elevated for 4-6 hours. When a single 2 mg dose of repaglinide is given to healthy subjects, the area under the curve (AUC) is 18.0 - 18.7 (ng/mL/h)^3. </p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Amide derivatives of phenylacetic acids.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002363\" rel=\"noopener\" target=\"_blank\">Phenylacetamides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic Compounds containing a benzene ring which bears at least one carboxyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002565\" rel=\"noopener\" target=\"_blank\">Benzoic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an aminobenzene moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000284\" rel=\"noopener\" target=\"_blank\">Aniline and substituted anilines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000321\" rel=\"noopener\" target=\"_blank\">Benzoyl derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003901\" rel=\"noopener\" target=\"_blank\">Dialkylarylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing an ether group substituted with a benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002341\" rel=\"noopener\" target=\"_blank\">Phenol ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds contaning a phenoxy group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004742\" rel=\"noopener\" target=\"_blank\">Phenoxy compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R\' , where R is an alkyl group and R\' is an aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000128\" rel=\"noopener\" target=\"_blank\">Alkyl aryl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds that contain at least one carboxyl group and one amino group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004176\" rel=\"noopener\" target=\"_blank\">Amino acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R\')H (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001663\" rel=\"noopener\" target=\"_blank\">Secondary carboxylic acid amides</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a carboxylic acid group with the formula -C(=O)OH.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001205\" rel=\"noopener\" target=\"_blank\">Carboxylic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 7 more</a>','Not Available','Not Available','50153520','135062-02-1','8805','CHEMBL1272','59377','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a ring with least one carbon atom and one non-carbon atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000002\" rel=\"noopener\" target=\"_blank\">Organoheterocyclic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000195\" rel=\"noopener\" target=\"_blank\">Piperidines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000303\" rel=\"noopener\" target=\"_blank\">Phenylpiperidines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000303\" rel=\"noopener\" target=\"_blank\">Phenylpiperidines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Amide derivatives of phenylacetic acids.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002363\" rel=\"noopener\" target=\"_blank\">Phenylacetamides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic Compounds containing a benzene ring which bears at least one carboxyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002565\" rel=\"noopener\" target=\"_blank\">Benzoic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an aminobenzene moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000284\" rel=\"noopener\" target=\"_blank\">Aniline and substituted anilines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000321\" rel=\"noopener\" target=\"_blank\">Benzoyl derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003901\" rel=\"noopener\" target=\"_blank\">Dialkylarylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing an ether group substituted with a benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002341\" rel=\"noopener\" target=\"_blank\">Phenol ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds contaning a phenoxy group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004742\" rel=\"noopener\" target=\"_blank\">Phenoxy compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R\' , where R is an alkyl group and R\' is an aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000128\" rel=\"noopener\" target=\"_blank\">Alkyl aryl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds that contain at least one carboxyl group and one amino group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004176\" rel=\"noopener\" target=\"_blank\">Amino acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R\')H (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001663\" rel=\"noopener\" target=\"_blank\">Secondary carboxylic acid amides</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a carboxylic acid group with the formula -C(=O)OH.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001205\" rel=\"noopener\" target=\"_blank\">Carboxylic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 7 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amino acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amino acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aniline or substituted anilines</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteromonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoic acid or derivatives</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Benzoyl</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxamide group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dialkylarylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocyclic benzene moiety</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenol ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenoxy compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenylacetamide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenylpiperidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary carboxylic acid amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic/aromatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary amine</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 23 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic heteromonocyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">piperidines (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8805\" rel=\"noopener\" target=\"_blank\">CHEBI:8805</a>) </span></span></dd></dl>','Piperidines','<p>33-38 L/hour following IV administration</p>','This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.','Phenylpiperidines','<li>Take before a meal. Repaglinide should be taken before each meal of the day.