(24,'Valproic acid','valproic-acid','Valproic acid is an anticonvulsant used to control complex partial seizures and both simple and complex absence seizures.','Depakene, Depakote, Epival','Valproic acid','<p>Valproic acid, or valproate, is an fatty acid derivative and anticonvulsant originally synthesized in 1881 by Beverly S. Burton.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lopez-Munoz F, Baumeister AA, Hawkins MF, Alamo C: The role of serendipity in the discovery of the clinical effects of psychotropic drugs: beyond of the myth. Actas Esp Psiquiatr. 2012 Jan-Feb;40(1):34-42. Epub 2012 Jan 1. (PubMed ID 22344494)\" href=\"#reference-A178051\">26</a></sup> It enjoyed use as a popular organic solvent in industry and pharmaceutical manufacturing for nearly a century. In 1963, a serendipitous discovery was made by George Carraz during his investigations into the anticonvulsant effects of khelline when he found that all of his samples, dissolved in valproic acid, exerted a similar degree of anticonvulsive activity. It first received approval on February 28, 1978 from the FDA under the trade name Depakene.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Depakene FDA\" href=\"#reference-L6190\">29</a></sup></p><p>Since then, it has been investigated for neuroprotective, anti-manic, and anti-migraine effects. It is currently a compound of interest in the field of oncology for its anti-proliferative effects and is the subject of many clinical trials in a variety of cancer types.</p>','C8H16O2','DB00313','Approved, Investigational','Small Molecule','Average: 144.2114 Monoisotopic: 144.115029756 ',' , N03AG — Fatty acid derivatives , N03A — ANTIEPILEPTICS , N03 — ANTIEPILEPTICS , N — NERVOUS SYSTEM','<p>The intravenous and oral forms of valproic acid are expected to produce the same AUC, Cmax, and Cmin at steady-state.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup> The oral delayed-release tablet formulation has a Tmax of 4 hours. Differences in absorption rate are expected from other formulations but are not considered to be clinically important in the context of chronic therapy beyond impacting frequency of dosing. Differences in absorption may create earlier Tmax or higher Cmax values on initiation of therapy and may be affected differently by meals.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Depakene FDA Label (2019)\" href=\"#reference-L6196\">30</a></sup> The extended release tablet formulation had Tmax increase from 4 hours to 8 hours when taken with food. In comparison, the sprinkle capsule formulation had Tmax increase from 3.3 hours to 4.8 hours. Bioavailability is reported to be approximately 90% with all oral formulations with enteric-coated forms possibly reaching 100%.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Zaccara G, Messori A, Moroni F: Clinical pharmacokinetics of valproic acid--1988. Clin Pharmacokinet. 1988 Dec;15(6):367-89. doi: 10.2165/00003088-198815060-00002. (PubMed ID 3149565)\" href=\"#reference-A178066\">27</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=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a carboxylic acid group with the formula -C(=O)OH.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001205\" rel=\"noopener\" target=\"_blank\">Carboxylic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span></span></span>','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsDNA polymerase subunit gamma-1A467T(A;A) / (A;G)G > AADR Directly StudiedThe presence of this polymorphism in POLG may indicate an increased risk of liver failure and death when treated with valproic acid.DetailsDNA polymerase subunit gamma-1W748S(C;C) / (C;G)G > CADR Directly StudiedThe presence of this polymorphism in POLG may indicate an increased risk of liver failure and death when treated with valproic acid.Details','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsDNA polymerase subunit gamma-1A467T(A;A) / (A;G)G > AADR Directly StudiedThe presence of this polymorphism in POLG may indicate an increased risk of liver failure and death when treated with valproic acid.DetailsDNA polymerase subunit gamma-1W748S(C;C) / (C;G)G > CADR Directly StudiedThe presence of this polymorphism in POLG may indicate an increased risk of liver failure and death when treated with valproic acid.Details','50003616','99-66-1','39867','CHEMBL109','3009','<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 methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.</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=\"Organic molecules synthesized by chain elongation of an acetyl-CoA primer with malonyl-CoA (or methylmalonyl-CoA) groups that might contain a cyclic functionality and/or are substituted with heteroatoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003909\" rel=\"noopener\" target=\"_blank\">Fatty Acyls</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=\"Aliphatic monocarboxylic acids with a saturated or unsaturated aliphatic tail (with at least 4 Carbon atoms).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000262\" rel=\"noopener\" target=\"_blank\">Fatty acids and conjugates</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=\"Fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003544\" rel=\"noopener\" target=\"_blank\">Methyl-branched fatty acids</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a carboxylic acid group with the formula -C(=O)OH.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001205\" rel=\"noopener\" target=\"_blank\">Carboxylic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Aliphatic acyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Methyl-branched fatty acid</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 oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aliphatic acyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">branched-chain fatty acid, branched-chain saturated fatty acid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:39867\" rel=\"noopener\" target=\"_blank\">CHEBI:39867</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Branched fatty acids (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMFA01020291\" rel=\"noopener\" target=\"_blank\">LMFA01020291</a>) </span></span></dd></dl>','Fatty Acyls','<p>0.56 L/hr/m<sup>2</sup><sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup></p><p>Pediatric patients between 3 months and 10 years of age have 50% higher clearances by weight. Pediatric patients 10 years of age or older approximate adult values.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup></p>','This compound belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.','Methyl-branched fatty acids','<li>Avoid alcohol.</li>\n<li>Avoid milk and dairy products.</li>\n<li>Take with food.</li>','Drugs.com Drug Page',' , Acids, Acyclic , Anti-epileptic Agent , Anticonvulsants , Antimanic Agents , Antineoplastic Agents , Central Nervous System Agents , Central Nervous System Depressants , Cytochrome P-450 CYP1A2 Inhibitors , Cytochrome P-450 CYP1A2 Inhibitors (strength unknown) , Cytochrome P-450 CYP2A6 Substrates , Cytochrome P-450 CYP2A6 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2B6 Substrates , Cytochrome P-450 CYP2B6 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2C19 Inhibitors , Cytochrome P-450 CYP2C19 Inhibitors (weak) , Cytochrome P-450 CYP2C19 Substrates , Cytochrome P-450 CYP2C19 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2C8 Inhibitors , Cytochrome P-450 CYP2C9 Inhibitors , Cytochrome P-450 CYP2C9 Inhibitors (moderate) , Cytochrome P-450 CYP2C9 Substrates , Cytochrome P-450 CYP2C9 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP3A Inhibitors , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Inhibitors , Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) , Cytochrome P-450 CYP3A5 Substrates , Cytochrome P-450 CYP3A5 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Decreased Central Nervous System Disorganized Electrical Activity , Drugs causing inadvertant photosensitivity , Enzyme Inhibitors , Fatty Acid Derivatives , Fatty Acids , Fatty Acids, Volatile , GABA Agents , Hepatotoxic Agents , Highest Risk QTc-Prolonging Agents , Histone Deacetylase Inhibitors , Lipids , Methemoglobinemia Associated Agents , Miscellaneous Anticonvulsants , Mood Stabilizer , Narrow Therapeutic Index Drugs , Nervous System , Neurotransmitter Agents , OAT1/SLC22A6 inhibitors , OAT3/SLC22A8 Inhibitors , OAT3/SLC22A8 Substrates , OAT3/SLC22A8 Substrates with a Narrow Therapeutic Index , Organic Anion Transporting Polypeptide 2B1 Inhibitors , Pentanoic Acids , Photosensitizing Agents , Psychotropic Drugs , QTc Prolonging Agents , Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome , Tranquilizing Agents , UGT1A1 Inhibitors , UGT1A1 Substrates , UGT1A1 Substrates with a Narrow Therapeutic Index , UGT1A3 substrates , UGT1A3 Substrates with a Narrow Therapeutic Index , UGT1A4 substrates , UGT1A6 substrate , UGT1A6 Substrates with a Narrow Therapeutic Index , UGT1A9 Substrates , UGT1A9 Substrates with a Narrow Therapeutic Index , UGT2B7 substrates , UGT2B7 Substrates with a Narrow Therapeutic Index , Valerates','<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>boiling point (°C)</td><td>222</td><td>ChemIDplus</td></tr><tr><td>water solubility</td><td>1.3 mg/mL</td><td>FDA label (2006)</td></tr><tr><td>logP</td><td>2.75</td><td>ChemIDplus</td></tr><tr><td>logS</td><td>-1.86</td><td>ADME Research, USCD</td></tr><tr><td>pKa</td><td>4.8</td><td>FDA label (2006)</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">branched-chain fatty acid, branched-chain saturated fatty acid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:39867\" rel=\"noopener\" target=\"_blank\">CHEBI:39867</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Branched fatty acids (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMFA01020291\" rel=\"noopener\" target=\"_blank\">LMFA01020291</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/HMDB0001877\" rel=\"noopener\" target=\"_blank\">HMDB0001877</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:D00399\" rel=\"noopener\" target=\"_blank\">D00399</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:C07185\" rel=\"noopener\" target=\"_blank\">C07185</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=3121\" rel=\"noopener\" target=\"_blank\">3121</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=46505925\" rel=\"noopener\" target=\"_blank\">46505925</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.3009.html\" rel=\"noopener\" target=\"_blank\">3009</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=50003616\" rel=\"noopener\" target=\"_blank\">50003616</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=11118\" rel=\"noopener\" target=\"_blank\">11118</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=39867\" rel=\"noopener\" target=\"_blank\">39867</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/CHEMBL109\" rel=\"noopener\" target=\"_blank\">CHEMBL109</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/ZINC000003008621\" rel=\"noopener\" target=\"_blank\">ZINC000003008621</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=DNC001659\" rel=\"noopener\" target=\"_blank\">DNC001659</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/PA451846\" rel=\"noopener\" target=\"_blank\">PA451846</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/2PP\" rel=\"noopener\" target=\"_blank\">2PP</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/depakene.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/valproate.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/dep1124.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/Valproate\" rel=\"noopener\" target=\"_blank\">Valproate</a></dd></dl>','<li>Avoid alcohol.</li>\n<li>Avoid milk and dairy products.</li>\n<li>Take with food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A457\">Rosenberg G: The mechanisms of action of valproate in neuropsychiatric disorders: can we see the forest for the trees? Cell Mol Life Sci. 2007 Aug;64(16):2090-103. [<a href=\"/articles/A457\" target=\"_blank\">Article</a>] </li><li id=\"reference-A458\">Lehrman G, Hogue IB, Palmer S, Jennings C, Spina CA, Wiegand A, Landay AL, Coombs RW, Richman DD, Mellors JW, Coffin JM, Bosch RJ, Margolis DM: Depletion of latent HIV-1 infection in vivo: a proof-of-concept study. Lancet. 2005 Aug 13-19;366(9485):549-55. [<a href=\"/articles/A458\" target=\"_blank\">Article</a>] </li><li id=\"reference-A459\">Schwartz C, Palissot V, Aouali N, Wack S, Brons NH, Leners B, Bosseler M, Berchem G: Valproic acid induces non-apoptotic cell death mechanisms in multiple myeloma cell lines. Int J Oncol. 2007 Mar;30(3):573-82. [<a href=\"/articles/A459\" target=\"_blank\">Article</a>] </li><li id=\"reference-A460\">Valentini A, Gravina P, Federici G, Bernardini S: Valproic acid induces apoptosis, p16INK4A upregulation and sensitization to chemotherapy in human melanoma cells. Cancer Biol Ther. 2007 Feb;6(2):185-91. 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[<a href=\"/articles/A177859\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177919\">Cipriani A, Reid K, Young AH, Macritchie K, Geddes J: Valproic acid, valproate and divalproex in the maintenance treatment of bipolar disorder. Cochrane Database Syst Rev. 2013 Oct 17;(10):CD003196. doi: 10.1002/14651858.CD003196.pub2. [<a href=\"/articles/A177919\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177928\">Ghaemi SN, Gilmer WS, Goldberg JF, Zablotsky B, Kemp DE, Kelley ME, Bauer AD, Fleck J, Filkowski MM, Stan VA, Dunn RT: Divalproex in the treatment of acute bipolar depression: a preliminary double-blind, randomized, placebo-controlled pilot study. J Clin Psychiatry. 2007 Dec;68(12):1840-4. [<a href=\"/articles/A177928\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177931\">Davis LL, Bartolucci A, Petty F: Divalproex in the treatment of bipolar depression: a placebo-controlled study. J Affect Disord. 2005 Apr;85(3):259-66. doi: 10.1016/j.jad.2004.09.009. [<a href=\"/articles/A177931\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177934\">Muzina DJ, Gao K, Kemp DE, Khalife S, Ganocy SJ, Chan PK, Serrano MB, Conroy CM, Calabrese JR: Acute efficacy of divalproex sodium versus placebo in mood stabilizer-naive bipolar I or II depression: a double-blind, randomized, placebo-controlled trial. J Clin Psychiatry. 2011 Jun;72(6):813-9. doi: 10.4088/JCP.09m05570gre. Epub 2010 Aug 24. [<a href=\"/articles/A177934\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177955\">Prasad M, Krishnan PR, Sequeira R, Al-Roomi K: Anticonvulsant therapy for status epilepticus. Cochrane Database Syst Rev. 2014 Sep 10;(9):CD003723. doi: 10.1002/14651858.CD003723.pub3. [<a href=\"/articles/A177955\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177991\">El-Habr EA, Dubois LG, Burel-Vandenbos F, Bogeas A, Lipecka J, Turchi L, Lejeune FX, Coehlo PL, Yamaki T, Wittmann BM, Fareh M, Mahfoudhi E, Janin M, Narayanan A, Morvan-Dubois G, Schmitt C, Verreault M, Oliver L, Sharif A, Pallud J, Devaux B, Puget S, Korkolopoulou P, Varlet P, Ottolenghi C, Plo I, Moura-Neto V, Virolle T, Chneiweiss H, Junier MP: A driver role for GABA metabolism in controlling stem and proliferative cell state through GHB production in glioma. Acta Neuropathol. 2017 Apr;133(4):645-660. doi: 10.1007/s00401-016-1659-5. Epub 2016 Dec 28. [<a href=\"/articles/A177991\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177997\">Yamada MK, Nakanishi K, Ohba S, Nakamura T, Ikegaya Y, Nishiyama N, Matsuki N: Brain-derived neurotrophic factor promotes the maturation of GABAergic mechanisms in cultured hippocampal neurons. J Neurosci. 2002 Sep 1;22(17):7580-5. [<a href=\"/articles/A177997\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178000\">Shaltiel G, Shamir A, Shapiro J, Ding D, Dalton E, Bialer M, Harwood AJ, Belmaker RH, Greenberg ML, Agam G: Valproate decreases inositol biosynthesis. Biol Psychiatry. 2004 Dec 1;56(11):868-74. doi: 10.1016/j.biopsych.2004.08.027. [<a href=\"/articles/A178000\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178003\">Yu W, Greenberg ML: Inositol depletion, GSK3 inhibition and bipolar disorder. Future Neurol. 2016 May;11(2):135-148. doi: 10.2217/fnl-2016-0003. Epub 2016 Apr 26. [<a href=\"/articles/A178003\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178015\">Manji HK, Etcheberrigaray R, Chen G, Olds JL: Lithium decreases membrane-associated protein kinase C in hippocampus: selectivity for the alpha isozyme. J Neurochem. 1993 Dec;61(6):2303-10. [<a href=\"/articles/A178015\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178018\">Yi L, Wu Q, Chen N, Song G, Wang C, Zou Q, Zhang Z: Valproate Plays a Protective Role against Migraine by Inhibiting Protein Kinase C Signalling in Nitroglycerin-treated Mice. Basic Clin Pharmacol Toxicol. 2018 Mar;122(3):310-316. doi: 10.1111/bcpt.12915. Epub 2017 Nov 12. [<a href=\"/articles/A178018\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178021\">Watterson JM, Watson DG, Meyer EM, Lenox RH: A role for protein kinase C and its substrates in the action of valproic acid in the brain: implications for neural plasticity. Brain Res. 2002 Apr 26;934(1):69-80. [<a href=\"/articles/A178021\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178024\">Bolanos JP, Medina JM: Effect of valproate on the metabolism of the central nervous system. Life Sci. 1997;60(22):1933-42. [<a href=\"/articles/A178024\" target=\"_blank\">Article</a>] </li><li id=\"reference-A14708\">Bazinet RP, Weis MT, Rapoport SI, Rosenberger TA: Valproic acid selectively inhibits conversion of arachidonic acid to arachidonoyl-CoA by brain microsomal long-chain fatty acyl-CoA synthetases: relevance to bipolar disorder. Psychopharmacology (Berl). 2006 Jan;184(1):122-9. Epub 2005 Dec 13. [<a href=\"/articles/A14708\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178027\">Tang Y, Glauser TA, Gilbert DL, Hershey AD, Privitera MD, Ficker DM, Szaflarski JP, Sharp FR: Valproic acid blood genomic expression patterns in children with epilepsy - a pilot study. Acta Neurol Scand. 2004 Mar;109(3):159-68. [<a href=\"/articles/A178027\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178030\">Phiel CJ, Zhang F, Huang EY, Guenther MG, Lazar MA, Klein PS: Histone deacetylase is a direct target of valproic acid, a potent anticonvulsant, mood stabilizer, and teratogen. J Biol Chem. 2001 Sep 28;276(39):36734-41. doi: 10.1074/jbc.M101287200. Epub 2001 Jul 25. [<a href=\"/articles/A178030\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178033\">Sharma RP, Rosen C, Kartan S, Guidotti A, Costa E, Grayson DR, Chase K: Valproic acid and chromatin remodeling in schizophrenia and bipolar disorder: preliminary results from a clinical population. Schizophr Res. 2006 Dec;88(1-3):227-31. doi: 10.1016/j.schres.2006.07.015. Epub 2006 Sep 25. [<a href=\"/articles/A178033\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178036\">Huang Y, Doherty JJ, Dingledine R: Altered histone acetylation at glutamate receptor 2 and brain-derived neurotrophic factor genes is an early event triggered by status epilepticus. J Neurosci. 2002 Oct 1;22(19):8422-8. [<a href=\"/articles/A178036\" target=\"_blank\">Article</a>] </li><li id=\"reference-A11814\">Kanai H, Sawa A, Chen RW, Leeds P, Chuang DM: Valproic acid inhibits histone deacetylase activity and suppresses excitotoxicity-induced GAPDH nuclear accumulation and apoptotic death in neurons. Pharmacogenomics J. 2004;4(5):336-44. [<a href=\"/articles/A11814\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178051\">Lopez-Munoz F, Baumeister AA, Hawkins MF, Alamo C: The role of serendipity in the discovery of the clinical effects of psychotropic drugs: beyond of the myth. Actas Esp Psiquiatr. 2012 Jan-Feb;40(1):34-42. Epub 2012 Jan 1. [<a href=\"/articles/A178051\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178066\">Zaccara G, Messori A, Moroni F: Clinical pharmacokinetics of valproic acid--1988. Clin Pharmacokinet. 1988 Dec;15(6):367-89. doi: 10.2165/00003088-198815060-00002. [<a href=\"/articles/A178066\" target=\"_blank\">Article</a>] </li><li id=\"reference-L6151\">Depacon FDA Label (2006) [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018081s42,18082s26,18723s32,19680s19,20593s11,21168s9lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L6190\">Depakene FDA [<a href=\"https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&amp;ApplNo=018081\" target=\"_blank\">Link</a>] </li><li id=\"reference-L6196\">Depakene FDA Label (2019) [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/018081s069,018082s052lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L3897\">FDA Approved Drug Products: Stavzor (valproic acid) delayed-release capsules for oral use [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/022152s009lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>13-19 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup></p><p>The half-life in neonates ranges from 10-67 hours while the half-life in pediatric patients under 2 months of age ranges from 7-13 hours.</p>','HMDB0001877','2-propylpentanoic acid','InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)','NIJJYAXOARWZEE-UHFFFAOYSA-N','<p><strong>Indicated</strong> for:<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup> </p><p>1) Use as monotherapy or adjunctive therapy in the management of complex partial seizures and simple or complex absence seizures. </p><p>2) Adjunctive therapy in the management of multiple seizure types that include absence seizures. </p><p>3) Prophylaxis of migraine headaches.</p><p>4) Acute management of mania associated with bipolar disorder.</p><p><strong>Off-label</strong> uses include:</p><p>1) Maintenance therapy for bipolar disorder.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Cipriani A, Reid K, Young AH, Macritchie K, Geddes J: Valproic acid, valproate and divalproex in the maintenance treatment of bipolar disorder. Cochrane Database Syst Rev. 2013 Oct 17;(10):CD003196. doi: 10.1002/14651858.CD003196.pub2. (PubMed ID 24132760)\" href=\"#reference-A177919\">7</a></sup></p><p>2) Treatment for acute bipolar depression.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Ghaemi SN, Gilmer WS, Goldberg JF, Zablotsky B, Kemp DE, Kelley ME, Bauer AD, Fleck J, Filkowski MM, Stan VA, Dunn RT: Divalproex in the treatment of acute bipolar depression: a preliminary double-blind, randomized, placebo-controlled pilot study. J Clin Psychiatry. 2007 Dec;68(12):1840-4. (PubMed ID 18162014)\" href=\"#reference-A177928\">8</a>,<a class=\"reference-popover-link\" data-content=\"Davis LL, Bartolucci A, Petty F: Divalproex in the treatment of bipolar depression: a placebo-controlled study. J Affect Disord. 2005 Apr;85(3):259-66. doi: 10.1016/j.jad.2004.09.009. (PubMed ID 15780695)\" href=\"#reference-A177931\">9</a>,<a class=\"reference-popover-link\" data-content=\"Muzina DJ, Gao K, Kemp DE, Khalife S, Ganocy SJ, Chan PK, Serrano MB, Conroy CM, Calabrese JR: Acute efficacy of divalproex sodium versus placebo in mood stabilizer-naive bipolar I or II depression: a double-blind, randomized, placebo-controlled trial. J Clin Psychiatry. 2011 Jun;72(6):813-9. doi: 10.4088/JCP.09m05570gre. Epub 2010 Aug 24. (PubMed ID 20816041)\" href=\"#reference-A177934\">10</a></sup></p><p>3) Emergency treatment of status epilepticus.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Prasad M, Krishnan PR, Sequeira R, Al-Roomi K: Anticonvulsant therapy for status epilepticus. Cochrane Database Syst Rev. 2014 Sep 10;(9):CD003723. doi: 10.1002/14651858.CD003723.pub3. (PubMed ID 25207925)\" href=\"#reference-A177955\">11</a></sup></p>','C07185','D00399','Organic compounds','<p>Most drug is metabolized to glucuronide conjugates (30-50%) of the parent drug or of metabolites.<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=\"Zaccara G, Messori A, Moroni F: Clinical pharmacokinetics of valproic acid--1988. Clin Pharmacokinet. 1988 Dec;15(6):367-89. doi: 10.2165/00003088-198815060-00002. (PubMed ID 3149565)\" href=\"#reference-A178066\">27</a></sup> Another large portion is metabolized through mitochondrial β-oxidation (40%). The remainder of metabolism (15-20%) occurs through oxidation, hydroxylation, and dehydrogenation at the ω, ω<sub>1</sub>, and ω<sub>2</sub> positions resulting in the formation of hydroxyls, ketones, carboxyls, a lactone metabolite, double bonds, and combinations. </p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aliphatic acyclic compounds','2PP','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000635?highlight[compounds][]=DB00313&amp;highlight[proteins][]=DB00313\">Valproic Acid Metabolism Pathway</a></td><td>Drug metabolism</td></tr></tbody>','PA451846','<p>Protein binding is linear at low concentrations with a free fraction of approximately 10% at 40 mcg/mL but becomes non-linear at higher concentrations with a free fraction of 18.5% at 135 mcg/mL.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup> This may be due to binding at separate high and low-affinity sites on albumin proteins.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Zaccara G, Messori A, Moroni F: Clinical pharmacokinetics of valproic acid--1988. Clin Pharmacokinet. 1988 Dec;15(6):367-89. doi: 10.2165/00003088-198815060-00002. (PubMed ID 3149565)\" href=\"#reference-A178066\">27</a></sup> Binding is expected to decrease in the elderly and patients with hepatic dysfunction.</p>','3121','46505925','<p>Most drug is eliminated through hepatic metabolism, about 30-50%.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup> The other major contributing pathway is mitochondrial β-oxidation, about 40%. Other oxidative pathways make up an additional 15-20%. Less than 3% is excreted unchanged in the urine.</p>','RxList Drug Page','11118','CCCC(CCC)C(O)=O','Solid','Fatty acids and conjugates','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Aliphatic acyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Methyl-branched fatty acid</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 oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span></span></span>','Lipids and lipid-like molecules','<span class=\"citations\"><p>Daniel Aubert, Francis Blanc, Henri Desmolin, Michel Morre, Lucette Sindely, \"Valproic acid preparations.\" U.S. Patent US5017613, issued January, 1965.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=5017613&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5017613</a>','DNC001659','<p><strong>LD<sub>50</sub> Values</strong></p><p>Oral, mouse: 1098 mg/kg</p><p>Oral, rat: 670 mg/kg</p><p><strong>Overdose</strong></p><p>Symptoms of overdose include somnolence, heart block, deep coma, and hypernatremia. Fatalities have been reported, however patients have recovered from valproate serum concentrations as high as 2120 mcg/mL. The unbound fraction may be removed by hemodialysis. Naloxone has been demonstrated to reverse the CNS depressant effects of overdose but may also reverse the anti-epileptic effects.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup></p><p><strong>Reproductive Toxicity</strong></p><p>Valproate use in pregnancy is known to increase the risk of neural tube defects and other structural abnormalities.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup> The risk of spina bifida increases from 0.06-0.07% in the normal population to 1-2% in valproate users. The North American Antiepileptic Drug (NAAED)\nPregnancy Registry reports a major malformation rate of 9-11%, 5 times the baseline rate. These malformations include neural tube defects, cardiovascular malformations, craniofacial defects (e.g., oral clefts, craniosynostosis), hypospadias, limb malformations (e.g., clubfoot, polydactyly), and other malformations of varying severity involving other body systems. Other antiepileptic drugs, lamotrigine, carbemazepine, and phenytoin, have been found to reduce IQ in children exposed in utero. Valproate was also studied however the results did not achieve statistical significance (97 IQ (CI: 94-101)). Observational studies report an absolute risk increase of 2.9% (relative risk 2.9 times baseline) of autism spectrum disorder in children exposed to valproate in utero. There have been case reports of fatal hepatic failure in children of mothers who used valproate during pregnancy.</p><p>There have been reports of male infertility when taking valproate.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup></p><p><strong>Lactation</strong></p><p>Valproate is excreted in human milk.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup> Data in the published literature describe the presence of valproate in human milk (range: 0.4 mcg/mL to 3.9 mcg/mL), corresponding to 1% to 10% of maternal serum levels. Valproate serum concentrations collected from breastfed infants aged 3 days postnatal to 12 weeks following delivery ranged from 0.7 mcg/mL to 4 mcg/mL, which were 1% to 6% of maternal serum valproate levels. A published study in children up to six years of age did not report adverse developmental or cognitive effects following exposure to valproate\nvia breast milk.</p><p><strong>Other Toxicity Considerations</strong></p><p>Use in pediatrics under 2 years of age increases the risk of fatal hepatotoxicity.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup></p>','614OI1Z5WI','<p>11 L/1.73m<sup>2</sup>.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup></p>','Valproate','ZINC000003008621'),(26,'Indomethacin','indomethacin','Indomethacin is a nonsteroidal anti-inflammatory (NSAID) used for symptomatic management of chronic musculoskeletal pain conditions and to induce closure of a hemodynamically significant patent ductus arteriosus in premature infants.','Indocin, Tivorbex','Indomethacin','<p>Indometacin, or indomethacin, is a non-steroidal anti-inflammatory drug (NSAID) with anti-inflammatory, analgesic, and antipyretic properties. NSAIDs consist of agents that are structurally unrelated; the NSAID chemical classification of indometacin is an indole-acetic acid derivative with the chemical name 1- (p-chlorobenzoyl)25-methoxy-2-methylindole-3-acetic acid.