(37,'Vincristine','vincristine','Vincristine is a vinca alkaloid used to treat acute leukemia, malignant lymphoma, Hodgkin\'s disease, acute erythraemia, and acute panmyelosis.','Marqibo, Vincasar','Vincristine','<p>Vincristine is an antitumor vinca alkaloid isolated from Vinca Rosea. It is marketed under several brand names, many of which have different formulations such as Marqibo (liposomal injection) and Vincasar. Vincristine is indicated for the treatment of acute leukaemia, malignant lymphoma, Hodgkin\'s disease, acute erythraemia, and acute panmyelosis. vincristine sulfate is often chosen as part of polychemotherapy because of lack of significant bone–marrow suppression (at recommended doses) and of unique clinical toxicity (neuropathy).</p>','C46H56N4O10','DB00541','Approved, Investigational','Small Molecule','Average: 824.972 Monoisotopic: 824.399644019 ',' , L01CA — Vinca alkaloids and analogues , L01C — PLANT ALKALOIDS AND OTHER NATURAL PRODUCTS , L01 — ANTINEOPLASTIC AGENTS , L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS','<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=\"Compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000210\" rel=\"noopener\" target=\"_blank\">Carbazoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an indole moiety that carries an alkyl chain at the 3-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004196\" rel=\"noopener\" target=\"_blank\">3-alkylindoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acids containing exactly three carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001986\" rel=\"noopener\" target=\"_blank\">Tricarboxylic acids and derivatives</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=\"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=\"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 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 a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003449\" rel=\"noopener\" target=\"_blank\">N-alkylpyrrolidines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR\', where R=H or organyl group and R\'=methyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003416\" rel=\"noopener\" target=\"_blank\">Methyl esters</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></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 pyrrole ring, which is a five-member aromatic heterocycle with one nitrogen atom and four carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000090\" rel=\"noopener\" target=\"_blank\">Pyrroles</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=\"Compounds containing an amide derivative of carboxylic acid, with the general structure RN(R1)C(R2)=O (R1-R2 any atom but H).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001664\" rel=\"noopener\" target=\"_blank\">Tertiary carboxylic acid amides</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=\"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=\"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 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=\"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 12 more</a>','Not Available','Not Available','38872','57-22-7','28445','CHEMBL499458','4535015','<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 vinca alkaloids. These are alkaloids with a dimeric chemical structure composed of an indole nucleus (catharanthine), and a dihydroindole nucleus (vindoline), joined together.</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 with a dimeric chemical structure composed of an indole nucleus (catharanthine), and a dihydroindole nucleus (vindoline), joined together.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002756\" rel=\"noopener\" target=\"_blank\">Vinca 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 with a dimeric chemical structure composed of an indole nucleus (catharanthine), and a dihydroindole nucleus (vindoline), joined together.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002756\" rel=\"noopener\" target=\"_blank\">Vinca 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=\"Compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000210\" rel=\"noopener\" target=\"_blank\">Carbazoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an indole moiety that carries an alkyl chain at the 3-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004196\" rel=\"noopener\" target=\"_blank\">3-alkylindoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acids containing exactly three carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001986\" rel=\"noopener\" target=\"_blank\">Tricarboxylic acids and derivatives</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=\"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=\"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 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 a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003449\" rel=\"noopener\" target=\"_blank\">N-alkylpyrrolidines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR\', where R=H or organyl group and R\'=methyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003416\" rel=\"noopener\" target=\"_blank\">Methyl esters</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></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 pyrrole ring, which is a five-member aromatic heterocycle with one nitrogen atom and four carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000090\" rel=\"noopener\" target=\"_blank\">Pyrroles</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=\"Compounds containing an amide derivative of carboxylic acid, with the general structure RN(R1)C(R2)=O (R1-R2 any atom but H).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001664\" rel=\"noopener\" target=\"_blank\">Tertiary carboxylic acid amides</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=\"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=\"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 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=\"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 12 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\">3-alkylindole</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\">Amino acid or derivatives</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 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\">Carbazole</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 class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclic alcohol</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\">Indole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Indole or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Methyl ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">N-alkylpyrrolidine</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 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\">Pyrrole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrrolidine</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\">Tertiary carboxylic acid amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tricarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinca alkaloid skeleton</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=\"not-available\">Not Available</span></dd></dl>','Vinca alkaloids','<p><span class=\"not-available\">Not Available</span></p>','This compound belongs to the class of organic compounds known as vinca alkaloids. These are alkaloids with a dimeric chemical structure composed of an indole nucleus (catharanthine), and a dihydroindole nucleus (vindoline), joined together.','Vinca alkaloids','<li>Exercise caution with grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum concentration of vincristine.</li>\n<li>Exercise caution with St. John\'s Wort. This herb induces CYP3A4 metabolism, which may reduce serum levels of vincristine.</li>','Drugs.com Drug Page',' , Agents Causing Muscle Toxicity , Alkaloids , Antimitotic Agents , Antineoplastic Agents , Antineoplastic Agents, Phytogenic , Antineoplastic and Immunomodulating Agents , BCRP/ABCG2 Substrates , BSEP/ABCB11 Substrates , BSEP/ABCB11 Substrates with a Narrow Therapeutic Index , Cardiotoxic antineoplastic agents , Cytochrome P-450 CYP3A Substrates , 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 CYP3A7 Substrates , Cytochrome P-450 CYP3A7 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 Substrates , Heterocyclic Compounds, Fused-Ring , Immunosuppressive Agents , Indole Alkaloids , Indoles , Indolizidines , Indolizines , Mitosis Modulators , Narrow Therapeutic Index Drugs , Neurotoxic agents , OATP1B1/SLCO1B1 Inhibitors , OATP1B3 inhibitors , P-glycoprotein inducers , P-glycoprotein inhibitors , P-glycoprotein substrates , P-glycoprotein substrates with a Narrow Therapeutic Index , Secologanin Tryptamine Alkaloids , Tubulin Modulators , Vinca Alkaloids','<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>logP</td><td>2.82</td><td>HANSCH,C ET AL. (1995)</td></tr><tr><td>pKa</td><td>5</td><td>MERCK INDEX (1996)</td></tr></tbody></table>','<span class=\"not-available\">Not Available</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/HMDB0014681\" rel=\"noopener\" target=\"_blank\">HMDB0014681</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:D08679\" rel=\"noopener\" target=\"_blank\">D08679</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:C07204\" rel=\"noopener\" target=\"_blank\">C07204</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=5978\" rel=\"noopener\" target=\"_blank\">5978</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=46507033\" rel=\"noopener\" target=\"_blank\">46507033</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.4535015.html\" rel=\"noopener\" target=\"_blank\">4535015</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=38872\" rel=\"noopener\" target=\"_blank\">38872</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=11202\" rel=\"noopener\" target=\"_blank\">11202</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=28445\" rel=\"noopener\" target=\"_blank\">28445</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/CHEMBL499458\" rel=\"noopener\" target=\"_blank\">CHEMBL499458</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/ZINC000085537024\" rel=\"noopener\" target=\"_blank\">ZINC000085537024</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=DAP000114\" rel=\"noopener\" target=\"_blank\">DAP000114</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/PA451879\" rel=\"noopener\" target=\"_blank\">PA451879</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/R1Q\" rel=\"noopener\" target=\"_blank\">R1Q</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/vincristine.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/vincristine.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/Vincristine\" rel=\"noopener\" target=\"_blank\">Vincristine</a></dd></dl>','<li>Exercise caution with grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum concentration of vincristine.</li>\n<li>Exercise caution with St. John\'s Wort. This herb induces CYP3A4 metabolism, which may reduce serum levels of vincristine.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A830\">Graf WD, Chance PF, Lensch MW, Eng LJ, Lipe HP, Bird TD: Severe vincristine neuropathy in Charcot-Marie-Tooth disease type 1A. Cancer. 1996 Apr 1;77(7):1356-62. [<a href=\"/articles/A830\" target=\"_blank\">Article</a>] </li><li id=\"reference-A831\">Qweider M, Gilsbach JM, Rohde V: Inadvertent intrathecal vincristine administration: a neurosurgical emergency. Case report. J Neurosurg Spine. 2007 Mar;6(3):280-3. [<a href=\"/articles/A831\" target=\"_blank\">Article</a>] </li><li id=\"reference-A832\">JOHNSON IS, ARMSTRONG JG, GORMAN M, BURNETT JP Jr: THE VINCA ALKALOIDS: A NEW CLASS OF ONCOLYTIC AGENTS. Cancer Res. 1963 Sep;23:1390-427. [<a href=\"/articles/A832\" target=\"_blank\">Article</a>] </li><li id=\"reference-A833\">Gidding CE, Kellie SJ, Kamps WA, de Graaf SS: Vincristine revisited. Crit Rev Oncol Hematol. 1999 Feb;29(3):267-87. [<a href=\"/articles/A833\" target=\"_blank\">Article</a>] </li><li id=\"reference-L20449\">FDA Approved Drug Products: Marqibo (vincristine sulfate liposome) for intravenous injection [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/202497s011lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>When intravenously injected into cancer patients, a triphasic serum decay patten was observed. The initial, middle, and terminal half-lives are 5 minutes, 2.3 hours, 85 hours respectively. The range of the terminal half-life is humans is 19 - 155 hours. </p>','HMDB0014681','methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(1R,13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,','InChI=1S/C46H56N4O10/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3/t28-,37-,38+,39+','OGWKCGZFUXNPDA-CFWMRBGOSA-N','<p>Treatment of acute lymphocytic leukemia (ALL), Hodgkin lymphoma, non-Hodgkin lymphomas, Wilms\' tumor, neuroblastoma, rhabdomyosarcoma. Liposomal vincristine is indicated for the treatment of relapsed Philadelphia chromosome-negative (Ph-) acute lymphoblastic leukemia (ALL). </p>','C07204','D08679','Organic compounds','<p>Hepatic. Cytochrome P450 isoenzymes of the CYP3A subfamily facilitate the metabolism of vincristine. </p>','Aromatic heteropolycyclic compounds','R1Q','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000437?highlight[compounds][]=DB00541&amp;highlight[proteins][]=DB00541\">Vincristine Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA451879','<p>~75%</p>','5978','46507033','<p>The liver is the major excretory organ in humans and animals. 80% of an injected dose of vincristine sulfate is excreted via feces. 10 - 20% is excreted via urine. </p>','RxList Drug Page','11202','[H][C@@]12N3CC[C@@]11C4=C(C=C(OC)C(=C4)[C@]4(C[C@H]5C[N@](C[C@](O)(CC)C5)CCC5=C4NC4=CC=CC=C54)C(=O)OC)N(C=O)[C@@]1([H])[C@](O)([C@H](OC(C)=O)[C@]2(CC)C=CC3)C(=O)OC','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\">3-alkylindole</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\">Amino acid or derivatives</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 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\">Carbazole</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 class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclic alcohol</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\">Indole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Indole or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Methyl ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">N-alkylpyrrolidine</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 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\">Pyrrole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrrolidine</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\">Tertiary carboxylic acid amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tricarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinca alkaloid skeleton</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>','Alkaloids and derivatives','<span class=\"citations\"><p>Homer L. Pearce, \"Method of preparing vincristine.\" U.S. Patent US4303584, issued November, 1967.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=4303584&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US4303584</a>','DAP000114','<p>IVN-RAT LD<sub>50</sub> 1300 mg/kg; IPR-MUS LD<sub>50</sub> 5.2 mg/kg. Marqibo® must only be administered IV because it is fatal if administered by other routes. Marqibo® also has different dosing than vincristine sulphate injection, so attention is needed to prevent overdoses. The most clinically significant adverse effect of vincristine is neurotoxicity. </p>','5J49Q6B70F','<p>Within 15 to 30 minutes after injection, over 90% of the drug is distributed from the blood into tissue, where it remains tightly, but not irreversibly, bound.</p>','Vincristine','ZINC000085537024'),(38,'Methotrexate','methotrexate','Methotrexate is an antineoplastic agent used the treatment of a wide variety of cancers as well as severe psoriasis, severe rheumatoid arthritis, and juvenile rheumatoid arthritis.','Metoject, Nordimet, Otrexup, Rasuvo, Reditrex, Trexall, Xatmep','Methotrexate','<p>Methotrexate is a folate derivative that inhibits several enzymes responsible for nucleotide synthesis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Inoue K, Yuasa H: Molecular basis for pharmacokinetics and pharmacodynamics of methotrexate in rheumatoid arthritis therapy. Drug Metab Pharmacokinet. 2014;29(1):12-9. Epub 2013 Nov 26. (PubMed ID 24284432)\" href=\"#reference-A180322\">1</a></sup> This inhibition leads to suppression of inflammation as well as prevention of cell division.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Inoue K, Yuasa H: Molecular basis for pharmacokinetics and pharmacodynamics of methotrexate in rheumatoid arthritis therapy. Drug Metab Pharmacokinet. 2014;29(1):12-9. Epub 2013 Nov 26. (PubMed ID 24284432)\" href=\"#reference-A180322\">1</a></sup> Because of these effects, methotrexate is often used to treat inflammation caused by arthritis or to control cell division in neoplastic diseases such as breast cancer and non-Hodgkin\'s lymphoma.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Inoue K, Yuasa H: Molecular basis for pharmacokinetics and pharmacodynamics of methotrexate in rheumatoid arthritis therapy. Drug Metab Pharmacokinet. 2014;29(1):12-9. Epub 2013 Nov 26. (PubMed ID 24284432)\" href=\"#reference-A180322\">1</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Oral Solution\" href=\"#reference-L7144\">4</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Subcutaneous Injection\" href=\"#reference-L7147\">5</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Prefilled Syringe for Subcutaneous Injection\" href=\"#reference-L7150\">6</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Injection\" href=\"#reference-L7180\">7</a></sup></p><p>Due to the toxic effects of methotrexate, it is indicated for treatment of some forms of arthritis and severe psoriasis only if first line treatment has failed or patients are intolerant of those treatments.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Injection\" href=\"#reference-L7180\">7</a></sup></p><p>Methotrexate was granted FDA approval on 7 December 1953.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Sodium Oral Tablets\" href=\"#reference-L7198\">8</a></sup></p>','C20H22N8O5','DB00563','Approved','Small Molecule','Average: 454.4393 Monoisotopic: 454.171315854 ',' , L04AX — Other immunosuppressants , L04A — IMMUNOSUPPRESSANTS , L04 — IMMUNOSUPPRESSANTS , L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS , L01BA — Folic acid analogues , L01B — ANTIMETABOLITES , L01 — ANTINEOPLASTIC AGENTS , L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS','<p>Methotrexate has a bioavailability of 64-90%, though this decreases at oral doses above 25mg due to saturation of the carrier mediated transport of methotrexate.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Inoue K, Yuasa H: Molecular basis for pharmacokinetics and pharmacodynamics of methotrexate in rheumatoid arthritis therapy. Drug Metab Pharmacokinet. 2014;29(1):12-9. Epub 2013 Nov 26. (PubMed ID 24284432)\" href=\"#reference-A180322\">1</a></sup>. Methotrexate has a T<sub>max</sub> of 1 to 2 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Inoue K, Yuasa H: Molecular basis for pharmacokinetics and pharmacodynamics of methotrexate in rheumatoid arthritis therapy. Drug Metab Pharmacokinet. 2014;29(1):12-9. Epub 2013 Nov 26. (PubMed ID 24284432)\" href=\"#reference-A180322\">1</a></sup> oral doses of 10-15µg reach serum levels of 0.01-0.1µM.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Inoue K, Yuasa H: Molecular basis for pharmacokinetics and pharmacodynamics of methotrexate in rheumatoid arthritis therapy. Drug Metab Pharmacokinet. 2014;29(1):12-9. Epub 2013 Nov 26. (PubMed ID 24284432)\" href=\"#reference-A180322\">1</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 an alpha amino acid which bears an acyl group at its terminal nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002402\" rel=\"noopener\" target=\"_blank\">N-acyl-alpha amino acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001318\" rel=\"noopener\" target=\"_blank\">Hippuric acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form  pyrimido(4,5-b)pyrazine.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000109\" rel=\"noopener\" target=\"_blank\">Pteridines and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a benzamide moiety with an amine group attached to the benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001917\" rel=\"noopener\" target=\"_blank\">Aminobenzamides</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=\"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=\"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 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=\"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 pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000067\" rel=\"noopener\" target=\"_blank\">Pyrazines</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 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=\"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 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 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 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=\"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=\"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 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 11 more</a>','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsCanalicular multispecific organic anion transporter 1ABCC2 IVS 23+56(C;C) / (C;T)T alleleADR Directly StudiedPatients with this genotype have increased risk of toxicity with methotrexate.DetailsMethylenetetrahydrofolate reductase---(T;T) / (C;T)T alleleADR Directly StudiedPatients with this genotype have increased risk of toxicity with methotrexate.Details','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsCanalicular multispecific organic anion transporter 1ABCC2 IVS 23+56(C;C) / (C;T)T alleleADR Directly StudiedPatients with this genotype have increased risk of toxicity with methotrexate.DetailsMethylenetetrahydrofolate reductase---(T;T) / (C;T)T alleleADR Directly StudiedPatients with this genotype have increased risk of toxicity with methotrexate.Details','66082','59-05-2','44185','CHEMBL34259','112728','<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 glutamic acid and derivatives. These are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</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=\"Compounds containing a carboxylic acid group with the formula -C(=O)OH or a derivative thereof.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000265\" rel=\"noopener\" target=\"_blank\">Carboxylic 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 an amino acid or a peptide backbone, or derivatives thereof.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000013\" rel=\"noopener\" target=\"_blank\">Amino acids, peptides, and analogues</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 glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004323\" rel=\"noopener\" target=\"_blank\">Glutamic acid and derivatives</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 an alpha amino acid which bears an acyl group at its terminal nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002402\" rel=\"noopener\" target=\"_blank\">N-acyl-alpha amino acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001318\" rel=\"noopener\" target=\"_blank\">Hippuric acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form  pyrimido(4,5-b)pyrazine.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000109\" rel=\"noopener\" target=\"_blank\">Pteridines and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a benzamide moiety with an amine group attached to the benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001917\" rel=\"noopener\" target=\"_blank\">Aminobenzamides</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=\"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=\"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 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=\"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 pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000067\" rel=\"noopener\" target=\"_blank\">Pyrazines</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 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=\"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 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 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 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=\"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=\"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 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 11 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\">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\">Aminobenzamide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminobenzoic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminopyrimidine</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\">Aralkylamine</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\">Benzamide</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\">Benzoic acid or derivatives</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\">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\">Dialkylarylamine</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\">Glutamic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Heteroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hippuric acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hippuric acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</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\">N-acyl-alpha amino acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">N-acyl-alpha-amino acid</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 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\">Primary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pteridine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrazine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrimidine</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 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\">monocarboxylic acid amide, dicarboxylic acid, pteridines (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:44185\" rel=\"noopener\" target=\"_blank\">CHEBI:44185</a>) </span></span></dd></dl>','Carboxylic acids and derivatives','<p>Methotrexate clearance varies widely between patients and decreases with increasing doses.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Muhrez K, Benz-de Bretagne I, Nadal-Desbarats L, Blasco H, Gyan E, Choquet S, Montigny F, Emond P, Barin-Le Guellec C: Endogenous metabolites that are substrates of organic anion transporter\'s (OATs) predict methotrexate clearance. Pharmacol Res. 2017 Apr;118:121-132. doi: 10.1016/j.phrs.2016.05.021. Epub 2016 May 19. (PubMed ID 27210722)\" href=\"#reference-A180400\">3</a></sup> Currently, predicting clearance of methotrexate is difficult and exceedingly high serum levels of methotrexate can still occur when all precautions are taken.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Muhrez K, Benz-de Bretagne I, Nadal-Desbarats L, Blasco H, Gyan E, Choquet S, Montigny F, Emond P, Barin-Le Guellec C: Endogenous metabolites that are substrates of organic anion transporter\'s (OATs) predict methotrexate clearance. Pharmacol Res. 2017 Apr;118:121-132. doi: 10.1016/j.phrs.2016.05.021. Epub 2016 May 19. (PubMed ID 27210722)\" href=\"#reference-A180400\">3</a></sup></p>','This compound belongs to the class of organic compounds known as glutamic acid and derivatives. These are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.','Glutamic acid and derivatives','<li>Avoid alcohol.</li>\n<li>Avoid milk and dairy products. Milk and dairy products reduce absorption.</li>\n<li>Exercise caution with St. John\'s Wort.</li>\n<li>Limit caffeine intake. Caffeine may reduce the effectiveness of methotrexate.</li>\n<li>Take with or without food.</li>','Drugs.com Drug Page',' , Abortifacient Agents , Abortifacient Agents, Nonsteroidal , Agents Causing Muscle Toxicity , Antimetabolites , Antineoplastic Agents , Antineoplastic and Immunomodulating Agents , Antirheumatic Agents , BCRP/ABCG2 Substrates , Biological Factors , Cancer immunotherapy , Cardiotoxic antineoplastic agents , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 Substrates , Dermatologicals , Drugs causing inadvertant photosensitivity , Drugs that are Mainly Renally Excreted , Enzyme Inhibitors , Folic Acid Analogues , Folic Acid Antagonists , Hepatotoxic Agents , Heterocyclic Compounds, Fused-Ring , Immunologic Factors , Immunosuppressive Agents , Immunotherapy , Myelosuppressive Agents , Narrow Therapeutic Index Drugs , Nephrotoxic agents , Noxae , Nucleic Acid Synthesis Inhibitors , OAT1/SLC22A6 inhibitors , OAT3/SLC22A8 Inhibitors , OAT3/SLC22A8 Substrates , OAT3/SLC22A8 Substrates with a Narrow Therapeutic Index , OATP1B1/SLCO1B1 Substrates , OATP1B3 substrates , P-glycoprotein substrates , P-glycoprotein substrates with a Narrow Therapeutic Index , Photosensitizing Agents , Pigments, Biological , Pteridines , Pterins , Reproductive Control Agents , Toxic Actions','<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>195 °C</td><td>http://www.chemspider.com/Chemical-Structure.112728.html?rid=5b5d388b-5afb-4024-803b-99539fa66a77</td></tr><tr><td>logP</td><td>-1.85</td><td>HANSCH,C ET AL. (1995)</td></tr><tr><td>Caco2 permeability</td><td>-5.92</td><td>ADME Research, USCD</td></tr><tr><td>pKa</td><td>4.7</td><td>SANGSTER (1994)</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">monocarboxylic acid amide, dicarboxylic acid, pteridines (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:44185\" rel=\"noopener\" target=\"_blank\">CHEBI:44185</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/HMDB0014703\" rel=\"noopener\" target=\"_blank\">HMDB0014703</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:D00142\" rel=\"noopener\" target=\"_blank\">D00142</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:C01937\" rel=\"noopener\" target=\"_blank\">C01937</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=126941\" rel=\"noopener\" target=\"_blank\">126941</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=46507678\" rel=\"noopener\" target=\"_blank\">46507678</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.112728.html\" rel=\"noopener\" target=\"_blank\">112728</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=66082\" rel=\"noopener\" target=\"_blank\">66082</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=6851\" rel=\"noopener\" target=\"_blank\">6851</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=44185\" rel=\"noopener\" target=\"_blank\">44185</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/CHEMBL34259\" rel=\"noopener\" target=\"_blank\">CHEMBL34259</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/ZINC000001529323\" rel=\"noopener\" target=\"_blank\">ZINC000001529323</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=DNC000933\" rel=\"noopener\" target=\"_blank\">DNC000933</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/PA450428\" rel=\"noopener\" target=\"_blank\">PA450428</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/MTX\" rel=\"noopener\" target=\"_blank\">MTX</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/mtx.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/methotrexate.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/met1257.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/Methotrexate\" rel=\"noopener\" target=\"_blank\">Methotrexate</a></dd></dl>','<li>Avoid alcohol.</li>\n<li>Avoid milk and dairy products. Milk and dairy products reduce absorption.</li>\n<li>Exercise caution with St. John\'s Wort.