</li>','Drugs.com Drug Page',' , Acids, Acyclic , Alimentary Tract and Metabolism , Blood Glucose Lowering Agents , BSEP/ABCB11 Substrates , Cytochrome P-450 CYP2C8 Substrates , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 Substrates , Drugs Used in Diabetes , Glinide , Hypoglycemia-Associated Agents , Meglitinides , OATP1B1/SLCO1B1 Substrates , Oral Hypoglycemics , Potassium Channel Blockers , Stereoisomerism','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>130-131 °C</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>logP</td><td>5.9</td><td><span class=\"not-available\">Not Available</span></td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">piperidines (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8805\" rel=\"noopener\" target=\"_blank\">CHEBI:8805</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0015048\" rel=\"noopener\" target=\"_blank\">HMDB0015048</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D00594\" rel=\"noopener\" target=\"_blank\">D00594</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C07670\" rel=\"noopener\" target=\"_blank\">C07670</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=65981\" rel=\"noopener\" target=\"_blank\">65981</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508150\" rel=\"noopener\" target=\"_blank\">46508150</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.59377.html\" rel=\"noopener\" target=\"_blank\">59377</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50153520\" rel=\"noopener\" target=\"_blank\">50153520</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=73044\" rel=\"noopener\" target=\"_blank\">73044</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=8805\" rel=\"noopener\" target=\"_blank\">8805</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL1272\" rel=\"noopener\" target=\"_blank\">CHEMBL1272</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000003798537\" rel=\"noopener\" target=\"_blank\">ZINC000003798537</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000133\" rel=\"noopener\" target=\"_blank\">DAP000133</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA451234\" rel=\"noopener\" target=\"_blank\">PA451234</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/BJX\" rel=\"noopener\" target=\"_blank\">BJX</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic/prandin.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/cdi/repaglinide.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdrhealth\">PDRhealth</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/pra1343.shtml\" rel=\"noopener\" target=\"_blank\">PDRhealth Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Repaglinide\" rel=\"noopener\" target=\"_blank\">Repaglinide</a></dd></dl>','<li>Take before a meal. Repaglinide should be taken before each meal of the day.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A1388\">Massi-Benedetti M, Damsbo P: Pharmacology and clinical experience with repaglinide. Expert Opin Investig Drugs. 2000 Apr;9(4):885-98. [<a href=\"/articles/A1388\" target=\"_blank\">Article</a>] </li><li id=\"reference-L35790\">FDA Approved Drug Products: PRANDIN (repaglinide) tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020741s044lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>1 hour</p>','HMDB0015048','2-ethoxy-4-({[(1S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbamoyl}methyl)benzoic acid','InChI=1S/C27H36N2O4/c1-4-33-25-17-20(12-13-22(25)27(31)32)18-26(30)28-23(16-19(2)3)21-10-6-7-11-24(21)29-14-8-5-9-15-29/h6-7,10-13,17,19,23H,4-5,8-9,14-16,18H2,1-3H3,(H,28,30)(H,31,32)/t23-/m0/s1','FAEKWTJYAYMJKF-QHCPKHFHSA-N','<p>As an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. </p>','C07670','D00594','Organic compounds','<p>Repaglinide is rapidly metabolized via oxidation and dealkylation by cytochrome P450 3A4 and 2C9 to form the major dicarboxylic acid derivative (M2). Further oxidation produces the aromatic amine derivative (M1). Glucuronidation of the carboxylic acid group of repaglinide yields an acyl glucuronide (M7). Several other unidentified metabolites have been detected. Repaglinide metabolites to not possess appreciable hypoglycemic activity. </p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteromonocyclic compounds','BJX','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000454?highlight[compounds][]=DB00912&amp;highlight[proteins][]=DB00912\">Repaglinide Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA451234','<p>&gt;98% (e.g. to to albumin and α1-acid glycoprotein)</p>','65981','46508150','<p>90% eliminated in feces (&lt;2% as unchanged drug), 8% in urine (0.1% as unchanged drug)</p>','RxList Drug Page','73044','CCOC1=C(C=CC(CC(=O)N[C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)=C1)C(O)=O','Solid','Phenylpiperidines','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amino acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amino acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aniline or substituted anilines</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteromonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoic acid or derivatives</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Benzoyl</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxamide group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dialkylarylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocyclic benzene moiety</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenol ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenoxy compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenylacetamide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenylpiperidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary carboxylic acid amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic/aromatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary amine</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 23 more</a>','Organoheterocyclic compounds','<span class=\"citations\"><p>Manne Reddy, \"Polymorphic forms of (S)-Repaglinide and the processes for preparation thereof.\" U.S. Patent US20040102477, issued May 27, 2004.