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lucas S: The Pharmacology of Indomethacin. Headache. 2016 Feb;56(2):436-46. doi: 10.1111/head.12769. Epub 2016 Feb 11. (PubMed ID 26865183)\" href=\"#reference-A177871\">1</a></sup> The pharmacological effect of indometacin is not fully understood, however, it is thought to be mediated through potent and nonselective inhibition of the enzyme cyclooxygenase (COX), which is the main enzyme responsible for catalyzes the rate-limiting step in prostaglandin and thromboxane biosynthesis via the arachidonic acid (AA) pathway. Indometacin was first discovered in 1963 and it was first approved for use in the U.S. by the Food and Drug Administration in 1965, <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"HART FD, BOARDMAN PL: INDOMETHACIN: A NEW NON-STEROID ANTI-INFLAMMATORY AGENT. Br Med J. 1963 Oct 19;2(5363):965-70. (PubMed ID 14056924)\" href=\"#reference-A486\">10</a></sup> along with other acetic acid derivatives such as <a href=\"https://go.drugbank.com/drugs/DB00586\">diclofenac</a> and <a href=\"https://go.drugbank.com/drugs/DB00605\">sulindac</a> that were also developed during the 1960s.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lucas S: The Pharmacology of Indomethacin. Headache. 2016 Feb;56(2):436-46. doi: 10.1111/head.12769. Epub 2016 Feb 11. (PubMed ID 26865183)\" href=\"#reference-A177871\">1</a></sup> Since then, indometacin has been extensively studied in clinical trials as one of the most potent NSAIDs in blocking prostaglandin synthesis and was among the first NSAIDs to be used in the symptomatic treatment of migraine and for headaches that eventually became known as “indomethacin-responsive” headache disorders.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lucas S: The Pharmacology of Indomethacin. Headache. 2016 Feb;56(2):436-46. doi: 10.1111/head.12769. Epub 2016 Feb 11. (PubMed ID 26865183)\" href=\"#reference-A177871\">1</a></sup> </p><p>Most commonly used in rheumatoid arthritis, ankylosing spondylitis, osteoarthritis, acute shoulder pains, and acute gouty arthritis, indometacin is currently available as oral capsules as well as other methods of administration, including rectal and intravenous formulations. Intravenous indometacin is administered to close a hemodynamically significant patent ductus arteriosus, as indicated by clinical evidence, in premature infants.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Indocin I.V. (indomethacin for injection) - FDA Label\" href=\"#reference-L10553\">14</a></sup> Ophthalmic indometacin has been studied and used in the symptomatic treatment of postoperative ocular inflammation and pain and/or complications after cataract surgery. Although deemed effective in reducing ocular inflammation in clinical studies, topical NSAIDs were also associated with a potential reduction in corneal sensitivity accompanied by an increased risk of superficial punctate keratitis and subjective symptoms of discomfort, including pain, burning or pricking, or a tingling sensation after instillation into the cul‐de‐sac.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Weber M, Kodjikian L, Kruse FE, Zagorski Z, Allaire CM: Efficacy and safety of indomethacin 0.1% eye drops compared with ketorolac 0.5% eye drops in the management of ocular inflammation after cataract surgery. Acta Ophthalmol. 2013 Feb;91(1):e15-21. doi: 10.1111/j.1755-3768.2012.02520.x. Epub 2012 Sep 12. (PubMed ID 22970738)\" href=\"#reference-A177949\">6</a></sup></p>','C19H16ClNO4','DB00328','Approved, Investigational','Small Molecule','Average: 357.788 Monoisotopic: 357.076785712 ',' , S01CC — Antiinflammatory agents, non-steroids and antiinfectives in combination , S01C — ANTIINFLAMMATORY AGENTS AND ANTIINFECTIVES IN COMBINATION , 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 , S01BC — Antiinflammatory agents, non-steroids , S01B — ANTIINFLAMMATORY AGENTS , S01 — OPHTHALMOLOGICALS , S — SENSORY ORGANS , 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 , C01EB — Other cardiac preparations , C01E — OTHER CARDIAC PREPARATIONS , C01 — CARDIAC THERAPY , C — CARDIOVASCULAR SYSTEM','<p>Indometacin displays a linear pharmacokinetics profile where the plasma concentrations and area under the curve (AUC) are dose-proportional, whereas half-life (T1/2) and plasma and renal clearance are dose-dependent.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lucas S: The Pharmacology of Indomethacin. Headache. 2016 Feb;56(2):436-46. doi: 10.1111/head.12769. Epub 2016 Feb 11. (PubMed ID 26865183)\" href=\"#reference-A177871\">1</a></sup> Indometacin is readily and rapidly absorbed from the gastrointestinal tract. The bioavailability is virtually 100% following oral administration <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lucas S: The Pharmacology of Indomethacin. Headache. 2016 Feb;56(2):436-46. doi: 10.1111/head.12769. Epub 2016 Feb 11. (PubMed ID 26865183)\" href=\"#reference-A177871\">1</a></sup> and about 90% of the dose is absorbed within 4 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Indomethacin Capsules (25 mg) - FDA Label\" href=\"#reference-L6778\">13</a></sup> The bioavailability is about 80-90% following rectal administration.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Jensen KM, Grenabo L: Bioavailability of indomethacin after intramuscular injection and rectal administration of solution and suppositories. Acta Pharmacol Toxicol (Copenh). 1985 Nov;57(5):322-7. (PubMed ID 4090993)\" href=\"#reference-A177901\">5</a></sup></p><p>The peak plasma concentrations following a single oral dose were achieved between 0.9 ± 0.4 and 1.5 ± 0.8 hours in a fasting state.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Jensen KM, Grenabo L: Bioavailability of indomethacin after intramuscular injection and rectal administration of solution and suppositories. Acta Pharmacol Toxicol (Copenh). 1985 Nov;57(5):322-7. (PubMed ID 4090993)\" href=\"#reference-A177901\">5</a></sup> Despite large intersubject variation as well using the same preparation, peak plasma concentrations are dose-proportional and averaged 1.54 ± 0.76 μg/mL, 2.65 ± 1.03 μg/mL, and 4.92 ± 1.88 μg/mL following 25 mg, 50 mg, and 75 mg single doses in fasting subjects, respectively.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Jensen KM, Grenabo L: Bioavailability of indomethacin after intramuscular injection and rectal administration of solution and suppositories. Acta Pharmacol Toxicol (Copenh). 1985 Nov;57(5):322-7. (PubMed ID 4090993)\" href=\"#reference-A177901\">5</a></sup> With a typical therapeutic regimen of 25 or 50 mg t.i.d., the steady-state plasma concentrations of indomethacin are an average 1.4 times those following the first dose.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Indomethacin Capsules (25 mg) - FDA Label\" href=\"#reference-L6778\">13</a></sup></p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001252\" rel=\"noopener\" target=\"_blank\">Indole-3-acetic acid 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 (or a derivative thereof) linked to an indole.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002013\" rel=\"noopener\" target=\"_blank\">Indolecarboxylic acids and derivatives</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=\"Benzoic acids or derivatives carrying a halogen atom at the 4-position of the benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003100\" rel=\"noopener\" target=\"_blank\">4-halobenzoic 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 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 the alkyl aryl ether functional group with the generic formula R-O-R\' , where R is an alkyl group and R\' is an aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000128\" rel=\"noopener\" target=\"_blank\">Alkyl aryl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing 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 class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Heterocyclic compounds containing a pyrrole ring substituted at one or more positions.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002257\" rel=\"noopener\" target=\"_blank\">Substituted pyrroles</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></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 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=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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 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 bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span><span 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><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 10 more</a>','Not Available','Not Available','17638','53-86-1','49662','CHEMBL6','3584','<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 benzoylindoles. These are organic compounds containing an indole attached to a benzoyl moiety through the acyl group.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a ring with least one carbon atom and one non-carbon atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000002\" rel=\"noopener\" target=\"_blank\">Organoheterocyclic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000211\" rel=\"noopener\" target=\"_blank\">Indoles 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 indole attached to a benzoyl moiety through the acyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001753\" rel=\"noopener\" target=\"_blank\">Benzoylindoles</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 indole attached to a benzoyl moiety through the acyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001753\" rel=\"noopener\" target=\"_blank\">Benzoylindoles</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 acetic acid (or a derivative) linked to the C3 carbon atom of an indole.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001252\" rel=\"noopener\" target=\"_blank\">Indole-3-acetic acid 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 (or a derivative thereof) linked to an indole.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002013\" rel=\"noopener\" target=\"_blank\">Indolecarboxylic acids and derivatives</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=\"Benzoic acids or derivatives carrying a halogen atom at the 4-position of the benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003100\" rel=\"noopener\" target=\"_blank\">4-halobenzoic 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 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 the alkyl aryl ether functional group with the generic formula R-O-R\' , where R is an alkyl group and R\' is an aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000128\" rel=\"noopener\" target=\"_blank\">Alkyl aryl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing 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 class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Heterocyclic compounds containing a pyrrole ring substituted at one or more positions.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002257\" rel=\"noopener\" target=\"_blank\">Substituted pyrroles</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></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 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=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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 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 bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span><span 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><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 10 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-alkylindole</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\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anisole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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\">Benzoic acid or derivatives</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Benzoyl</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoylindole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Chlorobenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</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 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\">Indole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Indole-3-acetic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Indolecarboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Indolyl carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocyclic benzene moiety</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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\">Pyrrole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Substituted pyrrole</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 27 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\">aromatic ether, monochlorobenzenes, N-acylindole, indole-3-acetic acids (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:49662\" rel=\"noopener\" target=\"_blank\">CHEBI:49662</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-10545\" rel=\"noopener\" target=\"_blank\">CPD-10545</a>) </span></span></dd></dl>','Indoles and derivatives','<p>In a clinical pharmacokinetic study, the plasma clearance of indometacin was reported to range from 1 to 2.5 mL/kg/min following oral administration.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Helleberg L: Clinical Pharmacokinetics of indomethacin. Clin Pharmacokinet. 1981 Jul-Aug;6(4):245-58. doi: 10.2165/00003088-198106040-00001. (PubMed ID 7249487)\" href=\"#reference-A177874\">2</a></sup></p>','This compound belongs to the class of organic compounds known as benzoylindoles. These are organic compounds containing an indole attached to a benzoyl moiety through the acyl group.','Benzoylindoles','<li>Avoid alcohol. Ingestion of alcohol can increase the risk of GI bleeding.</li>\n<li>Take with or without food. Food has no effect on drug absorption. However, food may decrease the extent of gastrointestinal irritation caused by indomethacin.</li>','Drugs.com Drug Page',' , Acetic Acid Derivatives and Related Substances , Agents causing hyperkalemia , Agents that produce hypertension , Analgesics , Analgesics, Non-Narcotic , Anti-Inflammatory Agents , Anti-Inflammatory Agents, Non-Steroidal , Anti-Inflammatory Agents, Non-Steroidal (Non-Selective) , Antigout Preparations , Antiinflammatory and Antirheumatic Products , Antiinflammatory and Antirheumatic Products, Non-Steroids , Antiinflammatory Preparations, Non-Steroids for Topical Use , Antirheumatic Agents , BSEP/ABCB11 Substrates , Cardiac Therapy , Cardiovascular Agents , Central Nervous System Agents , Cyclooxygenase Inhibitors , Cytochrome P-450 CYP2C19 Inhibitors , Cytochrome P-450 CYP2C19 inhibitors (strength unknown) , Cytochrome P-450 CYP2C19 Substrates , Cytochrome P-450 CYP2C9 Substrates , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Enzyme Inhibitors , Heterocyclic Compounds, Fused-Ring , Hypoglycemia-Associated Agents , Immunosuppressive Agents , Indoles , Musculo-Skeletal System , Myelosuppressive Agents , Nephrotoxic agents , Non COX-2 selective NSAIDS , OAT1/SLC22A6 inhibitors , OAT1/SLC22A6 Substrates , OAT3/SLC22A8 Inhibitors , OAT3/SLC22A8 Substrates , OATP1B1/SLCO1B1 Inhibitors , Ophthalmologicals , Other Nonsteroidal Anti-inflammatory Agents , P-glycoprotein inhibitors , P-glycoprotein substrates , Peripheral Nervous System Agents , Sensory Organs , Sensory System Agents , Tocolytic Agents , Topical Products for Joint and Muscular Pain , UGT1A1 Inhibitors , UGT1A1 Substrates , UGT1A9 Substrates , UGT2B7 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>151</td><td>U.S. Patent 3,161,654.</td></tr><tr><td>water solubility</td><td>0.937 mg/L (at 25 °C)</td><td>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</td></tr><tr><td>logP</td><td>4.27</td><td>HANSCH,C ET AL. (1995)</td></tr><tr><td>logS</td><td>-4.62</td><td>ADME Research, USCD</td></tr><tr><td>Caco2 permeability</td><td>-4.69</td><td>ADME Research, USCD</td></tr><tr><td>pKa</td><td>4.5</td><td>BUDAVARI,S ET AL. (1989)</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">aromatic ether, monochlorobenzenes, N-acylindole, indole-3-acetic acids (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:49662\" rel=\"noopener\" target=\"_blank\">CHEBI:49662</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-10545\" rel=\"noopener\" target=\"_blank\">CPD-10545</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/HMDB0014473\" rel=\"noopener\" target=\"_blank\">HMDB0014473</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:D00141\" rel=\"noopener\" target=\"_blank\">D00141</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:C01926\" rel=\"noopener\" target=\"_blank\">C01926</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=3715\" rel=\"noopener\" target=\"_blank\">3715</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=46508291\" rel=\"noopener\" target=\"_blank\">46508291</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.3584.html\" rel=\"noopener\" target=\"_blank\">3584</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=17638\" rel=\"noopener\" target=\"_blank\">17638</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=5781\" rel=\"noopener\" target=\"_blank\">5781</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=49662\" rel=\"noopener\" target=\"_blank\">49662</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/CHEMBL6\" rel=\"noopener\" target=\"_blank\">CHEMBL6</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/ZINC000000601283\" rel=\"noopener\" target=\"_blank\">ZINC000000601283</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=DAP000617\" rel=\"noopener\" target=\"_blank\">DAP000617</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/PA449982\" rel=\"noopener\" target=\"_blank\">PA449982</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=1909\" 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/IMN\" rel=\"noopener\" target=\"_blank\">IMN</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/indometh.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/indomethacin.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/Indometacin\" rel=\"noopener\" target=\"_blank\">Indometacin</a></dd></dl>','<li>Avoid alcohol. Ingestion of alcohol can increase the risk of GI bleeding.</li>\n<li>Take with or without food. Food has no effect on drug absorption. However, food may decrease the extent of gastrointestinal irritation caused by indomethacin.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A177871\">Lucas S: The Pharmacology of Indomethacin. Headache. 2016 Feb;56(2):436-46. doi: 10.1111/head.12769. Epub 2016 Feb 11. [<a href=\"/articles/A177871\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177874\">Helleberg L: Clinical Pharmacokinetics of indomethacin. Clin Pharmacokinet. 1981 Jul-Aug;6(4):245-58. doi: 10.2165/00003088-198106040-00001. [<a href=\"/articles/A177874\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177877\">Nalamachu S, Wortmann R: Role of indomethacin in acute pain and inflammation management: a review of the literature. Postgrad Med. 2014 Jul;126(4):92-7. doi: 10.3810/pgm.2014.07.2787. [<a href=\"/articles/A177877\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177880\">Pacifici GM: Clinical pharmacology of indomethacin in preterm infants: implications in patent ductus arteriosus closure. Paediatr Drugs. 2013 Oct;15(5):363-76. doi: 10.1007/s40272-013-0031-7. [<a href=\"/articles/A177880\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177901\">Jensen KM, Grenabo L: Bioavailability of indomethacin after intramuscular injection and rectal administration of solution and suppositories. Acta Pharmacol Toxicol (Copenh). 1985 Nov;57(5):322-7. [<a href=\"/articles/A177901\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177949\">Weber M, Kodjikian L, Kruse FE, Zagorski Z, Allaire CM: Efficacy and safety of indomethacin 0.1% eye drops compared with ketorolac 0.5% eye drops in the management of ocular inflammation after cataract surgery. Acta Ophthalmol. 2013 Feb;91(1):e15-21. doi: 10.1111/j.1755-3768.2012.02520.x. Epub 2012 Sep 12. [<a href=\"/articles/A177949\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177964\">Alvan G, Orme M, Bertilsson L, Ekstrand R, Palmer L: Pharmacokinetics of indomethacin. Clin Pharmacol Ther. 1975 Sep;18(3):364-73. [<a href=\"/articles/A177964\" target=\"_blank\">Article</a>] </li><li id=\"reference-A176366\">Ricciotti E, FitzGerald GA: Prostaglandins and inflammation. Arterioscler Thromb Vasc Biol. 2011 May;31(5):986-1000. doi: 10.1161/ATVBAHA.110.207449. [<a href=\"/articles/A176366\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177979\">Rouzer CA, Marnett LJ: Cyclooxygenases: structural and functional insights. J Lipid Res. 2009 Apr;50 Suppl:S29-34. doi: 10.1194/jlr.R800042-JLR200. Epub 2008 Oct 23. [<a href=\"/articles/A177979\" target=\"_blank\">Article</a>] </li><li id=\"reference-A486\">HART FD, BOARDMAN PL: INDOMETHACIN: A NEW NON-STEROID ANTI-INFLAMMATORY AGENT. Br Med J. 1963 Oct 19;2(5363):965-70. [<a href=\"/articles/A486\" target=\"_blank\">Article</a>] </li><li id=\"reference-A234429\">Brunelli C, Amici C, Angelini M, Fracassi C, Belardo G, Santoro MG: The non-steroidal anti-inflammatory drug indomethacin activates the eIF2alpha kinase PKR, causing a translational block in human colorectal cancer cells. Biochem J. 2012 Apr 15;443(2):379-86. doi: 10.1042/BJ20111236. [<a href=\"/articles/A234429\" target=\"_blank\">Article</a>] </li><li id=\"reference-A234434\">Amici C, La Frazia S, Brunelli C, Balsamo M, Angelini M, Santoro MG: Inhibition of viral protein translation by indomethacin in vesicular stomatitis virus infection: role of eIF2alpha kinase PKR. Cell Microbiol. 2015 Sep;17(9):1391-404. doi: 10.1111/cmi.12446. Epub 2015 May 13. [<a href=\"/articles/A234434\" target=\"_blank\">Article</a>] </li><li id=\"reference-L6778\">Indomethacin Capsules (25 mg) - FDA Label [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016059s100lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L10553\">Indocin I.V. (indomethacin for injection) - FDA Label [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018878s027lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L13269\">FDA Approved Drug Products: INDOCIN (indomethacin) Suppositories, for rectal use [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017814s041s042lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>Indometacin disposition from the plasma is reported to be biphasic, with a half-life of 1 hour during the initial phase and 2.6–11.2 hours during the second phase.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Weber M, Kodjikian L, Kruse FE, Zagorski Z, Allaire CM: Efficacy and safety of indomethacin 0.1% eye drops compared with ketorolac 0.5% eye drops in the management of ocular inflammation after cataract surgery. Acta Ophthalmol. 2013 Feb;91(1):e15-21. doi: 10.1111/j.1755-3768.2012.02520.x. Epub 2012 Sep 12. (PubMed ID 22970738)\" href=\"#reference-A177949\">6</a></sup> Interindividual and intraindividual variations are possible due to the extensive and sporadic nature of the enterohepatic recycling and biliary discharge of the drug.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Helleberg L: Clinical Pharmacokinetics of indomethacin. Clin Pharmacokinet. 1981 Jul-Aug;6(4):245-58. doi: 10.2165/00003088-198106040-00001. (PubMed ID 7249487)\" href=\"#reference-A177874\">2</a>,<a class=\"reference-popover-link\" data-content=\"Weber M, Kodjikian L, Kruse FE, Zagorski Z, Allaire CM: Efficacy and safety of indomethacin 0.1% eye drops compared with ketorolac 0.5% eye drops in the management of ocular inflammation after cataract surgery. Acta Ophthalmol. 2013 Feb;91(1):e15-21. doi: 10.1111/j.1755-3768.2012.02520.x. Epub 2012 Sep 12. (PubMed ID 22970738)\" href=\"#reference-A177949\">6</a></sup></p><p>The mean half-life of oral indomethacin is estimated to be about 4.5 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Indomethacin Capsules (25 mg) - FDA Label\" href=\"#reference-L6778\">13</a></sup> The disposition of intravenous indometacin in preterm neonates was shown to vary across premature infants. In neonates older than 7 days, the mean plasma half-life of intravenous indometacin was approximately 20 hours, ranging from 15 hours in infants weighing more than 1000 g and 21 hours in infants weighing less than 1000 g.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Indocin I.V. (indomethacin for injection) - FDA Label\" href=\"#reference-L10553\">14</a></sup></p>','HMDB0014473','2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid','InChI=1S/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)','CGIGDMFJXJATDK-UHFFFAOYSA-N','<p>Oral indometacin is indicated for symptomatic management of moderate to severe rheumatoid arthritis including acute flares of chronic disease, moderate to severe ankylosing spondylitis, moderate to severe osteoarthritis, acute painful shoulder (bursitis and/or tendinitis) and acute gouty arthritis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lucas S: The Pharmacology of Indomethacin. Headache. 2016 Feb;56(2):436-46. doi: 10.1111/head.12769. Epub 2016 Feb 11. (PubMed ID 26865183)\" href=\"#reference-A177871\">1</a>,<a class=\"reference-popover-link\" data-content=\"Indomethacin Capsules (25 mg) - FDA Label\" href=\"#reference-L6778\">13</a></sup></p><p>Intravenous indometacin is indicated to induce closure of a hemodynamically significant patent ductus arteriosus in premature infants weighing between 500 and 1750 g when after 48 hours usual medical management (e.g., fluid restriction, diuretics, digitalis, respiratory support, etc.) is ineffective.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Indocin I.V. (indomethacin for injection) - FDA Label\" href=\"#reference-L10553\">14</a></sup></p>','C01926','D00141','Organic compounds','<p>Indometacin undergoes hepatic metabolism involving glucuronidation, O-desmethylation, and N-deacylation.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Weber M, Kodjikian L, Kruse FE, Zagorski Z, Allaire CM: Efficacy and safety of indomethacin 0.1% eye drops compared with ketorolac 0.5% eye drops in the management of ocular inflammation after cataract surgery. Acta Ophthalmol. 2013 Feb;91(1):e15-21. doi: 10.1111/j.1755-3768.2012.02520.x. Epub 2012 Sep 12. (PubMed ID 22970738)\" href=\"#reference-A177949\">6</a></sup> O-desmethyl-indomethacin, N-deschlorobenzoyl-indomethacin, and O-desmethyl-N-deschlorobenzoyl-indomethacin metabolites and their glucuronides are primarily inactive and have no pharmacological activity.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Weber M, Kodjikian L, Kruse FE, Zagorski Z, Allaire CM: Efficacy and safety of indomethacin 0.1% eye drops compared with ketorolac 0.5% eye drops in the management of ocular inflammation after cataract surgery. Acta Ophthalmol. 2013 Feb;91(1):e15-21. doi: 10.1111/j.1755-3768.2012.02520.x. Epub 2012 Sep 12. (PubMed ID 22970738)\" href=\"#reference-A177949\">6</a>,<a class=\"reference-popover-link\" data-content=\"Indomethacin Capsules (25 mg) - FDA Label\" href=\"#reference-L6778\">13</a></sup> Unconjugated metabolites are also detected in the plasma.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Indomethacin Capsules (25 mg) - FDA Label\" href=\"#reference-L6778\">13</a></sup> Its high bioavailability indicates that indometacin is unlikely to be subject to the first-pass metabolism.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Weber M, Kodjikian L, Kruse FE, Zagorski Z, Allaire CM: Efficacy and safety of indomethacin 0.1% eye drops compared with ketorolac 0.5% eye drops in the management of ocular inflammation after cataract surgery. Acta Ophthalmol. 2013 Feb;91(1):e15-21. doi: 10.1111/j.1755-3768.2012.02520.x. Epub 2012 Sep 12. (PubMed ID 22970738)\" href=\"#reference-A177949\">6</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteropolycyclic compounds','IMN','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000104?highlight[compounds][]=DB00328&amp;highlight[proteins][]=DB00328\">Indomethacin Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA449982','<p>Indometacin is a weak organic acid that is 90-99% bound to protein in plasma over the expected range of therapeutic plasma concentrations <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Weber M, Kodjikian L, Kruse FE, Zagorski Z, Allaire CM: Efficacy and safety of indomethacin 0.1% eye drops compared with ketorolac 0.5% eye drops in the management of ocular inflammation after cataract surgery. Acta Ophthalmol. 2013 Feb;91(1):e15-21. doi: 10.1111/j.1755-3768.2012.02520.x. Epub 2012 Sep 12. (PubMed ID 22970738)\" href=\"#reference-A177949\">6</a>,<a class=\"reference-popover-link\" data-content=\"Indomethacin Capsules (25 mg) - FDA Label\" href=\"#reference-L6778\">13</a></sup>. Like other NSAIDs, indometacin is bound to plasma albumin <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Weber M, Kodjikian L, Kruse FE, Zagorski Z, Allaire CM: Efficacy and safety of indomethacin 0.1% eye drops compared with ketorolac 0.5% eye drops in the management of ocular inflammation after cataract surgery. Acta Ophthalmol. 2013 Feb;91(1):e15-21. doi: 10.1111/j.1755-3768.2012.02520.x. Epub 2012 Sep 12. (PubMed ID 22970738)\" href=\"#reference-A177949\">6</a></sup> but it does not bind to red blood cells. <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Helleberg L: Clinical Pharmacokinetics of indomethacin. Clin Pharmacokinet. 