</li>\n<li>Limit caffeine intake. Caffeine may reduce the effectiveness of methotrexate.</li>\n<li>Take with or without food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A180322\">Inoue K, Yuasa H: Molecular basis for pharmacokinetics and pharmacodynamics of methotrexate in rheumatoid arthritis therapy. Drug Metab Pharmacokinet. 2014;29(1):12-9. Epub 2013 Nov 26. [<a href=\"/articles/A180322\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180325\">Przekop PR Jr, Tulgan H, Przekop AA, Glantz M: Adverse drug reaction to methotrexate: pharmacogenetic origin. J Am Osteopath Assoc. 2006 Dec;106(12):706-7. [<a href=\"/articles/A180325\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180400\">Muhrez K, Benz-de Bretagne I, Nadal-Desbarats L, Blasco H, Gyan E, Choquet S, Montigny F, Emond P, Barin-Le Guellec C: Endogenous metabolites that are substrates of organic anion transporter\'s (OATs) predict methotrexate clearance. Pharmacol Res. 2017 Apr;118:121-132. doi: 10.1016/j.phrs.2016.05.021. Epub 2016 May 19. [<a href=\"/articles/A180400\" target=\"_blank\">Article</a>] </li><li id=\"reference-L7144\">FDA Approved Drug Products: Methotrexate Oral Solution [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208004s002lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7147\">FDA Approved Drug Products: Methotrexate Subcutaneous Injection [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/205776s002lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7150\">FDA Approved Drug Products: Methotrexate Prefilled Syringe for Subcutaneous Injection [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/204824s009lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7180\">FDA Approved Drug Products: Methotrexate Injection [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/011719s125lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7198\">FDA Approved Drug Products: Methotrexate Sodium Oral Tablets [<a href=\"https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&amp;ApplNo=008085\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7204\">Cayman Chemicals: Methotrexate MSDS [<a href=\"https://www.caymanchem.com/msdss/13960m.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L10457\">FDA Approved Drug Products: RediTrex Methotrexate Subcutaneous Injection [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210737s000lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L38854\">FDA Approved Drug Products: METHOTREXATE injection, for intravenous, intramuscular, subcutaneous, or intrathecal use [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/011719Orig1s131lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>The half life of low dose methotrexate is 3 to 10 hours in adults.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Oral Solution\" href=\"#reference-L7144\">4</a></sup> The half life for high dose methotrexate is 8 to 15 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Subcutaneous Injection\" href=\"#reference-L7147\">5</a></sup> Pediatric patients taking methotrexate for acute lymphoblastic anemia experience a terminal half life of 0.7 to 5.8 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Oral Solution\" href=\"#reference-L7144\">4</a></sup> Pediatric patients taking methotrexate for juvenile idiopathic arthritis experience a half life of 0.9 to 2.3 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Oral Solution\" href=\"#reference-L7144\">4</a></sup></p>','HMDB0014703','(2S)-2-[(4-{[(4-amino-2-imino-2,3-dihydropteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid','InChI=1S/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/t13-/m0/s1','FBOZXECLQNJBKD-ZDUSSCGKSA-N','<p>Methotrexate oral solution is indicated for pediatric acute lymphoblastic leukemia and pediatric polyarticular juvenile idiopathic arthritis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Oral Solution\" href=\"#reference-L7144\">4</a></sup> Methotrexate injections for subcutaneous use are indicated for severe active rheumatoid arthritis, polyarticular juvenile idiopathic arthritis and severe, recalcitrant, disabling psoriasis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Subcutaneous Injection\" href=\"#reference-L7147\">5</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Prefilled Syringe for Subcutaneous Injection\" href=\"#reference-L7150\">6</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: RediTrex Methotrexate Subcutaneous Injection\" href=\"#reference-L10457\">10</a></sup></p><p>Other formulations are indicated to treat gestational choriocarcinoma, chorioadenoma destruens, hydatiform mole, breast cancer, epidermoid cancer of the head and neck, advanced mycosis fungoides, lung cancer, and advanced non-Hodgkin\'s lymphoma.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Injection\" href=\"#reference-L7180\">7</a></sup> It is also used in the maintenance of acute lymphocytic leukemia.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Injection\" href=\"#reference-L7180\">7</a></sup> Methotrexate is also given before treatment with leucovorin to prolong relapse-free survival following surgical removal of a tumour in non-metastatic osteosarcoma.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Injection\" href=\"#reference-L7180\">7</a></sup></p>','C01937','D00142','Organic compounds','<p>Methotrexate is metabolized by folylpolyglutamate synthase to methotrexate polyglutamate in the liver as well as in tissues.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Inoue K, Yuasa H: Molecular basis for pharmacokinetics and pharmacodynamics of methotrexate in rheumatoid arthritis therapy. Drug Metab Pharmacokinet. 2014;29(1):12-9. Epub 2013 Nov 26. (PubMed ID 24284432)\" href=\"#reference-A180322\">1</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Injection\" href=\"#reference-L7180\">7</a></sup> Gamma-glutamyl hydrolase hydrolyzes the glutamyl chains of methotrexate polyglutamates converting them back to methotrexate.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Inoue K, Yuasa H: Molecular basis for pharmacokinetics and pharmacodynamics of methotrexate in rheumatoid arthritis therapy. Drug Metab Pharmacokinet. 2014;29(1):12-9. Epub 2013 Nov 26. (PubMed ID 24284432)\" href=\"#reference-A180322\">1</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Injection\" href=\"#reference-L7180\">7</a></sup> A small amount of methotrexate is also converted to 7-hydroxymethotrexate.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Inoue K, Yuasa H: Molecular basis for pharmacokinetics and pharmacodynamics of methotrexate in rheumatoid arthritis therapy. Drug Metab Pharmacokinet. 2014;29(1):12-9. Epub 2013 Nov 26. (PubMed ID 24284432)\" href=\"#reference-A180322\">1</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Injection\" href=\"#reference-L7180\">7</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteropolycyclic compounds','MTX','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000432?highlight[compounds][]=DB00563&amp;highlight[proteins][]=DB00563\">Methotrexate Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA450428','<p>Methotrexate is 46.5-54% bound to plasma proteins.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Inoue K, Yuasa H: Molecular basis for pharmacokinetics and pharmacodynamics of methotrexate in rheumatoid arthritis therapy. Drug Metab Pharmacokinet. 2014;29(1):12-9. Epub 2013 Nov 26. (PubMed ID 24284432)\" href=\"#reference-A180322\">1</a></sup></p>','126941','46507678','<p>Methotrexate is &gt;80% excreted as the unchanged drug and approximately 3% as the 7-hydroxylated metabolite.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Inoue K, Yuasa H: Molecular basis for pharmacokinetics and pharmacodynamics of methotrexate in rheumatoid arthritis therapy. Drug Metab Pharmacokinet. 2014;29(1):12-9. Epub 2013 Nov 26. (PubMed ID 24284432)\" href=\"#reference-A180322\">1</a></sup> Methotrexate is primarily excreted in the urine with 8.7-26% of an intravenous dose appearing in the bile.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Inoue K, Yuasa H: Molecular basis for pharmacokinetics and pharmacodynamics of methotrexate in rheumatoid arthritis therapy. Drug Metab Pharmacokinet. 2014;29(1):12-9. Epub 2013 Nov 26. (PubMed ID 24284432)\" href=\"#reference-A180322\">1</a></sup></p>','RxList Drug Page','6851','CN(CC1=CN=C2N=C(N)N=C(N)C2=N1)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C(O)=O','Solid','Amino acids, peptides, and analogues','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><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\">Aminobenzamide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminobenzoic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminopyrimidine</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\">Aralkylamine</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\">Benzamide</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\">Benzoic acid or derivatives</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\">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\">Dialkylarylamine</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\">Glutamic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Heteroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hippuric acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hippuric acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</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\">N-acyl-alpha amino acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">N-acyl-alpha-amino acid</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 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\">Primary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pteridine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrazine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrimidine</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 30 more</a>','Organic acids and derivatives','<a href=\"https://www.google.com/?tbm=pts#q=2512572&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US2512572</a>','DNC000933','<p>The oral LD<sub>50</sub> in rats is 135mg/kg and in mice is 146mg/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Cayman Chemicals: Methotrexate MSDS\" href=\"#reference-L7204\">9</a></sup></p><p>Symptoms of overdose include hematologic and gastrointestinal reactions like leukopenia, thombocytopenia, anemia, pancytopenia, bone marrow suppression, mucositis, stomatitis, oral ulceration, nausea, vomiting, gastrointestinal ulceration, and gastrointestinal bleeding.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Injection\" href=\"#reference-L7180\">7</a></sup> In the event of an overdose, patients should be treated with glucarpidase and not be given leucovorin for 2 hours before or after glucarpidase.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Methotrexate Injection\" href=\"#reference-L7180\">7</a></sup></p>','YL5FZ2Y5U1','<p>The volume of distribution of methotrexate at steady state is approximately 1L/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Inoue K, Yuasa H: Molecular basis for pharmacokinetics and pharmacodynamics of methotrexate in rheumatoid arthritis therapy. Drug Metab Pharmacokinet. 2014;29(1):12-9. Epub 2013 Nov 26. (PubMed ID 24284432)\" href=\"#reference-A180322\">1</a></sup></p>','Methotrexate','ZINC000001529323');
INSERT INTO `drugs_drugs` VALUES (39,'Carbamazepine','carbamazepine','Carbamazepine is an anticonvulsant used to treat various types of seizures and pain resulting from trigeminal neuralgia.','Carbatrol, Carnexiv, Epitol, Equetro, Tegretol','Carbamazepine','<p>Carbamazepine, also known as Tegretol, is an anticonvulsant drug and analgesic drug used to control seizures and to treat pain resulting from trigeminal neuralgia. It was initially approved by the FDA in 1965.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Tolou-Ghamari Z, Zare M, Habibabadi JM, Najafi MR: A quick review of carbamazepine pharmacokinetics in epilepsy from 1953 to 2012. J Res Med Sci. 2013 Mar;18(Suppl 1):S81-5. (PubMed ID 23961295)\" href=\"#reference-A180301\">3</a></sup> Aside from the above uses, this drug is also given to control the symptoms of bipolar 1.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup> Interestingly, carbamazepine was the first anticonvulsant used to treat individuals with bipolar disorder.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Chen CH, Lin SK: Carbamazepine treatment of bipolar disorder: a retrospective evaluation of naturalistic long-term outcomes. BMC Psychiatry. 2012 May 23;12:47. doi: 10.1186/1471-244X-12-47. (PubMed ID 22620289)\" href=\"#reference-A180319\">6</a></sup></p>','C15H12N2O','DB00564','Approved, Investigational','Small Molecule','Average: 236.2686 Monoisotopic: 236.094963016 ',' , N03AF — Carboxamide derivatives , N03A — ANTIEPILEPTICS , N03 — ANTIEPILEPTICS , N — NERVOUS SYSTEM','<p>The bioavailability of carbamazepine is in the range of 75-85% of an ingested dose.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Tolou-Ghamari Z, Zare M, Habibabadi JM, Najafi MR: A quick review of carbamazepine pharmacokinetics in epilepsy from 1953 to 2012. J Res Med Sci. 2013 Mar;18(Suppl 1):S81-5. (PubMed ID 23961295)\" href=\"#reference-A180301\">3</a></sup> After one 200 mg oral extended-release dose of carbamazepine in a pharmacokinetic study, the Cmax carbamazepine was measured to be 1.9 ± 0.3 mcg/mL. The Tmax was 19 ± 7 hours. After several doses of 800 mg every 12 hours, the peak concentrations of carbamazepine were measured to be 11.0 ± 2.5 mcg/mL. The Tmax was reduced to 5.9 ± 1.8 hours. Extended-release carbamazepine demonstrated linear pharmacokinetics over a range of 200–800 mg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup> </p><p><strong>Effect of food on absorption</strong></p><p>A meal containing high-fat content increased the rate of absorption of one 400 mg dose but not the AUC of carbamazepine.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup> The elimination half-life remained unchanged between fed and fasting state. The pharmacokinetics of an extended-release carbamazepine dose was demonstrated to be similar when administered in the fasted state or with food.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup> Based on these findings, food intake is unlikely to exert significant effects on carbamazepine absorption.</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 an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000069\" rel=\"noopener\" target=\"_blank\">Azepines</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=\"Compounds containing two amine groups joined by a carbonyl (C=O) functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000517\" rel=\"noopener\" target=\"_blank\">Ureas</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 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 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)DescriptionDetailsHeat shock 70 kDa protein 1-like---(T;T) / (C;T)T alleleADR Directly StudiedPatients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine.DetailsHeat shock 70 kDa protein 1A/1B---(C;G) / (C;C) / (C;T)C allele / C alleleADR Directly StudiedPatients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine.DetailsHLA class I histocompatibility antigen, B-15 alpha chain---(T;T) / (G;T)T alleleADR Directly StudiedPatients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine.DetailsHLA class I histocompatibility antigen, A-31 alpha chain---(G;G) / (C;G)G alleleADR Directly StudiedPatients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine.DetailsPromotilin---(A;A) / (A;C)A alleleADR Directly StudiedPatients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine.DetailsSodium channel protein type 1 subunit alpha---(A;A) / (A;G)IVS5N + 5 G>AEffect Directly StudiedPatients with this genotype have increased resistance to the anti-epileptic effects of carbamazepine.DetailsFlotillin-1HLA-B*1502(G;G) / (C;G)G > C / G > CADR Directly StudiedTaiwanese, Chinese, Indians, and Chinese–American patients with this genotype have increased risk of Stevens-Johnson syndrome or toxic epidermal necrolysis with carbamazepine.DetailsMucin-21HLA-B*1502(G;G) / (A;G)G>A / G>AADR Directly StudiedTaiwanese, Chinese, Indians, and Chinese–American patients with this genotype have increased risk of Stevens-Johnson syndrome or toxic epidermal necrolysis with carbamazepine.DetailsHLA class I histocompatibility antigen, B-15 alpha chainHLA-B*15:02Not AvailableHLA-B*15ADR Directly StudiedPatients who carry this allele may be at an increased risk of Stevens-Johnson Syndrome and toxic epidermal necrolysis when treated with carbamazepine.DetailsHLA class I histocompatibility antigen, A-3 alpha chainHLA-A*3101(T;T) / (A;T)A > TADR Directly StudiedPatients who carry this genotype in HLA-A are at a higher risk of experiencing a hypersensitivity reaction to carbamazepine.Details','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsHeat shock 70 kDa protein 1-like---(T;T) / (C;T)T alleleADR Directly StudiedPatients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine.DetailsHeat shock 70 kDa protein 1A/1B---(C;G) / (C;C) / (C;T)C allele / C alleleADR Directly StudiedPatients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine.DetailsHLA class I histocompatibility antigen, B-15 alpha chain---(T;T) / (G;T)T alleleADR Directly StudiedPatients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine.DetailsHLA class I histocompatibility antigen, A-31 alpha chain---(G;G) / (C;G)G alleleADR Directly StudiedPatients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine.DetailsPromotilin---(A;A) / (A;C)A alleleADR Directly StudiedPatients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine.DetailsSodium channel protein type 1 subunit alpha---(A;A) / (A;G)IVS5N + 5 G>AEffect Directly StudiedPatients with this genotype have increased resistance to the anti-epileptic effects of carbamazepine.DetailsFlotillin-1HLA-B*1502(G;G) / (C;G)G > C / G > CADR Directly StudiedTaiwanese, Chinese, Indians, and Chinese–American patients with this genotype have increased risk of Stevens-Johnson syndrome or toxic epidermal necrolysis with carbamazepine.DetailsMucin-21HLA-B*1502(G;G) / (A;G)G>A / G>AADR Directly StudiedTaiwanese, Chinese, Indians, and Chinese–American patients with this genotype have increased risk of Stevens-Johnson syndrome or toxic epidermal necrolysis with carbamazepine.DetailsHLA class I histocompatibility antigen, B-15 alpha chainHLA-B*15:02Not AvailableHLA-B*15ADR Directly StudiedPatients who carry this allele may be at an increased risk of Stevens-Johnson Syndrome and toxic epidermal necrolysis when treated with carbamazepine.DetailsHLA class I histocompatibility antigen, A-3 alpha chainHLA-A*3101(T;T) / (A;T)A > TADR Directly StudiedPatients who carry this genotype in HLA-A are at a higher risk of experiencing a hypersensitivity reaction to carbamazepine.Details','50003659','298-46-4','3387','CHEMBL108','2457','<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 dibenzazepines. These are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon 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 ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000293\" rel=\"noopener\" target=\"_blank\">Benzazepines</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 with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000320\" rel=\"noopener\" target=\"_blank\">Dibenzazepines</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 with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000320\" rel=\"noopener\" target=\"_blank\">Dibenzazepines</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 an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000069\" rel=\"noopener\" target=\"_blank\">Azepines</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=\"Compounds containing two amine groups joined by a carbonyl (C=O) functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000517\" rel=\"noopener\" target=\"_blank\">Ureas</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 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 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\">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\">Azepine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dibenzazepine</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></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 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\">ureas, dibenzoazepine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3387\" rel=\"noopener\" target=\"_blank\">CHEBI:3387</a>) </span></span></dd></dl>','Benzazepines','<p>In a pharmacokinetic study, the apparent oral clearance of carbamazepine was 25 ± 5 mL/min <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Rawlins MD, Collste P, Bertilsson L, Palmer L: Distribution and elimination kinetics of carbamazepine in man. Eur J Clin Pharmacol. 1975 Feb 28;8(2):91-6. (PubMed ID 1233212)\" href=\"#reference-A180424\">11</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup> after one dose of carbamazepine and 80 ± 30 mL/min after several doses.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup></p>','This compound belongs to the class of organic compounds known as dibenzazepines. These are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.','Dibenzazepines','<li>Avoid alcohol. Ingesting alcohol may increase drowsiness and dizziness.</li>\n<li>Avoid grapefruit products.</li>\n<li>Exercise caution with St. John\'s Wort. This herb induces the CYP3A metabolism of carbamazepine and may reduce its serum concentration.</li>\n<li>Take with or without food.</li>','Drugs.com Drug Page',' , Analgesics , Analgesics, Non-Narcotic , Anticonvulsants , Antimanic Agents , Carboxamide Derivatives , Cardiovascular Agents , Central Nervous System Agents , Central Nervous System Depressants , Cytochrome P-450 CYP1A2 Inducers , Cytochrome P-450 CYP1A2 Inducers (strong) , Cytochrome P-450 CYP1A2 Inhibitors , Cytochrome P-450 CYP1A2 Inhibitors (strength unknown) , Cytochrome P-450 CYP1A2 Substrates , Cytochrome P-450 CYP1A2 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2B6 Inducers , Cytochrome P-450 CYP2B6 Inducers (strong) , Cytochrome P-450 CYP2B6 Substrates , Cytochrome P-450 CYP2B6 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2C19 Inducers , Cytochrome P-450 CYP2C19 Inducers (moderate) , Cytochrome P-450 CYP2C19 Inhibitors , Cytochrome P-450 CYP2C19 inhibitors (strength unknown) , Cytochrome P-450 CYP2C8 Inducers , Cytochrome P-450 CYP2C8 Inducers (strength unknown) , Cytochrome P-450 CYP2C8 Substrates , Cytochrome P-450 CYP2C8 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2C9 Inducers , Cytochrome P-450 CYP2C9 Inducers (strength unknown) , Cytochrome P-450 CYP3A Inducers , Cytochrome P-450 CYP3A Inducers (strong) , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Inducers , Cytochrome P-450 CYP3A4 Inducers (strong) , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP3A5 Inducers , Cytochrome P-450 CYP3A5 Inducers (strength unknown) , Cytochrome P-450 CYP3A5 Inducers (strong) , 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 , Decreased Central Nervous System Disorganized Electrical Activity , Dibenzazepines , Drugs that are Mainly Renally Excreted , Drugs that are Mainly Renally Excreted with a Narrow Therapeutic Index , Enzyme Inducing Antiepileptic Drugs , Heterocyclic Compounds, Fused-Ring , Immunosuppressive Agents , Inducers of Drug Clearance , Membrane Transport Modulators , Miscellaneous Anticonvulsants , Mood Stabilizer , Myelosuppressive Agents , Narrow Therapeutic Index Drugs , P-glycoprotein inducers , P-glycoprotein substrates , Peripheral Nervous System Agents , Psychotropic Drugs , Sensory System Agents , Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome , Sodium Channel Blockers , Thyroxine-binding globulin substrates , UGT1A1 Inducers , UGT1A6 inducer , UGT2B7 substrates , UGT2B7 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>189-192</td><td>https://www.lookchem.com/Carbamazepine/</td></tr><tr><td>boiling point (°C)</td><td>399.6±45.0</td><td>https://www.lookchem.com/Carbamazepine/</td></tr><tr><td>logP</td><td>2.77</td><td>http://www.t3db.ca/toxins/T3D2826</td></tr><tr><td>logS</td><td>-3.2</td><td>http://www.t3db.ca/toxins/T3D2826</td></tr><tr><td>pKa</td><td>15.96, -3.8</td><td>http://www.t3db.ca/toxins/T3D2826</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">ureas, dibenzoazepine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3387\" rel=\"noopener\" target=\"_blank\">CHEBI:3387</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/HMDB0014704\" rel=\"noopener\" target=\"_blank\">HMDB0014704</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:D00252\" rel=\"noopener\" target=\"_blank\">D00252</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:C06868\" rel=\"noopener\" target=\"_blank\">C06868</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=2554\" rel=\"noopener\" target=\"_blank\">2554</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=46507583\" rel=\"noopener\" target=\"_blank\">46507583</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.2457.html\" rel=\"noopener\" target=\"_blank\">2457</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=50003659\" rel=\"noopener\" target=\"_blank\">50003659</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=2002\" rel=\"noopener\" target=\"_blank\">2002</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=3387\" rel=\"noopener\" target=\"_blank\">3387</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/CHEMBL108\" rel=\"noopener\" target=\"_blank\">CHEMBL108</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/ZINC000000004785\" rel=\"noopener\" target=\"_blank\">ZINC000000004785</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=DAP000129\" rel=\"noopener\" target=\"_blank\">DAP000129</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/PA448785\" rel=\"noopener\" target=\"_blank\">PA448785</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/N6W\" rel=\"noopener\" target=\"_blank\">N6W</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/carbam.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/carbamazepine.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/Carbamazepine\" rel=\"noopener\" target=\"_blank\">Carbamazepine</a></dd></dl>','<li>Avoid alcohol. Ingesting alcohol may increase drowsiness and dizziness.</li>\n<li>Avoid grapefruit products.</li>\n<li>Exercise caution with St. John\'s Wort. This herb induces the CYP3A metabolism of carbamazepine and may reduce its serum concentration.</li>\n<li>Take with or without food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A866\">Staines AG, Coughtrie MW, Burchell B: N-glucuronidation of carbamazepine in human tissues is mediated by UGT2B7. J Pharmacol Exp Ther. 2004 Dec;311(3):1131-7. Epub 2004 Aug 3. [<a href=\"/articles/A866\" target=\"_blank\">Article</a>] </li><li id=\"reference-A867\">Sisodiya SM, Goldstein DB: Drug resistance in epilepsy: more twists in the tale. Epilepsia. 2007 Dec;48(12):2369-70. [<a href=\"/articles/A867\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180301\">Tolou-Ghamari Z, Zare M, Habibabadi JM, Najafi MR: A quick review of carbamazepine pharmacokinetics in epilepsy from 1953 to 2012. J Res Med Sci. 2013 Mar;18(Suppl 1):S81-5. [<a href=\"/articles/A180301\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180304\">Marino SE, Birnbaum AK, Leppik IE, Conway JM, Musib LC, Brundage RC, Ramsay RE, Pennell PB, White JR, Gross CR, Rarick JO, Mishra U, Cloyd JC: Steady-state carbamazepine pharmacokinetics following oral and stable-labeled intravenous administration in epilepsy patients: effects of race and sex. Clin Pharmacol Ther. 2012 Mar;91(3):483-8. doi: 10.1038/clpt.2011.251. Epub 2012 Jan 25. [<a href=\"/articles/A180304\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180310\">Ambrosio AF, Soares-Da-Silva P, Carvalho CM, Carvalho AP: Mechanisms of action of carbamazepine and its derivatives, oxcarbazepine, BIA 2-093, and BIA 2-024. Neurochem Res. 2002 Feb;27(1-2):121-30. [<a href=\"/articles/A180310\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180319\">Chen CH, Lin SK: Carbamazepine treatment of bipolar disorder: a retrospective evaluation of naturalistic long-term outcomes. BMC Psychiatry. 2012 May 23;12:47. doi: 10.1186/1471-244X-12-47. [<a href=\"/articles/A180319\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180397\">Johnson DL, Gellman H, Waters RL, Tognella M: Brachioradialis transfer for wrist extension in tetraplegic patients who have fifth-cervical-level neurological function. J Bone Joint Surg Am. 1996 Jul;78(7):1063-7. doi: 10.2106/00004623-199607000-00011. [<a href=\"/articles/A180397\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180403\">Kuo CC, Chen RS, Lu L, Chen RC: Carbamazepine inhibition of neuronal Na+ currents: quantitative distinction from phenytoin and possible therapeutic implications. Mol Pharmacol. 1997 Jun;51(6):1077-83. doi: 10.1124/mol.51.6.1077. [<a href=\"/articles/A180403\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180415\">Barrons R, Roberts N: The role of carbamazepine and oxcarbazepine in alcohol withdrawal syndrome. J Clin Pharm Ther. 2010 Apr;35(2):153-67. doi: 10.1111/j.1365-2710.2009.01098.x. [<a href=\"/articles/A180415\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180421\">Aurora RN, Kristo DA, Bista SR, Rowley JA, Zak RS, Casey KR, Lamm CI, Tracy SL, Rosenberg RS: The treatment of restless legs syndrome and periodic limb movement disorder in adults--an update for 2012: practice parameters with an evidence-based systematic review and meta-analyses: an American Academy of Sleep Medicine Clinical Practice Guideline. Sleep. 2012 Aug 1;35(8):1039-62. doi: 10.5665/sleep.1988. [<a href=\"/articles/A180421\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180424\">Rawlins MD, Collste P, Bertilsson L, Palmer L: Distribution and elimination kinetics of carbamazepine in man. Eur J Clin Pharmacol. 1975 Feb 28;8(2):91-6. [<a href=\"/articles/A180424\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180427\">Yoshimura R, Yanagihara N, Terao T, Minami K, Toyohira Y, Ueno S, Uezono Y, Abe K, Izumi F: An active metabolite of carbamazepine, carbamazepine-10,11-epoxide, inhibits ion channel-mediated catecholamine secretion in cultured bovine adrenal medullary cells. Psychopharmacology (Berl). 1998 Feb;135(4):368-73. [<a href=\"/articles/A180427\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180436\">Thorn CF, Leckband SG, Kelsoe J, Leeder JS, Muller DJ, Klein TE, Altman RB: PharmGKB summary: carbamazepine pathway. Pharmacogenet Genomics. 2011 Dec;21(12):906-10. doi: 10.1097/FPC.0b013e328348c6f2. [<a href=\"/articles/A180436\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180439\">Lv Y, Zheng X, Shi M, Wang Z, Cui L: Different EPHX1 methylation levels in promoter area between carbamazepine-resistant epilepsy group and carbamazepine-sensitive epilepsy group in Chinese population. BMC Neurol. 2019 Jun 4;19(1):114. doi: 10.1186/s12883-019-1308-4. [<a href=\"/articles/A180439\" target=\"_blank\">Article</a>] </li><li id=\"reference-T634\">Jasdave S. Maan; Abdolreza Saadabadi (2019). Carbamazepine. Stat Pearls Publishing. </li><li id=\"reference-L1335\">FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021710s11s012lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7195\">Pharm KGB, carbamazepine pathway, pharmacokinetics [<a href=\"https://www.pharmgkb.org/pathway/PA165817070\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7156\">Carbamazepine MSDS [<a href=\"https://www.caymanchem.com/msdss/15422m.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7216\">ipolar Disorders and Carbamazepine: Pharmacokinetics,Pharmacodynamics, Therapeutic Effects and Indications of Carbamazepine: Review of Articles [<a href=\"https://www.omicsonline.org/open-access/bipolar-disorders-and-carbamazepine-pharmacokineticspharmacodynamics-therapeutic-effects-and-indications-ofcarbamazepine-review-of-2472-095X-1000112.php?aid=79291\" target=\"_blank\">Link</a>] </li><li id=\"reference-L11121\">FDA Approved Drug Products: Tegretol (carbamazepine) [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/016608s115_018281_s058_018927s055_020234_s047.