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=20040102477&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US20040102477</a>','DAP000133','<p>LD<sub>50</sub> &gt;1 g/kg (rat) (W. Grell)</p>','668Z8C33LU','<p>31 L following IV administration in healthy individuals</p>','Repaglinide','ZINC000003798537'),(60,'Aspirin','aspirin','Aspirin is a salicylate used to treat pain, fever, inflammation, migraines, and reducing the risk of major adverse cardiovascular events.','Aggrenox, Alka-seltzer, Alka-seltzer Fruit Chews, Anacin, Arthriten Inflammatory Pain, Ascomp, Aspi-cor, Aspir-low, Bayer Aspirin, Bayer Womens, Bc Arthritis, Bc Original Formula, Bufferin, Duoplavin, Durlaza, Ecotrin, Ecpirin, Endodan Reformulated May 2009, Equagesic, Exaprin, Excedrin, Excedrin PM Triple Action, Fasprin, Fiorinal, Fiorinal With Codeine, Goody\'s Body Pain, Goody\'s Extra Strength, Goody\'s PM, Miniprin, Norgesic Forte, Orphengesic, Pamprin Max Formula, Robaxisal, ST. Joseph Aspir','Acetylsalicylic acidCommonly known or available as Aspirin','<p>Also known as <em>Aspirin</em>, acetylsalicylic acid (ASA) is a commonly used drug for the treatment of pain and fever due to various causes. Acetylsalicylic acid has both anti-inflammatory and antipyretic effects. This drug also inhibits platelet aggregation and is used in the prevention of blood clots stroke, and myocardial infarction (MI) <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. </p><p>Interestingly, the results of various studies have demonstrated that long-term use of acetylsalicylic acid may decrease the risk of various cancers, including colorectal, esophageal, breast, lung, prostate, liver and skin cancer <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Alfonso L, Ai G, Spitale RC, Bhat GJ: Molecular targets of aspirin and cancer prevention. Br J Cancer. 2014 Jul 8;111(1):61-7. doi: 10.1038/bjc.2014.271. Epub 2014 May 29. (PubMed ID 24874482)\" href=\"#reference-A177325\">15</a></sup>. Aspirin is classified as a <em>non-selective cyclooxygenase (COX) inhibitor</em> <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Vane JR, Botting RM: The mechanism of action of aspirin. Thromb Res. 2003 Jun 15;110(5-6):255-8. (PubMed ID 14592543)\" href=\"#reference-A32682\">11</a>,<a class=\"reference-popover-link\" data-content=\"Ornelas A, Zacharias-Millward N, Menter DG, Davis JS, Lichtenberger L, Hawke D, Hawk E, Vilar E, Bhattacharya P, Millward S: Beyond COX-1: the effects of aspirin on platelet biology and potential mechanisms of chemoprevention. Cancer Metastasis Rev. 2017 Jun;36(2):289-303. doi: 10.1007/s10555-017-9675-z. (PubMed ID 28762014)\" href=\"#reference-A177268\">14</a></sup> and is available in many doses and forms, including chewable tablets, suppositories, extended release formulations, and others <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Mayo Clinic website: Salicylate\" href=\"#reference-L5968\">19</a></sup>. </p><p>Acetylsalicylic acid is a very common cause of accidental poisoning in young children. It should be kept out of reach from young children, toddlers, and infants <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','C9H8O4','DB00945','Approved, Vet approved','Small Molecule','Average: 180.1574 Monoisotopic: 180.042258744 ',' , B01AC — Platelet aggregation inhibitors excl. heparin , B01A — ANTITHROMBOTIC AGENTS , B01 — ANTITHROMBOTIC AGENTS , B — BLOOD AND BLOOD FORMING ORGANS , C07FX — Beta blocking agents, other combinations , C07F — BETA BLOCKING AGENTS, OTHER COMBINATIONS , C07 — BETA BLOCKING AGENTS , C — CARDIOVASCULAR SYSTEM , C10BX — HMG CoA reductase inhibitors, other combinations , C10B — LIPID MODIFYING AGENTS, COMBINATIONS , C10 — LIPID MODIFYING AGENTS , C — CARDIOVASCULAR SYSTEM , M01BA — Antiinflammatory/antirheumatic agents in combination with corticosteroids , M01B — ANTIINFLAMMATORY/ANTIRHEUMATIC AGENTS IN COMBINATION , M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS , M — MUSCULO-SKELETAL SYSTEM , N02BA — Salicylic acid and derivatives , N02B — OTHER ANALGESICS AND ANTIPYRETICS , N02 — ANALGESICS , N — NERVOUS SYSTEM , C10BX — HMG CoA reductase inhibitors, other combinations , C10B — LIPID MODIFYING AGENTS, COMBINATIONS , C10 — LIPID MODIFYING AGENTS , C — CARDIOVASCULAR SYSTEM , B01AC — Platelet aggregation inhibitors excl. heparin , B01A — ANTITHROMBOTIC AGENTS , B01 — ANTITHROMBOTIC AGENTS , B — BLOOD AND BLOOD FORMING ORGANS , N02AJ — Opioids in combination with non-opioid analgesics , N02A — OPIOIDS , N02 — ANALGESICS , N — NERVOUS SYSTEM , N02AJ — Opioids in combination with non-opioid analgesics , N02A — OPIOIDS , N02 — ANALGESICS , N — NERVOUS SYSTEM , N02BA — Salicylic acid and derivatives , N02B — OTHER ANALGESICS AND ANTIPYRETICS , N02 — ANALGESICS , N — NERVOUS SYSTEM , C10BX — HMG CoA reductase inhibitors, other combinations , C10B — LIPID MODIFYING AGENTS, COMBINATIONS , C10 — LIPID MODIFYING AGENTS , C — CARDIOVASCULAR SYSTEM , N02BA — Salicylic acid and derivatives , N02B — OTHER ANALGESICS AND ANTIPYRETICS , N02 — ANALGESICS , N — NERVOUS SYSTEM , A01AD — Other agents for local oral treatment , A01A — STOMATOLOGICAL PREPARATIONS , A01 — STOMATOLOGICAL PREPARATIONS , A — ALIMENTARY TRACT AND METABOLISM , C10BX — HMG CoA reductase inhibitors, other combinations , C10B — LIPID MODIFYING AGENTS, COMBINATIONS , C10 — LIPID MODIFYING AGENTS , C — CARDIOVASCULAR SYSTEM , C07FX — Beta blocking agents, other combinations , C07F — BETA BLOCKING AGENTS, OTHER COMBINATIONS , C07 — BETA BLOCKING AGENTS , C — CARDIOVASCULAR SYSTEM , N02AJ — Opioids in combination with non-opioid analgesics , N02A — OPIOIDS , N02 — ANALGESICS , N — NERVOUS SYSTEM , C10BX — HMG CoA reductase inhibitors, other combinations , C10B — LIPID MODIFYING AGENTS, COMBINATIONS , C10 — LIPID MODIFYING AGENTS , C — CARDIOVASCULAR SYSTEM , C10BX — HMG CoA reductase inhibitors, other combinations , C10B — LIPID MODIFYING AGENTS, COMBINATIONS , C10 — LIPID MODIFYING AGENTS , C — CARDIOVASCULAR SYSTEM , C10BX — HMG CoA reductase inhibitors, other combinations , C10B — LIPID MODIFYING AGENTS, COMBINATIONS , C10 — LIPID MODIFYING AGENTS , C — CARDIOVASCULAR SYSTEM , C07FX — Beta blocking agents, other combinations , C07F — BETA BLOCKING AGENTS, OTHER COMBINATIONS , C07 — BETA BLOCKING AGENTS , C — CARDIOVASCULAR SYSTEM','<p>Absorption is generally rapid and complete following oral administration but absorption may be variable depending on the route, dosage form, and other factors including but not limited to the rate of tablet dissolution, gastric contents, gastric emptying time, and gastric pH <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p><p><strong>Detailed absorption information</strong></p><p>When ingested orally, acetylsalicylic acid is rapidly absorbed in both the stomach and proximal small intestine. The non-ionized acetylsalicylic acid passes through the stomach lining by passive diffusion. Ideal absorption of salicylate in the stomach occurs in the pH range of 2.15 - 4.10. Intestinal absorption of acetylsalicylic acid occurs at a much faster rate. At least half of the ingested dose is hydrolyzed to salicylic acid in the first-hour post-ingestion by esterases found in the gastrointestinal tract. Peak plasma salicylate concentrations