1981 Jul-Aug;6(4):245-58. doi: 10.2165/00003088-198106040-00001. (PubMed ID 7249487)\" href=\"#reference-A177874\">2</a></sup></p>','3715','46508291','<p>Indometacin is eliminated via renal excretion, metabolism, and biliary excretion. It is also subject to enter the enterohepatic circulation through excretion of its glucuronide metabolites into bile followed by resorption of indometacin after hydrolysis <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Weber M, Kodjikian L, Kruse FE, Zagorski Z, Allaire CM: Efficacy and safety of indomethacin 0.1% eye drops compared with ketorolac 0.5% eye drops in the management of ocular inflammation after cataract surgery. Acta Ophthalmol. 2013 Feb;91(1):e15-21. doi: 10.1111/j.1755-3768.2012.02520.x. Epub 2012 Sep 12. (PubMed ID 22970738)\" href=\"#reference-A177949\">6</a></sup>. The extent of involvement in the enterohepatic circulation ranges from 27 to 115%.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Weber M, Kodjikian L, Kruse FE, Zagorski Z, Allaire CM: Efficacy and safety of indomethacin 0.1% eye drops compared with ketorolac 0.5% eye drops in the management of ocular inflammation after cataract surgery. Acta Ophthalmol. 2013 Feb;91(1):e15-21. doi: 10.1111/j.1755-3768.2012.02520.x. Epub 2012 Sep 12. (PubMed ID 22970738)\" href=\"#reference-A177949\">6</a></sup></p><p>About 60 percent of an oral dosage is recovered in urine as drug and metabolites (26 percent as indomethacin and its glucuronide), and 33 percent in the feces (1.5 percent as indomethacin).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Indomethacin Capsules (25 mg) - FDA Label\" href=\"#reference-L6778\">13</a></sup></p>','RxList Drug Page','5781','COC1=CC2=C(C=C1)N(C(=O)C1=CC=C(Cl)C=C1)C(C)=C2CC(O)=O','Solid','Benzoylindoles','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">3-alkylindole</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\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anisole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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\">Benzoic acid or derivatives</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Benzoyl</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoylindole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Chlorobenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</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 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\">Indole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Indole-3-acetic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Indolecarboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Indolyl carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocyclic benzene moiety</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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\">Pyrrole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Substituted pyrrole</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 27 more</a>','Organoheterocyclic compounds','<span class=\"citations\"><p>Hubertus L. Regtop, John R. Biffin, \"Preparation of divalent metal salts of indomethacin.\" U.S. Patent US5310936, issued November, 1917.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=5310936&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5310936</a>','DAP000617','<p>Acute oral LD50 is 2.42 mg/kg in rats and 13 mg/kg in mice.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Material Safety Data Sheet\" href=\"#msds-reference\">MSDS</a></sup> The oral LD50 of indomethacin in mice and rats (based on 14-day mortality response) was 50 and 12 mg/kg, respectively.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Indomethacin Capsules (25 mg) - FDA Label\" href=\"#reference-L6778\">13</a></sup> </p><p>Symptoms of overdose may be characterized by nausea, vomiting, intense headache, dizziness, mental confusion, disorientation, or lethargy. In addition, there have been reports of paresthesias, numbness, and convulsions. In case of an overdose, the patient should receive symptomatic and supportive treatment with stomach emptying through induced vomiting or gastric lavage.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Indomethacin Capsules (25 mg) - FDA Label\" href=\"#reference-L6778\">13</a></sup> The patient should then be closely monitored for any signs of gastrointestinal ulceration and hemorrhage. Antacids may be useful.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Indomethacin Capsules (25 mg) - FDA Label\" href=\"#reference-L6778\">13</a></sup></p>','XXE1CET956','<p>The volume of distribution ranged from 0.34 to 1.57 L/kg following oral, intravenous, or rectal administration of single and multiple doses of indometacin in healthy individuals.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Alvan G, Orme M, Bertilsson L, Ekstrand R, Palmer L: Pharmacokinetics of indomethacin. Clin Pharmacol Ther. 1975 Sep;18(3):364-73. (PubMed ID 1100305)\" href=\"#reference-A177964\">7</a></sup> Indometacin is distributed into the synovial fluid <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Helleberg L: Clinical Pharmacokinetics of indomethacin. Clin Pharmacokinet. 1981 Jul-Aug;6(4):245-58. doi: 10.2165/00003088-198106040-00001. (PubMed ID 7249487)\" href=\"#reference-A177874\">2</a></sup> and is extensively bound to tissues <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Weber M, Kodjikian L, Kruse FE, Zagorski Z, Allaire CM: Efficacy and safety of indomethacin 0.1% eye drops compared with ketorolac 0.5% eye drops in the management of ocular inflammation after cataract surgery. Acta Ophthalmol. 2013 Feb;91(1):e15-21. doi: 10.1111/j.1755-3768.2012.02520.x. Epub 2012 Sep 12. (PubMed ID 22970738)\" href=\"#reference-A177949\">6</a></sup>. It has been detected in human breast milk <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Helleberg L: Clinical Pharmacokinetics of indomethacin. Clin Pharmacokinet. 1981 Jul-Aug;6(4):245-58. doi: 10.2165/00003088-198106040-00001. (PubMed ID 7249487)\" href=\"#reference-A177874\">2</a></sup> and placenta.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Indomethacin Capsules (25 mg) - FDA Label\" href=\"#reference-L6778\">13</a></sup> Although indometacin has been shown to cross the blood-brain barrier (BBB)<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Indomethacin Capsules (25 mg) - FDA Label\" href=\"#reference-L6778\">13</a></sup>, its extensive plasma protein binding allows only the small fraction of free or unbound indometacin to diffuse across the BBB.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Weber M, Kodjikian L, Kruse FE, Zagorski Z, Allaire CM: Efficacy and safety of indomethacin 0.1% eye drops compared with ketorolac 0.5% eye drops in the management of ocular inflammation after cataract surgery. Acta Ophthalmol. 2013 Feb;91(1):e15-21. doi: 10.1111/j.1755-3768.2012.02520.x. Epub 2012 Sep 12. (PubMed ID 22970738)\" href=\"#reference-A177949\">6</a></sup></p>','Indometacin','ZINC000000601283'),(27,'Diltiazem','diltiazem','Diltiazem is a calcium channel blocker used to treat hypertension and to manage chronic stable angina.','Cardizem, Cartia, Matzim, Taztia, Tiadylt, Tiazac','Diltiazem','<p>Diltiazem is a benzothiazepine derivative with antihypertensive and vasodilating properties. Approved in 1982 by the FDA, it is a member of the non-dihydropyridine calcium channel blockers drug class. It works through various mechanisms of action, but it primarily works by inhibiting the calcium influx into cardiac and vascular smooth muscle during depolarization.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"CARDIZEM® LA (diltiazem hydrochloride) extended-release tablets - FDA Label\" href=\"#reference-L10556\">12</a></sup> Compared to dihydropyridine drugs, such as <a href=\"https://go.drugbank.com/drugs/DB01115\">nifedipine</a>, that preferentially act on vascular smooth muscle and <a href=\"https://go.drugbank.com/drugs/DB00661\">verapamil</a> that directly acts on the heart muscle, diltiazem displays an intermediate specificity to target both the cardiac and vascular smooth muscle.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Rang, H. P. and Dale, M. M. (2012). Rang and Dale\'s Pharmacology  (7th ed.). Edinburgh: Elsevier/Churchill Livingstone. (ISBN 978-0-7020-3471-8)\" href=\"#reference-T28\">8</a></sup> Being a potent vasodilator, diltiazem is used clinically as an antihypertensive, anti-arrhythmic, and as an anti-anginal agent <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Diltiazem - StatPearls - NCBI Bookshelf\" href=\"#reference-L6289\">9</a></sup> for the management of cardiovascular conditions such as hypertension, chronic stable angina, atrial fibrillation, atrial flutter. Apart from its main FDA-approved indications, diltiazem has also been used for numerous off-label indications, such as anal fissures (in topical formulations), migraine prophylaxis, pulmonary hypertension, and rest-related cramps in the lower extremities.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Diltiazem - StatPearls - NCBI Bookshelf\" href=\"#reference-L6289\">9</a></sup> Typically available in extended-release oral and intravenous formulations, diltiazem is marketed under various brand names with Cardizem and Tiazac being the most common ones.</p>','C22H26N2O4S','DB00343','Approved, Investigational','Small Molecule','Average: 414.518 Monoisotopic: 414.16132802 ',' , C08DB — Benzothiazepine derivatives , C08D — SELECTIVE CALCIUM CHANNEL BLOCKERS WITH DIRECT CARDIAC EFFECTS , C08 — CALCIUM CHANNEL BLOCKERS , C — CARDIOVASCULAR SYSTEM , C05AE — Muscle relaxants , C05A — AGENTS FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE , C05 — VASOPROTECTIVES , C — CARDIOVASCULAR SYSTEM','<p>Diltiazem is readily absorbed from the gastrointestinal tract. Minimum therapeutic plasma diltiazem concentrations appear to be in the range of 50 to 200 ng/mL. Following oral administration of extended formulations of 360 mg diltiazem, the drug in plasma was detectable within 3 to 4 hours and the peak plasma concentrations were reached between 11 and 18 hours post-dose. Diltiazem peak and systemic exposures were not affected by concurrent food intake.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"CARDIZEM® LA (diltiazem hydrochloride) extended-release tablets - FDA Label\" href=\"#reference-L10556\">12</a></sup> Due to hepatic first-pass metabolism, the absolute bioavailability following oral administration is about 40%,<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"CARDIZEM® LA (diltiazem hydrochloride) extended-release tablets - FDA Label\" href=\"#reference-L10556\">12</a></sup> with the value ranging from 24 to 74% due to high interindividual variation in the first pass effect.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Hermann P, Rodger SD, Remones G, Thenot JP, London DR, Morselli PL: Pharmacokinetics of diltiazem after intravenous and oral administration. Eur J Clin Pharmacol. 1983;24(3):349-52. (PubMed ID 6861848)\" href=\"#reference-A178420\">1</a></sup> The bioavailability may increase in patients with hepatic impairment.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"CARDIZEM® LA (diltiazem hydrochloride) extended-release tablets - FDA Label\" href=\"#reference-L10556\">12</a></sup></p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds contaning a phenoxy group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004742\" rel=\"noopener\" target=\"_blank\">Phenoxy compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic aromatic compounds containing a monocyclic benzene moiety carrying exactly or one more methoxy groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004113\" rel=\"noopener\" target=\"_blank\">Methoxybenzenes</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=\"Organosulfur compounds containing a thioether group that is substituted by an alkyl and an aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003863\" rel=\"noopener\" target=\"_blank\">Alkylarylthioethers</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 amine group, a carboxylic acid group (or a derivative thereof), and a side-chain that is specific to each amino acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000347\" rel=\"noopener\" target=\"_blank\">Amino acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a lactam ring, which is a cyclic amide of amino carboxylic acids, having a 1-azacycloalkan-2-one structure (or an analogue having unsaturation or heteroatoms replacing one or more carbon atoms of the ring).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000160\" rel=\"noopener\" target=\"_blank\">Lactams</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001238\" rel=\"noopener\" target=\"_blank\">Carboxylic acid esters</a></span></span></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=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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 6 more</a>','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsBeta-1 adrenergic receptor---(C;G) / (G;G)C > GEffect Directly StudiedPatients with this genotype require a lower dosage of diltiazem to achieve a favourable rate-control response when treating atrial fibrillation.Details','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsBeta-1 adrenergic receptor---(C;G) / (G;G)C > GEffect Directly StudiedPatients with this genotype require a lower dosage of diltiazem to achieve a favourable rate-control response when treating atrial fibrillation.Details','50004704','42399-41-7','101278','CHEMBL23','35850','<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 benzothiazepines. These are organic compounds containing a benzene fused to a thiazepine ring (a seven-membered ring with a nitrogen atom and a sulfur atom replacing two carbon atoms).</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a ring with least one carbon atom and one non-carbon atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000002\" rel=\"noopener\" target=\"_blank\">Organoheterocyclic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a benzene fused to a thiazepine ring (a seven-membered ring with a nitrogen atom and a sulfur atom replacing two carbon atoms).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000317\" rel=\"noopener\" target=\"_blank\">Benzothiazepines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"not-available\">Not Available</span></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a benzene fused to a thiazepine ring (a seven-membered ring with a nitrogen atom and a sulfur atom replacing two carbon atoms).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000317\" rel=\"noopener\" target=\"_blank\">Benzothiazepines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds contaning a phenoxy group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004742\" rel=\"noopener\" target=\"_blank\">Phenoxy compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic aromatic compounds containing a monocyclic benzene moiety carrying exactly or one more methoxy groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004113\" rel=\"noopener\" target=\"_blank\">Methoxybenzenes</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=\"Organosulfur compounds containing a thioether group that is substituted by an alkyl and an aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003863\" rel=\"noopener\" target=\"_blank\">Alkylarylthioethers</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 amine group, a carboxylic acid group (or a derivative thereof), and a side-chain that is specific to each amino acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000347\" rel=\"noopener\" target=\"_blank\">Amino acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a lactam ring, which is a cyclic amide of amino carboxylic acids, having a 1-azacycloalkan-2-one structure (or an analogue having unsaturation or heteroatoms replacing one or more carbon atoms of the ring).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000160\" rel=\"noopener\" target=\"_blank\">Lactams</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001238\" rel=\"noopener\" target=\"_blank\">Carboxylic acid esters</a></span></span></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=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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 6 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkylarylthioether</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\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl thioether</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\">Benzothiazepine</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxamide group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</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\">Lactam</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Methoxybenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocyclic benzene moiety</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenol ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenoxy compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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\">Thioether</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 22 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\">5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:101278\" rel=\"noopener\" target=\"_blank\">CHEBI:101278</a>) </span></span></dd></dl>','Benzothiazepines','<p>Following a single intravenous injection in healthy male volunteers, the systemic clearance of diltiazem was approximately 65 L/h. After constant rate intravenous infusion, the systemic clearance decreased to 48 L/h.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Diltiazem Hydrochloride Injection Label - Bedford Laboratories\" href=\"#reference-L6292\">10</a></sup></p>','This compound belongs to the class of organic compounds known as benzothiazepines. These are organic compounds containing a benzene fused to a thiazepine ring (a seven-membered ring with a nitrogen atom and a sulfur atom replacing two carbon atoms).','Benzothiazepines','<li>Avoid natural licorice. The risk of cardiovascular adverse effects may be increased.</li>','Drugs.com Drug Page',' , Agents causing hyperkalemia , Agents for Treatment of Hemorrhoids and Anal Fissures for Topical Use , Antiarrhythmic agents , Antihypertensive Agents , Antihypertensive Agents Indicated for Hypertension , Benzazepines , Benzothiazepine Derivatives , Bradycardia-Causing Agents , Calcium Channel Blockers , Calcium Channel Blockers (Nondihydropyridine) , Calcium-Regulating Hormones and Agents , Cardiovascular Agents , Cytochrome P-450 CYP2C19 Substrates , Cytochrome P-450 CYP2C8 Inhibitors , Cytochrome P-450 CYP2C8 Inhibitors (moderate) , Cytochrome P-450 CYP2C8 Substrates , Cytochrome P-450 CYP2C9 Substrates , Cytochrome P-450 CYP2D6 Substrates , Cytochrome P-450 CYP3A Inhibitors , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Inhibitors , Cytochrome P-450 CYP3A4 Inhibitors (moderate) , Cytochrome P-450 CYP3A4 Inhibitors (strong) , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A5 Inhibitors , Cytochrome P-450 CYP3A5 Inhibitors (moderate) , Cytochrome P-450 CYP3A5 Substrates , Cytochrome P-450 CYP3A7 Inhibitors , Cytochrome P-450 CYP3A7 Inhibitors (moderate) , Cytochrome P-450 CYP3A7 Inhibitors (strong) , Cytochrome P-450 CYP3A7 Substrates , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Drugs causing inadvertant photosensitivity , Heterocyclic Compounds, Fused-Ring , Hypotensive Agents , Membrane Transport Modulators , Miscellaneous Calcium-channel Blocking Agents , Moderate Risk QTc-Prolonging Agents , P-glycoprotein inhibitors , P-glycoprotein substrates , Photosensitizing Agents , QTc Prolonging Agents , Selective Calcium Channel Blockers With Direct Cardiac Effects , Vasodilating Agents , Vasoprotectives','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>187-188</td><td>Kugita, H., Inoue, H., Ikezaki, M. and Takeo, S.; U.S. Patent 3,562,257; assigned to Tanabe Seiyaku Co.,Ltd., Japan.</td></tr><tr><td>water solubility</td><td>465 mg/L</td><td>MCFARLAND,JW ET AL. (2001)</td></tr><tr><td>logP</td><td>2.8</td><td>Human Metabolome Database (HMDB)</td></tr><tr><td>Caco2 permeability</td><td>-4.38</td><td>ADME Research, USCD</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:101278\" rel=\"noopener\" target=\"_blank\">CHEBI:101278</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/HMDB0014487\" rel=\"noopener\" target=\"_blank\">HMDB0014487</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:D07845\" rel=\"noopener\" target=\"_blank\">D07845</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:C06958\" rel=\"noopener\" target=\"_blank\">C06958</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=39186\" rel=\"noopener\" target=\"_blank\">39186</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=46505667\" rel=\"noopener\" target=\"_blank\">46505667</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.35850.html\" rel=\"noopener\" target=\"_blank\">35850</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=50004704\" rel=\"noopener\" target=\"_blank\">50004704</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=3443\" rel=\"noopener\" target=\"_blank\">3443</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=101278\" rel=\"noopener\" target=\"_blank\">101278</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/CHEMBL23\" rel=\"noopener\" target=\"_blank\">CHEMBL23</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/ZINC000000621893\" rel=\"noopener\" target=\"_blank\">ZINC000000621893</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=DAP001262\" rel=\"noopener\" target=\"_blank\">DAP001262</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/PA449334\" rel=\"noopener\" target=\"_blank\">PA449334</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/C9F\" rel=\"noopener\" target=\"_blank\">C9F</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/diltiaz.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/diltiazem.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/car1068.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/Diltiazem\" rel=\"noopener\" target=\"_blank\">Diltiazem</a></dd></dl>','<li>Avoid natural licorice. The risk of cardiovascular adverse effects may be increased.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A178420\">Hermann P, Rodger SD, Remones G, Thenot JP, London DR, Morselli PL: Pharmacokinetics of diltiazem after intravenous and oral administration. Eur J Clin Pharmacol. 1983;24(3):349-52. [<a href=\"/articles/A178420\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178432\">Rodriguez Padial L, Baron-Esquivias G, Hernandez Madrid A, Marzal Martin D, Pallares-Carratala V, de la Sierra A: Clinical Experience with Diltiazem in the Treatment of Cardiovascular Diseases. Cardiol Ther. 2016 Jun;5(1):75-82. doi: 10.1007/s40119-016-0059-1. Epub 2016 Mar 25. [<a href=\"/articles/A178432\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178444\">Nayler WG, Dillon JS: Calcium antagonists and their mode of action: an historical overview. Br J Clin Pharmacol. 1986;21 Suppl 2:97S-107S. doi: 10.1111/j.1365-2125.1986.tb02859.x. [<a href=\"/articles/A178444\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178453\">Sutton MS, Morad M: Mechanisms of action of diltiazem in isolated human atrial and ventricular myocardium. J Mol Cell Cardiol. 1987 May;19(5):497-508. [<a href=\"/articles/A178453\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178492\">O\'Connor SE, Grosset A, Janiak P: The pharmacological basis and pathophysiological significance of the heart rate-lowering property of diltiazem. Fundam Clin Pharmacol. 1999;13(2):145-53. [<a href=\"/articles/A178492\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178516\">Yeung PK, Prescott C, Haddad C, Montague TJ, McGregor C, Quilliam MA, Xei M, Li R, Farmer P, Klassen GA: Pharmacokinetics and metabolism of diltiazem in healthy males and females following a single oral dose. Eur J Drug Metab Pharmacokinet. 1993 Apr-Jun;18(2):199-206. doi: 10.1007/BF03188796. [<a href=\"/articles/A178516\" target=\"_blank\">Article</a>] </li><li id=\"reference-A39292\">Molden E, Asberg A, Christensen H: Desacetyl-diltiazem displays severalfold higher affinity to CYP2D6 compared with CYP3A4. Drug Metab Dispos. 2002 Jan;30(1):1-3. [<a href=\"/articles/A39292\" target=\"_blank\">Article</a>] </li><li id=\"reference-T28\">4, 22. (2012). In Rang and Dale\'s Pharmacology (7th ed., pp. 50, 272). 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-L6289\">Diltiazem - StatPearls - NCBI Bookshelf [<a href=\"https://www.ncbi.nlm.nih.gov/books/NBK532937/\" target=\"_blank\">Link</a>] </li><li id=\"reference-L6292\">Diltiazem Hydrochloride Injection Label - Bedford Laboratories [<a href=\"https://docs.boehringer-ingelheim.com/Prescribing%20Information/PIs/Ben%20Venue_Bedford%20Labs/55390-565-10%20DLT%2050MG/5539056510\" target=\"_blank\">Link</a>] </li><li id=\"reference-L6298\">Cardizem (diltiazem hydrochloride) Drug Summary - PDR.net [<a href=\"https://www.pdr.net/drug-summary/Cardizem-diltiazem-hydrochloride-2077\" target=\"_blank\">Link</a>] </li><li id=\"reference-L10556\">CARDIZEM® LA (diltiazem hydrochloride) extended-release tablets - FDA Label [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021392s019lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L10559\">CARDIZEM® CD (diltiazem HCl) Capsules - FDA Label [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020062s040lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>The plasma elimination half-life is approximately 3.0 to 4.5 hours following single and multiple oral doses. The half-life may slightly increase with dose and the extent of hepatic impairment.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"CARDIZEM® LA (diltiazem hydrochloride) extended-release tablets - FDA Label\" href=\"#reference-L10556\">12</a></sup> The apparent elimination half-life for diltiazem as extended-release tablets after single or multiple dosing is 6 to 9 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"CARDIZEM® LA (diltiazem hydrochloride) extended-release tablets - FDA Label\" href=\"#reference-L10556\">12</a></sup> The plasma elimination half-life is approximately 3.4 hours following administration of a single intravenous injection.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Diltiazem Hydrochloride Injection Label - Bedford Laboratories\" href=\"#reference-L6292\">10</a></sup> The elimination half-lives of pharmacologically active metabolites are longer than that of diltiazem.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Yeung PK, Prescott C, Haddad C, Montague TJ, McGregor C, Quilliam MA, Xei M, Li R, Farmer P, Klassen GA: Pharmacokinetics and metabolism of diltiazem in healthy males and females following a single oral dose. Eur J Drug Metab Pharmacokinet. 1993 Apr-Jun;18(2):199-206. doi: 10.1007/BF03188796. (PubMed ID 8243504)\" href=\"#reference-A178516\">6</a></sup></p>','HMDB0014487','(2S,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate','InChI=1S/C22H26N2O4S/c1-15(25)28-20-21(16-9-11-17(27-4)12-10-16)29-19-8-6-5-7-18(19)24(22(20)26)14-13-23(2)3/h5-12,20-21H,13-14H2,1-4H3/t20-,21+/m1/s1','HSUGRBWQSSZJOP-RTWAWAEBSA-N','<p><strong>Oral</strong></p><p>Indicated for the management of hypertension, to lower blood pressure, alone or in combination with other antihypertensive agents.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"CARDIZEM® LA (diltiazem hydrochloride) extended-release tablets - FDA Label\" href=\"#reference-L10556\">12</a></sup></p><p>Indicated for use to improve exercise tolerance in patients with chronic stable angina.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"CARDIZEM® LA (diltiazem hydrochloride) extended-release tablets - FDA Label\" href=\"#reference-L10556\">12</a></sup></p><p>Indicated for the management of variant angina (Prinzmetal\'s angina).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Cardizem (diltiazem hydrochloride) Drug Summary - PDR.net\" href=\"#reference-L6298\">11</a></sup></p><p><strong>Intravenous</strong></p><p>Indicated for the short-term management of atrial fibrillation or atrial flutter for temporary control of rapid ventricular rate.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Diltiazem Hydrochloride Injection Label - Bedford Laboratories\" href=\"#reference-L6292\">10</a></sup></p><p>Indicated for the rapid conversion of paroxysmal supraventricular tachycardias (PSVT) to sinus rhythm. This includes AV nodal reentrant tachycardias and reciprocating tachycardias associated with an extranodal accessory pathway such as the WPW syndrome or short PR syndrome.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Diltiazem Hydrochloride Injection Label - Bedford Laboratories\" href=\"#reference-L6292\">10</a></sup></p><p><strong>Off-label</strong></p><p>Indicated for off-label uses in anal fissures (as topical formulation), migraine prophylaxis, cramps in lower leg related to rest, pulmonary hypertension,<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Diltiazem - StatPearls - NCBI Bookshelf\" href=\"#reference-L6289\">9</a></sup> idiopathic dilated cardiomyopathy, and proteinuria associated with diabetic nephropathy.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Cardizem (diltiazem hydrochloride) Drug Summary - PDR.net\" href=\"#reference-L6298\">11</a></sup></p>','C06958','D07845','Organic compounds','<p>Diltiazem is subject to extensive first-pass metabolism, which explains its relatively low absolute oral bioavailability. It undergoes N-demethylation primarily mediated by CYP3A4. CYP2D6 is responsible for O-demethylation and esterases mediate deacetylation.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Molden E, Asberg A, Christensen H: Desacetyl-diltiazem displays severalfold higher affinity to CYP2D6 compared with CYP3A4. Drug Metab Dispos. 