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L38274\">FDA Approved Drug Products: CARNEXIV (carbamazepine) injection [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/206030s002lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9713\">FDA Approved Drug Products: Carbatrol (carbamazepine) extended-release capsules for oral use [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020712s037lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>The mean elimination half-life of carbamazepine was 35 to 40 hours after one dose of carbamazepine extended-release formulations. The half-life ranged from 12-17 hours after several doses of carbamazepine.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup> One pharmacokinetic study determined the elimination half-life of carbamazepine to range between 27 to 36.8 hours in healthy volunteers.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Rawlins MD, Collste P, Bertilsson L, Palmer L: Distribution and elimination kinetics of carbamazepine in man. Eur J Clin Pharmacol. 1975 Feb 28;8(2):91-6. (PubMed ID 1233212)\" href=\"#reference-A180424\">11</a></sup></p>','HMDB0014704','2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide','InChI=1S/C15H12N2O/c16-15(18)17-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)17/h1-10H,(H2,16,18)','FFGPTBGBLSHEPO-UHFFFAOYSA-N','<p>Carbamazepine is indicated for the treatment of epilepsy and pain associated with true trigeminal neuralgia.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup> In particular, carbamazepine has shown efficacy in treating mixed seizures, partial seizures with complex symptoms, and generalized tonic-clonic seizures.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Tolou-Ghamari Z, Zare M, Habibabadi JM, Najafi MR: A quick review of carbamazepine pharmacokinetics in epilepsy from 1953 to 2012. J Res Med Sci. 2013 Mar;18(Suppl 1):S81-5. (PubMed ID 23961295)\" href=\"#reference-A180301\">3</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup> Carbamazepine is also indicated for the treatment of manic episodes and mixed manic-depressive episodes caused by bipolar I disorder.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup> Some off-label, unapproved uses of carbamazepine include the treatment of alcohol withdrawal syndrome and restless leg syndrome.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Barrons R, Roberts N: The role of carbamazepine and oxcarbazepine in alcohol withdrawal syndrome. J Clin Pharm Ther. 2010 Apr;35(2):153-67. doi: 10.1111/j.1365-2710.2009.01098.x. (PubMed ID 20456734)\" href=\"#reference-A180415\">9</a>,<a class=\"reference-popover-link\" data-content=\"Aurora RN, Kristo DA, Bista SR, Rowley JA, Zak RS, Casey KR, Lamm CI, Tracy SL, Rosenberg RS: The treatment of restless legs syndrome and periodic limb movement disorder in adults--an update for 2012: practice parameters with an evidence-based systematic review and meta-analyses: an American Academy of Sleep Medicine Clinical Practice Guideline. Sleep. 2012 Aug 1;35(8):1039-62. doi: 10.5665/sleep.1988. (PubMed ID 22851801)\" href=\"#reference-A180421\">10</a></sup></p>','C06868','D00252','Organic compounds','<p>Carbamazepine is largely metabolized in the liver. CYP3A4 hepatic enzyme is the major enzyme that metabolizes carbamazepine to its active metabolite, carbamazepine-10,11-epoxide<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Yoshimura R, Yanagihara N, Terao T, Minami K, Toyohira Y, Ueno S, Uezono Y, Abe K, Izumi F: An active metabolite of carbamazepine, carbamazepine-10,11-epoxide, inhibits ion channel-mediated catecholamine secretion in cultured bovine adrenal medullary cells. Psychopharmacology (Berl). 1998 Feb;135(4):368-73. (PubMed ID 9539261)\" href=\"#reference-A180427\">12</a></sup>, which is further metabolized to its trans-diol form by the enzyme epoxide hydrolase.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup> Other hepatic cytochrome enzymes that contribute to the metabolism of carbamazepine are CYP2C8, CYP3A5, and CYP2B6.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pharm KGB, carbamazepine pathway, pharmacokinetics\" href=\"#reference-L7195\">17</a></sup> Carbamazepine also undergoes hepatic glucuronidation by UGT2B7 enzyme and several other metabolic reactions occur, resulting in the formation of minor hydroxy metabolites and quinone metabolites.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pharm KGB, carbamazepine pathway, pharmacokinetics\" href=\"#reference-L7195\">17</a></sup> Interestingly, carbamazepine induces its own metabolism.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup> This leads to enhanced clearance, reduced half-life, and a reduction in serum levels of carbamazepine.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Tolou-Ghamari Z, Zare M, Habibabadi JM, Najafi MR: A quick review of carbamazepine pharmacokinetics in epilepsy from 1953 to 2012. J Res Med Sci. 2013 Mar;18(Suppl 1):S81-5. (PubMed ID 23961295)\" href=\"#reference-A180301\">3</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteropolycyclic compounds','N6W','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000634?highlight[compounds][]=DB00564&amp;highlight[proteins][]=DB00564\">Carbamazepine Metabolism Pathway</a></td><td>Drug metabolism</td></tr></tbody>','PA448785','<p>Carbamazepine is 75%-80% bound to plasma proteins.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Tolou-Ghamari Z, Zare M, Habibabadi JM, Najafi MR: A quick review of carbamazepine pharmacokinetics in epilepsy from 1953 to 2012. J Res Med Sci. 2013 Mar;18(Suppl 1):S81-5. (PubMed ID 23961295)\" href=\"#reference-A180301\">3</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup> One pharmacokinetic study indicates that it is 72% bound to plasma proteins.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Rawlins MD, Collste P, Bertilsson L, Palmer L: Distribution and elimination kinetics of carbamazepine in man. Eur J Clin Pharmacol. 1975 Feb 28;8(2):91-6. (PubMed ID 1233212)\" href=\"#reference-A180424\">11</a></sup></p>','2554','46507583','<p>After an oral dose of radiolabeled carbamazepine, 72% of the administered radioactive dose was detected in the urine and the remainder of the ingested dose was found in the feces. Carbamazepine is mainly excreted as hydroxylated and conjugated metabolites, and minimal amounts of unchanged drug.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup></p>','RxList Drug Page','2002','NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C12','Solid','Dibenzazepines','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><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\">Azepine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dibenzazepine</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></span>','Organoheterocyclic compounds','<span class=\"citations\"><p>Ketan Dhansukhlal Vyas, Wajid Sajjad Jafri, Ashok Krishna Kulkarni, \"Process for preparing carbamazepine from iminostilbene.\" U.S. Patent US6245908, issued February, 1998.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=6245908&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US6245908</a>','DAP000129','<p>Toxicity information\nOral LDLO (female): 1920 mg/kg/17W (intermittent); Oral LDLO (male): 54 mg/kg/9D (intermittent)<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Carbamazepine MSDS\" href=\"#reference-L7156\">18</a></sup>\nOral LD50 (rat): 1957 mg/kg <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Carbamazepine MSDS\" href=\"#reference-L7156\">18</a></sup></p><p>Overdose information</p><p>The initial signs of carbamazepine overdose occur 1-3 hours post ingestion. These signs and symptoms may vary in case of an overdose between carbamazepine and other drugs. Carbamazepine may cause various cardiovascular, neurological, respiratory, urinary symptoms as well as laboratory abnormalities including leukocytosis, reduced leucocytes, acetonuria, and glycosuria.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup></p><p>Neuromuscular symptoms may occur initially, followed by mild cardiac symptoms such as tachycardia, hypertension, or hypotension. Higher doses of carbamazepine may cause more severed cardiovascular effects. Restlessness, muscular twitching, tremor, dilated pupils, nystagmus, psychomotor disturbances, and other neurological symptoms may occur. Hyperreflexia in the initial stages of overdose may be followed by hyporeflexia. Nausea, vomiting, urinary retention, dizziness or drowsiness may also occur.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup> In cases of overdose, contact the local poison control center. Ensure to provide supportive and symptomatic treatment, which may include monitoring and careful supervision by a medical professional. The possibility of overdose with multiple drugs must be considered in the case of carbamazepine overdose. Maintain an adequate airway, oxygen, in addition to ventilation. Vital signs should be monitored.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup></p>','33CM23913M','<p>The volume of distribution of carbamazepine was found to be 1.0 L/kg in one pharmacokinetic study.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Marino SE, Birnbaum AK, Leppik IE, Conway JM, Musib LC, Brundage RC, Ramsay RE, Pennell PB, White JR, Gross CR, Rarick JO, Mishra U, Cloyd JC: Steady-state carbamazepine pharmacokinetics following oral and stable-labeled intravenous administration in epilepsy patients: effects of race and sex. Clin Pharmacol Ther. 2012 Mar;91(3):483-8. doi: 10.1038/clpt.2011.251. Epub 2012 Jan 25. (PubMed ID 22278332)\" href=\"#reference-A180304\">4</a></sup> Another study indicates that the volume of distribution of carbamazepine ranges between 0.7 to 1.4 L/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Rawlins MD, Collste P, Bertilsson L, Palmer L: Distribution and elimination kinetics of carbamazepine in man. Eur J Clin Pharmacol. 1975 Feb 28;8(2):91-6. (PubMed ID 1233212)\" href=\"#reference-A180424\">11</a></sup>. Carbamazepine crosses the placenta, and higher concentrations of this drug are found in the liver and kidney as opposed to lung and brain tissue.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules\" href=\"#reference-L1335\">16</a></sup> Carbamazepine crosses variably through the blood-brain barrier.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Thorn CF, Leckband SG, Kelsoe J, Leeder JS, Muller DJ, Klein TE, Altman RB: PharmGKB summary: carbamazepine pathway. Pharmacogenet Genomics. 2011 Dec;21(12):906-10. doi: 10.1097/FPC.0b013e328348c6f2. (PubMed ID 21738081)\" href=\"#reference-A180436\">13</a></sup></p>','Carbamazepine','ZINC000000004785'),(40,'Diclofenac','diclofenac','Diclofenac is an NSAID used to treat the signs and symptoms of osteoarthritis and rheumatoid arthritis.','Arthrotec, Cambia, Cataflam, Flector, Licart, Lofena, Pennsaid, Previdolrx Analgesic Pak, Salonpas Pain Relieving Patch, Solaraze, Voltaren, Voltaren Emulgel, Xrylix, Zipsor, Zorvolex','Diclofenac','<p>Diclofenac is a phenylacetic acid derivative and non-steroidal anti-inflammatory drug (NSAID).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup> NSAIDs inhibit cyclooxygenase (COX)-1 and-2 which are the enzyme responsible for producing prostaglandins (PGs). PGs contribute to inflammation and pain signalling. Diclofenac, like other NSAIDs, is often used as first line therapy for acute and chronic pain and inflammation from a variety of causes. Diclofenac was the product of rational drug design based on the structures of <a href=\"https://go.drugbank.com/drugs/DB00812\">phenylbutazone</a>, <a href=\"https://go.drugbank.com/drugs/DB00784\">mefenamic acid</a>, and <a href=\"https://go.drugbank.com/drugs/DB00328\">indomethacin</a>.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sallmann AR: The history of diclofenac. Am. J. Med. 1986 Apr 28;80(4):29-33.\" href=\"#reference-A180796\">12</a></sup> The addition of two chlorine groups in the ortho position of the phenyl ring locks the ring in maximal torsion which appears to be related to increased potency. It is often used in combination with <a href=\"https://go.drugbank.com/drugs/DB00929\">misoprostol</a> to prevent NSAID-induced gastric ulcers. Diclofenac was first approved by the FDA in July 1988 under the trade name Voltaren, marketed by Novartis (previously Ciba-Geigy).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Drugs@FDA: Voltaren Delayed Release\" href=\"#reference-L7360\">18</a></sup></p>','C14H11Cl2NO2','DB00586','Approved, Vet approved','Small Molecule','Average: 296.149 Monoisotopic: 295.016684015 ',' , S01CC — Antiinflammatory agents, non-steroids and antiinfectives in combination , S01C — ANTIINFLAMMATORY AGENTS AND ANTIINFECTIVES IN COMBINATION , S01 — OPHTHALMOLOGICALS , S — SENSORY ORGANS , S01BC — Antiinflammatory agents, non-steroids , S01B — ANTIINFLAMMATORY AGENTS , S01 — OPHTHALMOLOGICALS , S — SENSORY ORGANS , M01AB — Acetic acid derivatives and related substances , M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS , M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS , M — MUSCULO-SKELETAL SYSTEM , 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 , M01AB — Acetic acid derivatives and related substances , M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS , M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS , M — MUSCULO-SKELETAL SYSTEM , D11AX — Other dermatologicals , D11A — OTHER DERMATOLOGICAL PREPARATIONS , D11 — OTHER DERMATOLOGICAL PREPARATIONS , D — DERMATOLOGICALS','<p>Diclofenac is completely absorbed from the GI tract but likely undergoes significant first pass metabolism with only 60% of the drug reaching systemic circulation unchanged <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=\"Davies NM, Anderson KE: Clinical pharmacokinetics of diclofenac. Therapeutic insights and pitfalls. Clin Pharmacokinet. 1997 Sep;33(3):184-213. doi: 10.2165/00003088-199733030-00003. (PubMed ID 9314611)\" href=\"#reference-A178633\">7</a>,<a class=\"reference-popover-link\" data-content=\"Todd PA, Sorkin EM: Diclofenac sodium. A reappraisal of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1988 Mar;35(3):244-85. doi: 10.2165/00003495-198835030-00004. (PubMed ID 3286213)\" href=\"#reference-A180694\">8</a></sup>. Many topical formulations are absorbed percutaneous and produce clinically significant plasma concentrations. Absorption is dose proportional over the range of 25-150 mg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Davies NM, Anderson KE: Clinical pharmacokinetics of diclofenac. Therapeutic insights and pitfalls. Clin Pharmacokinet. 1997 Sep;33(3):184-213. doi: 10.2165/00003088-199733030-00003. (PubMed ID 9314611)\" href=\"#reference-A178633\">7</a></sup> Tmax varies between formulations with the oral solution reaching peak plasma concentrations in 10-40min, the enteric coated tablet in 1.5-2h, and the sustained- and extended-release formulations prolonging Tmax even further. Administration with food has no significant effects on AUC but does delay Tmax to 2.5-12h.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Davies NM, Anderson KE: Clinical pharmacokinetics of diclofenac. Therapeutic insights and pitfalls. Clin Pharmacokinet. 1997 Sep;33(3):184-213. doi: 10.2165/00003088-199733030-00003. (PubMed ID 9314611)\" href=\"#reference-A178633\">7</a>,<a class=\"reference-popover-link\" data-content=\"Todd PA, Sorkin EM: Diclofenac sodium. A reappraisal of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1988 Mar;35(3):244-85. doi: 10.2165/00003495-198835030-00004. (PubMed ID 3286213)\" href=\"#reference-A180694\">8</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 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 the acyl chloride functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001030\" rel=\"noopener\" target=\"_blank\">Aryl chlorides</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=\"Amines having the nitrogen atom linked to exactly two hydrocarbyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002451\" rel=\"noopener\" target=\"_blank\">Secondary amines</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=\"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=\"Compounds containing a chemical bond between a carbon atom and a chlorine atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001516\" rel=\"noopener\" target=\"_blank\">Organochlorides</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 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 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 1 more</a>','Not Available','Not Available','13066','15307-86-5','47381','CHEMBL139','2925','<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 dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.</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=\"Aromatic compounds containing a halogen atom linked to a benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000035\" rel=\"noopener\" target=\"_blank\">Halobenzenes</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 benzene with exactly two chlorine atoms attached to it.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002564\" rel=\"noopener\" target=\"_blank\">Dichlorobenzenes</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 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 the acyl chloride functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001030\" rel=\"noopener\" target=\"_blank\">Aryl chlorides</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=\"Amines having the nitrogen atom linked to exactly two hydrocarbyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002451\" rel=\"noopener\" target=\"_blank\">Secondary amines</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=\"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=\"Compounds containing a chemical bond between a carbon atom and a chlorine atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001516\" rel=\"noopener\" target=\"_blank\">Organochlorides</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 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 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 1 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\">1,3-dichlorobenzene</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 homomonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl chloride</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl halide</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></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\">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\">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\">Organochloride</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organohalogen 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\">Secondary 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 12 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 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\">monocarboxylic acid, secondary amino compound, dichlorobenzene, aromatic amine, amino acid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:47381\" rel=\"noopener\" target=\"_blank\">CHEBI:47381</a>) </span></span></dd></dl>','Benzene and substituted derivatives','<p>Diclofenac has a plasma clearance 16 L/h.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Todd PA, Sorkin EM: Diclofenac sodium. A reappraisal of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1988 Mar;35(3):244-85. doi: 10.2165/00003495-198835030-00004. (PubMed ID 3286213)\" href=\"#reference-A180694\">8</a></sup></p>','This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.','Dichlorobenzenes','<li>Avoid excessive or chronic alcohol consumption. Co-administration with alcohol may increase the risk of gastrointestinal side effects, such as ulceration.</li>\n<li>Take with food. Food reduces gastric irritation.</li>','Drugs.com Drug Page',' , Acetic Acid Derivatives and Related Substances , Acids, Carbocyclic , Agents causing angioedema , Agents causing hyperkalemia , Agents that produce hypertension , Amines , 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 , Antiinflammatory Preparations, Non-Steroids for Topical Use , Antimigraine Agents, Miscellaneous , Antirheumatic Agents , BSEP/ABCB11 Substrates , Central Nervous System Agents , Cyclooxygenase Inhibitors , Cyclooxygenase-2 (COX-2) Inhibitors , Cytochrome P-450 CYP1A2 Substrates , Cytochrome P-450 CYP2B6 Substrates , Cytochrome P-450 CYP2C18 Substrates , Cytochrome P-450 CYP2C19 Substrates , Cytochrome P-450 CYP2C8 Substrates , Cytochrome P-450 CYP2C9 Substrates , Cytochrome P-450 CYP2E1 Inhibitors , Cytochrome P-450 CYP2E1 Inhibitors (strength unknown) , 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 , Decreased Prostaglandin Production , Dermatologicals , Drugs causing inadvertant photosensitivity , Enzyme Inhibitors , Ethylamines , Musculo-Skeletal System , Nephrotoxic agents , Non COX-2 selective NSAIDS , OAT1/SLC22A6 inhibitors , OAT3/SLC22A8 Inhibitors , OATP1B1/SLCO1B1 Inhibitors , Ophthalmologicals , Other Nonsteroidal Anti-inflammatory Agents , P-glycoprotein inducers , Peripheral Nervous System Agents , Phenylacetates , Photosensitizing Agents , Sensory Organs , Sensory System Agents , Topical Products for Joint and Muscular Pain , UDP Glucuronosyltransferases Inhibitors , UGT1A1 Substrates , UGT1A3 substrates , UGT1A9 Substrates , UGT2B17 Inhibitors , 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>283-285 °C</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>water solubility</td><td>2.37 mg/L (at 25 °C)</td><td>FINI,A ET AL. (1986)</td></tr><tr><td>logP</td><td>4.51</td><td>AVDEEF,A (1997)</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, secondary amino compound, dichlorobenzene, aromatic amine, amino acid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:47381\" rel=\"noopener\" target=\"_blank\">CHEBI:47381</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/HMDB0014724\" rel=\"noopener\" target=\"_blank\">HMDB0014724</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:D07816\" rel=\"noopener\" target=\"_blank\">D07816</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:C01690\" rel=\"noopener\" target=\"_blank\">C01690</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=3033\" rel=\"noopener\" target=\"_blank\">3033</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=46504644\" rel=\"noopener\" target=\"_blank\">46504644</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.2925.html\" rel=\"noopener\" target=\"_blank\">2925</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=13066\" rel=\"noopener\" target=\"_blank\">13066</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=3355\" rel=\"noopener\" target=\"_blank\">3355</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=47381\" rel=\"noopener\" target=\"_blank\">47381</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/CHEMBL139\" rel=\"noopener\" target=\"_blank\">CHEMBL139</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/ZINC000000001281\" rel=\"noopener\" target=\"_blank\">ZINC000000001281</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=DAP000620\" rel=\"noopener\" target=\"_blank\">DAP000620</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/PA449293\" rel=\"noopener\" target=\"_blank\">PA449293</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=2714\" 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/DIF\" rel=\"noopener\" target=\"_blank\">DIF</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/diclofen.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/diclofenac-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/Diclofenac\" rel=\"noopener\" target=\"_blank\">Diclofenac</a></dd></dl>','<li>Avoid excessive or chronic alcohol consumption. Co-administration with alcohol may increase the risk of gastrointestinal side effects, such as ulceration.</li>\n<li>Take with food. Food reduces gastric 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-A913\">Solomon DH, Avorn J, Sturmer T, Glynn RJ, Mogun H, Schneeweiss S: Cardiovascular outcomes in new users of coxibs and nonsteroidal antiinflammatory drugs: high-risk subgroups and time course of risk. Arthritis Rheum. 2006 May;54(5):1378-89. [<a href=\"/articles/A913\" target=\"_blank\">Article</a>] </li><li id=\"reference-A914\">FitzGerald GA, Patrono C: The coxibs, selective inhibitors of cyclooxygenase-2. N Engl J Med. 2001 Aug 9;345(6):433-42. [<a href=\"/articles/A914\" target=\"_blank\">Article</a>] </li><li id=\"reference-A915\">Graham DJ: COX-2 inhibitors, other NSAIDs, and cardiovascular risk: the seduction of common sense. JAMA. 2006 Oct 4;296(13):1653-6. Epub 2006 Sep 12. [<a href=\"/articles/A915\" target=\"_blank\">Article</a>] </li><li id=\"reference-A916\">Brater DC: Renal effects of cyclooxygyenase-2-selective inhibitors. J Pain Symptom Manage. 2002 Apr;23(4 Suppl):S15-20; discussion S21-3. [<a href=\"/articles/A916\" target=\"_blank\">Article</a>] </li><li id=\"reference-A917\">Gan TJ: Diclofenac: an update on its mechanism of action and safety profile. Curr Med Res Opin. 2010 Jul;26(7):1715-31. doi: 10.1185/03007995.2010.486301. [<a href=\"/articles/A917\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178633\">Davies NM, Anderson KE: Clinical pharmacokinetics of diclofenac. Therapeutic insights and pitfalls. Clin Pharmacokinet. 1997 Sep;33(3):184-213. doi: 10.2165/00003088-199733030-00003. [<a href=\"/articles/A178633\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180694\">Todd PA, Sorkin EM: Diclofenac sodium. A reappraisal of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1988 Mar;35(3):244-85. doi: 10.2165/00003495-198835030-00004. [<a href=\"/articles/A180694\" target=\"_blank\">Article</a>] </li><li id=\"reference-A31847\">Kuehl GE, Lampe JW, Potter JD, Bigler J: Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab Dispos. 2005 Jul;33(7):1027-35. doi: 10.1124/dmd.104.002527. Epub 2005 Apr 20. [<a href=\"/articles/A31847\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179023\">Chen L, Yang G, Grosser T: Prostanoids and inflammatory pain. Prostaglandins Other Lipid Mediat. 2013 Jul-Aug;104-105:58-66. doi: 10.1016/j.prostaglandins.2012.08.006. Epub 2012 Sep 3. [<a href=\"/articles/A179023\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179044\">Hirata T, Narumiya S: Prostanoids as regulators of innate and adaptive immunity. Adv Immunol. 2012;116:143-74. doi: 10.1016/B978-0-12-394300-2.00005-3. [<a href=\"/articles/A179044\" target=\"_blank\">Article</a>] </li><li id=\"reference-A180796\">Sallmann AR: The history of diclofenac. Am. J. Med. 1986 Apr 28;80(4):29-33. [<a href=\"/articles/A180796\" target=\"_blank\">Article</a>] </li><li id=\"reference-A31196\">Bort R, Mace K, Boobis A, Gomez-Lechon MJ, Pfeifer A, Castell J: Hepatic metabolism of diclofenac: role of human CYP in the minor oxidative pathways. Biochem Pharmacol. 1999 Sep 1;58(5):787-96. [<a href=\"/articles/A31196\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181015\">Yan Z, Li J, Huebert N, Caldwell GW, Du Y, Zhong H: Detection of a novel reactive metabolite of diclofenac: evidence for CYP2C9-mediated bioactivation via arene oxides. Drug Metab Dispos. 2005 Jun;33(6):706-13. doi: 10.1124/dmd.104.003095. Epub 2005 Mar 11. [<a href=\"/articles/A181015\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181018\">Boerma JS, Vermeulen NP, Commandeur JN: One-electron oxidation of diclofenac by human cytochrome P450s as a potential bioactivation mechanism for formation of 2\'-(glutathion-S-yl)-deschloro-diclofenac. Chem Biol Interact. 2014 Jan 25;207:32-40. doi: 10.1016/j.cbi.2013.11.001. Epub 2013 Nov 15. [<a href=\"/articles/A181018\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181021\">Kamimura H, Ito S, Nozawa K, Nakamura S, Chijiwa H, Nagatsuka S, Kuronuma M, Ohnishi Y, Suemizu H, Ninomiya S: Formation of the accumulative human metabolite and human-specific glutathione conjugate of diclofenac in TK-NOG chimeric mice with humanized livers. Drug Metab Dispos. 2015 Mar;43(3):309-16. doi: 10.1124/dmd.114.061689. Epub 2014 Dec 11. [<a href=\"/articles/A181021\" target=\"_blank\">Article</a>] </li><li id=\"reference-T116\">Brunton LL, Hilal-Dandan R, Knollmann BC. eds (2018). Goodman &amp; Gilman\'s: The Pharmacological Basis of Therapeutics (13th ed.). McGraw-Hill Education. [<a href=\"https://www.google.com/search?tbo=p&amp;tbm=bks&amp;q=978-1-25-958473-2\" rel=\"noopener\" target=\"_blank\">ISBN:978-1-25-958473-2</a>] </li><li id=\"reference-L7360\">Drugs@FDA: Voltaren Delayed Release [<a href=\"https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&amp;ApplNo=019201\" target=\"_blank\">Link</a>] </li><li id=\"reference-L12693\">Health Canada Product Monograph: Diclofenac oral tablets [<a href=\"https://pdf.hres.ca/dpd_pm/00054964.PDF\" target=\"_blank\">Link</a>] </li></ol>','<p>The terminal half-life of diclofenac is approximately 2 h, however the apparent half-life including all metabolites is 25.8-33 h.<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=\"Todd PA, Sorkin EM: Diclofenac sodium. A reappraisal of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1988 Mar;35(3):244-85. doi: 10.2165/00003495-198835030-00004. (PubMed ID 3286213)\" href=\"#reference-A180694\">8</a></sup></p>','HMDB0014724','2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid','InChI=1S/C14H11Cl2NO2/c15-10-5-3-6-11(16)14(10)17-12-7-2-1-4-9(12)8-13(18)19/h1-7,17H,8H2,(H,18,19)','DCOPUUMXTXDBNB-UHFFFAOYSA-N','<p>Diclofenac is indicated for use in the treatment of pain and inflammation from varying sources including inflammatory conditions such as osteoarthritis, rheumatoid arthritis, and akylosing spondylitis, as well as injury-related inflammation due to surgery and physical trauma. It is often used in combination with <a href=\"https://go.drugbank.com/drugs/DB00929\">misoprostol</a> as a gastro-protective agent in patients with high risk of developing NSAID-induced ulcers.</p>','C01690','D07816','Organic compounds','<p>Diclofenac undergoes oxidative metabolism to hydroxy metabolites as well as conjugation to glucuronic acid, sulfate, and taurine.<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=\"Davies NM, Anderson KE: Clinical pharmacokinetics of diclofenac. Therapeutic insights and pitfalls. Clin Pharmacokinet. 1997 Sep;33(3):184-213. doi: 10.2165/00003088-199733030-00003. (PubMed ID 9314611)\" href=\"#reference-A178633\">7</a></sup> The primary metabolite is 4\'-hydroxy diclofenac which is generated by CYP2C9. This metabolite is very weakly active with one thirtieth the activity of diclofenac. Other metabolites include 3\'-hydroxy diclofenac, 3\'-hydroxy-4\'methoxy diclofenac, 4\',5-dihydroxy diclofenac, an acylglucuronide conjugate, and other conjugate metabolites.</p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic homomonocyclic compounds','DIF','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000093?highlight[compounds][]=DB00586&amp;highlight[proteins][]=DB00586\">Diclofenac Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA449293','<p>Diclofenac is over 99.7% bound to serum proteins, primarily albumin.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Davies NM, Anderson KE: Clinical pharmacokinetics of diclofenac. Therapeutic insights and pitfalls. Clin Pharmacokinet. 1997 Sep;33(3):184-213. doi: 10.2165/00003088-199733030-00003. (PubMed ID 9314611)\" href=\"#reference-A178633\">7</a></sup> It is undergoes limited binding to lipoproteins as well with 1.1% bound to HDL, 0.3% to LDL, and 0.15% to VLDL.</p>','3033','46504644','<p>Diclofenac is mainly eliminated via metabolism.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Davies NM, Anderson KE: Clinical pharmacokinetics of diclofenac. Therapeutic insights and pitfalls. Clin Pharmacokinet. 