occur between 1-2 hours post-administration <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002319\" rel=\"noopener\" target=\"_blank\">Phenol esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic Compounds containing a benzene ring which bears at least one carboxyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002565\" rel=\"noopener\" target=\"_blank\">Benzoic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds contaning a phenoxy group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004742\" rel=\"noopener\" target=\"_blank\">Phenoxy compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000321\" rel=\"noopener\" target=\"_blank\">Benzoyl derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing exactly two carboxylic acid groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000346\" rel=\"noopener\" target=\"_blank\">Dicarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001238\" rel=\"noopener\" target=\"_blank\">Carboxylic acid esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a carboxylic acid group with the formula -C(=O)OH.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001205\" rel=\"noopener\" target=\"_blank\">Carboxylic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span></span></span>','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsCytochrome P450 2C9CYP2C9*3(C;C) / (A;C)C AlleleEffect Directly StudiedPatients with this genotype have reduced metabolism of acetylsalicylic acid.DetailsLeukotriene C4 synthase---(A;C) / (C;C)C alleleADR Directly StudiedThe presence of this genotype in LTC4S may indicate an increased risk of chronic urticaria when treated with acetylsalicylic acid.DetailsIntegrin beta-3GPIIIa PlA2(C;C) / (C;T)T > CEffect Directly StudiedPatients with this genotype have increased resistance to the anti-thrombotic effects of aspirin.DetailsCytochrome P450 2C9CYP2C9*6Not Available818delAEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*15Not Available485C>AEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*25Not Available353_362delAGAAATGGAAEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*35Not Available374G>T / 430C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*2Not Available430C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*4Not Available1076T>CEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*5Not Available1080C>GEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*8Not Available449G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*11Not Available1003C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*12Not Available1465C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*13Not Available269T>CEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*14Not Available374G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*16Not Available895A>GEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*18Not Available1075A>C / 1190A>C  … show all Effect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*26Not Available389C>GEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*28Not Available641A>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*30Not Available1429G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*33Not Available395G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsCytochrome P450 2C9CYP2C9*3(C;C) / (A;C)C AlleleEffect Directly StudiedPatients with this genotype have reduced metabolism of acetylsalicylic acid.DetailsLeukotriene C4 synthase---(A;C) / (C;C)C alleleADR Directly StudiedThe presence of this genotype in LTC4S may indicate an increased risk of chronic urticaria when treated with acetylsalicylic acid.DetailsIntegrin beta-3GPIIIa PlA2(C;C) / (C;T)T > CEffect Directly StudiedPatients with this genotype have increased resistance to the anti-thrombotic effects of aspirin.DetailsCytochrome P450 2C9CYP2C9*6Not Available818delAEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*15Not Available485C>AEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*25Not Available353_362delAGAAATGGAAEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*35Not Available374G>T / 430C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*2Not Available430C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*4Not Available1076T>CEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*5Not Available1080C>GEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*8Not Available449G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*11Not Available1003C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*12Not Available1465C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*13Not Available269T>CEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*14Not Available374G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*16Not Available895A>GEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*18Not Available1075A>C / 1190A>C  … show all Effect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*26Not Available389C>GEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*28Not Available641A>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*30Not Available1429G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*33Not Available395G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails','22360','50-78-2','15365','CHEMBL25','2157','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as acylsalicylic acids. These are o-acylated derivatives of salicylic acid.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing one or more benzene rings.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002448\" rel=\"noopener\" target=\"_blank\">Benzenoids</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing one monocyclic ring system consisting of benzene.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002279\" rel=\"noopener\" target=\"_blank\">Benzene and substituted derivatives</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carboxylic acid substituent attached to a benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000176\" rel=\"noopener\" target=\"_blank\">Benzoic acids and derivatives</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"O-acylated derivatives of salicylic acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004577\" rel=\"noopener\" target=\"_blank\">Acylsalicylic acids</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002319\" rel=\"noopener\" target=\"_blank\">Phenol esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic Compounds containing a benzene ring which bears at least one carboxyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002565\" rel=\"noopener\" target=\"_blank\">Benzoic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds contaning a phenoxy group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004742\" rel=\"noopener\" target=\"_blank\">Phenoxy compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000321\" rel=\"noopener\" target=\"_blank\">Benzoyl derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing exactly two carboxylic acid groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000346\" rel=\"noopener\" target=\"_blank\">Dicarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001238\" rel=\"noopener\" target=\"_blank\">Carboxylic acid esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a carboxylic acid group with the formula -C(=O)OH.