2002 Jan;30(1):1-3. (PubMed ID 11744603)\" href=\"#reference-A39292\">7</a></sup> There was large inter-individual variability in the circulating plasma levels of metabolites in healthy volunteers.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Yeung PK, Prescott C, Haddad C, Montague TJ, McGregor C, Quilliam MA, Xei M, Li R, Farmer P, Klassen GA: Pharmacokinetics and metabolism of diltiazem in healthy males and females following a single oral dose. Eur J Drug Metab Pharmacokinet. 1993 Apr-Jun;18(2):199-206. doi: 10.1007/BF03188796. (PubMed ID 8243504)\" href=\"#reference-A178516\">6</a></sup></p><p>In healthy volunteers, the major circulating metabolites in the plasma are N-monodesmethyl diltilazem, deacetyl diltiazem, and deacetyl N-monodesmethyl diltiazem, which are all pharmacologically active.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Yeung PK, Prescott C, Haddad C, Montague TJ, McGregor C, Quilliam MA, Xei M, Li R, Farmer P, Klassen GA: Pharmacokinetics and metabolism of diltiazem in healthy males and females following a single oral dose. Eur J Drug Metab Pharmacokinet. 1993 Apr-Jun;18(2):199-206. doi: 10.1007/BF03188796. (PubMed ID 8243504)\" href=\"#reference-A178516\">6</a></sup> Deacetyl diltiazem retains about 25-50% of the pharmacological activity to that of the parent compound.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"CARDIZEM® LA (diltiazem hydrochloride) extended-release tablets - FDA Label\" href=\"#reference-L10556\">12</a></sup> Deacetyl diltiazem can be further transformed into deacetyl diltiazem N-oxide or deacetyl O-desmethyl diltiazem. N-monodesmethyl diltilazem can be further metabolized to N,O-didesmethyl diltiazem. Deacetyl N-monodesmethyl diltiazem can be further metabolized to deacetyl N,O-didesmethyl diltiazem, which can be glucuronidated or sulphated.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Yeung PK, Prescott C, Haddad C, Montague TJ, McGregor C, Quilliam MA, Xei M, Li R, Farmer P, Klassen GA: Pharmacokinetics and metabolism of diltiazem in healthy males and females following a single oral dose. Eur J Drug Metab Pharmacokinet. 1993 Apr-Jun;18(2):199-206. doi: 10.1007/BF03188796. (PubMed ID 8243504)\" href=\"#reference-A178516\">6</a></sup> Diltiazem can be O-demethylated by CYP2D6 to form O-desmethyl diltiazem.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Molden E, Asberg A, Christensen H: Desacetyl-diltiazem displays severalfold higher affinity to CYP2D6 compared with CYP3A4. Drug Metab Dispos. 2002 Jan;30(1):1-3. (PubMed ID 11744603)\" href=\"#reference-A39292\">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','C9F','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000359?highlight[compounds][]=DB00343&amp;highlight[proteins][]=DB00343\">Diltiazem Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA449334','<p>Diltiazem is about 70-80% bound to plasma proteins, according to <em>in vitro</em> binding studies.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"CARDIZEM® LA (diltiazem hydrochloride) extended-release tablets - FDA Label\" href=\"#reference-L10556\">12</a></sup> About 40% of the drug is thought to bind to alpha-1-glycoprotein at clinically significant concentrations while about 30% of the drug is bound to albumin.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Diltiazem Hydrochloride Injection Label - Bedford Laboratories\" href=\"#reference-L6292\">10</a></sup></p>','39186','46505667','<p>Due to its extensive metabolism, only 2% to 4% of the unchanged drug can be detected in the urine.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"CARDIZEM® LA (diltiazem hydrochloride) extended-release tablets - FDA Label\" href=\"#reference-L10556\">12</a></sup> The major urinary metabolite in healthy volunnteers was N-monodesmethyl diltiazem, followed by deacetyl N,O-didesmethyl diltiazem, deacetyl N-monodesmethyl diltiazem, and deacetyl diltiazem; however, there seems to be large inter-individual variability in the urinary excretion of DTZ and its metabolites.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Yeung PK, Prescott C, Haddad C, Montague TJ, McGregor C, Quilliam MA, Xei M, Li R, Farmer P, Klassen GA: Pharmacokinetics and metabolism of diltiazem in healthy males and females following a single oral dose. Eur J Drug Metab Pharmacokinet. 1993 Apr-Jun;18(2):199-206. doi: 10.1007/BF03188796. (PubMed ID 8243504)\" href=\"#reference-A178516\">6</a></sup></p>','RxList Drug Page','3443','COC1=CC=C(C=C1)[C@@H]1SC2=C(C=CC=C2)N(CCN(C)C)C(=O)[C@@H]1OC(C)=O','Solid','Not Available','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkylarylthioether</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\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl thioether</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\">Benzothiazepine</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxamide group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</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\">Lactam</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Methoxybenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocyclic benzene moiety</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenol ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenoxy compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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\">Thioether</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 22 more</a>','Organoheterocyclic compounds','<span class=\"citations\"><p>Kugita, H., Inoue, H., Ikezaki, M. and Takeo, S.; U.S. Patent 3,562,257; assigned to Tanabe Seiyaku Co.,Ltd., Japan.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=3562257&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US3562257</a>','DAP001262','<p><strong>Clinical Toxicity and Overdose</strong></p><p>The oral LD<sub>50</sub> ranges from 415 to 740mg/kg in mice and 560 to 810 mg/kg in rats. The oral LD<sub>50</sub> in dogs is considered to be in excess of 50 mg/kg. A dose of 360 mg/kg resulted in lethality in monkeys. The intravenous LD<sub>50</sub> is 60 mg/kg in mice and 38 mg/kg in rats. </p><p>Cases of overdose from doses ranging from less than 1 g to 18 g have been reported with diltiazem, with several cases involving multiple drug ingestions resulting in death. Overdoses were associated with bradycardia, hypotension, heart block, and cardiac failure that may manifest as dizziness, lightheadedness, and fatigue.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Diltiazem - StatPearls - NCBI Bookshelf\" href=\"#reference-L6289\">9</a></sup> Actual treatment and dosage should depend on the severity of the clinical situation and the judgment and experience of the treating physician. Diltiazem overdose should be responded with appropriate supportive measures and gastrointestinal decontamination. Bradycardia and heart block can be treated with atropine at doses ranging from 0.60 to 1.0 mg. In the case of bradycardia, if there is no response to vagal blockage, cautious administration of isoproterenol should be considered. Cardiac pacing can also be used to treat fixed high-degree AV block. In the case of heart failure, blood pressure may be maintained with the use of fluids and vasopressors, as well as inotropic agents such as <a href=\"https://go.drugbank.com/drugs/DB01064\">isoproterenol</a>, <a href=\"https://go.drugbank.com/drugs/DB00988\">dopamine</a>, or <a href=\"https://go.drugbank.com/drugs/DB00841\">dobutamine</a>. Other appropriate measures include ventilatory support, gastric lavage, activated charcoal, and/or intravenous calcium. Diltiazem does not appear to be removed by peritoneal or hemodialysis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"CARDIZEM® LA (diltiazem hydrochloride) extended-release tablets - FDA Label\" href=\"#reference-L10556\">12</a></sup></p><p><strong>Non-clinical toxicity</strong></p><p>In a 24-month study in rats receiving oral doses of up to 100 mg/kg/day, there was no evidence of carcinogenicity. There was also no mutagenic response <em>in vitro</em> or <em>in vivo</em> in mammalian cell assays or <em>in vitro</em> bacterial assays. No evidence of impaired fertility was observed in a study performed in male and female rats receiving oral doses of up to 100 mg/kg/day.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"CARDIZEM® LA (diltiazem hydrochloride) extended-release tablets - FDA Label\" href=\"#reference-L10556\">12</a></sup></p><p><strong>Pregnancy and Lactation</strong></p><p>In reproduction studies in animals, administration of diltiazem at doses ranging from five to twenty times the daily recommended human therapeutic dose resulted in cases of the embryo and fetal lethality and skeletal abnormalities, and an increase in the risk of stillbirths. There have been no up-to-date controlled studies that investigated the use of diltiazem in pregnant women. The use of diltiazem in pregnant women should be undertaken only if the potential benefit justifies the risk to the fetus.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"CARDIZEM® LA (diltiazem hydrochloride) extended-release tablets - FDA Label\" href=\"#reference-L10556\">12</a></sup> Diltiazem is excreted in human milk, where one report suggests that the concentrations in breast milk may approximate serum levels; therefore, the decision should be made to either discontinue nursing or the use of the drug after careful consideration of the clinical necessity of diltiazem therapy in the nursing mother.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"CARDIZEM® LA (diltiazem hydrochloride) extended-release tablets - FDA Label\" href=\"#reference-L10556\">12</a></sup></p><p><strong>Use in special populations</strong></p><p>As there is limited information on the variable effects of diltiazem in geriatric patients, the initial therapy of diltiazem should involve the low end of the dosing range, reflecting the greater frequency of decreased hepatic, renal, or cardiac function, and of concomitant disease or other drug therapy. Currently, there are no specific dosing guidelines for patients with renal or hepatic impairment.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"CARDIZEM® LA (diltiazem hydrochloride) extended-release tablets - FDA Label\" href=\"#reference-L10556\">12</a></sup></p>','EE92BBP03H','<p>The apparent volume of distribution of diltiazem was approximately 305 L following a single intravenous injection in healthy male volunteers.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Diltiazem Hydrochloride Injection Label - Bedford Laboratories\" href=\"#reference-L6292\">10</a></sup></p>','Diltiazem','ZINC000000621893'),(28,'Progesterone','progesterone','Progesterone is a hormone used for a variety of functions, including contraception, control of abnormal uterine bleeding, maintenance of pregnancy, and prevention of endometrial hyperplasia.','Bijuva, Crinone, Endometrin, Prochieve, Prometrium','Progesterone','<p>Progesterone is a hormone that occurs naturally in females, and is essential for endometrial receptivity, embryo implantation, and the successful establishment of pregnancy. A low progesterone concentration or an insufficient response to progesterone can cause infertility and pregnancy loss <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Young SL, Lessey BA: Progesterone function in human endometrium: clinical perspectives. Semin Reprod Med. 2010 Jan;28(1):5-16. doi: 10.1055/s-0029-1242988. Epub 2010 Jan 26. (PubMed ID 20104424)\" href=\"#reference-A175609\">7</a></sup>. Progesterone is used in various contraceptive preparations to prevent ovulation and fertilization <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Danielle B. Cooper; Rotimi Adigun (2018). Oral contraceptives. StatPearls Publishing.\" href=\"#reference-T481\">15</a></sup>, <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Lopez LM, Ramesh S, Chen M, Edelman A, Otterness C, Trussell J, Helmerhorst FM: Progestin-only contraceptives: effects on weight. Cochrane Database Syst Rev. 2016 Aug 28;(8):CD008815. doi: 10.1002/14651858.CD008815.pub4. (PubMed ID 27567593)\" href=\"#reference-A175612\">8</a></sup> as well as in other formulations to promote and support pregnancy. Please see <a href=\"https://go.drugbank.com/drugs/DB00603\">Medroxyprogesterone acetate</a>, <a href=\"https://go.drugbank.com/drugs/DB00351\">Megestrol acetate</a>, <a href=\"https://go.drugbank.com/drugs/DB00378\">Dydrogesterone</a> and <a href=\"https://go.drugbank.com/drugs/DB14570\">Hydroxyprogesterone</a> entries for information on various other forms of progesterone.</p><p>Pharmaceutical progesterone is made from a plant source as a starting material and is chemically identical to progesterone of human ovarian origin <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. Progesterone is available in gelatinized capsule form, vaginal gel form, tablet form, vaginal insert form, and injection form, all used for various purposes <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=\"Progesterone gel: Crinone® 4% and Crinone® 8%\" href=\"#reference-F3898\">20</a>,<a class=\"reference-popover-link\" data-content=\"Norethindrone FDA label\" href=\"#reference-F3904\">22</a>,<a class=\"reference-popover-link\" data-content=\"Endometrin FDA label, vaginal insert\" href=\"#reference-F3901\">21</a>,<a class=\"reference-popover-link\" data-content=\"Progesterone injection, FDA label\" href=\"#reference-F3907\">23</a></sup>.</p>','C21H30O2','DB00396','Approved, Vet approved','Small Molecule','Average: 314.4617 Monoisotopic: 314.224580204 ',' , G03FA — Progestogens and estrogens, fixed combinations , G03F — PROGESTOGENS AND ESTROGENS IN COMBINATION , G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM , G — GENITO URINARY SYSTEM AND SEX HORMONES , G03DA — Pregnen (4) derivatives , G03D — PROGESTOGENS , G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM , G — GENITO URINARY SYSTEM AND SEX HORMONES','<p><strong>Oral micronized capsules</strong></p><p>Following oral administration of progesterone in the micronized soft-gelatin capsule formulation, peak serum concentration was achieved in the first 3 hours. The absolute bioavailability of micronized progesterone is unknown at this time. In postmenopausal women, serum progesterone concentration increased in a dose-proportional and linear fashion after multiple doses of progesterone capsules, ranging from 100 mg/day to 300 mg/day <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. </p><p><strong>IM administration</strong></p><p>After intramuscular (IM) administration of 10 mg of progesterone in oil, the maximum plasma concentrations were achieved in about 8 hours post-injection and plasma concentrations stayed above baseline for approximately 24 hours post-injection. Injections of 10, 25, and 50 mg lead to geometric mean values for maximum plasma concentration (CMAX) of 7, 28, and 50 ng/mL, respectively <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"PROGESTERONE INJECTION USP IN SESAME OIL FOR INTRAMUSCULAR USE ONLY\" href=\"#reference-F3916\">25</a></sup>. Progesterone administered by the intramuscular (IM) route avoids significant first-pass hepatic metabolism. As a result, endometrial tissue concentrations of progesterone achieved with IM administration are higher when compared with oral administration. Despite this, the highest concentrations of progesterone in endometrial tissue are reached with vaginal administration <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Paulson RJ, Collins MG, Yankov VI: Progesterone pharmacokinetics and pharmacodynamics with 3 dosages and 2 regimens of an effervescent micronized progesterone vaginal insert. J Clin Endocrinol Metab. 2014 Nov;99(11):4241-9. doi: 10.1210/jc.2013-3937. Epub 2014 Feb 25. (PubMed ID 24606090)\" href=\"#reference-A175657\">11</a></sup>. </p><p><strong>Note on oral contraceptive tablet absorption</strong></p><p>Serum progestin levels peak about 2 hours after oral administration of progesterone-only contraceptive tablets, followed by rapid distribution and elimination. By 24 hours after drug administration, serum levels remain near the baseline, making efficacy dependent upon strict adherence to the dosing schedule. Large variations in serum progesterone levels occur among individuals. Progestin-only administration leads to lower steady-state serum progestin levels and a shorter elimination half-life than concurrent administration with estrogens <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Norethindrone FDA label\" href=\"#reference-F3904\">22</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=\"Steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003058\" rel=\"noopener\" target=\"_blank\">20-oxosteroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"3-oxo steroids containing a double bond between positions  3 and 4.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002974\" rel=\"noopener\" target=\"_blank\">3-oxo delta-4-steroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroids containing a double bond between positions 4 and 5.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002978\" rel=\"noopener\" target=\"_blank\">Delta-4-steroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004325\" rel=\"noopener\" target=\"_blank\">Cyclohexenones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span>','Not Available','Not Available','8903','57-83-0','17026','CHEMBL103','5773','<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 gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane 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=\"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=\"Steroids with a structure based on the 21-carbon pregnane skeleton.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003569\" rel=\"noopener\" target=\"_blank\">Pregnane steroids</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Steroids with a structure based on a hydroxylated prostane moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001468\" rel=\"noopener\" target=\"_blank\">Gluco/mineralocorticoids, progestogins and derivatives</a></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=\"Steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003058\" rel=\"noopener\" target=\"_blank\">20-oxosteroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"3-oxo steroids containing a double bond between positions  3 and 4.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002974\" rel=\"noopener\" target=\"_blank\">3-oxo delta-4-steroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroids containing a double bond between positions 4 and 5.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002978\" rel=\"noopener\" target=\"_blank\">Delta-4-steroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004325\" rel=\"noopener\" target=\"_blank\">Cyclohexenones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">20-oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">3-oxo-delta-4-steroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">3-oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aliphatic homopolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclic ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclohexenone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Delta-4-steroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ketone</span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aliphatic homopolycyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">3-oxo Delta(4)-steroid, 20-oxo steroid, C21-steroid hormone (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17026\" rel=\"noopener\" target=\"_blank\">CHEBI:17026</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Pregnane and derivatives [Fig], Progestagens (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C00410\" rel=\"noopener\" target=\"_blank\">C00410</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMST02030159\" rel=\"noopener\" target=\"_blank\">LMST02030159</a>) </span></span></dd></dl>','Steroids and steroid derivatives','<p><strong>Apparent clearance</strong></p><p>1367 ± 348 (50mg of progesterone administered by vaginal insert once daily) <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Paulson RJ, Collins MG, Yankov VI: Progesterone pharmacokinetics and pharmacodynamics with 3 dosages and 2 regimens of an effervescent micronized progesterone vaginal insert. J Clin Endocrinol Metab. 2014 Nov;99(11):4241-9. doi: 10.1210/jc.2013-3937. Epub 2014 Feb 25. (PubMed ID 24606090)\" href=\"#reference-A175657\">11</a></sup>.</p><p>106 ± 15 L/h (50mg/mL IM injection once daily) <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Paulson RJ, Collins MG, Yankov VI: Progesterone pharmacokinetics and pharmacodynamics with 3 dosages and 2 regimens of an effervescent micronized progesterone vaginal insert. J Clin Endocrinol Metab. 2014 Nov;99(11):4241-9. doi: 10.1210/jc.2013-3937. Epub 2014 Feb 25. (PubMed ID 24606090)\" href=\"#reference-A175657\">11</a></sup>.</p>','This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.','Gluco/mineralocorticoids, progestogins and derivatives','<li>Administer vitamin supplements.</li>\n<li>Avoid alcohol.</li>\n<li>Limit caffeine intake.</li>\n<li>Take at the same time every day.</li>\n<li>Take with food.</li>','Drugs.com Drug Page',' , Adrenal Cortex Hormones , BCRP/ABCG2 Inducers , BCRP/ABCG2 Inhibitors , BSEP/ABCB11 Inhibitors , Corpus Luteum Hormones , Cytochrome P-450 CYP2A6 Inducers , Cytochrome P-450 CYP2C19 Inhibitors , Cytochrome P-450 CYP2C19 inhibitors (strength unknown) , Cytochrome P-450 CYP2C19 Substrates , Cytochrome P-450 CYP2C9 Inhibitors , Cytochrome P-450 CYP2C9 Inhibitors (strength unknown) , Cytochrome P-450 CYP2C9 Substrates , Cytochrome P-450 CYP2D6 Substrates , 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 Substrates , Cytochrome P-450 CYP3A5 Substrates , Cytochrome P-450 CYP3A7 Inhibitors , Cytochrome P-450 CYP3A7 Inhibitors (strength unknown) , Cytochrome P-450 CYP3A7 Substrates , Cytochrome P-450 Enzyme Inducers , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Fused-Ring Compounds , Genito Urinary System and Sex Hormones , Gonadal Hormones , Gonadal Steroid Hormones , Hormonal Contraceptives for Systemic Use , Hormones , Hormones, Hormone Substitutes, and Hormone Antagonists , Hyperglycemia-Associated Agents , OATP1B1/SLCO1B1 Inhibitors , OATP1B3 inducers , OCT1 inhibitors , OCT2 Inhibitors , P-glycoprotein inducers , P-glycoprotein inhibitors , P-glycoprotein substrates , Pregnanes , Pregnenediones , Pregnenes , Progesterone and Derivatives , Progesterone, antagonists & inhibitors , Progestin-containing Intrauterine Device , Progestins , Sex Hormones and Modulators of the Genital System , 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>melting point (°C)</td><td>128-132</td><td>https://www.chemicalbook.com/ChemicalProductProperty_US_CB4224484.aspx</td></tr><tr><td>boiling point (°C)</td><td>394.13°C (rough estimate)</td><td>https://www.chemicalbook.com/ChemicalProductProperty_US_CB4224484.aspx</td></tr><tr><td>water solubility</td><td>&lt;0.1 g/100 mL at 19 ºC</td><td>https://www.chemicalbook.com/ChemicalProductProperty_US_CB4224484.aspx</td></tr><tr><td>logP</td><td>3.87</td><td>http://www.hmdb.ca/metabolites/HMDB0001830</td></tr><tr><td>logS</td><td>-4.43</td><td>http://www.hmdb.ca/metabolites/HMDB0001830</td></tr><tr><td>pKa</td><td>Strongest acidic: , Strongest basic: 18.92, -4.8</td><td>http://www.hmdb.ca/metabolites/HMDB0001830</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">3-oxo Delta(4)-steroid, 20-oxo steroid, C21-steroid hormone (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17026\" rel=\"noopener\" target=\"_blank\">CHEBI:17026</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Pregnane and derivatives [Fig], Progestagens (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C00410\" rel=\"noopener\" target=\"_blank\">C00410</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMST02030159\" rel=\"noopener\" target=\"_blank\">LMST02030159</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/HMDB0001830\" rel=\"noopener\" target=\"_blank\">HMDB0001830</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:D00066\" rel=\"noopener\" target=\"_blank\">D00066</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:C00410\" rel=\"noopener\" target=\"_blank\">C00410</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=5994\" rel=\"noopener\" target=\"_blank\">5994</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=46508968\" rel=\"noopener\" target=\"_blank\">46508968</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.5773.html\" rel=\"noopener\" target=\"_blank\">5773</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=8903\" rel=\"noopener\" target=\"_blank\">8903</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=8727\" rel=\"noopener\" target=\"_blank\">8727</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=17026\" rel=\"noopener\" target=\"_blank\">17026</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/CHEMBL103\" rel=\"noopener\" target=\"_blank\">CHEMBL103</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/ZINC000004428529\" rel=\"noopener\" target=\"_blank\">ZINC000004428529</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=DAP000549\" rel=\"noopener\" target=\"_blank\">DAP000549</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/PA451123\" rel=\"noopener\" target=\"_blank\">PA451123</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/STR\" rel=\"noopener\" target=\"_blank\">STR</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/progesterone.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/progesterone.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/pro1670.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/Progesterone\" rel=\"noopener\" target=\"_blank\">Progesterone</a></dd></dl>','<li>Administer vitamin supplements.</li>\n<li>Avoid alcohol.</li>\n<li>Limit caffeine intake.</li>\n<li>Take at the same time every day.</li>\n<li>Take with food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A599\">Allen WM: THE ISOLATION OF CRYSTALLINE PROGESTIN. Science. 1935 Aug 2;82(2118):89-93. [<a href=\"/articles/A599\" target=\"_blank\">Article</a>] </li><li id=\"reference-A600\">Allen WM: Progesterone: how did the name originate? South Med J. 1970 Oct;63(10):1151-5. [<a href=\"/articles/A600\" target=\"_blank\">Article</a>] </li><li id=\"reference-A601\">Schumacher M, Guennoun R, Robert F, Carelli C, Gago N, Ghoumari A, Gonzalez Deniselle MC, Gonzalez SL, Ibanez C, Labombarda F, Coirini H, Baulieu EE, De Nicola AF: Local synthesis and dual actions of progesterone in the nervous system: neuroprotection and myelination. Growth Horm IGF Res. 2004 Jun;14 Suppl A:S18-33. [<a href=\"/articles/A601\" target=\"_blank\">Article</a>] </li><li id=\"reference-A602\">Hould FS, Fried GM, Fazekas AG, Tremblay S, Mersereau WA: Progesterone receptors regulate gallbladder motility. J Surg Res. 1988 Dec;45(6):505-12. [<a href=\"/articles/A602\" target=\"_blank\">Article</a>] </li><li id=\"reference-A38631\">Payne VA, Chang YT, Loew GH: Homology modeling and substrate binding study of human CYP2C18 and CYP2C19 enzymes. Proteins. 1999 Nov 1;37(2):204-17. [<a href=\"/articles/A38631\" target=\"_blank\">Article</a>] </li><li id=\"reference-A38674\">Yamazaki H, Shimada T: Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9. doi: 10.1006/abbi.1997.0302. [<a href=\"/articles/A38674\" target=\"_blank\">Article</a>] </li><li id=\"reference-A175609\">Young SL, Lessey BA: Progesterone function in human endometrium: clinical perspectives. Semin Reprod Med. 2010 Jan;28(1):5-16. doi: 10.1055/s-0029-1242988. Epub 2010 Jan 26. [<a href=\"/articles/A175609\" target=\"_blank\">Article</a>] </li><li id=\"reference-A175612\">Lopez LM, Ramesh S, Chen M, Edelman A, Otterness C, Trussell J, Helmerhorst FM: Progestin-only contraceptives: effects on weight. Cochrane Database Syst Rev. 2016 Aug 28;(8):CD008815. doi: 10.1002/14651858.CD008815.pub4. [<a href=\"/articles/A175612\" target=\"_blank\">Article</a>] </li><li id=\"reference-A175645\">Khandelwal M: Vaginal progesterone in risk reduction of preterm birth in women with short cervix in the midtrimester of pregnancy. Int J Womens Health. 2012;4:481-90. doi: 10.2147/IJWH.S28944. Epub 2012 Sep 14. [<a href=\"/articles/A175645\" target=\"_blank\">Article</a>] </li><li id=\"reference-A175651\">Okada H, Tsuzuki T, Murata H: Decidualization of the human endometrium. Reprod Med Biol. 2018 Feb 1;17(3):220-227. doi: 10.1002/rmb2.12088. eCollection 2018 Jul. [<a href=\"/articles/A175651\" target=\"_blank\">Article</a>] </li><li id=\"reference-A175657\">Paulson RJ, Collins MG, Yankov VI: Progesterone pharmacokinetics and pharmacodynamics with 3 dosages and 2 regimens of an effervescent micronized progesterone vaginal insert. J Clin Endocrinol Metab. 2014 Nov;99(11):4241-9. doi: 10.1210/jc.2013-3937. Epub 2014 Feb 25. [<a href=\"/articles/A175657\" target=\"_blank\">Article</a>] </li><li id=\"reference-A175660\">Child T, Leonard SA, Evans JS, Lass A: Systematic review of the clinical efficacy of vaginal progesterone for luteal phase support in assisted reproductive technology cycles. Reprod Biomed Online. 2018 Jun;36(6):630-645. doi: 10.1016/j.rbmo.2018.02.001. Epub 2018 Feb 22. [<a href=\"/articles/A175660\" target=\"_blank\">Article</a>] </li><li id=\"reference-A175663\">Check JH: Luteal Phase Support in assisted reproductive technology treatment: focus on Endometrin(R) (progesterone) vaginal insert. Ther Clin Risk Manag. 