1997 Sep;33(3):184-213. doi: 10.2165/00003088-199733030-00003. (PubMed ID 9314611)\" href=\"#reference-A178633\">7</a>,<a class=\"reference-popover-link\" data-content=\"Todd PA, Sorkin EM: Diclofenac sodium. A reappraisal of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1988 Mar;35(3):244-85. doi: 10.2165/00003495-198835030-00004. (PubMed ID 3286213)\" href=\"#reference-A180694\">8</a></sup> Of the total dose, 60-70% is eliminated in the urine and 30% is eliminated in the feces. No significant enterohepatic recycling occurs.</p>','RxList Drug Page','3355','OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl','Solid','Halobenzenes','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1,3-dichlorobenzene</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 homomonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl chloride</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl halide</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></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\">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\">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\">Organochloride</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organohalogen 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\">Secondary 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 12 more</a>','Benzenoids','<span class=\"citations\"><p>Takuzo Kamishita, \"Gel preparations for topical application of diclofenac sodium.\" U.S. Patent US4670254, issued October, 1983.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=4670254&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US4670254</a>','DAP000620','<p>Symptoms of overdose include lethargy, drowsiness, nausea, vomiting, and epigastric pain, and gastrointestinal bleeding.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup> Hypertension, acute renal failure, respiratory depression and coma occur rarely. In case of overdose, provide supportive care and consider inducing emesis and administering activated charcoal if overdose occurred less than 4 hours prior.</p>','144O8QL0L1','<p>Diclofenac has a total volume of distribution of 5-10 L or 0.1-0.2 L/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Davies NM, Anderson KE: Clinical pharmacokinetics of diclofenac. Therapeutic insights and pitfalls. Clin Pharmacokinet. 1997 Sep;33(3):184-213. doi: 10.2165/00003088-199733030-00003. (PubMed ID 9314611)\" href=\"#reference-A178633\">7</a></sup> The volume of the central compartment is 0.04 L/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Todd PA, Sorkin EM: Diclofenac sodium. A reappraisal of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1988 Mar;35(3):244-85. doi: 10.2165/00003495-198835030-00004. (PubMed ID 3286213)\" href=\"#reference-A180694\">8</a></sup> Diclofenac distributes to the synovial fluid reaching peak concentration 2-4h after administration.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Davies NM, Anderson KE: Clinical pharmacokinetics of diclofenac. Therapeutic insights and pitfalls. Clin Pharmacokinet. 1997 Sep;33(3):184-213. doi: 10.2165/00003088-199733030-00003. (PubMed ID 9314611)\" href=\"#reference-A178633\">7</a></sup> There is limited crossing of the blood brain barrier and cerebrospinal fluid concentrations only reach 8.22% of plasma concentrations. Doses of 50 mg delivered via intramuscular injection produced no detectable diclofenac concentrations in breast milk, however metabolite concentrations were not investigated. Diclofenac has been shown to cross the placenta in mice and rats but human data is unavailable.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Todd PA, Sorkin EM: Diclofenac sodium. A reappraisal of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs. 1988 Mar;35(3):244-85. doi: 10.2165/00003495-198835030-00004. (PubMed ID 3286213)\" href=\"#reference-A180694\">8</a></sup></p>','Diclofenac','ZINC000000001281'),(41,'Amiloride','amiloride','Amiloride is a pyrizine compound used to treat hypertension and congestive heart failure.','Midamor','Amiloride','<p>A pyrazine compound inhibiting sodium reabsorption through sodium channels in renal epithelial cells. This inhibition creates a negative potential in the luminal membranes of principal cells, located in the distal convoluted tubule and collecting duct. Negative potential reduces secretion of potassium and hydrogen ions. Amiloride is used in conjunction with diuretics to spare potassium loss. (From Gilman et al., Goodman and Gilman\'s The Pharmacological Basis of Therapeutics, 9th ed, p705)</p>','C6H8ClN7O','DB00594','Approved','Small Molecule','Average: 229.627 Monoisotopic: 229.04788562 ',' , C03DB — Other potassium-sparing agents , C03D — POTASSIUM-SPARING AGENTS , C03 — DIURETICS , C — CARDIOVASCULAR SYSTEM','<p>Readily absorbed following oral administration.</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=\"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=\"Organic compounds containing the acyl chloride functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001030\" rel=\"noopener\" target=\"_blank\">Aryl chlorides</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 1,3-dipolar compounds with the general structure  X#N+-Z- &lt;-&gt; X-=N+=Z &lt;-&gt; X-=N-Z+ &lt;-&gt; X-N=Z (X = C or O, Z = C, N, or O).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003633\" rel=\"noopener\" target=\"_blank\">Propargyl-type 1,3-dipolar organic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organonitrogen compounds with the general formula RN=CN(R\')(R\'\'), (R,R\',R\'\' = H or organyl group).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003152\" rel=\"noopener\" target=\"_blank\">Carboximidamides</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=\"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=\"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 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=\"Compounds containing a chemical bond between a carbon atom and a chlorine atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001516\" rel=\"noopener\" target=\"_blank\">Organochlorides</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 an imine functional group, with the general structure RN=CR2 (R = H, hydrocarbyl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000117\" rel=\"noopener\" target=\"_blank\">Imines</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 2 more</a>','Not Available','Not Available','16173','2609-46-3','2639','CHEMBL945','15403','<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 aminopyrazines. These are organic compounds containing an amino group attached to a pyrazine ring.</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 five-member heterocyclic compound with five nitrogen atoms, and two nitrogen atoms at positions 1 and 2 (Pyridazines), 1 and 3 (Pyrimidines), or 1 and 4 (Pyrazines).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001346\" rel=\"noopener\" target=\"_blank\">Diazines</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 pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000067\" rel=\"noopener\" target=\"_blank\">Pyrazines</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 an amino group attached to a pyrazine ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001694\" rel=\"noopener\" target=\"_blank\">Aminopyrazines</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=\"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=\"Organic compounds containing the acyl chloride functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001030\" rel=\"noopener\" target=\"_blank\">Aryl chlorides</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 1,3-dipolar compounds with the general structure  X#N+-Z- &lt;-&gt; X-=N+=Z &lt;-&gt; X-=N-Z+ &lt;-&gt; X-N=Z (X = C or O, Z = C, N, or O).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003633\" rel=\"noopener\" target=\"_blank\">Propargyl-type 1,3-dipolar organic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organonitrogen compounds with the general formula RN=CN(R\')(R\'\'), (R,R\',R\'\' = H or organyl group).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003152\" rel=\"noopener\" target=\"_blank\">Carboximidamides</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=\"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=\"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 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=\"Compounds containing a chemical bond between a carbon atom and a chlorine atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001516\" rel=\"noopener\" target=\"_blank\">Organochlorides</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 an imine functional group, with the general structure RN=CR2 (R = H, hydrocarbyl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000117\" rel=\"noopener\" target=\"_blank\">Imines</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 2 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\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminopyrazine</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 chloride</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\">Carboximidamide</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\">Imidolactam</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\">Imine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic 1,3-dipolar compound</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\">Organochloride</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organohalogen 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\">Primary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Propargyl-type 1,3-dipolar organic compound</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 11 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\">pyrazines, monocarboxylic acid amide, organochlorine compound, guanidines, aromatic amine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2639\" rel=\"noopener\" target=\"_blank\">CHEBI:2639</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">a small molecule (<a href=\"http://metacyc.org/META/new-image?type=COMPOUND&amp;object=CPD-10324\" rel=\"noopener\" target=\"_blank\">CPD-10324</a>) </span></span></dd></dl>','Diazines','<p><span class=\"not-available\">Not Available</span></p>','This compound belongs to the class of organic compounds known as aminopyrazines. These are organic compounds containing an amino group attached to a pyrazine ring.','Aminopyrazines','<li>Avoid drastic dietary changes.</li>\n<li>Avoid natural licorice.</li>\n<li>Avoid potassium-containing products.</li>\n<li>Take with food. Food reduces irritation.</li>','Drugs.com Drug Page',' , Acid Sensing Ion Channel Blockers , Agents causing hyperkalemia , Cardiovascular Agents , Decreased Renal K+ Excretion , Diuretics , Epithelial Sodium Channel Blockers , Hypotensive Agents , Increased Diuresis , Membrane Transport Modulators , Natriuretic Agents , OCT2 Inhibitors , Potassium-Sparing Diuretics , Pyrazines , 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>240.5-241.5</td><td>Cragoe, E.J., Jr.; US. Patent 3,313,813; April 11,1967; assigned to Merck 81 Co., Inc.</td></tr><tr><td>water solubility</td><td>Slightly soluble</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>logP</td><td>-0.3</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>pKa</td><td>8.7</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\">pyrazines, monocarboxylic acid amide, organochlorine compound, guanidines, aromatic amine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2639\" rel=\"noopener\" target=\"_blank\">CHEBI:2639</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">a small molecule (<a href=\"http://metacyc.org/META/new-image?type=COMPOUND&amp;object=CPD-10324\" rel=\"noopener\" target=\"_blank\">CPD-10324</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/HMDB0014732\" rel=\"noopener\" target=\"_blank\">HMDB0014732</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:D07447\" rel=\"noopener\" target=\"_blank\">D07447</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:C06821\" rel=\"noopener\" target=\"_blank\">C06821</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=16231\" rel=\"noopener\" target=\"_blank\">16231</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=46508156\" rel=\"noopener\" target=\"_blank\">46508156</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.15403.html\" rel=\"noopener\" target=\"_blank\">15403</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=16173\" rel=\"noopener\" target=\"_blank\">16173</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=644\" rel=\"noopener\" target=\"_blank\">644</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=2639\" rel=\"noopener\" target=\"_blank\">2639</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/CHEMBL945\" rel=\"noopener\" target=\"_blank\">CHEMBL945</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/ZINC000004340269\" rel=\"noopener\" target=\"_blank\">ZINC000004340269</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=DAP000187\" rel=\"noopener\" target=\"_blank\">DAP000187</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/PA448368\" rel=\"noopener\" target=\"_blank\">PA448368</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=2421\" 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/AMR\" rel=\"noopener\" target=\"_blank\">AMR</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/amilor.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/amiloride.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/mod1272.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/Amiloride\" rel=\"noopener\" target=\"_blank\">Amiloride</a></dd></dl>','<li>Avoid drastic dietary changes.</li>\n<li>Avoid natural licorice.</li>\n<li>Avoid potassium-containing products.</li>\n<li>Take with food. Food reduces irritation.</li>','<span class=\"not-available\">Not Available</span>','<p>Plasma half-life varies from 6 to 9 hours.</p>','HMDB0014732','3,5-diamino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide','InChI=1S/C6H8ClN7O/c7-2-4(9)13-3(8)1(12-2)5(15)14-6(10)11/h(H4,8,9,13)(H4,10,11,14,15)','XSDQTOBWRPYKKA-UHFFFAOYSA-N','<p>For use as adjunctive treatment with thiazide diuretics or other kaliuretic-diuretic agents in congestive heart failure or hypertension.</p>','C06821','D07447','Organic compounds','<p>Amiloride is not metabolized by the liver but is excreted unchanged by the kidneys.</p>','Aromatic heteromonocyclic compounds','AMR','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000133?highlight[compounds][]=DB00594&amp;highlight[proteins][]=DB00594\">Amiloride Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA448368','<p><span class=\"not-available\">Not Available</span></p>','16231','46508156','<p>Amiloride HCl is not metabolized by the liver but is excreted unchanged by the kidneys. About 50 percent of a 20 mg dose of amiloride HCl is excreted in the urine and 40 percent in the stool within 72 hours.</p>','RxList Drug Page','644','NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N','Solid','Pyrazines','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminopyrazine</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 chloride</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\">Carboximidamide</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\">Imidolactam</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\">Imine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic 1,3-dipolar compound</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\">Organochloride</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organohalogen 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\">Primary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Propargyl-type 1,3-dipolar organic compound</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 11 more</a>','Organoheterocyclic compounds','<span class=\"citations\"><p>Cragoe, E.J., Jr.; US. Patent 3,313,813; April 11,1967; assigned to Merck 81 Co., Inc.</p>\n</span>','DAP000187','<p>No data are available in regard to overdosage in humans. The oral LD<sub>50</sub> of amiloride hydrochloride (calculated as the base) is 56 mg/kg in mice and 36 to 85 mg/kg in rats, depending on the strain. The most likely signs and symptoms to be expected with overdosage are dehydration and electrolyte imbalance.</p>','7DZO8EB0Z3','<p><span class=\"not-available\">Not Available</span></p>','Amiloride','ZINC000004340269'),(42,'Efavirenz','efavirenz','Efavirenz is a non-nucleoside reverse transcriptase inhibitor used to treat HIV infection or prevent the spread of HIV.','Atripla, Stocrin, Sustiva, Symfi','Efavirenz','<p>Efavirenz (brand names Sustiva® and Stocrin®) is a non-nucleoside reverse transcriptase inhibitor (NNRTI) and is used as part of highly active antiretroviral therapy (HAART) for the treatment of a human immunodeficiency virus (HIV) type 1.</p><p>For HIV infection that has not previously been treated, efavirenz and lamivudine in combination with zidovudine or tenofovir is the preferred NNRTI-based regimen.</p><p>Efavirenz is also used in combination with other antiretroviral agents as part of an expanded postexposure prophylaxis regimen to prevent HIV transmission for those exposed to materials associated with a high risk for HIV transmission.</p>','C14H9ClF3NO2','DB00625','Approved, Investigational','Small Molecule','Average: 315.675 Monoisotopic: 315.027390859 ',' , J05AR — Antivirals for treatment of HIV infections, combinations , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , J05AG — Non-nucleoside 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','<p><span class=\"not-available\">Not Available</span></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=\"Organic compounds containing the ynone functional group, an alpha,beta unsaturated ketone group with the general structure  RC#C-C(=O)R\' (R\'  not H).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001373\" rel=\"noopener\" target=\"_blank\">Ynones</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 the acyl chloride functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001030\" rel=\"noopener\" target=\"_blank\">Aryl chlorides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic 1,3-dipolar compounds with the general structure  X#N+-Z- &lt;-&gt; X-=N+=Z &lt;-&gt; X-=N-Z+ &lt;-&gt; X-N=Z (X = C or O, Z = C, N, or O).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003633\" rel=\"noopener\" target=\"_blank\">Propargyl-type 1,3-dipolar organic 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 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=\"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 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=\"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 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 chlorine atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001516\" rel=\"noopener\" target=\"_blank\">Organochlorides</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=\"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 the alkyl fluoride functional group with formula R-F , where R is an alkyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001027\" rel=\"noopener\" target=\"_blank\">Alkyl fluorides</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 2 more</a>','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsCytochrome P450 2B6CYP2B6*6Not AvailableG > T / A > GEffect Directly StudiedThe presence of this polymorphism in CYP2B6 is associated with reduction in efavirenz metabolism.Details','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsCytochrome P450 2B6CYP2B6*6Not AvailableG > T / A > GEffect Directly StudiedThe presence of this polymorphism in CYP2B6 is associated with reduction in efavirenz metabolism.Details','2483','154598-52-4','119486','CHEMBL223228','57715','<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 benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen 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 an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001396\" rel=\"noopener\" target=\"_blank\">Benzoxazines</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 an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001396\" rel=\"noopener\" target=\"_blank\">Benzoxazines</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 the ynone functional group, an alpha,beta unsaturated ketone group with the general structure  RC#C-C(=O)R\' (R\'  not H).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001373\" rel=\"noopener\" target=\"_blank\">Ynones</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 the acyl chloride functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001030\" rel=\"noopener\" target=\"_blank\">Aryl chlorides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic 1,3-dipolar compounds with the general structure  X#N+-Z- &lt;-&gt; X-=N+=Z &lt;-&gt; X-=N-Z+ &lt;-&gt; X-N=Z (X = C or O, Z = C, N, or O).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003633\" rel=\"noopener\" target=\"_blank\">Propargyl-type 1,3-dipolar organic 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 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=\"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 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=\"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 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 chlorine atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001516\" rel=\"noopener\" target=\"_blank\">Organochlorides</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=\"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 the alkyl fluoride functional group with formula R-F , where R is an alkyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001027\" rel=\"noopener\" target=\"_blank\">Alkyl fluorides</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 2 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 fluoride</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkyl halide</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\">Aryl chloride</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\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoxazine</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 1,3-dipolar 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\">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\">Organochloride</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\">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\">Propargyl-type 1,3-dipolar organic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ynone</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 11 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\">organofluorine compound, organochlorine compound, cyclopropanes, acetylenic compound, benzoxazine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:119486\" rel=\"noopener\" target=\"_blank\">CHEBI:119486</a>) </span></span></dd></dl>','Benzoxazines','<p><span class=\"not-available\">Not Available</span></p>','This compound belongs to the class of organic compounds known as benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom).','Benzoxazines','<li>Avoid excessive or chronic alcohol consumption. Alcohol may contribute to additive adverse effects when taken with efavirenz.</li>\n<li>Take on an empty stomach. Taking efavirenz with food increases efavirenz concentrations and may increase the frequency of adverse reactions. In patients who cannot swallow capsules, the capsule contents can be administered with a small amount of food or infant formula using the capsule sprinkle method of administration.</li>','Drugs.com Drug Page',' , 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 , BSEP/ABCB11 Substrates , Central Nervous System Depressants , Cycloparaffins , Cytochrome P-450 CYP1A2 Inhibitors , Cytochrome P-450 CYP1A2 Inhibitors (strength unknown) , Cytochrome P-450 CYP1A2 Substrates , Cytochrome P-450 CYP2B6 Inducers , Cytochrome P-450 CYP2B6 Inducers (strength unknown) , Cytochrome P-450 CYP2B6 Substrates , Cytochrome P-450 CYP2C19 Inducers , Cytochrome P-450 CYP2C19 Inducers (strength unknown) , Cytochrome P-450 CYP2C19 Inhibitors , Cytochrome P-450 CYP2C19 Inhibitors (moderate) , Cytochrome P-450 CYP2C8 Inhibitors , Cytochrome P-450 CYP2C8 Inhibitors (moderate) , Cytochrome P-450 CYP2C9 Inhibitors , Cytochrome P-450 CYP2C9 Inhibitors (moderate) , Cytochrome P-450 CYP2D6 Inhibitors , Cytochrome P-450 CYP2D6 Inhibitors (strength unknown) , 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 (moderate) , Cytochrome P-450 CYP3A4 Inhibitors , Cytochrome P-450 CYP3A4 Inhibitors (strong) , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A5 Inducers , Cytochrome P-450 CYP3A5 Inducers (moderate) , Cytochrome P-450 CYP3A7 Inducers , Cytochrome P-450 CYP3A7 Inducers (moderate) , Cytochrome P-450 Enzyme Inducers , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Direct Acting Antivirals , Enzyme Inhibitors , Heterocyclic Compounds, Fused-Ring , Human Immunodeficiency Virus 1 Non-Nucleoside Analog Reverse Transcriptase Inhibitor , Hydrocarbons, Acyclic , Inducers of Drug Clearance , Moderate Risk QTc-Prolonging Agents , Non-Nucleoside Reverse Transcriptase Inhibitors , Nonnucleoside Reverse Transcriptase Inhibitors , Nucleic Acid Synthesis Inhibitors , OCT1 inhibitors , Oxazines , QTc Prolonging Agents , Reverse Transcriptase Inhibitors , UGT1A1 Inducers','<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>139-141 °C</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>logP</td><td>4.6</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\">organofluorine compound, organochlorine compound, cyclopropanes, acetylenic compound, benzoxazine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:119486\" rel=\"noopener\" target=\"_blank\">CHEBI:119486</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/HMDB0014763\" rel=\"noopener\" target=\"_blank\">HMDB0014763</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:D00896\" rel=\"noopener\" target=\"_blank\">D00896</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:C08088\" rel=\"noopener\" target=\"_blank\">C08088</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=64139\" rel=\"noopener\" target=\"_blank\">64139</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=46506827\" rel=\"noopener\" target=\"_blank\">46506827</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.57715.html\" rel=\"noopener\" target=\"_blank\">57715</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=2483\" rel=\"noopener\" target=\"_blank\">2483</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=195085\" rel=\"noopener\" target=\"_blank\">195085</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=119486\" rel=\"noopener\" target=\"_blank\">119486</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/CHEMBL223228\" rel=\"noopener\" target=\"_blank\">CHEMBL223228</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/ZINC000002020233\" rel=\"noopener\" target=\"_blank\">ZINC000002020233</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=DAP000709\" rel=\"noopener\" target=\"_blank\">DAP000709</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/PA449441\" rel=\"noopener\" target=\"_blank\">PA449441</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/EFZ\" rel=\"noopener\" target=\"_blank\">EFZ</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/efaviren.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/efavirenz.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/Efavirenz\" rel=\"noopener\" target=\"_blank\">Efavirenz</a></dd></dl>','<li>Avoid excessive or chronic alcohol consumption. Alcohol may contribute to additive adverse effects when taken with efavirenz.</li>\n<li>Take on an empty stomach. Taking efavirenz with food increases efavirenz concentrations and may increase the frequency of adverse reactions. In patients who cannot swallow capsules, the capsule contents can be administered with a small amount of food or infant formula using the capsule sprinkle method of administration.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A953\">Ren J, Bird LE, Chamberlain PP, Stewart-Jones GB, Stuart DI, Stammers DK: Structure of HIV-2 reverse transcriptase at 2.35-A resolution and the mechanism of resistance to non-nucleoside inhibitors. Proc Natl Acad Sci U S A. 2002 Oct 29;99(22):14410-5. Epub 2002 Oct 17. [<a href=\"/articles/A953\" target=\"_blank\">Article</a>] </li><li id=\"reference-A33800\">Robertson SM, Penzak SR, Lane J, Pau AK, Mican JM: A potentially significant interaction between efavirenz and phenytoin: a case report and review of the literature. Clin Infect Dis. 2005 Jul 15;41(2):e15-8. doi: 10.1086/431208. Epub 2005 Jun 7. [<a href=\"/articles/A33800\" target=\"_blank\">Article</a>] </li><li id=\"reference-A38593\">Michaud V, Ogburn E, Thong N, Aregbe AO, Quigg TC, Flockhart DA, Desta Z: Induction of CYP2C19 and CYP3A activity following repeated administration of efavirenz in healthy volunteers. Clin Pharmacol Ther. 2012 Mar;91(3):475-82. doi: 10.1038/clpt.2011.249. Epub 2012 Feb 8. [<a href=\"/articles/A38593\" target=\"_blank\">Article</a>] </li><li id=\"reference-L9860\">FDA Approved Drugs: Sustiva® oral capsules/tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020972s057,021360s045lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>40-55 hours</p>','HMDB0014763','(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one','InChI=1S/C14H9ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-4,7-8H,1-2H2,(H,19,20)/t13-/m0/s1','XPOQHMRABVBWPR-ZDUSSCGKSA-N','<p>For use in combination treatment of HIV infection (AIDS)</p>','C08088','D00896','Organic compounds','<p>Efavirenz is principally metabolized by the cytochrome P450 system to hydroxylated metabolites with subsequent glucuronidation of these hydroxylated metabolites. These metabolites are essentially inactive against HIV-1.</p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteropolycyclic compounds','EFZ','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000740?highlight[compounds][]=DB00625&amp;highlight[proteins][]=DB00625\">Efavirenz Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA449441','<p>99.5-99.75%</p>','64139','46506827','<p>Nearly all of the urinary excretion of the radiolabeled drug was in the form of metabolites.</p>','RxList Drug Page','195085','FC(F)(F)[C@]1(OC(=O)NC2=C1C=C(Cl)C=C2)C#CC1CC1','Solid','Not Available','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Alkyl fluoride</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkyl halide</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\">Aryl chloride</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\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoxazine</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 1,3-dipolar 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\">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\">Organochloride</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\">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\">Propargyl-type 1,3-dipolar organic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ynone</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 11 more</a>','Organoheterocyclic compounds','<span class=\"citations\"><p>John Doney, \"Amorphous efavirenz and the production thereof.\" U.S. Patent US20070026073, issued February 01, 2007.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=20070026073&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US20070026073</a>','DAP000709','<p><span class=\"not-available\">Not Available</span></p>','JE6H2O27P8','<p><span class=\"not-available\">Not Available</span></p>','Efavirenz','ZINC000002020233'),(43,'Adenosine','adenosine','Adenosine is a medication used in myocardial perfusion scintigraphy and to treat supraventricular tachycardia.','Adenocard, Viva-drops Lubricating Eye Drops','Adenosine','<p>The structure of adenosine was first described in 1931,<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Levene PA, Tipson RS: THE RING STRUCTURE OF ADENOSINE. Science. 