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001205\" rel=\"noopener\" target=\"_blank\">Carboxylic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Acylsalicylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic homomonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoyl</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dicarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic homomonocyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">salicylates, acetate ester, benzoic acids (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15365\" rel=\"noopener\" target=\"_blank\">CHEBI:15365</a>) </span></span></dd></dl>','Benzene and substituted derivatives','<p>The clearance rate of acetylsalicylic acid is extremely variable, depending on several factors <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Levy G: Clinical pharmacokinetics of aspirin. Pediatrics. 1978 Nov;62(5 Pt 2 Suppl):867-72. (PubMed ID 724339)\" href=\"#reference-A177217\">6</a></sup>. Dosage adjustments may be required in patients with renal impairment <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. The extended-release tablet should not be administered to patients with eGFR of less than 10 mL/min <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Durlaza FDA label\" href=\"#reference-F4405\">21</a></sup>.</p>','This compound belongs to the class of organic compounds known as acylsalicylic acids. These are o-acylated derivatives of salicylic acid.','Acylsalicylic acids','<li>Avoid alcohol. Alcohol increases the risk of gastrointestinal bleeding.</li>\n<li>Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.</li>\n<li>Take after a meal. This reduces irritating gastrointestinal effects.</li>\n<li>Take with a full glass of water.</li>','Drugs.com Drug Page',' , Acids, Carbocyclic , Agents causing angioedema , Agents causing hyperkalemia , Agents that produce hypertension , Alimentary Tract and Metabolism , Analgesics , Analgesics, Non-Narcotic , Anti-Inflammatory Agents , Anti-Inflammatory Agents, Non-Steroidal , Anti-Inflammatory Agents, Non-Steroidal (Non-Selective) , Antiinflammatory and Antirheumatic Products , Antiplatelet agents , Antipyretics , Benzene Derivatives , Blood and Blood Forming Organs , Cardiovascular Agents , Cyclooxygenase Inhibitors , Cytochrome P-450 CYP2C19 Inducers , Cytochrome P-450 CYP2C19 Inducers (strength unknown) , Cytochrome P-450 CYP2C9 Substrates , Cytochrome P-450 Enzyme Inducers , Cytochrome P-450 Substrates , Decreased Platelet Aggregation , Decreased Prostaglandin Production , Drugs that are Mainly Renally Excreted , Hematologic Agents , Hydroxybenzoates , Musculo-Skeletal System , Nephrotoxic agents , Non COX-2 selective NSAIDS , OAT1/SLC22A6 inhibitors , OAT3/SLC22A8 Inhibitors , P-glycoprotein inducers , P-glycoprotein substrates , Peripheral Nervous System Agents , Platelet Aggregation Inhibitors Excl. Heparin , Salicylates , Salicylic Acid and Derivatives , Sensory System Agents , Stomatological Preparations , UGT1A6 substrate','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>138-140</td><td>http://www.rsc.org/learn-chemistry/content/filerepository/CMP/00/000/045/Aspirin.pdf</td></tr><tr><td>boiling point (°C)</td><td>140 °C</td><td>http://www.chemicalland21.com/lifescience/phar/ACETYLSALICYLIC%20ACID.htm</td></tr><tr><td>water solubility</td><td>10 mg/mL</td><td>https://www.sigmaaldrich.com/catalog/product/sigma/a5376?lang=en&amp;region=US</td></tr><tr><td>logP</td><td>1.18</td><td>https://www.fip.org/files/fip/BPS/BCS/Monographs/AcetylsalicylicAcid.pdf</td></tr><tr><td>pKa</td><td>3.5</td><td>https://www.fip.org/files/fip/BPS/BCS/Monographs/AcetylsalicylicAcid.pdf</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">salicylates, acetate ester, benzoic acids (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15365\" rel=\"noopener\" target=\"_blank\">CHEBI:15365</a>) </span></span>','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"human-metabolome-database\">Human Metabolome Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.hmdb.ca/metabolites/HMDB0001879\" rel=\"noopener\" target=\"_blank\">HMDB0001879</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-drug\">KEGG Drug</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?drug:D00109\" rel=\"noopener\" target=\"_blank\">D00109</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"kegg-compound\">KEGG Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C01405\" rel=\"noopener\" target=\"_blank\">C01405</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-compound\">PubChem Compound</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=2244\" rel=\"noopener\" target=\"_blank\">2244</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pubchem-substance\">PubChem Substance</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505803\" rel=\"noopener\" target=\"_blank\">46505803</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chemspider\">ChemSpider</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.chemspider.com/Chemical-Structure.2157.html\" rel=\"noopener\" target=\"_blank\">2157</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"bindingdb\">BindingDB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=22360\" rel=\"noopener\" target=\"_blank\">22360</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxnav\">RxNav</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://mor.nlm.nih.gov/RxNav/search?searchBy=RXCUI&amp;searchTerm=1191\" rel=\"noopener\" target=\"_blank\">1191</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chebi\">ChEBI</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=15365\" rel=\"noopener\" target=\"_blank\">15365</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"chembl\">ChEMBL</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL25\" rel=\"noopener\" target=\"_blank\">CHEMBL25</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"zinc\">ZINC</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://zinc.docking.org/substances/ZINC000000000053\" rel=\"noopener\" target=\"_blank\">ZINC000000000053</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"therapeutic-targets-database\">Therapeutic