2009 Aug;5(4):403-7. Epub 2009 Jun 4. [<a href=\"/articles/A175663\" target=\"_blank\">Article</a>] </li><li id=\"reference-A175666\">Grimm SL, Hartig SM, Edwards DP: Progesterone Receptor Signaling Mechanisms. J Mol Biol. 2016 Sep 25;428(19):3831-49. doi: 10.1016/j.jmb.2016.06.020. Epub 2016 Jul 2. [<a href=\"/articles/A175666\" target=\"_blank\">Article</a>] </li><li id=\"reference-T481\">Danielle B. Cooper; Rotimi Adigun (2018). Oral contraceptives. StatPearls Publishing. </li><li id=\"reference-T490\">Dhanalakshmi K. Thiyagarajan; Rebecca Jeanmonod (2019). Physiology, Menstrual Cycle. StatPearls publishing. </li><li id=\"reference-L5629\">Drug approval package FDA [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/020843_s000_PrometriumTOC.cfm\" target=\"_blank\">Link</a>] </li><li id=\"reference-L5638\">Merck Manuals: Abnormal Uterine Bleeding Due to Ovulatory Dysfunction (AUB-O) [<a href=\"https://www.merckmanuals.com/en-ca/professional/gynecology-and-obstetrics/menstrual-abnormalities/abnormal-uterine-bleeding-due-to-ovulatory-dysfunction-aub-o\" target=\"_blank\">Link</a>] </li><li id=\"reference-L5641\">AAFP: Abnormal uterine bleeding [<a href=\"https://www.aafp.org/afp/1999/1001/p1371.html\" target=\"_blank\">Link</a>] </li><li id=\"reference-F3898\">Progesterone gel: Crinone® 4% and Crinone® 8% [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/003/898/original/Progesterone_Gel.pdf?1552088547\" target=\"_blank\">File</a>] </li><li id=\"reference-F3901\">Endometrin FDA label, vaginal insert [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/003/901/original/Endometrin__vaginal_insert_FDA_label.pdf?1552088774\" target=\"_blank\">File</a>] </li><li id=\"reference-F3904\">Norethindrone FDA label [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/003/904/original/Norethindrone_FDA_label.pdf?1552320726\" target=\"_blank\">File</a>] </li><li id=\"reference-F3907\">Progesterone injection, FDA label [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/003/907/original/Progestrone_injection__FDA_label.pdf?1552321319\" target=\"_blank\">File</a>] </li><li id=\"reference-F3913\">Utrogestan capsules, medsafe NZ label [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/003/913/original/UtrogestanSunflowerOilcap.pdf?1552322296\" target=\"_blank\">File</a>] </li><li id=\"reference-F3916\">PROGESTERONE INJECTION USP IN SESAME OIL FOR INTRAMUSCULAR USE ONLY [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/003/916/original/FDA_Label__Progesterone_and_sesame_oil.pdf?1552338634\" target=\"_blank\">File</a>] </li></ol>','<p>Absorption half-life is approximately 25-50 hours and an elimination half-life of 5-20 minutes (progesterone gel) <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Progesterone gel: Crinone® 4% and Crinone® 8%\" href=\"#reference-F3898\">20</a></sup>. </p><p>Progesterone, administered orally, has a short serum half-life (approximately 5 minutes). It is rapidly metabolized to <em>17-hydroxyprogesterone</em> during its first pass through the liver <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Paulson RJ, Collins MG, Yankov VI: Progesterone pharmacokinetics and pharmacodynamics with 3 dosages and 2 regimens of an effervescent micronized progesterone vaginal insert. J Clin Endocrinol Metab. 2014 Nov;99(11):4241-9. doi: 10.1210/jc.2013-3937. Epub 2014 Feb 25. (PubMed ID 24606090)\" href=\"#reference-A175657\">11</a></sup>. </p>','HMDB0001830','(1S,3aS,3bS,9aR,9bS,11aS)-1-acetyl-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one','InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1','RJKFOVLPORLFTN-LEKSSAKUSA-N','<p><strong>Gelatinized capsules</strong></p><p>The gelatinized capsules are indicated for use in the prevention of endometrial hyperplasia in non-hysterectomized postmenopausal women who are receiving conjugated estrogens tablets. They are also indicated for use in secondary amenorrhea <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. </p><p><strong>Vaginal gel</strong></p><p>Progesterone gel (8%) is indicated as progesterone supplementation or replacement as part of an Assisted Reproductive Technology (“ART”) treatment for infertile women with progesterone deficiency. The lower concentration progesterone gel (4%) is used in the treatment of secondary amenorrhea, with the use of the 8% concentration if there is no therapeutic response to the 4% gel <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Progesterone gel: Crinone® 4% and Crinone® 8%\" href=\"#reference-F3898\">20</a></sup>.</p><p><strong>Vaginal insert</strong></p><p>This form is indicated to support embryo implantation and early pregnancy by supplementation of corpus luteal function as part of an Assisted Reproductive Technology (ART) treatment program for infertile women <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Endometrin FDA label, vaginal insert\" href=\"#reference-F3901\">21</a></sup>.</p><p><strong>Injection (intramuscular)</strong></p><p>This drug is indicated in amenorrhea and abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology, such as submucous fibroids or uterine cancer <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Progesterone injection, FDA label\" href=\"#reference-F3907\">23</a></sup>. </p><p><strong>Tablets, contraceptive</strong></p><p>The tablet form of progesterone in contraceptive formulations is indicated for the prevention of pregnancy <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Norethindrone FDA label\" href=\"#reference-F3904\">22</a></sup>. </p>','C00410','D00066','Organic compounds','<p>Progesterone is mainly metabolized by the liver. After oral administration, the major plasma metabolites found are 20 a hydroxy-Δ4 a-prenolone and 5 a-dihydroprogesterone. Some progesterone metabolites are found excreted in the bile and these metabolites may be deconjugated and subsequently metabolized in the gut by reduction, dehydroxylation, and epimerization <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. The major plasma and urinary metabolites are comparable to those found during the physiological progesterone secretion of the corpus luteum <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Utrogestan capsules, medsafe NZ label\" href=\"#reference-F3913\">24</a></sup>. </p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aliphatic homopolycyclic compounds','STR','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000371?highlight[compounds][]=DB00396&amp;highlight[proteins][]=DB00396\">Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000575?highlight[compounds][]=DB00396&amp;highlight[proteins][]=DB00396\">11-beta-Hydroxylase Deficiency (CYP11B1)</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000717?highlight[compounds][]=DB00396&amp;highlight[proteins][]=DB00396\">Apparent Mineralocorticoid Excess Syndrome</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000372?highlight[compounds][]=DB00396&amp;highlight[proteins][]=DB00396\">Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000577?highlight[compounds][]=DB00396&amp;highlight[proteins][]=DB00396\">Corticosterone Methyl Oxidase I Deficiency (CMO I)</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000718?highlight[compounds][]=DB00396&amp;highlight[proteins][]=DB00396\">3-beta-Hydroxysteroid Dehydrogenase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000130?highlight[compounds][]=DB00396&amp;highlight[proteins][]=DB00396\">Steroidogenesis</a></td><td>Metabolic</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000373?highlight[compounds][]=DB00396&amp;highlight[proteins][]=DB00396\">Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia Due to 21-Hydroxylase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000566?highlight[compounds][]=DB00396&amp;highlight[proteins][]=DB00396\">17-alpha-Hydroxylase Deficiency (CYP17)</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000576?highlight[compounds][]=DB00396&amp;highlight[proteins][]=DB00396\">21-Hydroxylase Deficiency (CYP21)</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000578?highlight[compounds][]=DB00396&amp;highlight[proteins][]=DB00396\">Corticosterone Methyl Oxidase II Deficiency (CMO II)</a></td><td>Disease</td></tr></tbody>','PA451123','<p>96%-99% bound to serum proteins, primarily to serum albumin (50%-54%) and transcortin (43%-48%) <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','5994','46508968','<p>Progesterone metabolites are excreted mainly by the kidneys. Urinary elimination is observed for 95% of patients in the form of glycuroconjugated metabolites, primarily 3 a, 5 ß–pregnanediol (<em>pregnandiol</em>) <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Utrogestan capsules, medsafe NZ label\" href=\"#reference-F3913\">24</a></sup>. The glucuronide and sulfate conjugates of pregnanediol and pregnanolone are excreted in the urine and bile. Progesterone metabolites, excreted in the bile, may undergo enterohepatic recycling or may be found excreted in the feces. </p>','RxList Drug Page','8727','[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C','Solid','Pregnane steroids','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">20-oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">3-oxo-delta-4-steroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">3-oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aliphatic homopolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclic ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclohexenone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Delta-4-steroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ketone</span></span></span>','Lipids and lipid-like molecules','<span class=\"citations\"><p>Nejib M. Nasraoui, Alain Piasco, \"Derivatives of 19-nor progesterone; process for producing them and the pharmaceutical compositions incorporating them.\" U.S. Patent US5223492, issued May, 1971.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=5223492&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5223492</a>','DAP000549','<p>Intraperitoneal LD50 (rat): 327 mg/kg <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Material Safety Data Sheet\" href=\"#msds-reference\">MSDS</a></sup>. </p><p><strong>Use in pregnancy</strong></p><p>Only forms of progesterone that are indicated on product labeling for pregnancy should be used. Some forms of progesterone should not be used in pregnancy <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>, <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Norethindrone FDA label\" href=\"#reference-F3904\">22</a></sup>. Refer to individual product monographs for information regarding use in pregnancy. Many studies have found no effects on fetal development associated with long-term use of contraceptive doses of oral progestins. Studies of infant growth and development that have been conducted have not demonstrated significant adverse effects, however, these studies are few in number. It is therefore advisable to rule out suspected pregnancy before starting any hormonal contraceptive <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Norethindrone FDA label\" href=\"#reference-F3904\">22</a></sup>. </p><p><strong>Effects on fertility</strong></p><p>Progesterone at high doses is an antifertility drug and high doses would be expected to impair fertility until cessation <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"PROGESTERONE INJECTION USP IN SESAME OIL FOR INTRAMUSCULAR USE ONLY\" href=\"#reference-F3916\">25</a></sup>. The progesterone contraceptive should not be used during pregnancy. </p><p><strong>Carcinogenicity</strong></p><p>Progesterone has been shown to induce or promote the formation of ovarian, uterine, mammary, and genital tract tumors in animals. The clinical relevance of these findings is unknown <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Utrogestan capsules, medsafe NZ label\" href=\"#reference-F3913\">24</a></sup>. Certain epidemiological studies of patients using oral contraceptives have reported an increased relative risk of developing breast cancer, especially at a younger age and associated with a longer duration of use. These studies have mainly involved combined oral contraceptives, and therefore, it is unknown whether this risk is attributable to progestins, estrogens, or a combination of both. At this time, there is insufficient data to determine whether the use of progestin-only contraceptives increases the risk in a similar way to combined contraceptives. A meta-analysis of 54 studies showed a small increase in the frequency of breast cancer diagnosis for women who were currently using combined oral contraceptives, or had used them within the past 10 years. There was no increase in the frequency of having breast cancer diagnosed ten or more years after cessation of hormone use. Women with breast cancer should not use oral contraceptives, as there is no sufficient data to fully establish or negate the risk of cancer with hormonal contraceptive use <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Norethindrone FDA label\" href=\"#reference-F3904\">22</a></sup>. </p><p><strong>Use in breastfeeding</strong></p><p>Progesterone has been detected in the milk of nursing mothers <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Endometrin FDA label, vaginal insert\" href=\"#reference-F3901\">21</a></sup>, <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Norethindrone FDA label\" href=\"#reference-F3904\">22</a></sup>. No adverse effects, in general, have been found on breastfeeding ability or on the health, growth, or development of the growing infant. Despite this, isolated post-marketing cases of decreased milk production have been reported <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Norethindrone FDA label\" href=\"#reference-F3904\">22</a></sup>. </p>','4G7DS2Q64Y','<p>When administered vaginally, progesterone is well absorbed by uterine endometrial tissue, and a small percentage is distributed into the systemic circulation.\nThe amount of progesterone in the systemic circulation appears to be of minimal importance, especially when implantation, pregnancy, and live birth outcomes appear similar for intramuscular and vaginal administration of progesterone <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Paulson RJ, Collins MG, Yankov VI: Progesterone pharmacokinetics and pharmacodynamics with 3 dosages and 2 regimens of an effervescent micronized progesterone vaginal insert. J Clin Endocrinol Metab. 2014 Nov;99(11):4241-9. doi: 10.1210/jc.2013-3937. Epub 2014 Feb 25. (PubMed ID 24606090)\" href=\"#reference-A175657\">11</a></sup>. </p>','Progesterone','ZINC000004428529'),(29,'Spironolactone','spironolactone','Spironolactone is an aldosterone receptor antagonist used for the treatment of hypertension, hyperaldosteronism, edema due to various conditions, hirsutism (off-label) and hypokalemia.','Aldactazide, Aldactone, Carospir','Spironolactone','<p>Spironolactone is a potassium sparing diuretic like <a href=\"https://go.drugbank.com/drugs/DB00700\">eplerenone</a> that competitively inhibits mineralocorticoid receptors in the distal convoluted tubule to promote sodium and water excretion and potassium retention.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sica DA: Pharmacokinetics and pharmacodynamics of mineralocorticoid blocking agents and their effects on potassium homeostasis. Heart Fail Rev. 2005 Jan;10(1):23-9. doi: 10.1007/s10741-005-2345-1. (PubMed ID 15947888)\" href=\"#reference-A11837\">8</a></sup>. Spironolactone was originally developed purely for this ability before other pharmacodynamic properties of the drug were discovered.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sica DA: Pharmacokinetics and pharmacodynamics of mineralocorticoid blocking agents and their effects on potassium homeostasis. Heart Fail Rev. 2005 Jan;10(1):23-9. doi: 10.1007/s10741-005-2345-1. (PubMed ID 15947888)\" href=\"#reference-A11837\">8</a>,<a class=\"reference-popover-link\" data-content=\"BOLTE E, VERDY M, MARC-AURELE J, BROUILLET J, BEAUREGARD P, GENEST J: Studies on new diuretic compounds: spirolactone and chlorothiazide. Can Med Assoc J. 1958 Dec 1;79(11):881-8. (PubMed ID 13608362)\" href=\"#reference-A178246\">11</a></sup> It is indicated to treat a number of conditions including heart failure, deem, hyperaldosteronism, adrenal hyperplasia, hypertension, and nephrotic syndrome.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup> Off label uses of spironolactone involving its antiandrogenic activity include hirsutism, female pattern hair loss, and adult acne vulgaris.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Kim GK, Del Rosso JQ: Oral Spironolactone in Post-teenage Female Patients with Acne Vulgaris: Practical Considerations for the Clinician Based on Current Data and Clinical Experience. J Clin Aesthet Dermatol. 2012 Mar;5(3):37-50. (PubMed ID 22468178)\" href=\"#reference-A178135\">4</a></sup> Spironolactone is also frequently used in medical gender transition.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Millington K, Liu E, Chan YM: The Utility of Potassium Monitoring in Gender-Diverse Adolescents Taking Spironolactone. J Endocr Soc. 2019 Apr 4;3(5):1031-1038. doi: 10.1210/js.2019-00030. eCollection 2019 May 1. (PubMed ID 31065620)\" href=\"#reference-A178138\">5</a></sup></p><p>Spironolactone was developed in 1957, marketed in 1959, and approved by the FDA on January 21, 1960.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Menard J: The 45-year story of the development of an anti-aldosterone more specific than spironolactone. Mol Cell Endocrinol. 2004 Mar 31;217(1-2):45-52. doi: 10.1016/j.mce.2003.10.008. (PubMed ID 15134800)\" href=\"#reference-A178243\">10</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Spironolactone\" href=\"#reference-L6187\">12</a></sup></p>','C24H32O4S','DB00421','Approved','Small Molecule','Average: 416.573 Monoisotopic: 416.202130202 ',' , C03DA — Aldosterone antagonists , C03D — POTASSIUM-SPARING AGENTS , C03 — DIURETICS , C — CARDIOVASCULAR SYSTEM','<p>Spironolactone reaches a maximum concentration in 2.6 hours and an active metabolite (canrenone) reaches a maximum concentration in 4.3 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup> When taken with food, the bioavailability of spironolactone increases to 95.4%.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup></p><p>Giving spironolactone with food increases the maximum concentration from 209ng/mL to 301ng/mL.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Karim A: Spironolactone: disposition, metabolism, pharmacodynamics, and bioavailability. Drug Metab Rev. 1978;8(1):151-88. doi: 10.3109/03602537808993782. (PubMed ID 363379)\" href=\"#reference-A178165\">6</a></sup> The time to maximum concentration also increases from 2.28 hours to 3.05 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Karim A: Spironolactone: disposition, metabolism, pharmacodynamics, and bioavailability. Drug Metab Rev. 1978;8(1):151-88. doi: 10.3109/03602537808993782. (PubMed ID 363379)\" href=\"#reference-A178165\">6</a></sup> The area under the curve varies from 2103ng/mL*hr to 4544ng/mL*hr.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Karim A: Spironolactone: disposition, metabolism, pharmacodynamics, and bioavailability. Drug Metab Rev. 1978;8(1):151-88. doi: 10.3109/03602537808993782. (PubMed ID 363379)\" href=\"#reference-A178165\">6</a></sup></p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"3-oxo steroids containing a double bond between positions  3 and 4.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002974\" rel=\"noopener\" target=\"_blank\">3-oxo delta-4-steroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroids containing a double bond between positions 4 and 5.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002978\" rel=\"noopener\" target=\"_blank\">Delta-4-steroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004325\" rel=\"noopener\" target=\"_blank\">Cyclohexenones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001245\" rel=\"noopener\" target=\"_blank\">Gamma butyrolactones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002648\" rel=\"noopener\" target=\"_blank\">Tetrahydrofurans</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an ester of thiocarboxylic acid, with the general structure RC(=S)XR\' (R=H, alkyl, aryl; R\'=alkyl, aryl; X=O,S).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001200\" rel=\"noopener\" target=\"_blank\">Thioesters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001238\" rel=\"noopener\" target=\"_blank\">Carboxylic acid esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Ester derivatives of carbothioic S-acids, with the general structure RSC(=O)R\' where R = organyl group and R\' = H or organyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003872\" rel=\"noopener\" target=\"_blank\">Carbothioic S-esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organosulfur compounds a sulfenyl group with the general formula RS (R = organyl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003260\" rel=\"noopener\" target=\"_blank\">Sulfenyl 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></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=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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 3 more</a>','Not Available','Not Available','50228080','52-01-7','9241','CHEMBL1393','5628','<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=\"3-oxo steroids containing a double bond between positions  3 and 4.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002974\" rel=\"noopener\" target=\"_blank\">3-oxo delta-4-steroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Steroids containing a double bond between positions 4 and 5.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002978\" rel=\"noopener\" target=\"_blank\">Delta-4-steroids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004325\" rel=\"noopener\" target=\"_blank\">Cyclohexenones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001245\" rel=\"noopener\" target=\"_blank\">Gamma butyrolactones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002648\" rel=\"noopener\" target=\"_blank\">Tetrahydrofurans</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an ester of thiocarboxylic acid, with the general structure RC(=S)XR\' (R=H, alkyl, aryl; R\'=alkyl, aryl; X=O,S).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001200\" rel=\"noopener\" target=\"_blank\">Thioesters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001238\" rel=\"noopener\" target=\"_blank\">Carboxylic acid esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Ester derivatives of carbothioic S-acids, with the general structure RSC(=O)R\' where R = organyl group and R\' = H or organyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003872\" rel=\"noopener\" target=\"_blank\">Carbothioic S-esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organosulfur compounds a sulfenyl group with the general formula RS (R = organyl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003260\" rel=\"noopener\" target=\"_blank\">Sulfenyl 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></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=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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 3 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-oxo-delta-4-steroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">3-oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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\">Carbothioic s-ester</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\">Delta-4-steroid</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\">Gamma butyrolactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Lactone</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 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\">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\">Oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Spironolactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Sulfenyl compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetrahydrofuran</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Thiocarboxylic acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Thiocarboxylic acid or derivatives</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 17 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\">thioester, 3-oxo steroid, methyl ketone, oxaspiro compound, steroid lactone (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9241\" rel=\"noopener\" target=\"_blank\">CHEBI:9241</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Pregnane and derivatives [Fig] (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C07310\" rel=\"noopener\" target=\"_blank\">C07310</a>) </span></span></dd></dl>','Steroids and steroid derivatives','<p>Clearance data is not readily available.<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=\"Carone L, Oxberry SG, Twycross R, Charlesworth S, Mihalyo M, Wilcock A: Spironolactone. J Pain Symptom Manage. 2017 Feb;53(2):288-292. doi: 10.1016/j.jpainsymman.2016.12.320. Epub 2016 Dec 23. (PubMed ID 28024992)\" href=\"#reference-A178192\">7</a></sup></p>','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 alcohol.</li>\n<li>Avoid potassium-containing products. Potassium products increase the risk of hyperkalemia.</li>\n<li>Take with or without food. Food increases the bioavailability of spironolactone by nearly 100%. It should be taken at a consistent time in regards to food.</li>','Drugs.com Drug Page',' , Agents causing hyperkalemia , Antihypertensive Agents , Antihypertensive Agents Indicated for Hypertension , BSEP/ABCB11 Substrates , Cardiovascular Agents , Cytochrome P-450 CYP2C8 Inhibitors , Cytochrome P-450 CYP2C8 Inhibitors (moderate) , Cytochrome P-450 Enzyme Inhibitors , Diuretics , Fused-Ring Compounds , Hormone Antagonists , Hormones, Hormone Substitutes, and Hormone Antagonists , Hypotensive Agents , Lactones , Mineralocorticoid (Aldosterone) Receptor Antagonists , Mineralocorticoid Receptor Antagonists , Natriuretic Agents , P-glycoprotein inducers , 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>melting point (°C)</td><td>134.5 °C</td><td>[MSDS]</td></tr><tr><td>boiling point (°C)</td><td>201</td><td>[MSDS]</td></tr><tr><td>logP</td><td>2.78</td><td>https://www.ncbi.nlm.nih.gov/pubmed/26642673</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">thioester, 3-oxo steroid, methyl ketone, oxaspiro compound, steroid lactone (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9241\" rel=\"noopener\" target=\"_blank\">CHEBI:9241</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Pregnane and derivatives [Fig] (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C07310\" rel=\"noopener\" target=\"_blank\">C07310</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/HMDB0014565\" rel=\"noopener\" target=\"_blank\">HMDB0014565</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:D00443\" rel=\"noopener\" target=\"_blank\">D00443</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:C07310\" rel=\"noopener\" target=\"_blank\">C07310</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=5833\" rel=\"noopener\" target=\"_blank\">5833</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=46508525\" rel=\"noopener\" target=\"_blank\">46508525</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.5628.html\" rel=\"noopener\" target=\"_blank\">5628</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=50228080\" rel=\"noopener\" target=\"_blank\">50228080</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=9997\" rel=\"noopener\" target=\"_blank\">9997</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=9241\" rel=\"noopener\" target=\"_blank\">9241</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/CHEMBL1393\" rel=\"noopener\" target=\"_blank\">CHEMBL1393</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/ZINC000003861599\" rel=\"noopener\" target=\"_blank\">ZINC000003861599</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=DAP000297\" rel=\"noopener\" target=\"_blank\">DAP000297</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/PA451483\" rel=\"noopener\" target=\"_blank\">PA451483</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=2875\" 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/SNL\" rel=\"noopener\" target=\"_blank\">SNL</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/spiron.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/spironolactone.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/ald1010.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/Spironolactone\" rel=\"noopener\" target=\"_blank\">Spironolactone</a></dd></dl>','<li>Avoid alcohol.</li>\n<li>Avoid potassium-containing products. Potassium products increase the risk of hyperkalemia.</li>\n<li>Take with or without food. Food increases the bioavailability of spironolactone by nearly 100%. It should be taken at a consistent time in regards to food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A178126\">Takamura N, Maruyama T, Ahmed S, Suenaga A, Otagiri M: Interactions of aldosterone antagonist diuretics with human serum proteins. Pharm Res. 1997 Apr;14(4):522-6. [<a href=\"/articles/A178126\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178069\">LaCagnin LB, Lutsie P, Colby HD: Conversion of spironolactone to 7 alpha-thiomethylspironolactone by hepatic and renal microsomes. Biochem Pharmacol. 1987 Oct 15;36(20):3439-44. [<a href=\"/articles/A178069\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178072\">Los LE, Pitzenberger SM, Ramjit HG, Coddington AB, Colby HD: Hepatic metabolism of spironolactone. Production of 3-hydroxy-thiomethyl metabolites. Drug Metab Dispos. 1994 Nov-Dec;22(6):903-8. [<a href=\"/articles/A178072\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178135\">Kim GK, Del Rosso JQ: Oral Spironolactone in Post-teenage Female Patients with Acne Vulgaris: Practical Considerations for the Clinician Based on Current Data and Clinical Experience. J Clin Aesthet Dermatol. 