1931 Nov 20;74(1925):521. doi: 10.1126/science.74.1925.521. (PubMed ID 17798867)\" href=\"#reference-A229823\">7</a></sup> though the vasodilating effects were not described in literature until the 1940s.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"SINGHER HO, MILLMAN N: The adenosine-triphosphatase activity of smooth muscle. Fed Proc. 1946;5(1 Pt 2):202. (PubMed ID 21064444)\" href=\"#reference-A229828\">8</a></sup> Adenosine is indicated as an adjunct to thallium-201 in myocardial perfusion scintigraphy,<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Adenoscan (Adenosine) Intravenous Injection (Discontinued)\" href=\"#reference-L31983\">12</a></sup> though it is rarely used in this indication, having largely been replaced by <a href=\"https://go.drugbank.com/drugs/DB00975\">dipyridamole</a> and [regadenson].<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Notghi A, Low CS: Myocardial perfusion scintigraphy: past, present and future. Br J Radiol. 2011 Dec;84 Spec No 3:S229-36. doi: 10.1259/bjr/14625142. (PubMed ID 22723530)\" href=\"#reference-A229833\">9</a>,<a class=\"reference-popover-link\" data-content=\"Palani G, Ananthasubramaniam K: Regadenoson: review of its established role in myocardial perfusion imaging and emerging applications. Cardiol Rev. 2013 Jan-Feb;21(1):42-8. doi: 10.1097/CRD.0b013e3182613db6. (PubMed ID 22643345)\" href=\"#reference-A229838\">10</a></sup> Adenosine is also indicated in the treatment of supraventricular tachycardia.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Dailymed: Adenocard (Adenosine) Intravenous Injection\" href=\"#reference-L31998\">13</a></sup></p><p>Adenosine was granted FDA approval on 30 October 1989.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Adenocard (Adenosine) Intravenous Injection (Discontinued)\" href=\"#reference-L31978\">11</a></sup></p>','C10H13N5O4','DB00640','Approved, Investigational','Small Molecule','Average: 267.2413 Monoisotopic: 267.096753929 ',' , C01EB — Other cardiac preparations , C01E — OTHER CARDIAC PREPARATIONS , C01 — CARDIAC THERAPY , C — CARDIOVASCULAR SYSTEM','<p>Data regarding the absorption of adenosine are not readily available.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Uematsu T, Kozawa O, Matsuno H, Niwa M, Yoshikoshi H, Oh-uchi M, Kohno K, Nagashima S, Kanamaru M: Pharmacokinetics and tolerability of intravenous infusion of adenosine (SUNY4001) in healthy volunteers. Br J Clin Pharmacol. 2000 Aug;50(2):177-81. doi: 10.1046/j.1365-2125.2000.00214.x. (PubMed ID 10930971)\" href=\"#reference-A229813\">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=\"Compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002203\" rel=\"noopener\" target=\"_blank\">Glycosylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Monosaccharides in which the carbohydrate moiety contains five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001497\" rel=\"noopener\" target=\"_blank\">Pentoses</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002987\" rel=\"noopener\" target=\"_blank\">6-aminopurines</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=\"Heterocyclic compounds containing an imidazole ring substituted at position 1.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002311\" rel=\"noopener\" target=\"_blank\">N-substituted imidazoles</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=\"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=\"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 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></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=\"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=\"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=\"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></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','14487','58-61-7','16335','CHEMBL477','54923','<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 purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl 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=\"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=\"Compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000479\" rel=\"noopener\" target=\"_blank\">Purine nucleosides</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 comprising a purine base attached to a ribosyl or deoxyribosyl moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000479\" rel=\"noopener\" target=\"_blank\">Purine 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 consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002203\" rel=\"noopener\" target=\"_blank\">Glycosylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Monosaccharides in which the carbohydrate moiety contains five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001497\" rel=\"noopener\" target=\"_blank\">Pentoses</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002987\" rel=\"noopener\" target=\"_blank\">6-aminopurines</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=\"Heterocyclic compounds containing an imidazole ring substituted at position 1.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002311\" rel=\"noopener\" target=\"_blank\">N-substituted imidazoles</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=\"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=\"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 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></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=\"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=\"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=\"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></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\">6-aminopurine</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 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\">Glycosyl compound</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></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\">Imidazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidazopyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidolactam</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monosaccharide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">N-glycosyl compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">N-substituted imidazole</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\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pentose monosaccharide</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\">Purine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Purine nucleoside</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrimidine</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></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 21 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\">adenosines (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16335\" rel=\"noopener\" target=\"_blank\">CHEBI:16335</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Ribonucleosides (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C00212\" rel=\"noopener\" target=\"_blank\">C00212</a>) </span></span></dd></dl>','Purine nucleosides','<p>Data regarding the clearance of adenosine are not readily available.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Uematsu T, Kozawa O, Matsuno H, Niwa M, Yoshikoshi H, Oh-uchi M, Kohno K, Nagashima S, Kanamaru M: Pharmacokinetics and tolerability of intravenous infusion of adenosine (SUNY4001) in healthy volunteers. Br J Clin Pharmacol. 2000 Aug;50(2):177-81. doi: 10.1046/j.1365-2125.2000.00214.x. (PubMed ID 10930971)\" href=\"#reference-A229813\">5</a></sup></p>','This compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.','Purine nucleosides','<li>Avoid caffeine. Caffeine may antagonise the activity of adenosine.</li>','Drugs.com Drug Page',' , Adenosine, antagonists & inhibitors , Agents producing tachycardia , Alkenes , Analgesics , Antiarrhythmic agents , Antiarrhythmics, Class V , Biological Factors , Carbohydrates , Cardiac Therapy , Cardiovascular Agents , Central Nervous System Agents , Cyclohexanes , Cyclohexenes , Cycloparaffins , Glycosides , Heterocyclic Compounds, Fused-Ring , Hydrocarbons, Acyclic , Miscellaneous Cardiac Drugs , Miscellaneous Therapeutic Agents , Moderate Risk QTc-Prolonging Agents , Neurotransmitter Agents , Nucleic Acids, Nucleotides, and Nucleosides , Nucleosides , Peripheral Nervous System Agents , Polyenes , Purine Nucleosides , Purinergic Agents , Purinergic Agonists , Purinergic P1 Receptor Agonists , Purines , QTc Prolonging Agents , Ribonucleosides , Sensory System Agents , Terpenes , Vasodilating Agents','<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>235.5 °C</td><td>PhysProp</td></tr><tr><td>logP</td><td>-1.05</td><td>HANSCH,C ET AL. (1995)</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">adenosines (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16335\" rel=\"noopener\" target=\"_blank\">CHEBI:16335</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Ribonucleosides (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C00212\" rel=\"noopener\" target=\"_blank\">C00212</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/HMDB0000050\" rel=\"noopener\" target=\"_blank\">HMDB0000050</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:D00045\" rel=\"noopener\" target=\"_blank\">D00045</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:C00212\" rel=\"noopener\" target=\"_blank\">C00212</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=60961\" rel=\"noopener\" target=\"_blank\">60961</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=46508728\" rel=\"noopener\" target=\"_blank\">46508728</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.54923.html\" rel=\"noopener\" target=\"_blank\">54923</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=14487\" rel=\"noopener\" target=\"_blank\">14487</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=296\" rel=\"noopener\" target=\"_blank\">296</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=16335\" rel=\"noopener\" target=\"_blank\">16335</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/CHEMBL477\" rel=\"noopener\" target=\"_blank\">CHEMBL477</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/ZINC000002169830\" rel=\"noopener\" target=\"_blank\">ZINC000002169830</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=DAP000223\" rel=\"noopener\" target=\"_blank\">DAP000223</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/PA448049\" rel=\"noopener\" target=\"_blank\">PA448049</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/ADN\" rel=\"noopener\" target=\"_blank\">ADN</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/adenos.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/adenosine.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/Adenosine\" rel=\"noopener\" target=\"_blank\">Adenosine</a></dd></dl>','<li>Avoid caffeine. Caffeine may antagonise the activity of adenosine.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A229788\">Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. [<a href=\"/articles/A229788\" target=\"_blank\">Article</a>] </li><li id=\"reference-A229793\">Maiuolo J, Oppedisano F, Gratteri S, Muscoli C, Mollace V: Regulation of uric acid metabolism and excretion. Int J Cardiol. 2016 Jun 15;213:8-14. doi: 10.1016/j.ijcard.2015.08.109. Epub 2015 Aug 14. [<a href=\"/articles/A229793\" target=\"_blank\">Article</a>] </li><li id=\"reference-A229808\">Cui F, Wang J, Li F, Fan J, Qu G, Yao X, Lei B: Investigation of the Interaction between Adenosine and Human Serum Albumin by Fluorescent Spectroscopy and Molecular Modeling Chinese Journal of Chemistry. 2008 Apr 16;26(4):661-665. [<a href=\"/articles/A229808\" target=\"_blank\">Article</a>] </li><li id=\"reference-A187466\">Singh S, McKintosh R: Adenosine . [<a href=\"/articles/A187466\" target=\"_blank\">Article</a>] </li><li id=\"reference-A229813\">Uematsu T, Kozawa O, Matsuno H, Niwa M, Yoshikoshi H, Oh-uchi M, Kohno K, Nagashima S, Kanamaru M: Pharmacokinetics and tolerability of intravenous infusion of adenosine (SUNY4001) in healthy volunteers. Br J Clin Pharmacol. 2000 Aug;50(2):177-81. doi: 10.1046/j.1365-2125.2000.00214.x. [<a href=\"/articles/A229813\" target=\"_blank\">Article</a>] </li><li id=\"reference-A229818\">Iskandrian AS: Adenosine myocardial perfusion imaging. J Nucl Med. 1994 Apr;35(4):734-6. [<a href=\"/articles/A229818\" target=\"_blank\">Article</a>] </li><li id=\"reference-A229823\">Levene PA, Tipson RS: THE RING STRUCTURE OF ADENOSINE. Science. 1931 Nov 20;74(1925):521. doi: 10.1126/science.74.1925.521. [<a href=\"/articles/A229823\" target=\"_blank\">Article</a>] </li><li id=\"reference-A229828\">SINGHER HO, MILLMAN N: The adenosine-triphosphatase activity of smooth muscle. Fed Proc. 1946;5(1 Pt 2):202. [<a href=\"/articles/A229828\" target=\"_blank\">Article</a>] </li><li id=\"reference-A229833\">Notghi A, Low CS: Myocardial perfusion scintigraphy: past, present and future. Br J Radiol. 2011 Dec;84 Spec No 3:S229-36. doi: 10.1259/bjr/14625142. [<a href=\"/articles/A229833\" target=\"_blank\">Article</a>] </li><li id=\"reference-A229838\">Palani G, Ananthasubramaniam K: Regadenoson: review of its established role in myocardial perfusion imaging and emerging applications. Cardiol Rev. 2013 Jan-Feb;21(1):42-8. doi: 10.1097/CRD.0b013e3182613db6. [<a href=\"/articles/A229838\" target=\"_blank\">Article</a>] </li><li id=\"reference-L31978\">FDA Approved Drug Products: Adenocard (Adenosine) Intravenous Injection (Discontinued) [<a href=\"https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&amp;ApplNo=019937\" target=\"_blank\">Link</a>] </li><li id=\"reference-L31983\">FDA Approved Drug Products: Adenoscan (Adenosine) Intravenous Injection (Discontinued) [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020059s017s018lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L31998\">Dailymed: Adenocard (Adenosine) Intravenous Injection [<a href=\"https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f0e32589-dad9-4887-8481-bcf7f6618466\" target=\"_blank\">Link</a>] </li><li id=\"reference-L32048\">Cayman Chemical: Adenosine MSDS [<a href=\"https://www.caymanchem.com/msdss/21232m.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>The half life of adenosine in blood is less than 10 seconds.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Adenoscan (Adenosine) Intravenous Injection (Discontinued)\" href=\"#reference-L31983\">12</a></sup></p>','HMDB0000050','(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol','InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1','OIRDTQYFTABQOQ-KQYNXXCUSA-N','<p>Adenosine is indicated as an adjunct to thallium-201 in myocardial perfusion scintigraphy in patients unable to adequately exercise.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Adenoscan (Adenosine) Intravenous Injection (Discontinued)\" href=\"#reference-L31983\">12</a></sup> It is also indicated to convert sinus rhythm of paroxysmal supraventricular tachycardia.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Dailymed: Adenocard (Adenosine) Intravenous Injection\" href=\"#reference-L31998\">13</a></sup></p>','C00212','D00045','Organic compounds','<p>Adenosine can be phosphorylated by adenosine kinase to form adenosine monophosphate.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. (PubMed ID 31821783)\" href=\"#reference-A229788\">1</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Adenoscan (Adenosine) Intravenous Injection (Discontinued)\" href=\"#reference-L31983\">12</a></sup> From there, it is phosphorylated again by adenylate kinase 1 to form adenosine diphosphate, and again by nucleoside diphosphate kinase A or B to form adenosine triphosphate.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. (PubMed ID 31821783)\" href=\"#reference-A229788\">1</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Adenoscan (Adenosine) Intravenous Injection (Discontinued)\" href=\"#reference-L31983\">12</a></sup></p><p>Alternatively, adenosine can be deaminated by adenosine deaminase to form inosine.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. (PubMed ID 31821783)\" href=\"#reference-A229788\">1</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Adenoscan (Adenosine) Intravenous Injection (Discontinued)\" href=\"#reference-L31983\">12</a></sup> Iosine is phosphorylated by purine nucleoside phosphorylase to form hypoxanthine.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. (PubMed ID 31821783)\" href=\"#reference-A229788\">1</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Adenoscan (Adenosine) Intravenous Injection (Discontinued)\" href=\"#reference-L31983\">12</a></sup> Hypoxanthine undergoes oxidation by xanthine dehydrogenase twice to form the metabolites xanthine, followed by uric acid.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Maiuolo J, Oppedisano F, Gratteri S, Muscoli C, Mollace V: Regulation of uric acid metabolism and excretion. Int J Cardiol. 2016 Jun 15;213:8-14. doi: 10.1016/j.ijcard.2015.08.109. Epub 2015 Aug 14. (PubMed ID 26316329)\" href=\"#reference-A229793\">2</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Adenoscan (Adenosine) Intravenous Injection (Discontinued)\" href=\"#reference-L31983\">12</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteropolycyclic compounds','ADN','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000033?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Methionine Metabolism</a></td><td>Metabolic</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000144?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Adenosine Deaminase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000168?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">AICA-Ribosiduria</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000203?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Molybdenum Cofactor Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000221?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Methionine Adenosyltransferase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000427?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Azathioprine Action Pathway</a></td><td>Drug action</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000430?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Thioguanine Action Pathway</a></td><td>Drug action</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000513?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Xanthinuria Type II</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000167?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Adenylosuccinate Lyase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000214?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">S-Adenosylhomocysteine (SAH) Hydrolase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000220?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Xanthine Dehydrogenase Deficiency (Xanthinuria)</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000222?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Glycine N-Methyltransferase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000340?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000341?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Hypermethioninemia</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000512?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Xanthinuria Type I</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000536?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Mitochondrial DNA Depletion Syndrome</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000537?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Myoadenylate Deaminase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000570?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Homocystinuria-Megaloblastic Anemia Due to Defect in Cobalamin Metabolism, cblG Complementation Type</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000029?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Selenoamino Acid Metabolism</a></td><td>Metabolic</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000050?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Purine Metabolism</a></td><td>Metabolic</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000123?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Betaine Metabolism</a></td><td>Metabolic</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000177?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Cystathionine beta-Synthase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000210?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Purine Nucleoside Phosphorylase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000320?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Intracellular Signalling Through Adenosine Receptor A2a and Adenosine</a></td><td>Signaling</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000321?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Intracellular Signalling Through Adenosine Receptor A2b and Adenosine</a></td><td>Signaling</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000364?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Lesch-Nyhan Syndrome (LNS)</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000365?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Gout or Kelley-Seegmiller Syndrome</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000428?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Mercaptopurine Action Pathway</a></td><td>Drug action</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000535?highlight[compounds][]=DB00640&amp;highlight[proteins][]=DB00640\">Adenine Phosphoribosyltransferase Deficiency (APRT)</a></td><td>Disease</td></tr></tbody>','PA448049','<p>Adenosine is bound to albumin in plasma, however data regarding the extent of binding are not readily available.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Cui F, Wang J, Li F, Fan J, Qu G, Yao X, Lei B: Investigation of the Interaction between Adenosine and Human Serum Albumin by Fluorescent Spectroscopy and Molecular Modeling Chinese Journal of Chemistry. 2008 Apr 16;26(4):661-665.\" href=\"#reference-A229808\">3</a></sup></p>','60961','46508728','<p>Adenosine is predominantly eliminated in the urine as uric acid.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Maiuolo J, Oppedisano F, Gratteri S, Muscoli C, Mollace V: Regulation of uric acid metabolism and excretion. Int J Cardiol. 2016 Jun 15;213:8-14. doi: 10.1016/j.ijcard.2015.08.109. Epub 2015 Aug 14. (PubMed ID 26316329)\" href=\"#reference-A229793\">2</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Adenoscan (Adenosine) Intravenous Injection (Discontinued)\" href=\"#reference-L31983\">12</a></sup></p>','RxList Drug Page','296','NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1','Solid','Not Available','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">6-aminopurine</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 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\">Glycosyl compound</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></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\">Imidazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidazopyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidolactam</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monosaccharide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">N-glycosyl compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">N-substituted imidazole</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\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pentose monosaccharide</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\">Purine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Purine nucleoside</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrimidine</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></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 21 more</a>','Nucleosides, nucleotides, and analogues','<span class=\"citations\"><p>Giorgio Stramentinoli, Federico Gennari, \"Process for preparing adenosine derivatives of anti-inflammatory and analgesic activity.\" U.S. Patent US4373097, issued October, 1965.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=4373097&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US4373097</a>','DAP000223','<p>Patients experiencing an overdose of adenosine may present with asystole, heart block, or cardiac ischemia; though the effects are generally short lived.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Singh S, McKintosh R: Adenosine . (PubMed ID 30085591)\" href=\"#reference-A187466\">4</a></sup> Patients experiencing an overdose should be treated with symptomatic and supportive care, which may include a slow intravenous injection of <a href=\"https://go.drugbank.com/drugs/DB00277\">theophylline</a>.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Adenoscan (Adenosine) Intravenous Injection (Discontinued)\" href=\"#reference-L31983\">12</a></sup></p><p>The LD<sub>50</sub> in mice is &gt;20 g/kg subcutaneously, 500mg/kg intraperitoneally, and 39.6 µg/kg subcutaneously.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Cayman Chemical: Adenosine MSDS\" href=\"#reference-L32048\">14</a></sup></p>','K72T3FS567','<p>Data regarding the volume of distribution of adenosine are not readily available.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Uematsu T, Kozawa O, Matsuno H, Niwa M, Yoshikoshi H, Oh-uchi M, Kohno K, Nagashima S, Kanamaru M: Pharmacokinetics and tolerability of intravenous infusion of adenosine (SUNY4001) in healthy volunteers. Br J Clin Pharmacol. 2000 Aug;50(2):177-81. doi: 10.1046/j.1365-2125.2000.00214.x. (PubMed ID 10930971)\" href=\"#reference-A229813\">5</a></sup></p>','Adenosine','ZINC000002169830'),(44,'Tamoxifen','tamoxifen','Tamoxifen is a selective estrogen receptor modulator used to treat estrogen receptor positive breast cancer, reduce the risk of invasive breast cancer following surgery, or reduce the risk of breast cancer in high risk women.','Nolvadex-D, Soltamox','Tamoxifen','<p>Tamoxifen is a non-steroidal antiestrogen used to treat estrogen receptor positive breast cancers as well as prevent the incidence of breast cancer in high risk populations.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Jordan VC: Fourteenth Gaddum Memorial Lecture. A current view of tamoxifen for the treatment and prevention of breast cancer. Br J Pharmacol. 1993 Oct;110(2):507-17. (PubMed ID 8242225)\" href=\"#reference-A1025\">1</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Tablets\" href=\"#reference-L7799\">15</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Solution\" href=\"#reference-L7802\">16</a></sup> Tamoxifen is used alone or as an adjuvant in these treatments.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Tablets\" href=\"#reference-L7799\">15</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Solution\" href=\"#reference-L7802\">16</a></sup> Tamoxifen may no longer be the preferred treatment for these types of cancers as patients generally have better survival, side effect profiles, and compliance with <a href=\"https://go.drugbank.com/drugs/DB01217\">anastrozole</a>.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Howell A, Cuzick J, Baum M, Buzdar A, Dowsett M, Forbes JF, Hoctin-Boes G, Houghton J, Locker GY, Tobias JS: Results of the ATAC (Arimidex, Tamoxifen, Alone or in Combination) trial after completion of 5 years\' adjuvant treatment for breast cancer. Lancet. 2005 Jan 1-7;365(9453):60-2. (PubMed ID 15639680)\" href=\"#reference-A1026\">2</a></sup></p><p>Tamoxifen was granted FDA approval on 30 December 1977.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Tablets\" href=\"#reference-L7799\">15</a></sup></p>','C26H29NO','DB00675','Approved','Small Molecule','Average: 371.5146 Monoisotopic: 371.224914555 ',' , L02BA — Anti-estrogens , L02B — HORMONE ANTAGONISTS AND RELATED AGENTS , L02 — ENDOCRINE THERAPY , L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS','<p>An oral dose of 20mg reaches a C<sub>max</sub> of 40ng/mL with a T<sub>max</sub> of 5 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Tablets\" href=\"#reference-L7799\">15</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Solution\" href=\"#reference-L7802\">16</a></sup> The metabolite N-desmethyltamoxifen reaches a C<sub>max</sub> of 15ng/mL.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Tablets\" href=\"#reference-L7799\">15</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Solution\" href=\"#reference-L7802\">16</a></sup> 10mg of tamoxifen orally twice daily for 3 months results in a C<sub>ss</sub> of 120ng/mL and a C<sub>ss</sub> of 336ng/mL.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Tablets\" href=\"#reference-L7799\">15</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Solution\" href=\"#reference-L7802\">16</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 diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000369\" rel=\"noopener\" target=\"_blank\">Diphenylmethanes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a phenylpropane moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002811\" rel=\"noopener\" target=\"_blank\">Phenylpropanes</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=\"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=\"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 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 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></span>','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsCytochrome P450 2D6CYP2D6*4(A;A)A Allele, homozygoteEffect Directly StudiedPatients with this genotype have reduced metabolism of tamoxifen resulting in reduced plasma concentrations its active form endoxifen.DetailsCoagulation factor V---(A;A) / (A;G)A alleleADR Directly StudiedPatients with this genotype have increased risk of a thromboembolic event with tamoxifen.DetailsCytochrome P450 2D6CYP2D6*3Not AvailableC alleleEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*6Not Available1707delTEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*31Not Available-1770G>A / -1584C>G  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*51Not Available-1584C>G / -1235A>G  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*68ANot Available-1426C>T / -1235A>G  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*68BNot AvailableSimilar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4.Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*100Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*101Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetails','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsCytochrome P450 2D6CYP2D6*4(A;A)A Allele, homozygoteEffect Directly StudiedPatients with this genotype have reduced metabolism of tamoxifen resulting in reduced plasma concentrations its active form endoxifen.DetailsCoagulation factor V---(A;A) / (A;G)A alleleADR Directly StudiedPatients with this genotype have increased risk of a thromboembolic event with tamoxifen.DetailsCytochrome P450 2D6CYP2D6*3Not AvailableC alleleEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*6Not Available1707delTEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*31Not Available-1770G>A / -1584C>G  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*51Not Available-1584C>G / -1235A>G  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*68ANot Available-1426C>T / -1235A>G  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*68BNot AvailableSimilar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4.Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*100Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetailsCytochrome P450 2D6CYP2D6*101Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetails','20607','10540-29-1','41774','CHEMBL83','2015313','<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 stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.