Targets Database</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000843\" rel=\"noopener\" target=\"_blank\">DAP000843</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pharmgkb\">PharmGKB</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pharmgkb.org/drug/PA448497\" rel=\"noopener\" target=\"_blank\">PA448497</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"guide-to-pharmacology\">Guide to Pharmacology</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=4139\" rel=\"noopener\" target=\"_blank\">GtP Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdbe-ligand\">PDBe Ligand</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.ebi.ac.uk/pdbe-srv/pdbechem/chemicalCompound/show/AIN\" rel=\"noopener\" target=\"_blank\">AIN</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"rxlist\">RxList</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.rxlist.com/cgi/generic/asa.htm\" rel=\"noopener\" target=\"_blank\">RxList Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"drugs-com\">Drugs.com</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://www.drugs.com/aspirin.html\" rel=\"noopener\" target=\"_blank\">Drugs.com Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"pdrhealth\">PDRhealth</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/asp1033.shtml\" rel=\"noopener\" target=\"_blank\">PDRhealth Drug Page</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"wikipedia\">Wikipedia</dt><dd class=\"col-md-8 col-sm-7\"><a href=\"https://en.wikipedia.org/wiki/Aspirin\" rel=\"noopener\" target=\"_blank\">Aspirin</a></dd></dl>','<li>Avoid alcohol. Alcohol increases the risk of gastrointestinal bleeding.</li>\n<li>Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.</li>\n<li>Take after a meal. This reduces irritating gastrointestinal effects.</li>\n<li>Take with a full glass of water.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A1440\">Macdonald S: Aspirin use to be banned in under 16 year olds. BMJ. 2002 Nov 2;325(7371):988. [<a href=\"/articles/A1440\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1441\">Sneader W: The discovery of aspirin: a reappraisal. BMJ. 2000 Dec 23-30;321(7276):1591-4. [<a href=\"/articles/A1441\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1442\">Aukerman G, Knutson D, Miser WF: Management of the acute migraine headache. Am Fam Physician. 2002 Dec 1;66(11):2123-30. [<a href=\"/articles/A1442\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1443\">Authors unspecified: Randomised trial of intravenous streptokinase, oral aspirin, both, or neither among 17,187 cases of suspected acute myocardial infarction: ISIS-2. ISIS-2 (Second International Study of Infarct Survival) Collaborative Group. Lancet. 1988 Aug 13;2(8607):349-60. [<a href=\"/articles/A1443\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1444\">Dorsch MP, Lee JS, Lynch DR, Dunn SP, Rodgers JE, Schwartz T, Colby E, Montague D, Smyth SS: Aspirin resistance in patients with stable coronary artery disease with and without a history of myocardial infarction. Ann Pharmacother. 2007 May;41(5):737-41. Epub 2007 Apr 24. [<a href=\"/articles/A1444\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177217\">Levy G: Clinical pharmacokinetics of aspirin. Pediatrics. 1978 Nov;62(5 Pt 2 Suppl):867-72. [<a href=\"/articles/A177217\" target=\"_blank\">Article</a>] </li><li id=\"reference-A35408\">Authors unspecified: Guidance document: management priorities in salicylate toxicity. J Med Toxicol. 2015 Mar;11(1):149-52. doi: 10.1007/s13181-013-0362-3. [<a href=\"/articles/A35408\" target=\"_blank\">Article</a>] </li><li id=\"reference-A32954\">Durnas C, Cusack BJ: Salicylate intoxication in the elderly. Recognition and recommendations on how to prevent it. Drugs Aging. 1992 Jan-Feb;2(1):20-34. [<a href=\"/articles/A32954\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177241\">Flower R: What are all the things that aspirin does? BMJ. 2003 Sep 13;327(7415):572-3. doi: 10.1136/bmj.327.7415.572. [<a href=\"/articles/A177241\" target=\"_blank\">Article</a>] </li><li id=\"reference-A10989\">Hall MN, Campos H, Li H, Sesso HD, Stampfer MJ, Willett WC, Ma J: Blood levels of long-chain polyunsaturated fatty acids, aspirin, and the risk of colorectal cancer. Cancer Epidemiol Biomarkers Prev. 2007 Feb;16(2):314-21. [<a href=\"/articles/A10989\" target=\"_blank\">Article</a>] </li><li id=\"reference-A32682\">Vane JR, Botting RM: The mechanism of action of aspirin. Thromb Res. 2003 Jun 15;110(5-6):255-8. [<a href=\"/articles/A32682\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177256\">Vane JR, Bakhle YS, Botting RM: Cyclooxygenases 1 and 2. Annu Rev Pharmacol Toxicol. 1998;38:97-120. doi: 10.1146/annurev.pharmtox.38.1.97. [<a href=\"/articles/A177256\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177265\">Varga Z, Sabzwari SRA, Vargova V: Cardiovascular Risk of Nonsteroidal Anti-Inflammatory Drugs: An Under-Recognized Public Health Issue. Cureus. 2017 Apr 8;9(4):e1144. doi: 10.7759/cureus.1144. [<a href=\"/articles/A177265\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177268\">Ornelas A, Zacharias-Millward N, Menter DG, Davis JS, Lichtenberger L, Hawke D, Hawk E, Vilar E, Bhattacharya P, Millward S: Beyond COX-1: the effects of aspirin on platelet biology and potential mechanisms of chemoprevention. Cancer Metastasis Rev. 2017 Jun;36(2):289-303. doi: 10.1007/s10555-017-9675-z. [<a href=\"/articles/A177268\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177325\">Alfonso L, Ai G, Spitale RC, Bhat GJ: Molecular targets of aspirin and cancer prevention. Br J Cancer. 2014 Jul 8;111(1):61-7. doi: 10.1038/bjc.2014.271. Epub 2014 May 29. [<a href=\"/articles/A177325\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177400\">Tsoi KKF, Ho JMW, Chan FCH, Sung JJY: Long-term use of low-dose aspirin for cancer prevention: A 10-year population cohort study in Hong Kong. Int J Cancer. 2018 Dec 21. doi: 10.1002/ijc.32083. [<a href=\"/articles/A177400\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177403\">Li D, Wang P, Yu Y, Huang B, Zhang X, Xu C, Zhao X, Yin Z, He Z, Jin M, Liu C: Tumor-preventing activity of aspirin in multiple cancers based on bioinformatic analyses. PeerJ. 