2012 Mar;5(3):37-50. [<a href=\"/articles/A178135\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178138\">Millington K, Liu E, Chan YM: The Utility of Potassium Monitoring in Gender-Diverse Adolescents Taking Spironolactone. J Endocr Soc. 2019 Apr 4;3(5):1031-1038. doi: 10.1210/js.2019-00030. eCollection 2019 May 1. [<a href=\"/articles/A178138\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178165\">Karim A: Spironolactone: disposition, metabolism, pharmacodynamics, and bioavailability. Drug Metab Rev. 1978;8(1):151-88. doi: 10.3109/03602537808993782. [<a href=\"/articles/A178165\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178192\">Carone L, Oxberry SG, Twycross R, Charlesworth S, Mihalyo M, Wilcock A: Spironolactone. J Pain Symptom Manage. 2017 Feb;53(2):288-292. doi: 10.1016/j.jpainsymman.2016.12.320. Epub 2016 Dec 23. [<a href=\"/articles/A178192\" target=\"_blank\">Article</a>] </li><li id=\"reference-A11837\">Sica DA: Pharmacokinetics and pharmacodynamics of mineralocorticoid blocking agents and their effects on potassium homeostasis. Heart Fail Rev. 2005 Jan;10(1):23-9. doi: 10.1007/s10741-005-2345-1. [<a href=\"/articles/A11837\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178207\">Gardiner P, Schrode K, Quinlan D, Martin BK, Boreham DR, Rogers MS, Stubbs K, Smith M, Karim A: Spironolactone metabolism: steady-state serum levels of the sulfur-containing metabolites. J Clin Pharmacol. 1989 Apr;29(4):342-7. [<a href=\"/articles/A178207\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178243\">Menard J: The 45-year story of the development of an anti-aldosterone more specific than spironolactone. Mol Cell Endocrinol. 2004 Mar 31;217(1-2):45-52. doi: 10.1016/j.mce.2003.10.008. [<a href=\"/articles/A178243\" target=\"_blank\">Article</a>] </li><li id=\"reference-A178246\">BOLTE E, VERDY M, MARC-AURELE J, BROUILLET J, BEAUREGARD P, GENEST J: Studies on new diuretic compounds: spirolactone and chlorothiazide. Can Med Assoc J. 1958 Dec 1;79(11):881-8. [<a href=\"/articles/A178246\" target=\"_blank\">Article</a>] </li><li id=\"reference-L6187\">FDA Approved Drug Products: Spironolactone [<a href=\"https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&amp;ApplNo=012151\" target=\"_blank\">Link</a>] </li><li id=\"reference-L4449\">FDA Approved Drug Products: Aldactone (spironolactone) tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/012151s062lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>1.4 hours.<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=\"Carone L, Oxberry SG, Twycross R, Charlesworth S, Mihalyo M, Wilcock A: Spironolactone. J Pain Symptom Manage. 2017 Feb;53(2):288-292. doi: 10.1016/j.jpainsymman.2016.12.320. Epub 2016 Dec 23. (PubMed ID 28024992)\" href=\"#reference-A178192\">7</a></sup></p><p>Canrenone has a half life of 16.5 hours, 7-α-thiomethylspirolactone has a half life of 13.8 hours, and 6-ß-hydroxy-7-α-thiomethylspirolactone has a half life of 15 hours.<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=\"Carone L, Oxberry SG, Twycross R, Charlesworth S, Mihalyo M, Wilcock A: Spironolactone. J Pain Symptom Manage. 2017 Feb;53(2):288-292. doi: 10.1016/j.jpainsymman.2016.12.320. Epub 2016 Dec 23. (PubMed ID 28024992)\" href=\"#reference-A178192\">7</a></sup></p>','HMDB0014565','(1R,3aS,3bR,4R,9aR,9bS,11aS)-4-(acetylsulfanyl)-9a,11a-dimethyl-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydrospiro[cyclopenta[a]phenanthrene-1,2\'-oxolane]-5\',7-dione','InChI=1S/C24H32O4S/c1-14(25)29-19-13-15-12-16(26)4-8-22(15,2)17-5-9-23(3)18(21(17)19)6-10-24(23)11-7-20(27)28-24/h12,17-19,21H,4-11,13H2,1-3H3/t17-,18-,19+,21+,22-,23-,24+/m0/s1','LXMSZDCAJNLERA-ZHYRCANASA-N','<p>Spironolactone is indicated for the treatment of New York Heart Association Class III-IV heart failure, management of edema in cirrhotic adults not responsive to fluid and sodium restrictions, primary hyperaldosteronism short-term preoperatively, primary hyperaldosteronism long-term in patients with aldosterone producing adrenal adenomas that are not candidates for surgery or patients with bilarteral micro/macronodular adrenal hyperplasia, as an add-on therapy in hypertension, and in nephrotic syndrome when treatment of the disease as well as fluid and sodium restriction with other diuretics is inadequate.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup></p><p>Spironolactone has antiandrogenic activity which leads to many of its off label uses. Spironolactone is used off label in the treatment of hirsutism, female pattern hair loss, and adult acne vulgaris.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Kim GK, Del Rosso JQ: Oral Spironolactone in Post-teenage Female Patients with Acne Vulgaris: Practical Considerations for the Clinician Based on Current Data and Clinical Experience. J Clin Aesthet Dermatol. 2012 Mar;5(3):37-50. (PubMed ID 22468178)\" href=\"#reference-A178135\">4</a></sup></p><p>Spironolactone is also frequently used for its antiandrogenic effects in transgender female patients due to its low cost and reducing male-pattern hair growth.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Millington K, Liu E, Chan YM: The Utility of Potassium Monitoring in Gender-Diverse Adolescents Taking Spironolactone. J Endocr Soc. 2019 Apr 4;3(5):1031-1038. doi: 10.1210/js.2019-00030. eCollection 2019 May 1. (PubMed ID 31065620)\" href=\"#reference-A178138\">5</a></sup></p>','C07310','D00443','Organic compounds','<p>Spironolactone is deacetylated to 7α-thiospironolactone.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"LaCagnin LB, Lutsie P, Colby HD: Conversion of spironolactone to 7 alpha-thiomethylspironolactone by hepatic and renal microsomes. Biochem Pharmacol. 1987 Oct 15;36(20):3439-44. (PubMed ID 3675606)\" href=\"#reference-A178069\">2</a>,<a class=\"reference-popover-link\" data-content=\"Los LE, Pitzenberger SM, Ramjit HG, Coddington AB, Colby HD: Hepatic metabolism of spironolactone. Production of 3-hydroxy-thiomethyl metabolites. Drug Metab Dispos. 1994 Nov-Dec;22(6):903-8. (PubMed ID 7895608)\" href=\"#reference-A178072\">3</a></sup> 7α-thiospironolactone is S-methylated to 7α-thiomethylspironolactone or undergoes an elimination reaction to canrenone.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"LaCagnin LB, Lutsie P, Colby HD: Conversion of spironolactone to 7 alpha-thiomethylspironolactone by hepatic and renal microsomes. Biochem Pharmacol. 1987 Oct 15;36(20):3439-44. (PubMed ID 3675606)\" href=\"#reference-A178069\">2</a>,<a class=\"reference-popover-link\" data-content=\"Los LE, Pitzenberger SM, Ramjit HG, Coddington AB, Colby HD: Hepatic metabolism of spironolactone. Production of 3-hydroxy-thiomethyl metabolites. Drug Metab Dispos. 1994 Nov-Dec;22(6):903-8. (PubMed ID 7895608)\" href=\"#reference-A178072\">3</a></sup> 7α-thiomethylspironolactone is reduced to 3α-hydroxythiomethylspironolactone or 3β-hydroxythiomethylspironolactone.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"LaCagnin LB, Lutsie P, Colby HD: Conversion of spironolactone to 7 alpha-thiomethylspironolactone by hepatic and renal microsomes. Biochem Pharmacol. 1987 Oct 15;36(20):3439-44. (PubMed ID 3675606)\" href=\"#reference-A178069\">2</a>,<a class=\"reference-popover-link\" data-content=\"Los LE, Pitzenberger SM, Ramjit HG, Coddington AB, Colby HD: Hepatic metabolism of spironolactone. Production of 3-hydroxy-thiomethyl metabolites. Drug Metab Dispos. 1994 Nov-Dec;22(6):903-8. (PubMed ID 7895608)\" href=\"#reference-A178072\">3</a></sup></p><p>Canrenone was originally thought to be the primary circulating metabolite, however more recent studies have demonstrated that the primary metabolite is actually 7α-thiomethylspironolactone.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sica DA: Pharmacokinetics and pharmacodynamics of mineralocorticoid blocking agents and their effects on potassium homeostasis. Heart Fail Rev. 2005 Jan;10(1):23-9. doi: 10.1007/s10741-005-2345-1. (PubMed ID 15947888)\" href=\"#reference-A11837\">8</a>,<a class=\"reference-popover-link\" data-content=\"Gardiner P, Schrode K, Quinlan D, Martin BK, Boreham DR, Rogers MS, Stubbs K, Smith M, Karim A: Spironolactone metabolism: steady-state serum levels of the sulfur-containing metabolites. J Clin Pharmacol. 1989 Apr;29(4):342-7. (PubMed ID 2723123)\" href=\"#reference-A178207\">9</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aliphatic heteropolycyclic compounds','SNL','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000134?highlight[compounds][]=DB00421&amp;highlight[proteins][]=DB00421\">Spironolactone Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA451483','<p>&gt;90%.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup> Canrenone is as much as 98% protein bound.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Karim A: Spironolactone: disposition, metabolism, pharmacodynamics, and bioavailability. Drug Metab Rev. 1978;8(1):151-88. doi: 10.3109/03602537808993782. (PubMed ID 363379)\" href=\"#reference-A178165\">6</a></sup></p>','5833','46508525','<p>Metabolites of spironolactone are excreted 42-56% in urine, and 14.2-14.6% in the feces.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Karim A: Spironolactone: disposition, metabolism, pharmacodynamics, and bioavailability. Drug Metab Rev. 1978;8(1):151-88. doi: 10.3109/03602537808993782. (PubMed ID 363379)\" href=\"#reference-A178165\">6</a></sup> No unmetabolized spironolactone is present in the urine.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Karim A: Spironolactone: disposition, metabolism, pharmacodynamics, and bioavailability. Drug Metab Rev. 1978;8(1):151-88. doi: 10.3109/03602537808993782. (PubMed ID 363379)\" href=\"#reference-A178165\">6</a></sup></p>','RxList Drug Page','9997','[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@]([H])(CC2=CC(=O)CC[C@]12C)SC(C)=O','Solid','Steroid lactones','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">3-oxo-delta-4-steroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">3-oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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\">Carbothioic s-ester</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\">Delta-4-steroid</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\">Gamma butyrolactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Lactone</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 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\">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\">Oxosteroid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Spironolactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Sulfenyl compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetrahydrofuran</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Thiocarboxylic acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Thiocarboxylic acid or derivatives</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 17 more</a>','Lipids and lipid-like molecules','<span class=\"citations\"><p>Giuseppe Bernini, \"Process for preparing micronized spironolactone.\" U.S. Patent US4332721, issued July, 1975.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=4332721&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US4332721</a>','DAP000297','<p>Patients experiencing an overdose may present with drowsiness, mental confusion, maculopapular or erythematous rash, nausea, vomiting, dizziness, or diarrhea. Vomiting is generally induced or a gastric lavage is performed.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup> Supportive treatment involves maintining hydration, electrolyte balance, and vital functions<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p><p>The oral LD50 in mice, rats, and rabbits is &gt;1g/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup></p><p>Spironolactone should be avoided in pregnancy due to reports of feminization of male fetuses in animal studies.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup> Active metabolites of spironolactone are present in breast milk and levels that are likely inconsequential, though the long term effects have not been studied.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup></p><p>In animal studies, spironolactone slowed follicle development, ovulation, and implantation.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup> Spironolactone increased the incidence of benign adenomas in the testes of male rats, benign uterine endometrial stromal polyps in female rats, and thyroid follicular cell adenomas in both sexes of rats.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup> Spironolactone and canrenone are generally not considered to be mutagenic in tests but canrenone occasionally tests positive for mutagenicity with metabolic activation and spironolactone has occasionally tested inconclusive though slightly positive for mutagenicity.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup></p>','27O7W4T232','<p>Volume of distribution data is not readily available.<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=\"Carone L, Oxberry SG, Twycross R, Charlesworth S, Mihalyo M, Wilcock A: Spironolactone. J Pain Symptom Manage. 2017 Feb;53(2):288-292. doi: 10.1016/j.jpainsymman.2016.12.320. Epub 2016 Dec 23. (PubMed ID 28024992)\" href=\"#reference-A178192\">7</a></sup></p>','Spironolactone','ZINC000003861599'),(30,'Chloramphenicol','chloramphenicol','Chloramphenicol is a broad spectrum antibiotic that is effective against a variety of susceptible and serious bacterial infections but is not frequently used because of its high risk of bone marrow toxicity.','Chloromycetin','Chloramphenicol','<p>An antibiotic first isolated from cultures of <em>Streptomyces venequelae</em> in 1947 but now produced synthetically. It has a relatively simple structure and was the first broad-spectrum antibiotic to be discovered. It acts by interfering with bacterial protein synthesis and is mainly bacteriostatic. (From Martindale, The Extra Pharmacopoeia, 29th ed, p106)</p>','C11H12Cl2N2O5','DB00446','Approved, Vet approved','Small Molecule','Average: 323.129 Monoisotopic: 322.012326918 ',' , D06AX — Other antibiotics for topical use , D06A — ANTIBIOTICS FOR TOPICAL USE , D06 — ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE , D — DERMATOLOGICALS , S02AA — Antiinfectives , S02A — ANTIINFECTIVES , S02 — OTOLOGICALS , S — SENSORY ORGANS , D10AF — Antiinfectives for treatment of acne , D10A — ANTI-ACNE PREPARATIONS FOR TOPICAL USE , D10 — ANTI-ACNE PREPARATIONS , D — DERMATOLOGICALS , S01AA — Antibiotics , S01A — ANTIINFECTIVES , S01 — OPHTHALMOLOGICALS , S — SENSORY ORGANS , G01AA — Antibiotics , G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS , G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS , G — GENITO URINARY SYSTEM AND SEX HORMONES , J01BA — Amphenicols , J01B — AMPHENICOLS , J01 — ANTIBACTERIALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , S03AA — Antiinfectives , S03A — ANTIINFECTIVES , S03 — OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS , S — SENSORY ORGANS','<p>Rapidly and completely absorbed from gastrointestinal tract following oral administration (bioavailability 80%). Well absorbed following intramuscular administration (bioavailability 70%). Intraocular and some systemic absorption also occurs after topical application to the eye.</p>','','Enteric bacteria and other eubacteria\nGram negative and gram positive bacteria\nStreptococcus pneumoniae\nNeisseria meningitidis\nHaemophilus influenzae\nEnterococcus faecium','<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=\"C-nitro compounds where the nitro group is C-substituted with an aromatic group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004612\" rel=\"noopener\" target=\"_blank\">Nitroaromatic 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 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 comprising the oxoazanium cation, with the formula N+=O.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001508\" rel=\"noopener\" target=\"_blank\">Organic oxoazanium compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic acids with the general formula RC(=N)-OH (R=H, organic group).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002484\" rel=\"noopener\" target=\"_blank\">Carboximidic acids</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 class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic neutral compounds having formal unit electrical charges of opposite sign.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003610\" rel=\"noopener\" target=\"_blank\">Organic zwitterions</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 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=\"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 class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the alkyl chloride functional group with formula R-Cl , where R is an alkyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001026\" rel=\"noopener\" target=\"_blank\">Alkyl chlorides</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 4 more</a>','Not Available','Not Available','23447','56-75-7','17698','CHEMBL130','5744','<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 nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"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=\"Compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000036\" rel=\"noopener\" target=\"_blank\">Nitrobenzenes</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 nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000036\" rel=\"noopener\" target=\"_blank\">Nitrobenzenes</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=\"C-nitro compounds where the nitro group is C-substituted with an aromatic group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004612\" rel=\"noopener\" target=\"_blank\">Nitroaromatic 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 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 comprising the oxoazanium cation, with the formula N+=O.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001508\" rel=\"noopener\" target=\"_blank\">Organic oxoazanium compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic acids with the general formula RC(=N)-OH (R=H, organic group).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002484\" rel=\"noopener\" target=\"_blank\">Carboximidic acids</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 class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic neutral compounds having formal unit electrical charges of opposite sign.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003610\" rel=\"noopener\" target=\"_blank\">Organic zwitterions</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 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=\"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 class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the alkyl chloride functional group with formula R-Cl , where R is an alkyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001026\" rel=\"noopener\" target=\"_blank\">Alkyl chlorides</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 4 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkyl chloride</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkyl halide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Allyl-type 1,3-dipolar organic compound</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 homomonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">C-nitro compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboximidic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboximidic acid derivative</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\">Nitroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Nitrobenzene</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 nitro 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 oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxoazanium</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 zwitterion</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 alcohol</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\">Secondary alcohol</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 17 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\">organochlorine compound (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17698\" rel=\"noopener\" target=\"_blank\">CHEBI:17698</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Aromatic compounds (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C00918\" rel=\"noopener\" target=\"_blank\">C00918</a>) </span></span></dd></dl>','Benzene and substituted derivatives','<p><span class=\"not-available\">Not Available</span></p>','This compound belongs to the class of organic compounds known as nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.','Nitrobenzenes','<li>Take on an empty stomach.</li>','Drugs.com Drug Page',' , Alcohols , Amphenicols , Anti-Acne Preparations , Anti-Acne Preparations for Topical Use , Anti-Bacterial Agents , Anti-Infective Agents , Antibacterials for Systemic Use , Antibiotics for Topical Use , Antiinfectives for Systemic Use , Antiinfectives for Treatment of Acne , Benzene Derivatives , Cytochrome P-450 CYP2C19 Inhibitors , Cytochrome P-450 CYP2C19 Inhibitors (strong) , Cytochrome P-450 CYP3A Inhibitors , Cytochrome P-450 CYP3A4 Inhibitors , Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) , Cytochrome P-450 CYP3A5 Inhibitors , Cytochrome P-450 CYP3A5 Inhibitors (strength unknown) , Cytochrome P-450 CYP3A7 Inhibitors , Cytochrome P-450 CYP3A7 Inhibitors (strength unknown) , Cytochrome P-450 Enzyme Inhibitors , Dermatologicals , Enzyme Inhibitors , Genito Urinary System and Sex Hormones , Glycols , Gynecological Antiinfectives and Antiseptics , Immunosuppressive Agents , Myelosuppressive Agents , Nitro Compounds , Nitrobenzenes , OAT1/SLC22A6 inhibitors , Ophthalmological and Otological Preparations , Ophthalmologicals , Otologicals , Propylene Glycols , Protein Synthesis Inhibitors , Sensory Organs','<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>171</td><td>Bartz, Q.R.; U.S. Patent 2,483,871; October 4, 1949; assigned to Parke, Davis &amp; Company Crooks, H.M., Jr., Rebstock, M.C., Controulis, J. and Bartz, Q.R.; U.S. Patent 2,483,884;\nOctober 4, 1949; assigned to Parke, Davis &amp; Company.\nEhrlich, J., Smith, R.M. and Penner, M.A.; U.S. Patent 2,483,892; October 4, 1949; assigned to Parke, Davis &amp; Company.\nCarrara, G.; U.S. Patent 2,776,312; January 1, 1957\nSlack, R.; U.S. Patent 2,786,870; March 26, 1957; assigned to Parke, Davis &amp; Company.</td></tr><tr><td>water solubility</td><td>2500 mg/L (at 25 °C)</td><td>MERCK INDEX (2001)</td></tr><tr><td>logP</td><td>1.14</td><td>HANSCH,C ET AL. (1995)</td></tr><tr><td>logS</td><td>-2.11</td><td>ADME Research, USCD</td></tr><tr><td>Caco2 permeability</td><td>-4.69</td><td>ADME Research, USCD</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">organochlorine compound (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17698\" rel=\"noopener\" target=\"_blank\">CHEBI:17698</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Aromatic compounds (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C00918\" rel=\"noopener\" target=\"_blank\">C00918</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/HMDB0014589\" rel=\"noopener\" target=\"_blank\">HMDB0014589</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:D00104\" rel=\"noopener\" target=\"_blank\">D00104</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:C00918\" rel=\"noopener\" target=\"_blank\">C00918</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=5959\" rel=\"noopener\" target=\"_blank\">5959</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=46505318\" rel=\"noopener\" target=\"_blank\">46505318</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.5744.html\" rel=\"noopener\" target=\"_blank\">5744</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=23447\" rel=\"noopener\" target=\"_blank\">23447</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=2348\" rel=\"noopener\" target=\"_blank\">2348</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=17698\" rel=\"noopener\" target=\"_blank\">17698</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/CHEMBL130\" rel=\"noopener\" target=\"_blank\">CHEMBL130</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/ZINC000000113382\" rel=\"noopener\" target=\"_blank\">ZINC000000113382</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=DAP001356\" rel=\"noopener\" target=\"_blank\">DAP001356</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/PA448927\" rel=\"noopener\" target=\"_blank\">PA448927</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/CLM\" rel=\"noopener\" target=\"_blank\">CLM</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/chloramphenicol.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/mtm/chloramphenicol-ophthalmic.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/Chloramphenicol\" rel=\"noopener\" target=\"_blank\">Chloramphenicol</a></dd></dl>','<li>Take on an empty stomach.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A675\">Bhutta ZA, Niazi SK, Suria A: Chloramphenicol clearance in typhoid fever: implications for therapy. Indian J Pediatr. 1992 Mar-Apr;59(2):213-9. [<a href=\"/articles/A675\" target=\"_blank\">Article</a>] </li><li id=\"reference-A676\">Wali SS, Macfarlane JT, Weir WR, Cleland PG, Ball PA, Hassan-King M, Whittle HC, Greenwood BM: Single injection treatment of meningococcal meningitis. 2. Long-acting chloramphenicol. Trans R Soc Trop Med Hyg. 1979;73(6):698-702. [<a href=\"/articles/A676\" target=\"_blank\">Article</a>] </li><li id=\"reference-A677\">Puddicombe JB, Wali SS, Greenwood BM: A field trial of a single intramuscular injection of long-acting chloramphenicol in the treatment of meningococcal meningitis. Trans R Soc Trop Med Hyg. 1984;78(3):399-403. [<a href=\"/articles/A677\" target=\"_blank\">Article</a>] </li><li id=\"reference-A678\">Pecoul B, Varaine F, Keita M, Soga G, Djibo A, Soula G, Abdou A, Etienne J, Rey M: Long-acting chloramphenicol versus intravenous ampicillin for treatment of bacterial meningitis. Lancet. 1991 Oct 5;338(8771):862-6. [<a href=\"/articles/A678\" target=\"_blank\">Article</a>] </li><li id=\"reference-A679\">Nathan N, Borel T, Djibo A, Evans D, Djibo S, Corty JF, Guillerm M, Alberti KP, Pinoges L, Guerin PJ, Legros D: Ceftriaxone as effective as long-acting chloramphenicol in short-course treatment of meningococcal meningitis during epidemics: a randomised non-inferiority study. Lancet. 2005 Jul 23-29;366(9482):308-13. [<a href=\"/articles/A679\" target=\"_blank\">Article</a>] </li></ol>','<p>Half-life in adults with normal hepatic and renal function is 1.5 - 3.5 hours. In patients with impaired renal function half-life is 3 - 4 hours. In patients with severely impaired hepatic function half-life is 4.6 - 11.6 hours. Half-life in children 1 month to 16 years old is 3 - 6.5 hours, while half-life in infants 1 to 2 days old is 24 hours or longer and is highly variable, especially in low birth-weight infants.</p>','HMDB0014589','2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide','InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1','WIIZWVCIJKGZOK-RKDXNWHRSA-N','<p>Used in treatment of cholera, as it destroys the vibrios and decreases the diarrhea. It is effective against tetracycline-resistant vibrios. It is also used in eye drops or ointment to treat bacterial conjunctivitis.</p>','C00918','D00104','Organic compounds','<p>Hepatic, with 90% conjugated to inactive glucuronide.</p>','Aromatic homomonocyclic compounds','CLM','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000729?highlight[compounds][]=DB00446&amp;highlight[proteins][]=DB00446\">Chloramphenicol Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA448927','<p>Plasma protein binding is 50-60% in adults and 32% is premature neonates.</p>','5959','46505318','<p><span class=\"not-available\">Not Available</span></p>','RxList Drug Page','2348','OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C(C=C1)[N+]([O-])=O','Solid','Nitrobenzenes','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkyl chloride</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkyl halide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Allyl-type 1,3-dipolar organic compound</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 homomonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">C-nitro compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboximidic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboximidic acid derivative</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\">Nitroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Nitrobenzene</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 nitro 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 oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxoazanium</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 zwitterion</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 alcohol</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\">Secondary alcohol</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 17 more</a>','Benzenoids','<span class=\"citations\"><p>Guang-Zhong Wu, Wanda I. Tormos, \"Asymmetric process for preparing florfenicol, thiamphenicol chloramphenicol and oxazoline intermediates.\" U.S. Patent US5352832, issued May, 1992.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=5352832&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5352832</a>','DAP001356','<p>Oral, mouse: LD<sub>50</sub> = 1500 mg/kg; Oral, rat: LD<sub>50</sub> = 2500 mg/kg. Toxic reactions including fatalities have occurred in the premature and newborn; the signs and symptoms associated with these reactions have been referred to as the gray syndrome. Symptoms include (in order of appearance) abdominal distension with or without emesis, progressive pallid cyanosis, vasomotor collapse frequently accompanied by irregular respiration, and death within a few hours of onset of these symptoms.