</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=\"Organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups  to a phenyl ring lead to stilbenoids.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000253\" rel=\"noopener\" target=\"_blank\">Stilbenes</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 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups  to a phenyl ring lead to stilbenoids.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000253\" rel=\"noopener\" target=\"_blank\">Stilbenes</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 diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000369\" rel=\"noopener\" target=\"_blank\">Diphenylmethanes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a phenylpropane moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002811\" rel=\"noopener\" target=\"_blank\">Phenylpropanes</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=\"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=\"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 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 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></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\">Amine</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\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Diphenylmethane</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\">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 oxygen 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 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\">tertiary amino compound, stilbenoid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:41774\" rel=\"noopener\" target=\"_blank\">CHEBI:41774</a>) </span></span></dd></dl>','Stilbenes','<p>The clearance of tamoxifen was 189mL/min in a study of six postmenopausal women.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lien EA, Anker G, Lonning PE, Solheim E, Ueland PM: Decreased serum concentrations of tamoxifen and its metabolites induced by aminoglutethimide. Cancer Res. 1990 Sep 15;50(18):5851-7. (PubMed ID 2393854)\" href=\"#reference-A182213\">12</a></sup></p>','This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.','Stilbenes','<li>Exercise caution with St. John\'s Wort. This herb induces CYP3A4 metabolism, which may reduce the serum concentration of tamoxifen.</li>\n<li>Take with a full glass of water.</li>\n<li>Take with or without food.</li>','Drugs.com Drug Page',' , Anti-Estrogens , Antineoplastic Agents , Antineoplastic Agents, Hormonal , Antineoplastic and Immunomodulating Agents , BCRP/ABCG2 Substrates , Benzene Derivatives , Benzylidene Compounds , BSEP/ABCB11 Inhibitors , Cardiotoxic antineoplastic agents , Cytochrome P-450 CYP1A2 Substrates , Cytochrome P-450 CYP1A2 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2A6 Substrates , Cytochrome P-450 CYP2A6 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2B6 Inhibitors , Cytochrome P-450 CYP2B6 Inhibitors (moderate) , Cytochrome P-450 CYP2B6 Substrates , Cytochrome P-450 CYP2B6 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2C19 Substrates , Cytochrome P-450 CYP2C19 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2C8 Inhibitors , Cytochrome P-450 CYP2C8 Inhibitors (moderate) , Cytochrome P-450 CYP2C9 Inhibitors , Cytochrome P-450 CYP2C9 Inhibitors (strength unknown) , 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 (strength unknown) , Cytochrome P-450 CYP2D6 Substrates , Cytochrome P-450 CYP2D6 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 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 , Endocrine Therapy , Estrogen Agonist/Antagonist , Estrogen Antagonists , Estrogen Receptor Modulators , Hormone Antagonists , Hormone Antagonists and Related Agents , Hormones, Hormone Substitutes, and Hormone Antagonists , Narrow Therapeutic Index Drugs , P-glycoprotein inducers , P-glycoprotein inhibitors , P-glycoprotein substrates , P-glycoprotein substrates with a Narrow Therapeutic Index , Potential QTc-Prolonging Agents , QTc Prolonging Agents , Selective Estrogen Receptor Modulators , Stilbenes , Thyroxine-binding globulin inducers , UGT2B17 substrates , UGT2B7 substrates , UGT2B7 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>97 °C</td><td>http://www.chemspider.com/Chemical-Structure.2015313.html?rid=1b2fa2ba-dc6c-450e-bcf7-467741bd4eb1</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">tertiary amino compound, stilbenoid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:41774\" rel=\"noopener\" target=\"_blank\">CHEBI:41774</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/HMDB0014813\" rel=\"noopener\" target=\"_blank\">HMDB0014813</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:D08559\" rel=\"noopener\" target=\"_blank\">D08559</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:C07108\" rel=\"noopener\" target=\"_blank\">C07108</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=2733526\" rel=\"noopener\" target=\"_blank\">2733526</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=46505515\" rel=\"noopener\" target=\"_blank\">46505515</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.2015313.html\" rel=\"noopener\" target=\"_blank\">2015313</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=20607\" rel=\"noopener\" target=\"_blank\">20607</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=10324\" rel=\"noopener\" target=\"_blank\">10324</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=41774\" rel=\"noopener\" target=\"_blank\">41774</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/CHEMBL83\" rel=\"noopener\" target=\"_blank\">CHEMBL83</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/ZINC000001530689\" rel=\"noopener\" target=\"_blank\">ZINC000001530689</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=DAP000108\" rel=\"noopener\" target=\"_blank\">DAP000108</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/PA451581\" rel=\"noopener\" target=\"_blank\">PA451581</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=1016\" 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/CTX\" rel=\"noopener\" target=\"_blank\">CTX</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/tamox.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/tamoxifen.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/Tamoxifen\" rel=\"noopener\" target=\"_blank\">Tamoxifen</a></dd></dl>','<li>Exercise caution with St. John\'s Wort. This herb induces CYP3A4 metabolism, which may reduce the serum concentration of tamoxifen.</li>\n<li>Take with a full glass of water.</li>\n<li>Take with or without food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A1025\">Jordan VC: Fourteenth Gaddum Memorial Lecture. A current view of tamoxifen for the treatment and prevention of breast cancer. Br J Pharmacol. 1993 Oct;110(2):507-17. [<a href=\"/articles/A1025\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1026\">Howell A, Cuzick J, Baum M, Buzdar A, Dowsett M, Forbes JF, Hoctin-Boes G, Houghton J, Locker GY, Tobias JS: Results of the ATAC (Arimidex, Tamoxifen, Alone or in Combination) trial after completion of 5 years\' adjuvant treatment for breast cancer. Lancet. 2005 Jan 1-7;365(9453):60-2. [<a href=\"/articles/A1026\" target=\"_blank\">Article</a>] </li><li id=\"reference-A14873\">Crewe HK, Notley LM, Wunsch RM, Lennard MS, Gillam EM: Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4\'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos. 2002 Aug;30(8):869-74. [<a href=\"/articles/A14873\" target=\"_blank\">Article</a>] </li><li id=\"reference-A182102\">Squirewell EJ, Qin X, Duffel MW: Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50. doi: 10.1124/dmd.114.059709. Epub 2014 Aug 25. [<a href=\"/articles/A182102\" target=\"_blank\">Article</a>] </li><li id=\"reference-A182105\">Cronin-Fenton DP, Damkier P, Lash TL: Metabolism and transport of tamoxifen in relation to its effectiveness: new perspectives on an ongoing controversy. Future Oncol. 2014 Jan;10(1):107-22. doi: 10.2217/fon.13.168. [<a href=\"/articles/A182105\" target=\"_blank\">Article</a>] </li><li id=\"reference-A182108\">White IN: The tamoxifen dilemma. Carcinogenesis. 1999 Jul;20(7):1153-60. doi: 10.1093/carcin/20.7.1153. [<a href=\"/articles/A182108\" target=\"_blank\">Article</a>] </li><li id=\"reference-A182111\">Parte P, Kupfer D: Oxidation of tamoxifen by human flavin-containing monooxygenase (FMO) 1 and FMO3 to tamoxifen-N-oxide and its novel reduction back to tamoxifen by human cytochromes P450 and hemoglobin. Drug Metab Dispos. 2005 Oct;33(10):1446-52. doi: 10.1124/dmd.104.000802. Epub 2005 Jun 29. [<a href=\"/articles/A182111\" target=\"_blank\">Article</a>] </li><li id=\"reference-A182195\">Radin DP, Patel P: Delineating the molecular mechanisms of tamoxifen\'s oncolytic actions in estrogen receptor-negative cancers. Eur J Pharmacol. 2016 Jun 15;781:173-80. doi: 10.1016/j.ejphar.2016.04.017. Epub 2016 Apr 12. [<a href=\"/articles/A182195\" target=\"_blank\">Article</a>] </li><li id=\"reference-A182201\">Fromson JM, Pearson S, Bramah S: The metabolism of tamoxifen (I.C.I. 46,474). I. In laboratory animals. Xenobiotica. 1973 Nov;3(11):693-709. doi: 10.3109/00498257309151594. [<a href=\"/articles/A182201\" target=\"_blank\">Article</a>] </li><li id=\"reference-A182204\">Kisanga ER, Mellgren G, Lien EA: Excretion of hydroxylated metabolites of tamoxifen in human bile and urine. Anticancer Res. 2005 Nov-Dec;25(6C):4487-92. [<a href=\"/articles/A182204\" target=\"_blank\">Article</a>] </li><li id=\"reference-A182207\">Lien EA, Solheim E, Lea OA, Lundgren S, Kvinnsland S, Ueland PM: Distribution of 4-hydroxy-N-desmethyltamoxifen and other tamoxifen metabolites in human biological fluids during tamoxifen treatment. Cancer Res. 1989 Apr 15;49(8):2175-83. [<a href=\"/articles/A182207\" target=\"_blank\">Article</a>] </li><li id=\"reference-A182213\">Lien EA, Anker G, Lonning PE, Solheim E, Ueland PM: Decreased serum concentrations of tamoxifen and its metabolites induced by aminoglutethimide. Cancer Res. 1990 Sep 15;50(18):5851-7. [<a href=\"/articles/A182213\" target=\"_blank\">Article</a>] </li><li id=\"reference-A182183\">Klein DJ, Thorn CF, Desta Z, Flockhart DA, Altman RB, Klein TE: PharmGKB summary: tamoxifen pathway, pharmacokinetics. Pharmacogenet Genomics. 2013 Nov;23(11):643-7. doi: 10.1097/FPC.0b013e3283656bc1. [<a href=\"/articles/A182183\" target=\"_blank\">Article</a>] </li><li id=\"reference-A182249\">Kemp JV, Adam HK, Wakeling AE, Slater R: Identification and biological activity of tamoxifen metabolites in human serum. Biochem Pharmacol. 1983 Jul 1;32(13):2045-52. doi: 10.1016/0006-2952(83)90425-2. [<a href=\"/articles/A182249\" target=\"_blank\">Article</a>] </li><li id=\"reference-L7799\">FDA Approved Drug Products: Tamoxifen Oral Tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/17970s37s44s49lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7802\">FDA Approved Drug Products: Tamoxifen Oral Solution [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021807s006lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>The terminal elimination half-life of tamoxifen is 5 to 7 days, while the half-life of N-desmethyltamoxifen, the primary circulating metabolite, is approximately 14 days.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Tablets\" href=\"#reference-L7799\">15</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Solution\" href=\"#reference-L7802\">16</a></sup></p>','HMDB0014813','(2-{4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylamine','InChI=1S/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25-','NKANXQFJJICGDU-QPLCGJKRSA-N','<p>Tamoxifen is indicated to treat estrogen receptor positive metastatic breast cancer in adults, as an adjuvant in the treatment of early stage estrogen receptor positive breast cancer in adults, to reduce the risk of invasive breast cancer after surgery and radiation in adult women with ductal carcinoma in situ.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Solution\" href=\"#reference-L7802\">16</a></sup></p>','C07108','D08559','Organic compounds','<p>Tamoxifen can by hydroxylated to α-hydroxytamoxifen which is then glucuronidated or undergoes sulfate conjugation by sulfotransferase 2A1.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Squirewell EJ, Qin X, Duffel MW: Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50. doi: 10.1124/dmd.114.059709. Epub 2014 Aug 25. (PubMed ID 25157097)\" href=\"#reference-A182102\">4</a>,<a class=\"reference-popover-link\" data-content=\"White IN: The tamoxifen dilemma. Carcinogenesis. 1999 Jul;20(7):1153-60. doi: 10.1093/carcin/20.7.1153. (PubMed ID 10383884)\" href=\"#reference-A182108\">6</a></sup> Tamoxifen can also undergo N-oxidation by flavin monooxygenases 1 and 3 to tamoxifen N-oxide.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Squirewell EJ, Qin X, Duffel MW: Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50. doi: 10.1124/dmd.114.059709. Epub 2014 Aug 25. (PubMed ID 25157097)\" href=\"#reference-A182102\">4</a>,<a class=\"reference-popover-link\" data-content=\"White IN: The tamoxifen dilemma. Carcinogenesis. 1999 Jul;20(7):1153-60. doi: 10.1093/carcin/20.7.1153. (PubMed ID 10383884)\" href=\"#reference-A182108\">6</a>,<a class=\"reference-popover-link\" data-content=\"Parte P, Kupfer D: Oxidation of tamoxifen by human flavin-containing monooxygenase (FMO) 1 and FMO3 to tamoxifen-N-oxide and its novel reduction back to tamoxifen by human cytochromes P450 and hemoglobin. Drug Metab Dispos. 2005 Oct;33(10):1446-52. doi: 10.1124/dmd.104.000802. Epub 2005 Jun 29. (PubMed ID 15987777)\" href=\"#reference-A182111\">7</a></sup> Tamoxifen is N-dealkylated to N-desmethyltamoxifen by CYP2D6, CYP1A1, CYP1A2, CYP3A4, CYP1B1, CYP2C9, CYP2C19, and CYP3A5.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Crewe HK, Notley LM, Wunsch RM, Lennard MS, Gillam EM: Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4\'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos. 2002 Aug;30(8):869-74. (PubMed ID 12124303)\" href=\"#reference-A14873\">3</a>,<a class=\"reference-popover-link\" data-content=\"Squirewell EJ, Qin X, Duffel MW: Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50. doi: 10.1124/dmd.114.059709. Epub 2014 Aug 25. (PubMed ID 25157097)\" href=\"#reference-A182102\">4</a>,<a class=\"reference-popover-link\" data-content=\"Cronin-Fenton DP, Damkier P, Lash TL: Metabolism and transport of tamoxifen in relation to its effectiveness: new perspectives on an ongoing controversy. Future Oncol. 2014 Jan;10(1):107-22. doi: 10.2217/fon.13.168. (PubMed ID 24328412)\" href=\"#reference-A182105\">5</a>,<a class=\"reference-popover-link\" data-content=\"White IN: The tamoxifen dilemma. Carcinogenesis. 1999 Jul;20(7):1153-60. doi: 10.1093/carcin/20.7.1153. (PubMed ID 10383884)\" href=\"#reference-A182108\">6</a>,<a class=\"reference-popover-link\" data-content=\"Parte P, Kupfer D: Oxidation of tamoxifen by human flavin-containing monooxygenase (FMO) 1 and FMO3 to tamoxifen-N-oxide and its novel reduction back to tamoxifen by human cytochromes P450 and hemoglobin. Drug Metab Dispos. 2005 Oct;33(10):1446-52. doi: 10.1124/dmd.104.000802. Epub 2005 Jun 29. (PubMed ID 15987777)\" href=\"#reference-A182111\">7</a></sup> N-desmethyltamoxifen can be sulfate conjugated to form N-desmethyltamoxifen sulfate, 4-hydroxylated by CYP2D6 to form endoxifen, or N-dealkylated again by CYP3A4 and CYP3A5 to N,N-didesmethyltamoxifen.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Squirewell EJ, Qin X, Duffel MW: Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50. doi: 10.1124/dmd.114.059709. Epub 2014 Aug 25. (PubMed ID 25157097)\" href=\"#reference-A182102\">4</a>,<a class=\"reference-popover-link\" data-content=\"Cronin-Fenton DP, Damkier P, Lash TL: Metabolism and transport of tamoxifen in relation to its effectiveness: new perspectives on an ongoing controversy. Future Oncol. 2014 Jan;10(1):107-22. doi: 10.2217/fon.13.168. (PubMed ID 24328412)\" href=\"#reference-A182105\">5</a>,<a class=\"reference-popover-link\" data-content=\"Klein DJ, Thorn CF, Desta Z, Flockhart DA, Altman RB, Klein TE: PharmGKB summary: tamoxifen pathway, pharmacokinetics. Pharmacogenet Genomics. 2013 Nov;23(11):643-7. doi: 10.1097/FPC.0b013e3283656bc1. (PubMed ID 23962908)\" href=\"#reference-A182183\">13</a></sup> N,N-didesmethyltamoxifen undergoes a substitution reaction to form tamoxifen metabolite Y, followed by ether cleavage to metabolite E, which can then be sulfate conjugated by sulfotransferase 1A1 and 1E1 or O-glucuronidated.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Klein DJ, Thorn CF, Desta Z, Flockhart DA, Altman RB, Klein TE: PharmGKB summary: tamoxifen pathway, pharmacokinetics. Pharmacogenet Genomics. 2013 Nov;23(11):643-7. doi: 10.1097/FPC.0b013e3283656bc1. (PubMed ID 23962908)\" href=\"#reference-A182183\">13</a>,<a class=\"reference-popover-link\" data-content=\"Kemp JV, Adam HK, Wakeling AE, Slater R: Identification and biological activity of tamoxifen metabolites in human serum. Biochem Pharmacol. 1983 Jul 1;32(13):2045-52. doi: 10.1016/0006-2952(83)90425-2. (PubMed ID 6870933)\" href=\"#reference-A182249\">14</a></sup></p><p>Tamoxifen can also by 4-hydroxylated by CYP2D6, CYP2B6, CYP3A4, CYP2C9, and CYP2C19 to form 4-hydroxytamoxifen.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Crewe HK, Notley LM, Wunsch RM, Lennard MS, Gillam EM: Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4\'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos. 2002 Aug;30(8):869-74. (PubMed ID 12124303)\" href=\"#reference-A14873\">3</a>,<a class=\"reference-popover-link\" data-content=\"Squirewell EJ, Qin X, Duffel MW: Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50. doi: 10.1124/dmd.114.059709. Epub 2014 Aug 25. (PubMed ID 25157097)\" href=\"#reference-A182102\">4</a>,<a class=\"reference-popover-link\" data-content=\"Cronin-Fenton DP, Damkier P, Lash TL: Metabolism and transport of tamoxifen in relation to its effectiveness: new perspectives on an ongoing controversy. Future Oncol. 2014 Jan;10(1):107-22. doi: 10.2217/fon.13.168. (PubMed ID 24328412)\" href=\"#reference-A182105\">5</a>,<a class=\"reference-popover-link\" data-content=\"White IN: The tamoxifen dilemma. Carcinogenesis. 1999 Jul;20(7):1153-60. doi: 10.1093/carcin/20.7.1153. (PubMed ID 10383884)\" href=\"#reference-A182108\">6</a></sup> 4-hydroxytamoxifen can undergo glucuronidation by UGT1A8, UGT1A10, UGT2B7, and UGT2B17 to tamoxifen glucuronides, sulfate conjugation by sulfotransferase 1A1 and 1E1 to 4-hydroxytamoxifen sulfate, or N-dealkylation by CYP3A4 and CYP3A5 to endoxifen.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Squirewell EJ, Qin X, Duffel MW: Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50. doi: 10.1124/dmd.114.059709. Epub 2014 Aug 25. (PubMed ID 25157097)\" href=\"#reference-A182102\">4</a>,<a class=\"reference-popover-link\" data-content=\"Cronin-Fenton DP, Damkier P, Lash TL: Metabolism and transport of tamoxifen in relation to its effectiveness: new perspectives on an ongoing controversy. Future Oncol. 2014 Jan;10(1):107-22. doi: 10.2217/fon.13.168. (PubMed ID 24328412)\" href=\"#reference-A182105\">5</a></sup></p><p>Endoxifen undergoes demethylation to norendoxifen, a reversible sulfate conjugation reaction via sulfotransferase 1A1 and 1E1 to 4-hydroxytamoxifen sulfate, sulfate conjugation via sulfotransferase 2A1 to 4-endoxifen sulfate, or glucuronidation via UGT1A8, UGT1A10, UGT2B7, or UGT2B15 to tamoxifen glucuronides.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Klein DJ, Thorn CF, Desta Z, Flockhart DA, Altman RB, Klein TE: PharmGKB summary: tamoxifen pathway, pharmacokinetics. Pharmacogenet Genomics. 2013 Nov;23(11):643-7. doi: 10.1097/FPC.0b013e3283656bc1. (PubMed ID 23962908)\" href=\"#reference-A182183\">13</a>,<a class=\"reference-popover-link\" data-content=\"Squirewell EJ, Qin X, Duffel MW: Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50. doi: 10.1124/dmd.114.059709. Epub 2014 Aug 25. (PubMed ID 25157097)\" href=\"#reference-A182102\">4</a>,<a class=\"reference-popover-link\" data-content=\"Cronin-Fenton DP, Damkier P, Lash TL: Metabolism and transport of tamoxifen in relation to its effectiveness: new perspectives on an ongoing controversy. Future Oncol. 2014 Jan;10(1):107-22. doi: 10.2217/fon.13.168. (PubMed ID 24328412)\" href=\"#reference-A182105\">5</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic homomonocyclic compounds','CTX','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000606?highlight[compounds][]=DB00675&amp;highlight[proteins][]=DB00675\">Tamoxifen Metabolism Pathway</a></td><td>Drug metabolism</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000471?highlight[compounds][]=DB00675&amp;highlight[proteins][]=DB00675\">Tamoxifen Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA451581','<p>The protein binding of tamoxifen in plasma is over 98% and mostly to serum albumin.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lien EA, Solheim E, Lea OA, Lundgren S, Kvinnsland S, Ueland PM: Distribution of 4-hydroxy-N-desmethyltamoxifen and other tamoxifen metabolites in human biological fluids during tamoxifen treatment. Cancer Res. 1989 Apr 15;49(8):2175-83. (PubMed ID 2702659)\" href=\"#reference-A182207\">11</a></sup></p>','2733526','46505515','<p>Tamoxifen is mainly eliminated in the feces.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Tablets\" href=\"#reference-L7799\">15</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Solution\" href=\"#reference-L7802\">16</a></sup> Animal studies have shown 75% of radiolabelled tamoxifen recovered in the feces, with negligible collection from urine.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Fromson JM, Pearson S, Bramah S: The metabolism of tamoxifen (I.C.I. 46,474). I. In laboratory animals. Xenobiotica. 1973 Nov;3(11):693-709. doi: 10.3109/00498257309151594. (PubMed ID 4361333)\" href=\"#reference-A182201\">9</a></sup> However, 1 human study showed 26.7% recovery in the urine and 24.7% in the feces.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Kisanga ER, Mellgren G, Lien EA: Excretion of hydroxylated metabolites of tamoxifen in human bile and urine. Anticancer Res. 2005 Nov-Dec;25(6C):4487-92. (PubMed ID 16334131)\" href=\"#reference-A182204\">10</a></sup></p>','RxList Drug Page','10324','CC\\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C1','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\">Amine</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\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Diphenylmethane</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\">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 oxygen compound</span></span></span>','Phenylpropanoids and polyketides','<span class=\"citations\"><p>Chengjian Mao, \"Tamoxifen and 4-hydroxytamoxifen-activated system for regulated production of proteins in eukaryotic cells.\" U.S. Patent US20030199022, issued October 23, 2003.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=20030199022&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US20030199022</a>','DAP000108','<p>High doses of tamoxifen in animals lead to respiratory difficulty and convulsions.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Tablets\" href=\"#reference-L7799\">15</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Solution\" href=\"#reference-L7802\">16</a></sup> High doses in advanced metastatic cancer patients resulted in acute neurotoxicity seen by tremor, hyperreflexia, unsteady gait, and dizziness.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Tablets\" href=\"#reference-L7799\">15</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Solution\" href=\"#reference-L7802\">16</a></sup> Patients experiencing and overdose should be given supportive treatment as no specific treatment for overdose is suggested.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Tablets\" href=\"#reference-L7799\">15</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Tamoxifen Oral Solution\" href=\"#reference-L7802\">16</a></sup></p>','094ZI81Y45','<p>The volume of distribution of tamoxifen is approximately 50-60L/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lien EA, Solheim E, Lea OA, Lundgren S, Kvinnsland S, Ueland PM: Distribution of 4-hydroxy-N-desmethyltamoxifen and other tamoxifen metabolites in human biological fluids during tamoxifen treatment. Cancer Res. 1989 Apr 15;49(8):2175-83. (PubMed ID 2702659)\" href=\"#reference-A182207\">11</a></sup></p>','Tamoxifen','ZINC000001530689'),(45,'Losartan','losartan','Losartan is an angiotensin receptor blocker used to treat hypertension and diabetic nephropathy, and is used to reduce the risk of stroke.','Cozaar, Hyzaar','Losartan','<p>Losartan is an angiotensin II receptor blocker (ARB) used to treat hypertension.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan Oral Tablets\" href=\"#reference-L7423\">3</a></sup> Angiotensin-converting enzyme (ACE) inhibitors are used for a similar indication but are associated with a cough.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan Oral Tablets\" href=\"#reference-L7423\">3</a></sup> When patients with ACE inhibitor associated coughs are switched to ARBs like losartan, they have an incidence of cough similar to placebo or <a href=\"https://go.drugbank.com/drugs/DB00999\">hydrochlorothiazide</a>.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan Oral Tablets\" href=\"#reference-L7423\">3</a></sup> Losartan is available as losartan potassium oral tablets as well as a combination tablet of losartan potassium and hydrochlorothiazide.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan Oral Tablets\" href=\"#reference-L7423\">3</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan and Hydrochlorothiazide Oral Tablets\" href=\"#reference-L7426\">4</a></sup> Patients taking losartan should have their renal function and potassium levels monitored.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan Oral Tablets\" href=\"#reference-L7423\">3</a></sup> Losartan was granted FDA approval on 14 April 1995.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan Oral Tablets\" href=\"#reference-L7423\">3</a></sup></p>','C22H23ClN6O','DB00678','Approved','Small Molecule','Average: 422.911 Monoisotopic: 422.162187095 ',' , C09CA — Angiotensin II receptor blockers (ARBs), plain , C09C — ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), PLAIN , C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM , C — CARDIOVASCULAR SYSTEM , C09DA — Angiotensin II receptor blockers (ARBs) and diuretics , C09D — ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), COMBINATIONS , C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM , C — CARDIOVASCULAR SYSTEM , C09DB — Angiotensin II receptor blockers (ARBs) and calcium channel blockers , C09D — ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), COMBINATIONS , C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM , C — CARDIOVASCULAR SYSTEM','<p>Losartan is approximately 33% orally bioavailable.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. (PubMed ID 16029066)\" href=\"#reference-A1033\">1</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan Oral Tablets\" href=\"#reference-L7423\">3</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan and Hydrochlorothiazide Oral Tablets\" href=\"#reference-L7426\">4</a></sup> Losartan has a T<sub>max</sub> of 1 hour and the active metabolite has a T<sub>max</sub> of 3-4 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. (PubMed ID 16029066)\" href=\"#reference-A1033\">1</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan Oral Tablets\" href=\"#reference-L7423\">3</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan and Hydrochlorothiazide Oral Tablets\" href=\"#reference-L7426\">4</a></sup> Taking losartan with food decreases the C<sub>max</sub> but does only results in a 10% decrease in the AUC of losartan and its active metabolite.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. (PubMed ID 16029066)\" href=\"#reference-A1033\">1</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan Oral Tablets\" href=\"#reference-L7423\">3</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan and Hydrochlorothiazide Oral Tablets\" href=\"#reference-L7426\">4</a></sup> A 50-80mg oral dose of losartan leads to a C<sub>max</sub> of 200-250ng/mL.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. (PubMed ID 16029066)\" href=\"#reference-A1033\">1</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 phenyltetrazole skeleton, which consists of a tetrazole bound to a phenyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000306\" rel=\"noopener\" target=\"_blank\">Phenyltetrazoles and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Imidazoles in which the imidazole ring is substituted at for positions 1,2,4, and 5.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002633\" rel=\"noopener\" target=\"_blank\">1,2,4,5-tetrasubstituted imidazoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Heterocyclic compounds containing an imidazole ring substituted at position 1.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002311\" rel=\"noopener\" target=\"_blank\">N-substituted imidazoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the acyl chloride functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001030\" rel=\"noopener\" target=\"_blank\">Aryl chlorides</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 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=\"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 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=\"Compounds containing a chemical bond between a carbon atom and a chlorine atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001516\" rel=\"noopener\" target=\"_blank\">Organochlorides</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=\"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 2 more</a>','Not Available','Not Available','82258','114798-26-4','6541','CHEMBL191','3824','<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 biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.</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 to benzene rings linked together by a C-C bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000041\" rel=\"noopener\" target=\"_blank\">Biphenyls 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=\"Organic compounds containing to benzene rings linked together by a C-C bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000041\" rel=\"noopener\" target=\"_blank\">Biphenyls and derivatives</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 phenyltetrazole skeleton, which consists of a tetrazole bound to a phenyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000306\" rel=\"noopener\" target=\"_blank\">Phenyltetrazoles and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Imidazoles in which the imidazole ring is substituted at for positions 1,2,4, and 5.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002633\" rel=\"noopener\" target=\"_blank\">1,2,4,5-tetrasubstituted imidazoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Heterocyclic compounds containing an imidazole ring substituted at position 1.