2018 Sep 26;6:e5667. doi: 10.7717/peerj.5667. eCollection 2018. [<a href=\"/articles/A177403\" target=\"_blank\">Article</a>] </li><li id=\"reference-T562\">Hasan Arif; Sandeep Aggarwal (2018). Salicylic Acid (Aspirin): StatPearls. StatPearls Publishing. </li><li id=\"reference-L5968\">Mayo Clinic website: Salicylate [<a href=\"https://www.mayoclinic.org/drugs-supplements/salicylate-oral-route-rectal-route/proper-use/drg-20070551\" target=\"_blank\">Link</a>] </li><li id=\"reference-L12282\">Health Canada Product Monograph: Aspirin (acetylsalicylic acid) for oral administration [<a href=\"https://pdf.hres.ca/dpd_pm/00000653.PDF\" target=\"_blank\">Link</a>] </li><li id=\"reference-F4405\">Durlaza FDA label [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/004/405/original/Durlaza_%28Extended_Release%29.pdf?1555433930\" target=\"_blank\">File</a>] </li></ol>','<p>The half-life of ASA in the circulation ranges from 13 - 19 minutes. Blood concentrations drop rapidly after complete absorption. The half-life of the salicylate ranges between 3.5 and 4.5 hours <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','HMDB0001879','2-(acetyloxy)benzoic acid','InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)','BSYNRYMUTXBXSQ-UHFFFAOYSA-N','<p><strong>Pain, fever, and inflammation</strong></p><p>Acetylsalicylic acid (ASA), in the regular tablet form (immediate-release), is indicated to relieve pain, fever, and inflammation associated with many conditions, including the flu, the common cold, neck and back pain, dysmenorrhea, headache, tooth pain, sprains, fractures, myositis, neuralgia, synovitis, arthritis, bursitis, burns, and various injuries. It is also used for symptomatic pain relief after surgical and dental procedures <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. </p><p>The <em>extra strength</em> formulation of acetylsalicylic acid is also indicated for the management migraine pain with photophobia (sensitivity to light) and phonophobia (sensitivity to sound)<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p><p><strong>Other indications</strong></p><p>ASA is also indicated for various other purposes, due to its ability to inhibit platelet aggregation. These include: </p><p>Reducing the risk of cardiovascular death in suspected cases of myocardial infarction (MI) <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. </p><p>Reducing the risk of a first non-fatal myocardial infarction in patients, and for reducing the risk of morbidity and mortality in cases of unstable angina and in those who have had a prior myocardial infarction <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p><p>For reducing the risk of transient ischemic attacks (TIA) and to prevent atherothrombotic cerebral infarction (in conjunction with other treatments) <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p><p>For the prevention of thromboembolism after hip replacement surgery <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. </p><p>For decreasing platelet to platelet adhesion following carotid endarterectomy, aiding in the prevention of transient ischemic attacks (TIA) <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p><p>Used for patients undergoing hemodialysis with a silicone rubber arteriovenous cannula inserted to prevent thrombosis at the insertion site <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. </p><p><strong>Important note regarding use of the extended-release formulation <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Durlaza FDA label\" href=\"#reference-F4405\">21</a></sup></strong></p><p>In the setting of acute myocardial infarction, or before percutaneous interventions, the extended-release form of acetylsalicylic acid should not be used. Use immediate-release formulations in scenarios requiring rapid onset of action <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a>,<a class=\"reference-popover-link\" data-content=\"Durlaza FDA label\" href=\"#reference-F4405\">21</a></sup>. The extended-release form is taken to decrease the incidence of mortality and myocardial infarction (MI) for individuals diagnosed with chronic coronary artery disease (CAD), including patients with previous myocardial infarction (MI) or unstable angina or with chronic stable angina. Additionally, the extended-release form is used to decrease the risk of death and recurrent episodes of stroke in patients with a history of stroke or TIA <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Durlaza FDA label\" href=\"#reference-F4405\">21</a></sup>.</p>','C01405','D00109','Organic compounds','<p>Acetylsalicylic acid is hydrolyzed in the plasma to salicylic acid. Plasma concentrations of aspirin following after administration of the extended-release form are mostly undetectable 4-8 hours after ingestion of a single dose. Salicylic acid was measured at 24 hours following a single dose of extended-release acetylsalicylic acid <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Durlaza FDA label\" href=\"#reference-F4405\">21</a></sup>.</p><p>Salicylate is mainly metabolized in the liver, although other tissues may also be involved in this process <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. The major metabolites of acetylsalicylic acid are salicylic acid, salicyluric acid, the ether or phenolic glucuronide and the ester or acyl glucuronide. A small portion is converted to gentisic acid and other hydroxybenzoic acids <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic homomonocyclic compounds','AIN','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000083?highlight[compounds][]=DB00945&amp;highlight[proteins][]=DB00945\">Acetylsalicylic Acid Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA448497','<p>50% to 90% of a normal therapeutic concentration salicylate (a main metabolite of acetylsalicylic acid <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>) binds plasma proteins, particularly albumin, while acetylsalicylic acid itself binds negligibly <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. Acetylsalicylic acid has the ability to bind to and acetylate many proteins, hormones, DNA, platelets, and hemoglobin <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','2244','46505803','<p>Excretion of salicylates occurs mainly through the kidney, by the processes of glomerular filtration and tubular excretion, in the form of free salicylic acid, salicyluric acid, and, additionally, phenolic and acyl glucuronides <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. </p><p>Salicylate can be found in the urine soon after administration, however, the entire dose takes about 48 hours to be completely eliminated. The rate of salicylate is often variable, ranging from 10% to 85% in the urine, and heavily depends on urinary pH. Acidic urine generally aids in reabsorption of salicylate by the renal tubules, while alkaline urine increases excretion <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p><p>After the administration of a typical 325mg dose, the elimination of ASA is found to follow first order kinetics in a linear fashion. At high concentrations, the elimination half-life increases <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','RxList Drug Page','1191','CC(=O)OC1=CC=CC=C1C(O)=O','Solid','Benzoic acids and derivatives','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Acylsalicylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic homomonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoyl</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dicarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span></span></span>','Benzenoids','<span class=\"citations\"><p>Marino Gobetti, Guido Vandoni, \"Acetylsalicylic acid thioesters, a process for their preparation and pharmaceutical compositions containing them.