</p>','66974FR9Q1','<p><span class=\"not-available\">Not Available</span></p>','Chloramphenicol','ZINC000000113382'),(31,'Levothyroxine','levothyroxine','Levothyroxine is a synthetic T4 hormone used to treat hypothyroidism that can be used along with surgery and radioiodine therapy to manage thyrotropin-dependent well-differentiated thyroid cancer.','Eltroxin, Euthyrox, Levo-T, Levothroid, Levoxyl, Np Thyroid, Synthroid, Thyquidity, Tirosint, Unithroid','Levothyroxine','<p>Levothyroxine is a synthetically produced form of thyroxine, a major endogenous hormone secreted by the thyroid gland.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Label - levothyroxine\" href=\"#reference-F4633\">14</a></sup> Also known as L-thyroxine or the brand name product Synthroid, levothyroxine is used primarily to treat hypothyroidism, a condition where the thyroid gland is no longer able to produce sufficient quantities of the thyroid hormones T<sub>4</sub> (tetraiodothyronine or thyroxine) and T<sub>3</sub> (triiodothyronine or <a href=\"https://go.drugbank.com/drugs/DB00279\">Liothyronine</a>), resulting in diminished down-stream effects of these hormones. Without sufficient quantities of circulating thyroid hormones, symptoms of hypothyroidism begin to develop such as fatigue, increased heart rate, depression<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Tang R, Wang J, Yang L, Ding X, Zhong Y, Pan J, Yang H, Mu L, Chen X, Chen Z: Subclinical Hypothyroidism and Depression: A Systematic Review and Meta-Analysis. Front Endocrinol (Lausanne). 2019 Jun 4;10:340. doi: 10.3389/fendo.2019.00340. eCollection 2019. (PubMed ID 31214119)\" href=\"#reference-A179620\">4</a></sup>, dry skin and hair, muscle cramps, constipation, weight gain, memory impairment, and poor tolerance to cold temperatures.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"American Association of Clinical Endocrinologists (AACE): Clinical Practice Guidelines for Hypothyroidism in Adults\" href=\"#reference-F4636\">15</a>,<a class=\"reference-popover-link\" data-content=\"Jonklaas J, Bianco AC, Bauer AJ, Burman KD, Cappola AR, Celi FS, Cooper DS, Kim BW, Peeters RP, Rosenthal MS, Sawka AM: Guidelines for the treatment of hypothyroidism: prepared by the american thyroid association task force on thyroid hormone replacement. Thyroid. 2014 Dec;24(12):1670-751. doi: 10.1089/thy.2014.0028. (PubMed ID 25266247)\" href=\"#reference-A35722\">10</a></sup></p><p>In response to Thyroid Stimulating Hormone (TSH) release by the pituitary gland, a normally functioning thyroid gland will produce and secrete T<sub>4</sub>, which is then converted through deiodination (by type I or type II 5′-deiodinases)<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Kaplan MM, Breitbart R: Conversion of thyroxine to triiodothyronine in the anterior pituitary gland and the influence of this process on thyroid status. Horm Metab Res Suppl. 1984;14:79-85. (PubMed ID 6595194)\" href=\"#reference-A179941\">8</a></sup> into its active metabolite T<sub>3</sub>. While T<sub>4</sub> is the major product secreted by the thyroid gland, T<sub>3</sub> exerts the majority of the physiological effects of the thyroid hormones; T<sub>4</sub> and T<sub>3</sub> have a relative potency of ~1:4 (T4:T3).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Label - levothyroxine\" href=\"#reference-F4633\">14</a></sup> T<sub>4</sub> and T<sub>3</sub> act on nearly every cell of the body, but have a particularly strong effect on the cardiac system.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Osmak-Tizon L, Poussier M, Cottin Y, Rochette L: Non-genomic actions of thyroid hormones: Molecular aspects. Arch Cardiovasc Dis. 2014 Apr;107(4):207-11. doi: 10.1016/j.acvd.2014.02.001. Epub 2014 Mar 26. (PubMed ID 24680385)\" href=\"#reference-A179935\">6</a></sup> As a result, many cardiac functions including heart rate, cardiac output, and systemic vascular resistance are closely linked to thyroid status.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Klein I, Ojamaa K: Thyroid hormone and the cardiovascular system. N Engl J Med. 2001 Feb 15;344(7):501-9. doi: 10.1056/NEJM200102153440707. (PubMed ID 11172193)\" href=\"#reference-A179938\">7</a></sup></p><p>Prior to the development of levothyroxine, <a href=\"https://go.drugbank.com/drugs/DB09100\">Thyroid, porcine</a> or desiccated thyroid, used to be the mainstay of treatment for hypothyroidism. However, this is no longer recommended for the majority of patients due to several clinical concerns including limited controlled trials supporting its use. Desiccated thyroid products contain a ratio of T4 to T3 of 4.2:1, which is significantly lower than the 14:1 ratio of secretion by the human thyroid gland. This higher proportion of T3 in desiccated thyroid products can lead to supraphysiologic levels of T3 which may put patients at risk of thyrotoxicosis if thyroid extract therapy is not adjusted according to the serum TSH.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Jonklaas J, Bianco AC, Bauer AJ, Burman KD, Cappola AR, Celi FS, Cooper DS, Kim BW, Peeters RP, Rosenthal MS, Sawka AM: Guidelines for the treatment of hypothyroidism: prepared by the american thyroid association task force on thyroid hormone replacement. Thyroid. 2014 Dec;24(12):1670-751. doi: 10.1089/thy.2014.0028. (PubMed ID 25266247)\" href=\"#reference-A35722\">10</a>,<a class=\"reference-popover-link\" data-content=\"American Association of Clinical Endocrinologists (AACE): Clinical Practice Guidelines for Hypothyroidism in Adults\" href=\"#reference-F4636\">15</a></sup></p>','C15H11I4NO4','DB00451','Approved','Small Molecule','Average: 776.87 Monoisotopic: 776.686681525 ',' , H03AA — Thyroid hormones , H03A — THYROID PREPARATIONS , H03 — THYROID THERAPY , H — SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS','<p>Absorption of orally administered T4 from the gastrointestinal tract ranges from 40% to 80% with the majority of the levothyroxine dose absorbed from the jejunum and upper ileum. T4 absorption is increased by fasting, and decreased in malabsorption syndromes and by certain foods such as soybeans, milk, and dietary fiber. Absorption may also decrease with age. In addition, many drugs affect T4 absorption including bile acide sequestrants, sucralfate, proton pump inhibitors, and minerals such as calcium (including in yogurt and milk products)<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Chon DA, Reisman T, Weinreb JE, Hershman JM, Leung AM: Concurrent Milk Ingestion Decreases Absorption of Levothyroxine. Thyroid. 2018 Apr;28(4):454-457. doi: 10.1089/thy.2017.0428. Epub 2018 Mar 28. (PubMed ID 29589994)\" href=\"#reference-A179617\">3</a></sup>, magnesium, iron, and aluminum supplements. To prevent the formation of insoluble chelates, levothyroxine should generally be taken on an empty stomach at least 2 hours before a meal and separated by at least 4 hours from any interacting agents. </p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing two benzene rings linked to each other through an ether group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004155\" rel=\"noopener\" target=\"_blank\">Diphenylethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds with a structure containing a benzene ring conjugated to a propanoic acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002551\" rel=\"noopener\" target=\"_blank\">Phenylpropanoic acids</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 aryl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002463\" rel=\"noopener\" target=\"_blank\">Diarylethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing or derived from 1-phenylpropan-2-amine.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000188\" rel=\"noopener\" target=\"_blank\">Amphetamines and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Alpha amino acids which have the L-configuration of the alpha-carbon atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004146\" rel=\"noopener\" target=\"_blank\">L-alpha-amino acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds contaning a phenoxy group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004742\" rel=\"noopener\" target=\"_blank\">Phenoxy compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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=\"Iodophenols carrying a iodine at the C2 position of the benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002777\" rel=\"noopener\" target=\"_blank\">O-iodophenols</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=\"Aromatic compounds containing one or more iodine atoms attached to a benzene.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001101\" rel=\"noopener\" target=\"_blank\">Iodobenzenes</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 the acyl iodide functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001032\" rel=\"noopener\" target=\"_blank\">Aryl iodides</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=\"Compounds containing a chemical bond between a carbon atom and an iodine atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001518\" rel=\"noopener\" target=\"_blank\">Organoiodides</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=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an primary aliphatic amine group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000469\" rel=\"noopener\" target=\"_blank\">Monoalkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></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 10 more</a>','Not Available','Not Available','408980','51-48-9','18332','CHEMBL1624','5614','<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 phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine 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 phenylalanine or a derivative thereof resulting from reaction of phenylalanine 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/C0004321\" rel=\"noopener\" target=\"_blank\">Phenylalanine 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=\"Aromatic compounds containing two benzene rings linked to each other through an ether group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004155\" rel=\"noopener\" target=\"_blank\">Diphenylethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds with a structure containing a benzene ring conjugated to a propanoic acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002551\" rel=\"noopener\" target=\"_blank\">Phenylpropanoic acids</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 aryl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002463\" rel=\"noopener\" target=\"_blank\">Diarylethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing or derived from 1-phenylpropan-2-amine.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000188\" rel=\"noopener\" target=\"_blank\">Amphetamines and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Alpha amino acids which have the L-configuration of the alpha-carbon atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004146\" rel=\"noopener\" target=\"_blank\">L-alpha-amino acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds contaning a phenoxy group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004742\" rel=\"noopener\" target=\"_blank\">Phenoxy compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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=\"Iodophenols carrying a iodine at the C2 position of the benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002777\" rel=\"noopener\" target=\"_blank\">O-iodophenols</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=\"Aromatic compounds containing one or more iodine atoms attached to a benzene.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001101\" rel=\"noopener\" target=\"_blank\">Iodobenzenes</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 the acyl iodide functional group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001032\" rel=\"noopener\" target=\"_blank\">Aryl iodides</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=\"Compounds containing a chemical bond between a carbon atom and an iodine atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001518\" rel=\"noopener\" target=\"_blank\">Organoiodides</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=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an primary aliphatic amine group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000469\" rel=\"noopener\" target=\"_blank\">Monoalkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></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 10 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">2-halophenol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">2-iodophenol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">3-phenylpropanoic-acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alpha-amino acid</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\">Amphetamine or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aralkylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic homomonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl halide</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\">Aryl iodide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Diaryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Diphenylether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Halobenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Iodobenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">L-alpha-amino acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocyclic benzene moiety</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organohalogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoiodide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenol ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenoxy compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenylalanine or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary amine</span></span></span></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 27 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\">non-proteinogenic L-alpha-amino acid, L-phenylalanine derivative, iodophenol, 2-halophenol, thyroxine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:18332\" rel=\"noopener\" target=\"_blank\">CHEBI:18332</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">thyroxine, Other amino acids, Biogenic amines (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C01829\" rel=\"noopener\" target=\"_blank\">C01829</a>) </span></span></dd></dl>','Carboxylic acids and derivatives','<p><span class=\"not-available\">Not Available</span></p>','This compound belongs to the class of organic compounds known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.','Phenylalanine and derivatives','<li>Avoid calcium supplements/calcium rich foods. Calcium may interfere with the absorption of this drug by forming an insoluble complex. Separate medication administration by at least 4 hours.</li>\n<li>Avoid grapefruit products. Grapefruit may delay the absorption of this medication.</li>\n<li>Avoid iron supplements. Iron may interfere with the absorption of this drug by forming an insoluble complex. Separate medication administration by at least 4 hours.</li>\n<li>Avoid multivalent ions. Examples include iron, magnesium, and calcium. These are often found in antacids, vitamins, and supplements - separate medication administration by at least 4 hours.</li>\n<li>Do not take with bran and high fiber foods. Dietary fiber, soybean flour, cottonseed meal, and walnuts may reduce the absorption of levothyroxine.</li>\n<li>Take on an empty stomach. Levothyroxine should be taken on an empty stomach 30-60 minutes prior to the first meal of the day.</li>','Drugs.com Drug Page',' , Agents used to treat hypothyroidism , Amino Acids , Amino Acids, Aromatic , Amino Acids, Cyclic , Amino Acids, Peptides, and Proteins , Cytochrome P-450 CYP2C8 Inhibitors , Cytochrome P-450 CYP2C8 Inhibitors (moderate) , Cytochrome P-450 Enzyme Inhibitors , Hormones , Hormones, Hormone Substitutes, and Hormone Antagonists , Narrow Therapeutic Index Drugs , OATP1B1/SLCO1B1 Inhibitors , OATP1B3 inhibitors , Organic Anion Transporting Polypeptide 2B1 Inhibitors , P-glycoprotein inducers , Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins , Thyroid Products , Thyroxine-binding globulin substrates , UGT1A1 Substrates , UGT1A1 Substrates with a Narrow Therapeutic Index','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>235.5 °C</td><td>PhysProp</td></tr><tr><td>water solubility</td><td>0.105 mg/mL</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>logP</td><td>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\">non-proteinogenic L-alpha-amino acid, L-phenylalanine derivative, iodophenol, 2-halophenol, thyroxine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:18332\" rel=\"noopener\" target=\"_blank\">CHEBI:18332</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">thyroxine, Other amino acids, Biogenic amines (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C01829\" rel=\"noopener\" target=\"_blank\">C01829</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/HMDB0000248\" rel=\"noopener\" target=\"_blank\">HMDB0000248</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:D08125\" rel=\"noopener\" target=\"_blank\">D08125</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:C01829\" rel=\"noopener\" target=\"_blank\">C01829</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=5819\" rel=\"noopener\" target=\"_blank\">5819</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=46507672\" rel=\"noopener\" target=\"_blank\">46507672</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.5614.html\" rel=\"noopener\" target=\"_blank\">5614</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=408980\" rel=\"noopener\" target=\"_blank\">408980</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=10582\" rel=\"noopener\" target=\"_blank\">10582</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=18332\" rel=\"noopener\" target=\"_blank\">18332</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/CHEMBL1624\" rel=\"noopener\" target=\"_blank\">CHEMBL1624</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/ZINC000003830993\" rel=\"noopener\" target=\"_blank\">ZINC000003830993</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=DAP000083\" rel=\"noopener\" target=\"_blank\">DAP000083</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/PA450221\" rel=\"noopener\" target=\"_blank\">PA450221</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=2635\" 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/T44\" rel=\"noopener\" target=\"_blank\">T44</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/levothy.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/levothyroxine.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/syn1421.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/Levothyroxine\" rel=\"noopener\" target=\"_blank\">Levothyroxine</a></dd></dl>','<li>Avoid calcium supplements/calcium rich foods. Calcium may interfere with the absorption of this drug by forming an insoluble complex. Separate medication administration by at least 4 hours.</li>\n<li>Avoid grapefruit products. Grapefruit may delay the absorption of this medication.</li>\n<li>Avoid iron supplements. Iron may interfere with the absorption of this drug by forming an insoluble complex. Separate medication administration by at least 4 hours.</li>\n<li>Avoid multivalent ions. Examples include iron, magnesium, and calcium. These are often found in antacids, vitamins, and supplements - separate medication administration by at least 4 hours.</li>\n<li>Do not take with bran and high fiber foods. Dietary fiber, soybean flour, cottonseed meal, and walnuts may reduce the absorption of levothyroxine.</li>\n<li>Take on an empty stomach. Levothyroxine should be taken on an empty stomach 30-60 minutes prior to the first meal of the day.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A400\">Uchino H, Kanai Y, Kim DK, Wempe MF, Chairoungdua A, Morimoto E, Anders MW, Endou H: Transport of amino acid-related compounds mediated by L-type amino acid transporter 1 (LAT1): insights into the mechanisms of substrate recognition. Mol Pharmacol. 2002 Apr;61(4):729-37. [<a href=\"/articles/A400\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179605\">Cheng SY, Leonard JL, Davis PJ: Molecular aspects of thyroid hormone actions. Endocr Rev. 2010 Apr;31(2):139-70. doi: 10.1210/er.2009-0007. Epub 2010 Jan 5. [<a href=\"/articles/A179605\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179617\">Chon DA, Reisman T, Weinreb JE, Hershman JM, Leung AM: Concurrent Milk Ingestion Decreases Absorption of Levothyroxine. Thyroid. 2018 Apr;28(4):454-457. doi: 10.1089/thy.2017.0428. Epub 2018 Mar 28. [<a href=\"/articles/A179617\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179620\">Tang R, Wang J, Yang L, Ding X, Zhong Y, Pan J, Yang H, Mu L, Chen X, Chen Z: Subclinical Hypothyroidism and Depression: A Systematic Review and Meta-Analysis. Front Endocrinol (Lausanne). 2019 Jun 4;10:340. doi: 10.3389/fendo.2019.00340. eCollection 2019. [<a href=\"/articles/A179620\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179623\">Gottwald-Hostalek U, Uhl W, Wolna P, Kahaly GJ: New levothyroxine formulation meeting 95-105% specification over the whole shelf-life: results from two pharmacokinetic trials. Curr Med Res Opin. 2017 Feb;33(2):169-174. doi: 10.1080/03007995.2016.1246434. Epub 2016 Oct 21. [<a href=\"/articles/A179623\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179935\">Osmak-Tizon L, Poussier M, Cottin Y, Rochette L: Non-genomic actions of thyroid hormones: Molecular aspects. Arch Cardiovasc Dis. 2014 Apr;107(4):207-11. doi: 10.1016/j.acvd.2014.02.001. Epub 2014 Mar 26. [<a href=\"/articles/A179935\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179938\">Klein I, Ojamaa K: Thyroid hormone and the cardiovascular system. N Engl J Med. 2001 Feb 15;344(7):501-9. doi: 10.1056/NEJM200102153440707. [<a href=\"/articles/A179938\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179941\">Kaplan MM, Breitbart R: Conversion of thyroxine to triiodothyronine in the anterior pituitary gland and the influence of this process on thyroid status. Horm Metab Res Suppl. 1984;14:79-85. [<a href=\"/articles/A179941\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179950\">Hammes SR, Davis PJ: Overlapping nongenomic and genomic actions of thyroid hormone and steroids. Best Pract Res Clin Endocrinol Metab. 2015 Aug;29(4):581-93. doi: 10.1016/j.beem.2015.04.001. Epub 2015 Apr 22. [<a href=\"/articles/A179950\" target=\"_blank\">Article</a>] </li><li id=\"reference-A35722\">Jonklaas J, Bianco AC, Bauer AJ, Burman KD, Cappola AR, Celi FS, Cooper DS, Kim BW, Peeters RP, Rosenthal MS, Sawka AM: Guidelines for the treatment of hypothyroidism: prepared by the american thyroid association task force on thyroid hormone replacement. Thyroid. 2014 Dec;24(12):1670-751. doi: 10.1089/thy.2014.0028. [<a href=\"/articles/A35722\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179956\">Davis PJ, Leonard JL, Davis FB: Mechanisms of nongenomic actions of thyroid hormone. Front Neuroendocrinol. 2008 May;29(2):211-8. doi: 10.1016/j.yfrne.2007.09.003. Epub 2007 Oct 5. [<a href=\"/articles/A179956\" target=\"_blank\">Article</a>] </li><li id=\"reference-A179959\">Bergh JJ, Lin HY, Lansing L, Mohamed SN, Davis FB, Mousa S, Davis PJ: Integrin alphaVbeta3 contains a cell surface receptor site for thyroid hormone that is linked to activation of mitogen-activated protein kinase and induction of angiogenesis. Endocrinology. 2005 Jul;146(7):2864-71. doi: 10.1210/en.2005-0102. Epub 2005 Mar 31. [<a href=\"/articles/A179959\" target=\"_blank\">Article</a>] </li><li id=\"reference-L10562\">FDA Approved Drug Products: Synthroid® oral tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021402s024s028lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-F4633\">FDA Label - levothyroxine [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/004/633/original/FDA_Label_-_levothyroxine.pdf?1561401737\" target=\"_blank\">File</a>] </li><li id=\"reference-F4636\">American Association of Clinical Endocrinologists (AACE): Clinical Practice Guidelines for Hypothyroidism in Adults [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/004/636/original/CPG_for_hypothyroidism.pdf?1561402165\" target=\"_blank\">File</a>] </li></ol>','<p>T<sub>4</sub> half-life is 6 to 7 days. T<sub>3</sub> half-life is 1 to 2 days.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"American Association of Clinical Endocrinologists (AACE): Clinical Practice Guidelines for Hypothyroidism in Adults\" href=\"#reference-F4636\">15</a></sup></p>','HMDB0000248','(2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid','InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m0/s1','XUIIKFGFIJCVMT-LBPRGKRZSA-N','<p>Levothyroxine is indicated as replacement therapy in primary (thyroidal), secondary (pituitary) and tertiary (hypothalamic) congenital or acquired hypothyroidism. It is also indicated as an adjunct to surgery and radioiodine therapy in the management of thyrotropin-dependent well-differentiated thyroid cancer.</p>','C01829','D08125','Organic compounds','<p>Approximately 70% of secreted T<sub>4</sub> is deiodinated to equal amounts of T<sub>3</sub> and reverse triiodothyronine (rT<sub>3</sub>), which is calorigenically inactive. T<sub>4</sub> is slowly eliminated through its major metabolic pathway to T<sub>3</sub> via sequential deiodination, where approximately 80% of circulating T<sub>3</sub> is derived from peripheral T<sub>4</sub>. The liver is the major site of degradation for both T<sub>4</sub> and T<sub>3</sub>, with T<sub>4</sub> deiodination also occurring at a number of additional sites, including the kidney and other tissues.</p><p>Elimination of T<sub>4</sub> and T<sub>3</sub> involves hepatic conjugation to glucuronic and sulfuric acids. The hormones undergo enterohepatic circulation as conjugates are hydrolyzed in the intestine and reabsorbed. Conjugated compounds that reach the colon are hydrolyzed and eliminated as free compounds in the feces. Other minor T<sub>4</sub> metabolites have been identified. <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"American Association of Clinical Endocrinologists (AACE): Clinical Practice Guidelines for Hypothyroidism in Adults\" href=\"#reference-F4636\">15</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic homomonocyclic compounds','T44','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000716?highlight[compounds][]=DB00451&amp;highlight[proteins][]=DB00451\">Thyroid Hormone Synthesis</a></td><td>Metabolic</td></tr></tbody>','PA450221','<p>Circulating thyroid hormones are greater than 99% bound to plasma proteins, including thyroxine-binding globulin (TBG), thyroxine-binding prealbumin (TBPA) and albumin (TBA). The higher affinity of both TBG and TBPA for T4 partially explains the higher serum levels, slower metabolic clearance and longer half-life of T4 compared to T3. Protein-bound thyroid hormones exist in reverse equilibrium with small amounts of free hormone where only unbound hormone is metabolically active.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"American Association of Clinical Endocrinologists (AACE): Clinical Practice Guidelines for Hypothyroidism in Adults\" href=\"#reference-F4636\">15</a></sup></p>','5819','46507672','<p>Thyroid hormones are primarily eliminated by the kidneys. A portion of the conjugated hormone reaches the colon unchanged and is eliminated in the feces. Approximately 20% of T<sub>4</sub> is eliminated in the stool. Urinary excretion of T<sub>4</sub> decreases with age.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"American Association of Clinical Endocrinologists (AACE): Clinical Practice Guidelines for Hypothyroidism in Adults\" href=\"#reference-F4636\">15</a></sup></p>','RxList Drug Page','10582','N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)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\">2-halophenol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">2-iodophenol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">3-phenylpropanoic-acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alpha-amino acid</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\">Amphetamine or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aralkylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic homomonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl halide</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\">Aryl iodide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Diaryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Diphenylether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Halobenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Iodobenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">L-alpha-amino acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Monocyclic benzene moiety</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organohalogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoiodide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenol ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenoxy compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Phenylalanine or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary amine</span></span></span></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 27 more</a>','Organic acids and derivatives','<span class=\"citations\"><p>Jivn-Ren Chen, Dimitri C. Papadimitriou, \"Stable dosage of levothyroxine sodium and process of production.\" U.S. Patent US5225204, issued November, 1991.