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002311\" rel=\"noopener\" target=\"_blank\">N-substituted imidazoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the acyl chloride functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001030\" rel=\"noopener\" target=\"_blank\">Aryl chlorides</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 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=\"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 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=\"Compounds containing a chemical bond between a carbon atom and a chlorine atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001516\" rel=\"noopener\" target=\"_blank\">Organochlorides</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=\"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 2 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\">1,2,4,5-tetrasubstituted imidazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</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 heteromonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl chloride</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\">Azole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Biphenyl</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\">Imidazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">N-substituted imidazole</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\">Organochloride</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\">Phenyltetrazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetrazole</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=\"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\">imidazoles, biphenylyltetrazole (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6541\" rel=\"noopener\" target=\"_blank\">CHEBI:6541</a>) </span></span></dd></dl>','Benzene and substituted derivatives','<p>Losartan has a total plasma clearance of 600mL/min and a renal clearance of 75mL/min.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. (PubMed ID 16029066)\" href=\"#reference-A1033\">1</a></sup> E-3174, the active metabolite, has a total plasma clearance of 50mL/min and a renal clearance of 25mL/min.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. (PubMed ID 16029066)\" href=\"#reference-A1033\">1</a></sup></p>','This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.','Biphenyls and derivatives','<li>Take at the same time every day.</li>\n<li>Take with or without food. Food delays absorption, but does not affect the extent of absorption.</li>','Drugs.com Drug Page',' , Agents Acting on the Renin-Angiotensin System , Agents causing angioedema , Agents causing hyperkalemia , Angiotensin 2 Receptor Blocker , Angiotensin II receptor antagonists , Angiotensin II receptor blockers (ARBs) and calcium channel blockers , Angiotensin II receptor blockers (ARBs) and diuretics , Angiotensin II receptor blockers (ARBs), plain , Angiotensin II Type 1 Receptor Blockers , Angiotensin II Type 2 Receptor Blockers , Angiotensin Receptor Antagonists , Antiarrhythmic agents , Antihypertensive Agents , Antihypertensive Agents Indicated for Hypertension , Benzene Derivatives , Biphenyl Compounds , BSEP/ABCB11 Substrates , Cardiovascular Agents , Cytochrome P-450 CYP2C19 Inhibitors , Cytochrome P-450 CYP2C19 inhibitors (strength unknown) , Cytochrome P-450 CYP2C8 Inhibitors , Cytochrome P-450 CYP2C8 Inhibitors (strength unknown) , Cytochrome P-450 CYP2C9 Substrates , 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 , Drugs causing inadvertant photosensitivity , Hypotensive Agents , Imidazoles , OAT1/SLC22A6 inhibitors , P-glycoprotein inhibitors , P-glycoprotein substrates , Photosensitizing Agents , Potential QTc-Prolonging Agents , QTc Prolonging Agents , Tetrazoles , UGT1A1 Substrates , UGT1A3 substrates , UGT2B17 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>178-184</td><td>http://www.chemspider.com/Chemical-Structure.3824.html</td></tr><tr><td>boiling point (°C)</td><td>682</td><td>http://www.chemspider.com/Chemical-Structure.3824.html</td></tr><tr><td>water solubility</td><td>&lt;1mg/mL</td><td>http://www.chemspider.com/Chemical-Structure.3824.html</td></tr><tr><td>logP</td><td>1.19</td><td>https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/20-386S019_Cozaar_EAFONSI.pdf</td></tr><tr><td>pKa</td><td>5.5</td><td>MERCK INDEX (1996); approx.</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">imidazoles, biphenylyltetrazole (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6541\" rel=\"noopener\" target=\"_blank\">CHEBI:6541</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/HMDB0014816\" rel=\"noopener\" target=\"_blank\">HMDB0014816</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:D08146\" rel=\"noopener\" target=\"_blank\">D08146</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:C07072\" rel=\"noopener\" target=\"_blank\">C07072</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=3961\" rel=\"noopener\" target=\"_blank\">3961</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=46506538\" rel=\"noopener\" target=\"_blank\">46506538</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.3824.html\" rel=\"noopener\" target=\"_blank\">3824</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=82258\" rel=\"noopener\" target=\"_blank\">82258</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=52175\" rel=\"noopener\" target=\"_blank\">52175</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=6541\" rel=\"noopener\" target=\"_blank\">6541</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/CHEMBL191\" rel=\"noopener\" target=\"_blank\">CHEMBL191</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/ZINC000003873160\" rel=\"noopener\" target=\"_blank\">ZINC000003873160</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=DAP000523\" rel=\"noopener\" target=\"_blank\">DAP000523</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/PA450268\" rel=\"noopener\" target=\"_blank\">PA450268</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=590\" 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/LSN\" rel=\"noopener\" target=\"_blank\">LSN</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/losar.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/losartan.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/Losartan\" rel=\"noopener\" target=\"_blank\">Losartan</a></dd></dl>','<li>Take at the same time every day.</li>\n<li>Take with or without food. Food delays absorption, but does not affect the extent of absorption.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A1033\">Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. [<a href=\"/articles/A1033\" target=\"_blank\">Article</a>] </li><li id=\"reference-A415\">Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [<a href=\"/articles/A415\" target=\"_blank\">Article</a>] </li><li id=\"reference-L7423\">FDA Approved Drug Products: Losartan Oral Tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020386s062lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7426\">FDA Approved Drug Products: Losartan and Hydrochlorothiazide Oral Tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020387s063lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7441\">Cayman Chemicals: Losartan Potassium MSDS [<a href=\"https://www.caymanchem.com/msdss/10006594m.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>The terminal elimination half life of losartan is 1.5-2.5 hours while the active metabolite has a half life of 6-9 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. (PubMed ID 16029066)\" href=\"#reference-A1033\">1</a></sup></p>','HMDB0014816','(2-butyl-4-chloro-1-{[2\'-(2H-1,2,3,4-tetrazol-5-yl)-[1,1\'-biphenyl]-4-yl]methyl}-1H-imidazol-5-yl)methanol','InChI=1S/C22H23ClN6O/c1-2-3-8-20-24-21(23)19(14-30)29(20)13-15-9-11-16(12-10-15)17-6-4-5-7-18(17)22-25-27-28-26-22/h4-7,9-12,30H,2-3,8,13-14H2,1H3,(H,25,26,27,28)','PSIFNNKUMBGKDQ-UHFFFAOYSA-N','<p>Losartan is indicated to treat hypertension in patients older than 6 years, reduce the risk of stroke in patients with hypertension and left ventricular hypertrophy (though this benefit may not extend to patients with African heritage), and to treat diabetic nephropathy with elevated serum creatinine and proteinuria in patients with type 2 diabetes and hypertension.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan Oral Tablets\" href=\"#reference-L7423\">3</a></sup> Losartan with hydrochlorothiazide is indicated to treat hypertension and to reduce the risk of stroke in patients with hypertension and left ventricular hypertrophy (though this benefit may not extend to patients with African heritage).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan and Hydrochlorothiazide Oral Tablets\" href=\"#reference-L7426\">4</a></sup></p>','C07072','D08146','Organic compounds','<p>Losartan is metabolized to an aldehyde intermediate, E-3179, which is further metabolized to a carboxylic acid, E-3174, by cytochrome P450s like CYP2C9.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. (PubMed ID 16029066)\" href=\"#reference-A1033\">1</a></sup> Losartan can also be hydroxylated to an inactive metabolite, P1.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. (PubMed ID 16029066)\" href=\"#reference-A1033\">1</a></sup> Approximately 14% of losartan is metabolized to E-3174.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. (PubMed ID 16029066)\" href=\"#reference-A1033\">1</a></sup> Losartan can be metabolized by CYP3A4, CYP2C9, and CYP2C10.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. (PubMed ID 16029066)\" href=\"#reference-A1033\">1</a></sup> Losartan can also be glucuronidated by UGT1A1, UGT1A3, UGT1A10, UGT2B7, and UGT 2B17.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. (PubMed ID 19515014)\" href=\"#reference-A415\">2</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteromonocyclic compounds','LSN','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000162?highlight[compounds][]=DB00678&amp;highlight[proteins][]=DB00678\">Losartan Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA450268','<p>Losartan is 98.6-98.8% protein bound and the active metabolite (E-3174) is 99.7% protein bound in serum.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. (PubMed ID 16029066)\" href=\"#reference-A1033\">1</a></sup></p>','3961','46506538','<p>A single oral dose of losartan leads to 4% recovery in the urine as unchanged losartan, 6% in the urine as the active metabolite.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan Oral Tablets\" href=\"#reference-L7423\">3</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan and Hydrochlorothiazide Oral Tablets\" href=\"#reference-L7426\">4</a></sup> Oral radiolabelled losartan is 35% recovered in urine and 60% in feces.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan Oral Tablets\" href=\"#reference-L7423\">3</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan and Hydrochlorothiazide Oral Tablets\" href=\"#reference-L7426\">4</a></sup> Intravenous radiolabelled losartan is 45% recovered in urine and 50% in feces.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan Oral Tablets\" href=\"#reference-L7423\">3</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan and Hydrochlorothiazide Oral Tablets\" href=\"#reference-L7426\">4</a></sup></p>','RxList Drug Page','52175','CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1','Solid','Biphenyls and derivatives','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1,2,4,5-tetrasubstituted imidazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</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 heteromonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl chloride</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\">Azole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Biphenyl</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\">Imidazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">N-substituted imidazole</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\">Organochloride</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\">Phenyltetrazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetrazole</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>','Benzenoids','<span class=\"citations\"><p>Gordon C. Campbell, Jr., Anil M. Dwivedi, Dorothy A. Levorse, James A. McCauley, Krishnaswamy S. Raghavan, \"Polymorphs of losartan and the process for the preparation of form II of losartan.\" U.S. Patent US5608075, issued May, 1994.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=5608075&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5608075</a>','DAP000523','<p>The oral TDLO in mice is 1000mg/kg and in rats is 2000mg/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan Oral Tablets\" href=\"#reference-L7423\">3</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan and Hydrochlorothiazide Oral Tablets\" href=\"#reference-L7426\">4</a></sup> In humans the TDLO for men is 10mg/kg/2W and for women is 1mg/kg/1D.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Cayman Chemicals: Losartan Potassium MSDS\" href=\"#reference-L7441\">5</a></sup></p><p>Symptoms of overdose are likely to include hypotension, tachycardia, or bradycardia due to vagal stimulation.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan Oral Tablets\" href=\"#reference-L7423\">3</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan and Hydrochlorothiazide Oral Tablets\" href=\"#reference-L7426\">4</a></sup> Supportive treatment should be instituted for symptomatic hypotension.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan Oral Tablets\" href=\"#reference-L7423\">3</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan and Hydrochlorothiazide Oral Tablets\" href=\"#reference-L7426\">4</a></sup> Hemodialysis will not remove losartan or its active metabolite due to their high rates of protein binding.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan Oral Tablets\" href=\"#reference-L7423\">3</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Losartan and Hydrochlorothiazide Oral Tablets\" href=\"#reference-L7426\">4</a></sup></p>','JMS50MPO89','<p>The volume of distribution of losartan is 34.4±17.9L and 10.3±1.1L for the active metabolite (E-3174).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. (PubMed ID 16029066)\" href=\"#reference-A1033\">1</a></sup></p>','Losartan','ZINC000003873160'),(46,'Furosemide','furosemide','Furosemide is a loop diuretic used to treat hypertension and edema in congestive heart failure, liver cirrhosis, renal disease, and hypertension.','Lasix','Furosemide','<p>Furosemide is a potent loop diuretic that acts on the kidneys to ultimately increase water loss from the body. It is an anthranilic acid derivative.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Furosemide - FDA Label\" href=\"#reference-L7958\">9</a></sup> Furosemide is used for edema secondary to various clinical conditions, such as congestive heart failure exacerbation, liver failure, renal failure, and high blood pressure.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Furosemide - StatPearls - NCBI Bookshelf\" href=\"#reference-L7961\">10</a></sup> It mainly works by inhibiting electrolyte reabsorption from the kidneys and enhancing the excretion of water from the body. Furosemide has a fast onset and short duration of action and has been used safely and effectively in both pediatric and adult patients.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Prandota J: Clinical pharmacology of furosemide in children: a supplement. Am J Ther. 2001 Jul-Aug;8(4):275-89. (PubMed ID 11441327)\" href=\"#reference-A182495\">1</a></sup> The use of furosemide is particularly beneficial in clinical settings that require a drug with a higher diuretic potential. In addition to oral formulations, the solution for intravenous and intramuscular administration is also available, which is typically limited to patients who are unable to take oral medication or for patients in emergency clinical situations.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Furosemide - FDA Label\" href=\"#reference-L7958\">9</a></sup></p>','C12H11ClN2O5S','DB00695','Approved, Vet approved','Small Molecule','Average: 330.744 Monoisotopic: 330.007719869 ',' , C03EB — High-ceiling diuretics and potassium-sparing agents , C03E — DIURETICS AND POTASSIUM-SPARING AGENTS IN COMBINATION , C03 — DIURETICS , C — CARDIOVASCULAR SYSTEM , C03CA — Sulfonamides, plain , C03C — HIGH-CEILING DIURETICS , C03 — DIURETICS , C — CARDIOVASCULAR SYSTEM , G01AE — Sulfonamides , G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS , G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS , G — GENITO URINARY SYSTEM AND SEX HORMONES , C03CB — Sulfonamides and potassium in combination , C03C — HIGH-CEILING DIURETICS , C03 — DIURETICS , C — CARDIOVASCULAR SYSTEM','<p>Following oral administration, furosemide is absorbed from the gastrointestinal tract.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lasix Oral (furosemide) Product Monograph\" href=\"#reference-L9659\">12</a></sup> It displays variable bioavailability from oral dosage forms, ranging from 10 to 90%.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Oh SW, Han SY: Loop Diuretics in Clinical Practice. Electrolyte Blood Press. 2015 Jun;13(1):17-21. doi: 10.5049/EBP.2015.13.1.17. Epub 2015 Jun 30. (PubMed ID 26240596)\" href=\"#reference-A31831\">4</a></sup> The oral bioavailability of furosemide from oral tablets or oral solution is about 64% and 60%, respectively, of that from an intravenous injection of the drug.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Furosemide - FDA Label\" href=\"#reference-L7958\">9</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=\"Benzoic acids carrying a halogen atom at the 4-position of the benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003103\" rel=\"noopener\" target=\"_blank\">4-halobenzoic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Benzoic acids containing an amine group attached to the benzene moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002948\" rel=\"noopener\" target=\"_blank\">Aminobenzoic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Benzoic acids carrying a halogen atom on the benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003097\" rel=\"noopener\" target=\"_blank\">Halobenzoic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing a benzenesulfonyl group, which consists of a monocyclic benzene moiety that carries a sulfonyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004233\" rel=\"noopener\" target=\"_blank\">Benzenesulfonyl compounds</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=\"Organic amines where the amine group is secondary and linked on one end to a phenyl group and on the other end, to an alkyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003924\" rel=\"noopener\" target=\"_blank\">Phenylalkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Secondary alkylarylamines with the general formula HN(R)R\' (R = alkyl, R\' = aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002458\" rel=\"noopener\" target=\"_blank\">Secondary alkylarylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing one or more chlorine atoms attached to a benzene moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001099\" rel=\"noopener\" target=\"_blank\">Chlorobenzenes</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 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=\"Organic compounds containing the acyl chloride functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001030\" rel=\"noopener\" target=\"_blank\">Aryl chlorides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a furan ring, which is a five-member aromatic ring with one oxygen atom, four carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000076\" rel=\"noopener\" target=\"_blank\">Furans</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003890\" rel=\"noopener\" target=\"_blank\">Vinylogous amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organosulfur compounds with the general formula RS(=O)(=O)N(R\')R\'\'  (R = organyl, R\'-R\\&quot; = any atom but N).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003137\" rel=\"noopener\" target=\"_blank\">Aminosulfonyl compounds</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 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=\"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 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=\"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 chlorine atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001516\" rel=\"noopener\" target=\"_blank\">Organochlorides</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=\"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></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>','Not Available','Not Available','25902','54-31-9','47426','CHEMBL35','3322','<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 aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.</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 sulfonamide group that is S-linked to a benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000031\" rel=\"noopener\" target=\"_blank\">Benzenesulfonamides</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 a benzenesulfonamide moiety with an amine group attached to the benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001925\" rel=\"noopener\" target=\"_blank\">Aminobenzenesulfonamides</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=\"Benzoic acids carrying a halogen atom at the 4-position of the benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003103\" rel=\"noopener\" target=\"_blank\">4-halobenzoic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Benzoic acids containing an amine group attached to the benzene moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002948\" rel=\"noopener\" target=\"_blank\">Aminobenzoic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Benzoic acids carrying a halogen atom on the benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003097\" rel=\"noopener\" target=\"_blank\">Halobenzoic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing a benzenesulfonyl group, which consists of a monocyclic benzene moiety that carries a sulfonyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004233\" rel=\"noopener\" target=\"_blank\">Benzenesulfonyl compounds</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=\"Organic amines where the amine group is secondary and linked on one end to a phenyl group and on the other end, to an alkyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003924\" rel=\"noopener\" target=\"_blank\">Phenylalkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Secondary alkylarylamines with the general formula HN(R)R\' (R = alkyl, R\' = aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002458\" rel=\"noopener\" target=\"_blank\">Secondary alkylarylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing one or more chlorine atoms attached to a benzene moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001099\" rel=\"noopener\" target=\"_blank\">Chlorobenzenes</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 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=\"Organic compounds containing the acyl chloride functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001030\" rel=\"noopener\" target=\"_blank\">Aryl chlorides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a furan ring, which is a five-member aromatic ring with one oxygen atom, four carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000076\" rel=\"noopener\" target=\"_blank\">Furans</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003890\" rel=\"noopener\" target=\"_blank\">Vinylogous amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organosulfur compounds with the general formula RS(=O)(=O)N(R\')R\'\'  (R = organyl, R\'-R\\&quot; = any atom but N).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003137\" rel=\"noopener\" target=\"_blank\">Aminosulfonyl compounds</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 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=\"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 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=\"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 chlorine atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001516\" rel=\"noopener\" target=\"_blank\">Organochlorides</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=\"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></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=\"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\">4-halobenzoic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">4-halobenzoic acid or derivatives</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\">Aminobenzenesulfonamide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminobenzoic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminobenzoic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminosulfonyl compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aniline or substituted anilines</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\">Aralkylamine</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 chloride</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl halide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenesulfonyl group</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 class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoyl</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\">Chlorobenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Furan</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Halobenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Halobenzoic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Halobenzoic acid or derivatives</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\">Monocarboxylic acid or derivatives</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\">Organochloride</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\">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\">Organosulfur compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenylalkylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary aliphatic/aromatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Sulfonyl</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous amide</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 37 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\">sulfonamide, furans, chlorobenzoic acid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:47426\" rel=\"noopener\" target=\"_blank\">CHEBI:47426</a>) </span></span></dd></dl>','Benzene and substituted derivatives','<p>Following intravenous administration of 400 mg furosemide, the plasma clearance was 1.23 mL/kg/min in patients with heart failure and 2.34 mL/kg/min in healthy subjects, respectively.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Andreasen F, Mikkelsen E: Distribution, elimination and effect of furosemide in normal subjects and in patients with heart failure. Eur J Clin Pharmacol. 1977 Aug 17;12(1):15-22. doi: 10.1007/bf00561400. (PubMed ID 902673)\" href=\"#reference-A188838\">6</a></sup></p>','This compound belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.','Aminobenzenesulfonamides','<li>Avoid excessive or chronic alcohol consumption. Alcohol increases the risk of orthostatic hypotension.</li>\n<li>Avoid natural licorice. Avoid licorice in large amounts, as it may lead to hypokalemia.</li>\n<li>Increase consumption of potassium-rich foods. This medication may cause potassium depletion. Foods containing potassium include bananas and orange juice.</li>','Drugs.com Drug Page',' , Acids, Carbocyclic , Amides , Amines , Aminobenzoates , Aniline Compounds , Antihypertensive Agents , Antihypertensive Agents Indicated for Hypertension , Benzene Derivatives , Benzoates , Cardiovascular Agents , Diuretics , Drugs causing inadvertant photosensitivity , Drugs that are Mainly Renally Excreted , High-Ceiling Diuretics , High-Ceiling Diuretics and Potassium-Sparing Agents , Hyperglycemia-Associated Agents , Hypotensive Agents , Increased Diuresis at Loop of Henle , Membrane Transport Modulators , Natriuretic Agents , Nephrotoxic agents , Non Potassium Sparing Diuretics , OAT1/SLC22A6 inhibitors , OAT3/SLC22A8 Inhibitors , Ototoxic agents , Photosensitizing Agents , Sodium Potassium Chloride Symporter Inhibitors , Sulfanilamides , Sulfonamides , Sulfones , Sulfur Compounds , Thyroxine-binding globulin substrates , UGT1A1 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>220</td><td>MSDS</td></tr><tr><td>water solubility</td><td>73.1 mg/L (at 30 °C)</td><td>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</td></tr><tr><td>logP</td><td>2.03</td><td>SANGSTER (1993)</td></tr><tr><td>logS</td><td>-3.66</td><td>ADME Research, USCD</td></tr><tr><td>Caco2 permeability</td><td>-6.5</td><td>ADME Research, USCD</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">sulfonamide, furans, chlorobenzoic acid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:47426\" rel=\"noopener\" target=\"_blank\">CHEBI:47426</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/HMDB0001933\" rel=\"noopener\" target=\"_blank\">HMDB0001933</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:D00331\" rel=\"noopener\" target=\"_blank\">D00331</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:C07017\" rel=\"noopener\" target=\"_blank\">C07017</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=3440\" rel=\"noopener\" target=\"_blank\">3440</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=46506779\" rel=\"noopener\" target=\"_blank\">46506779</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.3322.html\" rel=\"noopener\" target=\"_blank\">3322</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=25902\" rel=\"noopener\" target=\"_blank\">25902</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=4603\" rel=\"noopener\" target=\"_blank\">4603</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=47426\" rel=\"noopener\" target=\"_blank\">47426</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/CHEMBL35\" rel=\"noopener\" target=\"_blank\">CHEMBL35</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/ZINC000000035804\" rel=\"noopener\" target=\"_blank\">ZINC000000035804</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=DAP000043\" rel=\"noopener\" target=\"_blank\">DAP000043</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/PA449719\" rel=\"noopener\" target=\"_blank\">PA449719</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/FUN\" rel=\"noopener\" target=\"_blank\">FUN</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/furos.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/furosemide.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/Furosemide\" rel=\"noopener\" target=\"_blank\">Furosemide</a></dd></dl>','<li>Avoid excessive or chronic alcohol consumption. Alcohol increases the risk of orthostatic hypotension.</li>\n<li>Avoid natural licorice. Avoid licorice in large amounts, as it may lead to hypokalemia.</li>\n<li>Increase consumption of potassium-rich foods. This medication may cause potassium depletion. Foods containing potassium include bananas and orange juice.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A182495\">Prandota J: Clinical pharmacology of furosemide in children: a supplement. Am J Ther. 2001 Jul-Aug;8(4):275-89. [<a href=\"/articles/A182495\" target=\"_blank\">Article</a>] </li><li id=\"reference-A183281\">Ponto LL, Schoenwald RD: Furosemide (frusemide). A pharmacokinetic/pharmacodynamic review (Part I). Clin Pharmacokinet. 1990 May;18(5):381-408. doi: 10.2165/00003088-199018050-00004. [<a href=\"/articles/A183281\" target=\"_blank\">Article</a>] </li><li id=\"reference-A183284\">Prandota J: Furosemide: progress in understanding its diuretic, anti-inflammatory, and bronchodilating mechanism of action, and use in the treatment of respiratory tract diseases. Am J Ther. 2002 Jul-Aug;9(4):317-28. [<a href=\"/articles/A183284\" target=\"_blank\">Article</a>] </li><li id=\"reference-A31831\">Oh SW, Han SY: Loop Diuretics in Clinical Practice. Electrolyte Blood Press. 2015 Jun;13(1):17-21. doi: 10.5049/EBP.2015.13.1.17. Epub 2015 Jun 30. [<a href=\"/articles/A31831\" target=\"_blank\">Article</a>] </li><li id=\"reference-A183563\">Pichette V, du Souich P: Role of the kidneys in the metabolism of furosemide: its inhibition by probenecid. J Am Soc Nephrol. 1996 Feb;7(2):345-9. [<a href=\"/articles/A183563\" target=\"_blank\">Article</a>] </li><li id=\"reference-A188838\">Andreasen F, Mikkelsen E: Distribution, elimination and effect of furosemide in normal subjects and in patients with heart failure. Eur J Clin Pharmacol. 