\" U.S. Patent US4563443, issued March, 1981.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=4563443&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US4563443</a>','DAP000843','<p><strong>Lethal doses</strong></p><p>Acute oral LD50 values have been reported as over 1.0 g/kg in humans, cats, and dogs, 0.92 g/kg - 1.48 g/kg in albino rats, 1.19 g/kg in guinea pigs, 1.1 g/kg in mice, and 1.8 g/kg in rabbit models <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p><p><strong>Acute toxicity</strong></p><p>Salicylate toxicity is a problem that may develop with both acute and chronic salicylate exposure <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Authors unspecified: Guidance document: management priorities in salicylate toxicity. J Med Toxicol. 2015 Mar;11(1):149-52. doi: 10.1007/s13181-013-0362-3. (PubMed ID 25715929)\" href=\"#reference-A35408\">7</a></sup>.\nMultiple organ systems may be affected by salicylate toxicity, including the central nervous system, the pulmonary system, and the gastrointestinal system. Severe bleeding may occur. In the majority of cases, patients suffering from salicylate toxicity are volume-depleted at the time of presentation for medical attention. Fluid resuscitation should occur immediately and volume status should be monitored closely. Disruptions in acid-base balance are frequent in ASA toxicity <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Authors unspecified: Guidance document: management priorities in salicylate toxicity. J Med Toxicol. 2015 Mar;11(1):149-52. doi: 10.1007/s13181-013-0362-3. (PubMed ID 25715929)\" href=\"#reference-A35408\">7</a></sup>. </p><p>The acute toxicity of acetylsalicylic in animals has been widely studied. The signs of poisoning in rats from lethal doses are mild to severe gastroenteritis, hepatitis, nephritis, pulmonary edema, encephalopathy, shock and some toxic effects on other organs and tissues. Mortality has been observed following convulsions or cardiovascular shock. An important differentiating property between various animal species is the ability to vomit toxic doses. Humans, cats and dogs have this ability, but rodents or rabbits do not <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. </p><p><strong>Chronic toxicity and carcinogenesis</strong></p><p>Chronic ASA toxicity is frequently accompanied by atypical clinical presentations that may be similar to diabetic ketoacidosis, delirium, cerebrovascular accident (CVA), myocardial infarction (MI) or cardiac failure. Plasma salicylate concentrations should be measured if salicylate intoxication is suspected, even if there no documentation available to suggest ASA was ingested. In older age, nephrotoxicity from salicylates increases, and the risk of upper gastrointestinal hemorrhage is increased, with higher rates of mortality <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Durnas C, Cusack BJ: Salicylate intoxication in the elderly. Recognition and recommendations on how to prevent it. Drugs Aging. 1992 Jan-Feb;2(1):20-34. (PubMed ID 1554971)\" href=\"#reference-A32954\">8</a></sup>. It is also important to note that ASA toxicity may occur even with close to normal serum concentrations. Prevention of chronic ASA includes the administration of smallest possible doses, avoidance of concurrent use of salicylate drugs, and therapeutic drug monitoring. Renal function should be regularly monitored and screening for gastrointestinal bleeding should be done at regular intervals <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Durnas C, Cusack BJ: Salicylate intoxication in the elderly. Recognition and recommendations on how to prevent it. Drugs Aging. 1992 Jan-Feb;2(1):20-34. (PubMed ID 1554971)\" href=\"#reference-A32954\">8</a></sup>. </p><p>Chronic toxicity studies were performed in rodents. ASA was administered at doses measured to be 2 to 20 times the maximum tolerated clinical dose to mice for up to one year. Negative dose-related effects were seen. These include decreased mean survival time, decreased number of births and progeny reaching an appropriate age for weaning. No evidence of carcinogenesis was found in 1-year studies <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. At daily doses of 0.24 g/kg/day given for 100 days to albino rats, ASA led to signs to excessive thirst, aciduria, diuresis, drowsiness, hyperreflexia, piloerection, changes in respiration, tachycardia, followed by soft stools, epistaxis, sialorrhea, dacryorrhea and mortality during hypothermic coma in the second study month <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p><p><strong>Use in pregnancy and lactation</strong></p><p>While teratogenic effects were observed in animals nearly lethal doses, no evidence suggests that this drug is teratogenic in humans <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. It is advisable, however, to avoid ASA use the first and second trimester of pregnancy, unless it is clearly required. If acetylsalicylic acid containing drugs are ingested by a patient attempting to conceive, or during the first and second trimester of pregnancy, the lowest possible dose at the shortest possible duration should be taken <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. This drug is contraindicated in the 3rd trimester of pregnancy <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. </p>','R16CO5Y76E','<p>This drug is distributed to body tissues shortly after administration. It is known to cross the placenta. The plasma contains high levels of salicylate, as well as tissues such as spinal, peritoneal and synovial fluids, saliva and milk. The kidney, liver, heart, and lungs are also found to be rich in salicylate concentration after dosing. Low concentrations of salicylate are usually low, and minimal concentrations are found in feces, bile, and sweat <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','Aspirin','ZINC000000000053'),