1977 Aug 17;12(1):15-22. doi: 10.1007/bf00561400. [<a href=\"/articles/A188838\" target=\"_blank\">Article</a>] </li><li id=\"reference-A189315\">Perez J, Sitar DS, Ogilvie RI: Biotransformation of furosemide in patients with acute pulmonary edema. Drug Metab Dispos. 1979 Nov-Dec;7(6):383-7. [<a href=\"/articles/A189315\" target=\"_blank\">Article</a>] </li><li id=\"reference-T28\">28. (2012). In Rang and Dale\'s Pharmacology (7th ed., pp. 352-354). Edinburgh: Elsevier/Churchill Livingstone. [<a href=\"https://www.google.com/search?tbo=p&amp;tbm=bks&amp;q=978-0-7020-3471-8\" rel=\"noopener\" target=\"_blank\">ISBN:978-0-7020-3471-8</a>] </li><li id=\"reference-L7958\">Furosemide - FDA Label [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018667s036lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7961\">Furosemide - StatPearls - NCBI Bookshelf [<a href=\"https://www.ncbi.nlm.nih.gov/books/NBK499921/\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7964\">Furosemide SAFETY DATA SHEET - Cayman Chemical [<a href=\"https://www.caymanchem.com/msdss/17273m.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L9659\">Lasix Oral (furosemide) Product Monograph [<a href=\"http://products.sanofi.ca/en/lasix.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>The half-life from the dose of 40 mg furosemide was 4 hours following oral administration and 4.5 hours following intravenous administration. The terminal half-life of furosemide is approximately 2 hours following parenteral administration.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Furosemide - FDA Label\" href=\"#reference-L7958\">9</a></sup> The terminal half-life may be increased up to 24 hours in patients with severe renal failure.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lasix Oral (furosemide) Product Monograph\" href=\"#reference-L9659\">12</a></sup></p>','HMDB0001933','4-chloro-2-{[(furan-2-yl)methyl]amino}-5-sulfamoylbenzoic acid','InChI=1S/C12H11ClN2O5S/c13-9-5-10(15-6-7-2-1-3-20-7)8(12(16)17)4-11(9)21(14,18)19/h1-5,15H,6H2,(H,16,17)(H2,14,18,19)','ZZUFCTLCJUWOSV-UHFFFAOYSA-N','<p>Furosemide is indicated for the treatment of edema associated with congestive heart failure, cirrhosis of the liver, and renal disease, including the nephrotic syndrome, in adults and pediatric patients.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Furosemide - FDA Label\" href=\"#reference-L7958\">9</a></sup> </p><p>Oral furosemide is indicated alone for the management of mild to moderate hypertension or severe hypertension in combination with other antihypertensive medications.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lasix Oral (furosemide) Product Monograph\" href=\"#reference-L9659\">12</a></sup></p><p>Intravenous furosemide is indicated as adjunctive therapy in acute pulmonary edema when a rapid onset of diuresis is desired.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Furosemide - FDA Label\" href=\"#reference-L7958\">9</a></sup></p>','C07017','D00331','Organic compounds','<p>The metabolism of furosemide occurs mainly in the kidneys and the liver, to a smaller extent. The kidneys are responsible for about 85% of total furosemide total clearance, where about 40% involves biotransformation.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pichette V, du Souich P: Role of the kidneys in the metabolism of furosemide: its inhibition by probenecid. J Am Soc Nephrol. 1996 Feb;7(2):345-9. (PubMed ID 8785407)\" href=\"#reference-A183563\">5</a></sup> Two major metabolites of furosemide are furosemide glucuronide, which is pharmacologically active, and saluamine (CSA) or 4-chloro-5-sulfamoylanthranilic acid.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Ponto LL, Schoenwald RD: Furosemide (frusemide). A pharmacokinetic/pharmacodynamic review (Part I). Clin Pharmacokinet. 1990 May;18(5):381-408. doi: 10.2165/00003088-199018050-00004. (PubMed ID 2185908)\" href=\"#reference-A183281\">2</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteromonocyclic compounds','FUN','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000115?highlight[compounds][]=DB00695&amp;highlight[proteins][]=DB00695\">Furosemide Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA449719','<p>Plasma concentrations ranging from 1 to 400 mcg/mL are about 91-99% bound in healthy individuals. The unbound fraction is about 2.3-4.1% at therapeutic concentrations.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lasix Oral (furosemide) Product Monograph\" href=\"#reference-L9659\">12</a></sup> Furosemide mainly binds to serum albumin.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Furosemide - FDA Label\" href=\"#reference-L7958\">9</a></sup></p>','3440','46506779','<p>The kidneys are responsible for 85% of total furosemide total clearance, where about 43% of the drug undergoes renal excretion.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pichette V, du Souich P: Role of the kidneys in the metabolism of furosemide: its inhibition by probenecid. J Am Soc Nephrol. 1996 Feb;7(2):345-9. (PubMed ID 8785407)\" href=\"#reference-A183563\">5</a></sup> Significantly more furosemide is excreted in urine following the I.V. injection than after the tablet or oral solution. Approximately 50% of the furosemide load is excreted unchanged in urine, and the rest is metabolized into glucuronide in the kidney.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Oh SW, Han SY: Loop Diuretics in Clinical Practice. Electrolyte Blood Press. 2015 Jun;13(1):17-21. doi: 10.5049/EBP.2015.13.1.17. Epub 2015 Jun 30. (PubMed ID 26240596)\" href=\"#reference-A31831\">4</a></sup></p>','RxList Drug Page','4603','NS(=O)(=O)C1=C(Cl)C=C(NCC2=CC=CO2)C(=C1)C(O)=O','Solid','Benzenesulfonamides','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">4-halobenzoic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">4-halobenzoic acid or derivatives</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\">Aminobenzenesulfonamide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminobenzoic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminobenzoic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminosulfonyl compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aniline or substituted anilines</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\">Aralkylamine</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 chloride</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl halide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenesulfonyl group</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 class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoyl</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\">Chlorobenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Furan</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Halobenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Halobenzoic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Halobenzoic acid or derivatives</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\">Monocarboxylic acid or derivatives</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\">Organochloride</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\">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\">Organosulfur compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenylalkylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary aliphatic/aromatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Sulfonyl</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous amide</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 37 more</a>','Benzenoids','<span class=\"citations\"><p>Angelo Signor, Alfredo Guerrato, Giovanni Signor, \"Process for the preparation of furosemide.\" U.S. Patent US5739361, issued June, 1971.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=5739361&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5739361</a>','DAP000043','<p>Clinical consequences from overdose depend on the extent of electrolyte and fluid loss and include dehydration, blood volume reduction, hypotension, electrolyte imbalance, hypokalemia, hypochloremic alkalosis,<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Furosemide - FDA Label\" href=\"#reference-L7958\">9</a></sup> hemoconcentration, cardiac arrhythmias (including A-V block and ventricular fibrillation).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lasix Oral (furosemide) Product Monograph\" href=\"#reference-L9659\">12</a></sup> Symptoms of overdose include acute renal failure, thrombosis, delirious states, flaccid paralysis, apathy and confusion. In cirrhotic patients, overdosage might precipitate hepatic coma.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lasix Oral (furosemide) Product Monograph\" href=\"#reference-L9659\">12</a></sup></p><p>In rats, the oral LD<sub>50</sub>, intraperitoneal LD<sub>50</sub>, and subcutaneous LD<sub>50</sub> is 2600 mg/kg, 800 mg/kg, and 4600 mg/kg, respectively. The Lowest published toxic dose (TDLo) in a female is 6250 μg/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Furosemide SAFETY DATA SHEET - Cayman Chemical\" href=\"#reference-L7964\">11</a></sup></p>','7LXU5N7ZO5','<p>The volume of distribution following intravenous administration of 40 mg furosemide were 0.181 L/kg in healthy subjects and 0.140 L/kg in patients with heart failure.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Andreasen F, Mikkelsen E: Distribution, elimination and effect of furosemide in normal subjects and in patients with heart failure. Eur J Clin Pharmacol. 1977 Aug 17;12(1):15-22. doi: 10.1007/bf00561400. (PubMed ID 902673)\" href=\"#reference-A188838\">6</a></sup></p>','Furosemide','ZINC000000035804'),(47,'Eplerenone','eplerenone','Eplerenone is an aldosterone receptor antagonist used to improve survival of patients with symptomatic heart failure and to reduce blood pressure.','Inspra','Eplerenone','<p>Eplerenone, an aldosterone receptor antagonist similar to spironolactone, has been shown to produce sustained increases in plasma renin and serum aldosterone, consistent with inhibition of the negative regulatory feedback of aldosterone on renin secretion. The resulting increased plasma renin activity and aldosterone circulating levels do not overcome the effects of eplerenone. Eplerenone selectively binds to recombinant human mineralocorticoid receptors relative to its binding to recombinant human glucocorticoid, progesterone and androgen receptors.</p>','C24H30O6','DB00700','Approved','Small Molecule','Average: 414.4914 Monoisotopic: 414.204238692 ',' , C03DA — Aldosterone antagonists , C03D — POTASSIUM-SPARING AGENTS , C03 — DIURETICS , C — CARDIOVASCULAR SYSTEM','<p>The absolute bioavailability of eplerenone is unknown.</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 an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001729\" rel=\"noopener\" target=\"_blank\">Oxepanes</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 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=\"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=\"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=\"Organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR\', where R=H or organyl group and R\'=methyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003416\" rel=\"noopener\" target=\"_blank\">Methyl esters</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 containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000159\" rel=\"noopener\" target=\"_blank\">Epoxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the dialkyl ether functional group, with the formula ROR\', where R and R\' are alkyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001167\" rel=\"noopener\" target=\"_blank\">Dialkyl ethers</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></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=\"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 1 more</a>','Not Available','Not Available','50318300','107724-20-9','31547','CHEMBL1095097','10203511','<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 spironolactones and derivatives. These are steroid lactones with a structure based on the spironolactone skeleton.</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=\"Sterol lipids containing a lactone moiety linked to the steroid skeleton.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001125\" rel=\"noopener\" target=\"_blank\">Steroid lactones</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=\"Steroid lactones with a structure based on the spironolactone skeleton.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001807\" rel=\"noopener\" target=\"_blank\">Spironolactones and derivatives</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 an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001729\" rel=\"noopener\" target=\"_blank\">Oxepanes</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 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=\"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=\"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=\"Organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR\', where R=H or organyl group and R\'=methyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003416\" rel=\"noopener\" target=\"_blank\">Methyl esters</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 containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000159\" rel=\"noopener\" target=\"_blank\">Epoxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the dialkyl ether functional group, with the formula ROR\', where R and R\' are alkyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001167\" rel=\"noopener\" target=\"_blank\">Dialkyl ethers</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></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=\"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 1 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\">Aliphatic heteropolycyclic 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 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\">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\">Dialkyl ether</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\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Gamma butyrolactone</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\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Lactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Methyl ester</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\">Oxepane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxirane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Spironolactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetrahydrofuran</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 13 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 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\">3-oxo steroid, epoxide, methyl ester, gamma-lactone, oxaspiro compound, steroid acid ester (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31547\" rel=\"noopener\" target=\"_blank\">CHEBI:31547</a>) </span></span></dd></dl>','Steroids and steroid derivatives','','This compound belongs to the class of organic compounds known as spironolactones and derivatives. These are steroid lactones with a structure based on the spironolactone skeleton.','Spironolactones and derivatives','<li>Avoid grapefruit products. Grapefruit juice may increase the serum levels of eplerenone by 25% by inhibiting CYP3A4.</li>\n<li>Take with or without food.</li>','Drugs.com Drug Page',' , Agents causing hyperkalemia , Antihypertensive Agents , Antihypertensive Agents Indicated for Hypertension , Cardiovascular Agents , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A5 Substrates , Cytochrome P-450 CYP3A7 Substrates , Cytochrome P-450 Substrates , Diuretics , Fused-Ring Compounds , Hormone Antagonists , Hormones, Hormone Substitutes, and Hormone Antagonists , Hypotensive Agents , Lactones , Mineralocorticoid (Aldosterone) Receptor Antagonists , Mineralocorticoid Receptor Antagonists , Natriuretic Agents , Potassium-Sparing Diuretics , Pregnanes , Pregnenes , Steroids','<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>water solubility</td><td>Slightly soluble</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>logP</td><td>1.3</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\">3-oxo steroid, epoxide, methyl ester, gamma-lactone, oxaspiro compound, steroid acid ester (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31547\" rel=\"noopener\" target=\"_blank\">CHEBI:31547</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/HMDB0014838\" rel=\"noopener\" target=\"_blank\">HMDB0014838</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:D01115\" rel=\"noopener\" target=\"_blank\">D01115</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:C12512\" rel=\"noopener\" target=\"_blank\">C12512</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=443872\" rel=\"noopener\" target=\"_blank\">443872</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=46509053\" rel=\"noopener\" target=\"_blank\">46509053</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.10203511.html\" rel=\"noopener\" target=\"_blank\">10203511</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=50318300\" rel=\"noopener\" target=\"_blank\">50318300</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=298869\" rel=\"noopener\" target=\"_blank\">298869</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=31547\" rel=\"noopener\" target=\"_blank\">31547</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/CHEMBL1095097\" rel=\"noopener\" target=\"_blank\">CHEMBL1095097</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/ZINC000003985982\" rel=\"noopener\" target=\"_blank\">ZINC000003985982</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=DAP000085\" rel=\"noopener\" target=\"_blank\">DAP000085</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/PA164749044\" rel=\"noopener\" target=\"_blank\">PA164749044</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=2876\" 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/YNU\" rel=\"noopener\" target=\"_blank\">YNU</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/inspra.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/eplerenone.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/ins1681.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/Eplerenone\" rel=\"noopener\" target=\"_blank\">Eplerenone</a></dd></dl>','<li>Avoid grapefruit products. Grapefruit juice may increase the serum levels of eplerenone by 25% by inhibiting CYP3A4.</li>\n<li>Take with or without food.</li>','<span class=\"not-available\">Not Available</span>','<p>4-6 hours</p>','HMDB0014838','methyl (1\'R,2R,2\'S,9\'R,10\'R,11\'S,15\'S,17\'R)-2\',15\'-dimethyl-5,5\'-dioxo-18\'-oxaspiro[oxolane-2,14\'-pentacyclo[8.8.0.0^{1,17}.0^{2,7}.0^{11,15}]octadecan]-6\'-ene-9\'-carboxylate','InChI=1S/C24H30O6/c1-21-7-4-14(25)10-13(21)11-15(20(27)28-3)19-16-5-8-23(9-6-18(26)30-23)22(16,2)12-17-24(19,21)29-17/h10,15-17,19H,4-9,11-12H2,1-3H3/t15-,16+,17-,19+,21+,22+,23-,24-/m1/s1','JUKPWJGBANNWMW-VWBFHTRKSA-N','<p>For improvement of survival of stable patients with left ventricular systolic dysfunction (ejection fraction &lt;40%) and clinical evidence of congestive heart failure after an acute myocardial infarction.</p>','C12512','D01115','Organic compounds','<p>Eplerenone is metabolized primarily by CYP3A4, however, no active metabolites have been identified in human plasma.</p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aliphatic heteropolycyclic compounds','YNU','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000135?highlight[compounds][]=DB00700&amp;highlight[proteins][]=DB00700\">Eplerenone Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA164749044','<p>50%</p>','443872','46509053','<p><span class=\"not-available\">Not Available</span></p>','RxList Drug Page','298869','[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)C[C@H]1O[C@@]11[C@@]2([H])[C@@H](CC2=CC(=O)CC[C@]12C)C(=O)OC','Solid','Steroid lactones','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Aliphatic heteropolycyclic 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 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\">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\">Dialkyl ether</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\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Gamma butyrolactone</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\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Lactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Methyl ester</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\">Oxepane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxirane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Spironolactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetrahydrofuran</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 13 more</a>','Lipids and lipid-like molecules','<span class=\"citations\"><p>Bhaskar Reddy Guntoori, Svetoslav S. Bratovanov, Mohamed Ibrahim Zaki, Elena Bejan, Stephen E. Horne, \"Process for the preparation and purification of eplerenone.\" U.S. Patent US20080234478, issued September 25, 2008.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=20080234478&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US20080234478</a>','DAP000085','<p>The most likely symptoms of human overdosage would be anticipated to be hypotension or hyperkalemia. However, no cases of human overdosage with eplerenone have been reported.</p>','6995V82D0B','','Eplerenone','ZINC000003985982'),(48,'Lamivudine','lamivudine','Lamivudine is a reverse transcriptase inhibitor used to treat HIV and hepatitis B infections.','Cimduo, Combivir, Delstrigo, Dovato, Epivir, Epivir Hbv, Epzicom, Heptovir, Kivexa, Symfi, Triumeq, Trizivir, Zeffix','Lamivudine','<p>A reverse transcriptase inhibitor and zalcitabine analog in which a sulfur atom replaces the 3\' carbon of the pentose ring. It is used to treat Human Immunodeficiency Virus Type 1 (HIV-1) and hepatitis B (HBV).</p>','C8H11N3O3S','DB00709','Approved, Investigational','Small Molecule','Average: 229.256 Monoisotopic: 229.052111923 ',' , 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 , 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 , J05AF — Nucleoside and nucleotide reverse transcriptase inhibitors , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE','<p>Lamivudine was rapidly absorbed after oral administration in HIV-infected patients. Absolute bioavailability in 12 adult patients was 86% ± 16% (mean ± SD) for the 150-mg tablet and 87% ± 13% for the oral solution. The peak serum lamivudine concentration (Cmax) was 1.5 ± 0.5 mcg/mL when an oral dose of 2 mg/kg twice a day was given to HIV-1 patients. When given with food, absorption is slower, compared to the fasted state. </p>','','Human Immunodeficiency Virus\nHepatitis B 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=\"Organic compounds containing a hydroxyl 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/C0004161\" rel=\"noopener\" target=\"_blank\">Hydroxypyrimidines</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=\"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 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=\"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 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=\"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 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=\"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 a nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000278\" rel=\"noopener\" target=\"_blank\">Organonitrogen 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=\"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 1 more</a>','Not Available','Not Available','50366817','134678-17-4','63577','CHEMBL141','54812','<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=\"Organic compounds containing a hydroxyl 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/C0004161\" rel=\"noopener\" target=\"_blank\">Hydroxypyrimidines</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=\"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 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=\"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 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=\"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 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=\"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 a nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000278\" rel=\"noopener\" target=\"_blank\">Organonitrogen 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=\"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 1 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\">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\">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\">Hydropyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydroxypyrimidine</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></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\">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\">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\">Pyrimidine</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 9 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\">primary alcohol, oxacycle, monothioacetal (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63577\" rel=\"noopener\" target=\"_blank\">CHEBI:63577</a>) </span></span></dd></dl>','Nucleoside and nucleotide analogues','','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. Food delays drug absorption, but not to a clinically significant extent.</li>','Drugs.com Drug Page',' , Agents Causing Muscle Toxicity , 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 , BCRP/ABCG2 Substrates , Deoxycytidine , Deoxyribonucleosides , Dideoxynucleosides , Direct Acting Antivirals , Drugs that are Mainly Renally Excreted , Enzyme Inhibitors , Hepatitis B Virus Nucleoside Analog Reverse Transcriptase Inhibitor , Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor , Nucleic Acid Synthesis Inhibitors , Nucleic Acids, Nucleotides, and Nucleosides , Nucleoside and Nucleotide Reverse Transcriptase Inhibitors , Nucleoside Reverse Transcriptase Inhibitors , Nucleosides , OAT1/SLC22A6 Substrates , OCT1 substrates , OCT2 Substrates , P-glycoprotein substrates , Pyrimidine Nucleosides , Pyrimidines , Reverse Transcriptase Inhibitors','<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>160-162 °C</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>water solubility</td><td>70 mg/ml</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>logP</td><td>-1.4</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\">primary alcohol, oxacycle, monothioacetal (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63577\" rel=\"noopener\" target=\"_blank\">CHEBI:63577</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/HMDB0014847\" rel=\"noopener\" target=\"_blank\">HMDB0014847</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:D00353\" rel=\"noopener\" target=\"_blank\">D00353</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:C07065\" rel=\"noopener\" target=\"_blank\">C07065</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=60825\" rel=\"noopener\" target=\"_blank\">60825</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=46507855\" rel=\"noopener\" target=\"_blank\">46507855</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.54812.html\" rel=\"noopener\" target=\"_blank\">54812</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=50366817\" rel=\"noopener\" target=\"_blank\">50366817</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=68244\" rel=\"noopener\" target=\"_blank\">68244</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=63577\" rel=\"noopener\" target=\"_blank\">63577</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/CHEMBL141\" rel=\"noopener\" target=\"_blank\">CHEMBL141</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/ZINC000000012346\" rel=\"noopener\" target=\"_blank\">ZINC000000012346</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=DAP000167\" rel=\"noopener\" target=\"_blank\">DAP000167</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/PA450163\" rel=\"noopener\" target=\"_blank\">PA450163</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/3TC\" rel=\"noopener\" target=\"_blank\">3TC</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/lamivudine.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/lamivudine.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/com1513.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/Lamivudine\" rel=\"noopener\" target=\"_blank\">Lamivudine</a></dd></dl>','<li>Take with or without food. Food delays drug absorption, but not to a clinically significant extent.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A1081\">Fox Z, Dragsted UB, Gerstoft J, Phillips AN, Kjaer J, Mathiesen L, Youle M, Katlama C, Hill A, Bruun JN, Clumeck N, Dellamonica P, Lundgren JD: A randomized trial to evaluate continuation versus discontinuation of lamivudine in individuals failing a lamivudine-containing regimen: the COLATE trial. Antivir Ther. 2006;11(6):761-70. [<a href=\"/articles/A1081\" target=\"_blank\">Article</a>] </li></ol>','<p>5 to 7 hours (healthy or HBV-infected patients) </p>','HMDB0014847','4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one','InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m0/s1','JTEGQNOMFQHVDC-NKWVEPMBSA-N','<p>For the treatment of HIV infection and chronic hepatitis B (HBV).</p>','C07065','D00353','Organic compounds','<p>Metabolism of lamivudine is a minor route of elimination. In man, the only known metabolite of lamivudine is the trans-sulfoxide metabolite. This biotransformation is catalyzed by sulfotransferases. </p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteromonocyclic compounds','3TC','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000649?highlight[compounds][]=DB00709&amp;highlight[proteins][]=DB00709\">Lamivudine Metabolism Pathway</a></td><td>Drug metabolism</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000742?highlight[compounds][]=DB00709&amp;highlight[proteins][]=DB00709\">Lamivudine Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA450163','<p>&lt;36% bound to plasma protein. </p>','60825','46507855','<p>The majority of lamivudine is eliminated unchanged in urine by active organic cationic secretion. 5.2% ± 1.4% (mean ± SD) of the dose was excreted as the trans-sulfoxide metabolite in the urine. Lamivudine is excreted in human breast milk and into the milk of lactating rats.</p>','RxList Drug Page','68244','NC1=NC(=O)N(C=C1)[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\">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\">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\">Hydropyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydroxypyrimidine</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></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\">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\">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\">Pyrimidine</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 9 more</a>','Nucleosides, nucleotides, and analogues','<span class=\"citations\"><p>Jinliang LI, Feng LV, \"PROCESS FOR STEREOSELECTIVE SYNTHESIS OF LAMIVUDINE.\" U.S. Patent US20100249409, issued September 30, 2010.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=20100249409&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US20100249409</a>','DAP000167','<p>The most common reported adverse reactions (incidence ≥15%) in adults were headache, nausea, malaise and fatigue, nasal signs and symptoms, diarrhea, and cough. </p>','2T8Q726O95','<p>Apparent volume of distribution, IV administration = 1.3 ± 0.4 L/kg. Volume of distribution was independent of dose and did not correlate with body weight.</p>','Lamivudine','ZINC000000012346'),