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=5225204&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5225204</a>','DAP000083','<p>LD<sub>50</sub>=20 mg/kg (orally in rat). Hypermetabolic state indistinguishable from thyrotoxicosis of endogenous origin. Symptoms of thyrotoxicosis include weight loss, increased appetite, palpitations, nervousness, diarrhea, abdominal cramps, sweating, tachycardia, increased pulse and blood pressure, cardiac arrhythmias, tremors, insomnia, heat intolerance, fever, and menstrual irregularities.</p>','Q51BO43MG4','<p><span class=\"not-available\">Not Available</span></p>','Levothyroxine','ZINC000003830993'),(32,'Imipramine','imipramine','Imipramine is a tricyclic antidepressant indicated for the treatment of depression and to reduce childhood enuresis.','Tofranil','Imipramine','<p>Imipramine, the prototypical tricyclic antidepressant (TCA), is a dibenzazepine-derivative TCA. TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, imipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, imipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as imipramine and amitriptyline, are more potent inhibitors of serotonin reuptake than secondary amine TCAs, such as nortriptyline and desipramine. TCAs also block histamine H<sub>1</sub> receptors, α<sub>1</sub>-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Gillman PK: Tricyclic antidepressant pharmacology and therapeutic drug interactions updated. Br J Pharmacol. 2007 Jul;151(6):737-48. Epub 2007 Apr 30. (PubMed ID 17471183)\" href=\"#reference-A6584\">5</a></sup>. Imipramine has less sedative and anticholinergic effects than the tertiary amine TCAs, amitriptyline and clomipramine. Imipramine may be used to treat depression and nocturnal enuresis in children <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. Unlabeled indications include chronic and neuropathic pain (including diabetic neuropathy), panic disorder, attention-deficit/hyperactivity disorder (ADHD), and post-traumatic stress disorder (PTSD) <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"APA: Practice Guideline for the Treatment of Patients with Panic Disorder\" href=\"#reference-L1349\">12</a>,<a class=\"reference-popover-link\" data-content=\"AACAP: Practice Parameter for the Assessment and Treatment of Children and Adolescents With Attention-Deficit/ Hyperactivity Disorder\" href=\"#reference-L1348\">11</a>,<a class=\"reference-popover-link\" data-content=\"Authors unspecified: Treatment of patients with eating disorders,third edition. American Psychiatric Association. Am J Psychiatry. 2006 Jul;163(7 Suppl):4-54. (PubMed ID 16925191)\" href=\"#reference-A31900\">1</a>,<a class=\"reference-popover-link\" data-content=\"APA: Practice Guideline for the Treatment of Patients with Schizophrenia Second Edition\" href=\"#reference-L1351\">13</a>,<a class=\"reference-popover-link\" data-content=\"APA: Practice Guideline for the Treatment of Patients with Bipolar Disorder Second Edition\" href=\"#reference-L1352\">14</a>,<a class=\"reference-popover-link\" data-content=\"APA: Practice Guideline for the Treatment of Patients with Acute Stress Disorder and Posttraumatic Stress Disorder\" href=\"#reference-L1353\">15</a>,<a class=\"reference-popover-link\" data-content=\"Low PA, Dotson RM: Symptomatic treatment of painful neuropathy. JAMA. 1998 Dec 2;280(21):1863-4. (PubMed ID 9846782)\" href=\"#reference-A31904\">2</a></sup>.</p>','C19H24N2','DB00458','Approved','Small Molecule','Average: 280.4073 Monoisotopic: 280.193948778 ',' , N06AA — Non-selective monoamine reuptake inhibitors , N06A — ANTIDEPRESSANTS , N06 — PSYCHOANALEPTICS , N — NERVOUS SYSTEM','<p>Rapidly and well absorbed (&gt;95%) after oral administration <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sallee FR, Pollock BG: Clinical pharmacokinetics of imipramine and desipramine. Clin Pharmacokinet. 1990 May;18(5):346-64. (PubMed ID 2185906)\" href=\"#reference-A31907\">3</a></sup>. The primary site of absorption is the small intestine as the basic amine groups are ionized in the acidic environment of the stomach, preventing movement across tissues. Bioavailability ranges from 29-77% due to high inter-individual variability. Peak plasma concentration is usually attained 2-6 hours following oral administration. Absorption is unaffected by food. </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=\"Tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003902\" rel=\"noopener\" target=\"_blank\">Alkyldiarylamines</a></span><span class=\"list-separator\"> / </span><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=\"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 heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span>','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsCytochrome P450 2D6CYP2D6*4(A;A)A AlleleEffect Directly StudiedPatients with this genotype have reduced metabolism of imipramine.DetailsCytochrome P450 2D6CYP2D6*3Not Available2549delAEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of imipramine.DetailsCytochrome P450 2D6CYP2D6*4Not AvailableA alleleEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of imipramine.DetailsCytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of imipramine.DetailsCytochrome P450 2D6CYP2D6*6Not Available1707delTEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of imipramine.DetailsCytochrome P450 2C19CYP2C19*2Not Available681G>AEffect Directly StudiedThe presence of this polymorphism in CYP2C19 is associated with poor metabolism of imipramine.DetailsCytochrome P450 2C19CYP2C19*3Not Available636G>AEffect Directly StudiedThe presence of this polymorphism in CYP2C19 is associated with reduced or poor metabolism of imipramine.DetailsCytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*31Not Available-1770G>A / -1584C>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*51Not Available-1584C>G / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*68ANot Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*68BNot AvailableSimilar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4.Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*100Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*101Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*2ANot Available681G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*2BNot Available681G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*4Not Available1A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*5Not Available1297C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*6Not Available395G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*7Not Available19294T>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*22Not Available557G>C / 991A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*24Not Available99C>T / 991A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*35Not Available12662A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*3Not AvailableC alleleEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*6Not Available1707delTEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*31Not Available-1770G>A / -1584C>G  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*51Not Available-1584C>G / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*68ANot Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*68BNot AvailableSimilar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4.Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*100Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*101Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*3Not AvailableG alleleEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of imipramine.DetailsCytochrome P450 2D6CYP2D6*4Not Available3877G>AEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of imipramine.Details','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsCytochrome P450 2D6CYP2D6*4(A;A)A AlleleEffect Directly StudiedPatients with this genotype have reduced metabolism of imipramine.DetailsCytochrome P450 2D6CYP2D6*3Not Available2549delAEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of imipramine.DetailsCytochrome P450 2D6CYP2D6*4Not AvailableA alleleEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of imipramine.DetailsCytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of imipramine.DetailsCytochrome P450 2D6CYP2D6*6Not Available1707delTEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of imipramine.DetailsCytochrome P450 2C19CYP2C19*2Not Available681G>AEffect Directly StudiedThe presence of this polymorphism in CYP2C19 is associated with poor metabolism of imipramine.DetailsCytochrome P450 2C19CYP2C19*3Not Available636G>AEffect Directly StudiedThe presence of this polymorphism in CYP2C19 is associated with reduced or poor metabolism of imipramine.DetailsCytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*31Not Available-1770G>A / -1584C>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*51Not Available-1584C>G / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*68ANot Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*68BNot AvailableSimilar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4.Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*100Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*101Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*2ANot Available681G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*2BNot Available681G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*4Not Available1A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*5Not Available1297C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*6Not Available395G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*7Not Available19294T>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*22Not Available557G>C / 991A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*24Not Available99C>T / 991A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2C19CYP2C19*35Not Available12662A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*3Not AvailableC alleleEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*6Not Available1707delTEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*31Not Available-1770G>A / -1584C>G  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*51Not Available-1584C>G / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*68ANot Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*68BNot AvailableSimilar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4.Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*100Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*101Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for adverse side effectsDetailsCytochrome P450 2D6CYP2D6*3Not AvailableG alleleEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of imipramine.DetailsCytochrome P450 2D6CYP2D6*4Not Available3877G>AEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of imipramine.Details','50010859','50-49-7','47499','CHEMBL11','3568','<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=\"Tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003902\" rel=\"noopener\" target=\"_blank\">Alkyldiarylamines</a></span><span class=\"list-separator\"> / </span><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=\"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 heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></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\">Alkyldiarylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</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\">Azepine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</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\">Organonitrogen compound</span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic 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\">dibenzoazepine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:47499\" rel=\"noopener\" target=\"_blank\">CHEBI:47499</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-11438\" rel=\"noopener\" target=\"_blank\">CPD-11438</a>) </span></span></dd></dl>','Benzazepines','<p>Imipramine has a mean clearance of 1 L/h/kg. Its active metabolite, desipramine has a mean clearance of 1.8 L/h/kg <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sallee FR, Pollock BG: Clinical pharmacokinetics of imipramine and desipramine. Clin Pharmacokinet. 1990 May;18(5):346-64. (PubMed ID 2185906)\" href=\"#reference-A31907\">3</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.</li>\n<li>Avoid St. John\'s Wort.</li>\n<li>Do not take with bran and high fiber foods.</li>\n<li>Limit caffeine intake.</li>\n<li>Take with food.</li>','Drugs.com Drug Page',' , Adrenergic Agents , Adrenergic alpha-1 Receptor Antagonists , Adrenergic alpha-Antagonists , Adrenergic Antagonists , Adrenergic Uptake Inhibitors , Agents producing tachycardia , Agents that produce hypertension , Agents that reduce seizure threshold , Anticholinergic Agents , Antidepressive Agents , Antidepressive Agents, Tricyclic , Central Nervous System Agents , Central Nervous System Depressants , Combined Inhibitors of Serotonin/Norepinephrine Reuptake , Cytochrome P-450 CYP1A2 Inhibitors , Cytochrome P-450 CYP1A2 Inhibitors (moderate) , 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 Substrates , Cytochrome P-450 CYP2B6 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2C18 Substrates , Cytochrome P-450 CYP2C18 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2C19 Inhibitors , Cytochrome P-450 CYP2C19 inhibitors (strength unknown) , Cytochrome P-450 CYP2C19 Inhibitors (strong) , Cytochrome P-450 CYP2C19 Substrates , Cytochrome P-450 CYP2C19 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2D6 Inhibitors , Cytochrome P-450 CYP2D6 Inhibitors (moderate) , Cytochrome P-450 CYP2D6 Inhibitors (weak) , Cytochrome P-450 CYP2D6 Substrates , Cytochrome P-450 CYP2D6 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2E1 Inhibitors , Cytochrome P-450 CYP2E1 Inhibitors (strength unknown) , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP3A7 Substrates , Cytochrome P-450 CYP3A7 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Dibenzazepines , Drugs that are Mainly Renally Excreted , Heterocyclic Compounds, Fused-Ring , Histamine Antagonists , Histamine H1 Antagonists , Hypotensive Agents , Membrane Transport Modulators , Moderate Risk QTc-Prolonging Agents , Muscarinic Antagonists , Narrow Therapeutic Index Drugs , Nervous System , Neurotoxic agents , Neurotransmitter Agents , Neurotransmitter Uptake Inhibitors , Non-Selective Monoamine Reuptake Inhibitors , OCT2 Inhibitors , P-glycoprotein substrates , P-glycoprotein substrates with a Narrow Therapeutic Index , Psychoanaleptics , Psychotropic Drugs , QTc Prolonging Agents , Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome , Serotonin 5-HT2 Receptor Antagonists , Serotonin 5-HT2A Receptor Antagonists , Serotonin 5-HT2C Receptor Antagonists , Serotonin Agents , Serotonin Modulators , Serotonin Receptor Antagonists , Tertiary amine tricyclic antidepressants , Tricyclics and Other Norepinephrine-reuptake 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>174-175</td><td>U.S. Patent 2,554,736.</td></tr><tr><td>boiling point (°C)</td><td>160 °C at 1.00E-01 mm Hg</td><td>PhysProp</td></tr><tr><td>water solubility</td><td>18.2 mg/L (at 24 °C)</td><td>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</td></tr><tr><td>logP</td><td>4.80</td><td>HANSCH,C ET AL. (1995)</td></tr><tr><td>logS</td><td>-4.19</td><td>ADME Research, USCD</td></tr><tr><td>Caco2 permeability</td><td>-4.85</td><td>ADME Research, USCD</td></tr><tr><td>pKa</td><td>9.4</td><td>SANGSTER (1994)</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">dibenzoazepine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:47499\" rel=\"noopener\" target=\"_blank\">CHEBI:47499</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-11438\" rel=\"noopener\" target=\"_blank\">CPD-11438</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/HMDB0001848\" rel=\"noopener\" target=\"_blank\">HMDB0001848</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:D08070\" rel=\"noopener\" target=\"_blank\">D08070</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:C07049\" rel=\"noopener\" target=\"_blank\">C07049</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=3696\" rel=\"noopener\" target=\"_blank\">3696</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=46507351\" rel=\"noopener\" target=\"_blank\">46507351</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.3568.html\" rel=\"noopener\" target=\"_blank\">3568</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=50010859\" rel=\"noopener\" target=\"_blank\">50010859</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=5691\" rel=\"noopener\" target=\"_blank\">5691</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=47499\" rel=\"noopener\" target=\"_blank\">47499</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/CHEMBL11\" rel=\"noopener\" target=\"_blank\">CHEMBL11</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/ZINC000000020245\" rel=\"noopener\" target=\"_blank\">ZINC000000020245</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=DAP001154\" rel=\"noopener\" target=\"_blank\">DAP001154</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/PA449969\" rel=\"noopener\" target=\"_blank\">PA449969</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=357\" 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/IXX\" rel=\"noopener\" target=\"_blank\">IXX</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/imip.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/imipramine.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/tof1448.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/Imipramine\" rel=\"noopener\" target=\"_blank\">Imipramine</a></dd></dl>','<li>Avoid alcohol.</li>\n<li>Avoid St. John\'s Wort.</li>\n<li>Do not take with bran and high fiber foods.</li>\n<li>Limit caffeine intake.</li>\n<li>Take with food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A31900\">Authors unspecified: Treatment of patients with eating disorders,third edition. American Psychiatric Association. Am J Psychiatry. 2006 Jul;163(7 Suppl):4-54. [<a href=\"/articles/A31900\" target=\"_blank\">Article</a>] </li><li id=\"reference-A31904\">Low PA, Dotson RM: Symptomatic treatment of painful neuropathy. JAMA. 1998 Dec 2;280(21):1863-4. [<a href=\"/articles/A31904\" target=\"_blank\">Article</a>] </li><li id=\"reference-A31907\">Sallee FR, Pollock BG: Clinical pharmacokinetics of imipramine and desipramine. Clin Pharmacokinet. 1990 May;18(5):346-64. [<a href=\"/articles/A31907\" target=\"_blank\">Article</a>] </li><li id=\"reference-A31915\">Gardiner SJ, Begg EJ: Pharmacogenetics, drug-metabolizing enzymes, and clinical practice. Pharmacol Rev. 2006 Sep;58(3):521-90. doi: 10.1124/pr.58.3.6. [<a href=\"/articles/A31915\" target=\"_blank\">Article</a>] </li><li id=\"reference-A6584\">Gillman PK: Tricyclic antidepressant pharmacology and therapeutic drug interactions updated. Br J Pharmacol. 2007 Jul;151(6):737-48. Epub 2007 Apr 30. [<a href=\"/articles/A6584\" target=\"_blank\">Article</a>] </li><li id=\"reference-A31931\">Schmidt HD, Duman RS: The role of neurotrophic factors in adult hippocampal neurogenesis, antidepressant treatments and animal models of depressive-like behavior. Behav Pharmacol. 2007 Sep;18(5-6):391-418. doi: 10.1097/FBP.0b013e3282ee2aa8. [<a href=\"/articles/A31931\" target=\"_blank\">Article</a>] </li><li id=\"reference-A31933\">Heninger GR, Delgado PL, Charney DS: The revised monoamine theory of depression: a modulatory role for monoamines, based on new findings from monoamine depletion experiments in humans. Pharmacopsychiatry. 1996 Jan;29(1):2-11. doi: 10.1055/s-2007-979535. [<a href=\"/articles/A31933\" target=\"_blank\">Article</a>] </li><li id=\"reference-A31938\">Wamsley JK, Byerley WF, McCabe RT, McConnell EJ, Dawson TM, Grosser BI: Receptor alterations associated with serotonergic agents: an autoradiographic analysis. J Clin Psychiatry. 1987 Mar;48 Suppl:19-25. [<a href=\"/articles/A31938\" target=\"_blank\">Article</a>] </li><li id=\"reference-A31939\">Shelton RC: Cellular mechanisms in the vulnerability to depression and response to antidepressants. Psychiatr Clin North Am. 2000 Dec;23(4):713-29. [<a href=\"/articles/A31939\" 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-L1348\">AACAP: Practice Parameter for the Assessment and Treatment of Children and Adolescents With Attention-Deficit/ Hyperactivity Disorder [<a href=\"http://www.aacap.org/App_Themes/AACAP/docs/practice_parameters/jaacap_adhd_2007.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L1349\">APA: Practice Guideline for the Treatment of Patients with Panic Disorder [<a href=\"https://psychiatryonline.org/pb/assets/raw/sitewide/practice_guidelines/guidelines/panicdisorder.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L1351\">APA: Practice Guideline for the Treatment of Patients with Schizophrenia Second Edition [<a href=\"https://psychiatryonline.org/pb/assets/raw/sitewide/practice_guidelines/guidelines/schizophrenia.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L1352\">APA: Practice Guideline for the Treatment of Patients with Bipolar Disorder Second Edition [<a href=\"https://psychiatryonline.org/pb/assets/raw/sitewide/practice_guidelines/guidelines/bipolar.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L1353\">APA: Practice Guideline for the Treatment of Patients with Acute Stress Disorder and Posttraumatic Stress Disorder [<a href=\"https://psychiatryonline.org/pb/assets/raw/sitewide/practice_guidelines/guidelines/acutestressdisorderptsd.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L1360\">TOXNET: Imipramine [<a href=\"http://toxnet.nlm.nih.gov/cgi-bin/sis/search2/r?dbs+hsdb:@term+@DOCNO+3100\" target=\"_blank\">Link</a>] </li></ol>','<p>Imipramine has a mean half life of 12 h. Its active metabolite, desipramine has a mean half life of 22.5 h <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sallee FR, Pollock BG: Clinical pharmacokinetics of imipramine and desipramine. Clin Pharmacokinet. 1990 May;18(5):346-64. (PubMed ID 2185906)\" href=\"#reference-A31907\">3</a></sup>.</p>','HMDB0001848','(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)dimethylamine','InChI=1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3','BCGWQEUPMDMJNV-UHFFFAOYSA-N','<p>For the relief of symptoms of depression and as temporary adjunctive therapy in reducing enuresis in children aged 6 years and older <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. </p><p>May also be used off-label to manage panic disorders with or without agoraphobia, as a second line agent for ADHD in children and adolescents, to manage bulimia nervosa, for short-term management of acute depressive episodes in bipolar disorder and schizophrenia, for the treatment of acute stress disorder and posttraumatic stress disorder, and for symptomatic treatment of postherpetic neuralgia and painful diabetic neuropathy <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"APA: Practice Guideline for the Treatment of Patients with Panic Disorder\" href=\"#reference-L1349\">12</a>,<a class=\"reference-popover-link\" data-content=\"AACAP: Practice Parameter for the Assessment and Treatment of Children and Adolescents With Attention-Deficit/ Hyperactivity Disorder\" href=\"#reference-L1348\">11</a>,<a class=\"reference-popover-link\" data-content=\"Authors unspecified: Treatment of patients with eating disorders,third edition. American Psychiatric Association. Am J Psychiatry. 2006 Jul;163(7 Suppl):4-54. (PubMed ID 16925191)\" href=\"#reference-A31900\">1</a>,<a class=\"reference-popover-link\" data-content=\"APA: Practice Guideline for the Treatment of Patients with Schizophrenia Second Edition\" href=\"#reference-L1351\">13</a>,<a class=\"reference-popover-link\" data-content=\"APA: Practice Guideline for the Treatment of Patients with Bipolar Disorder Second Edition\" href=\"#reference-L1352\">14</a>,<a class=\"reference-popover-link\" data-content=\"APA: Practice Guideline for the Treatment of Patients with Acute Stress Disorder and Posttraumatic Stress Disorder\" href=\"#reference-L1353\">15</a>,<a class=\"reference-popover-link\" data-content=\"Low PA, Dotson RM: Symptomatic treatment of painful neuropathy. JAMA. 1998 Dec 2;280(21):1863-4. (PubMed ID 9846782)\" href=\"#reference-A31904\">2</a></sup>. </p>','C07049','D08070','Organic compounds','<p>Imipramine is nearly exclusively metabolized by the liver <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sallee FR, Pollock BG: Clinical pharmacokinetics of imipramine and desipramine. Clin Pharmacokinet. 1990 May;18(5):346-64. (PubMed ID 2185906)\" href=\"#reference-A31907\">3</a></sup>. Imipramine is converted to desipramine by CYP1A2, CYP3A4, CYP2C19. Both imipramine and desipramine are hydroxylated by CYP2D6 <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Gardiner SJ, Begg EJ: Pharmacogenetics, drug-metabolizing enzymes, and clinical practice. Pharmacol Rev. 2006 Sep;58(3):521-90. doi: 10.1124/pr.58.3.6. (PubMed ID 16968950)\" href=\"#reference-A31915\">4</a></sup>. Desipramine is an active metabolite.</p><p>Minor metabolic pathways include dealkylation to form an imidodibenzyl product as well as demethylation of desipramine to didemethylimipramine and subsequent hydroxylation <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sallee FR, Pollock BG: Clinical pharmacokinetics of imipramine and desipramine. Clin Pharmacokinet. 1990 May;18(5):346-64. (PubMed ID 2185906)\" href=\"#reference-A31907\">3</a></sup>.</p><p>Less than 5% of orally administered imipramine is excreted unchanged.</p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteropolycyclic compounds','IXX','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000422?highlight[compounds][]=DB00458&amp;highlight[proteins][]=DB00458\">Imipramine Action Pathway</a></td><td>Drug action</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000625?highlight[compounds][]=DB00458&amp;highlight[proteins][]=DB00458\">Imipramine Metabolism Pathway</a></td><td>Drug metabolism</td></tr></tbody>','PA449969','<p>Imipramine is 60-96% bound to plasma proteins in circulation <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sallee FR, Pollock BG: Clinical pharmacokinetics of imipramine and desipramine. Clin Pharmacokinet. 1990 May;18(5):346-64. (PubMed ID 2185906)\" href=\"#reference-A31907\">3</a></sup>. It is known to bind albumin, α1-acid glycoprotein, and lipoproteins.</p>','3696','46507351','<p>Imipramine is primarily excreted in the urine with less than 5% present as the parent compound <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sallee FR, Pollock BG: Clinical pharmacokinetics of imipramine and desipramine. Clin Pharmacokinet. 1990 May;18(5):346-64. (PubMed ID 2185906)\" href=\"#reference-A31907\">3</a></sup></p>','RxList Drug Page','5691','CN(C)CCCN1C2=CC=CC=C2CCC2=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\">Alkyldiarylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</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\">Azepine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</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\">Organonitrogen compound</span></span></span>','Organoheterocyclic compounds','<span class=\"citations\"><p>U.S. Patent 2,554,736.</p>\n</span>','DAP001154','<p>The anticholinergic actvity of imipramine can produce dry mucous membranes, blurred vision, increased intraocular pressure, hyperthermia, constipation, adynamic ileus, urinary retention, delayed micturition, and dilation of the urinary tract <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"TOXNET: Imipramine\" href=\"#reference-L1360\">16</a></sup>.</p><p>Central nervous system and neuromuscular effects include drowsiness, lethargy, fatigue, agitation, excitement, nightmares, restlessness, insomnia, confusion, disturbed concentration, disorientation, delusions, and hallucinations.</p><p>Effects on the GI tract include anorexia, nausea and vomiting, diarrhea, abdominal cramps, increases in pancreatic enzymes, epigastric distress, stomatitis, peculiar taste, and black tongue.</p><p>Rarely agranulocytosis, thrombocytopenia, eosinophilia, leukopenia, and purpura have occured.</p><p>Infants whose mothers were receiving tricyclic antidepressants prior to delivery have experienced cardiac problems, irritability, respiratory distress, muscle spasms, seizures, and urinary retention.</p><p>Serotonin syndrome can occur when used in conjunction with other pro-serotonergic drugs.</p><p>Rat\n- Oral 250 mg/kg\n- Intraperitoneal 79mg/kg\n- Subcutaneous 250 mg/kg\n- Intravenous 15.9 mg/kg</p><p>Mouse\n- Oral 188 mg/kg\n- Intraperitoneal 51.6 mg/kg\n- Subcutaneous 195 μg/kg\n- Intravenous 21 mg/kg</p><p>Human range of toxicity is considered to include single dosages greater than 5 mg/kg.</p>','OGG85SX4E4','<p>Imipramine has a high apparent volume of distribution of 10-20 L/kg <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sallee FR, Pollock BG: Clinical pharmacokinetics of imipramine and desipramine. Clin Pharmacokinet. 1990 May;18(5):346-64. (PubMed ID 2185906)\" href=\"#reference-A31907\">3</a></sup>. The drug is known to accumulate in the brain at concentrations 30-40 times that in systemic circulation.</p>','Imipramine','ZINC000000020245'),(33,'Celecoxib','celecoxib','Celecoxib is an NSAID used to treat osteoarthritis, rheumatoid arthritis, acute pain, menstrual symptoms, and to reduce polyps is familial adenomatous polyposis.','Celebrex, Consensi, Elyxyb, Seglentis','Celecoxib','<p>Celecoxib, a selective cyclooxygenase-2 (COX-2) inhibitor, is a nonsteroidal anti-inflammatory drug (NSAID) which is known for its decreased risk of causing gastrointestinal bleeding compared to other NSAIDS.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Shin S: Safety of celecoxib versus traditional nonsteroidal anti-inflammatory drugs in older patients with arthritis. J Pain Res. 2018 Dec 14;11:3211-3219. doi: 10.2147/JPR.S186000. eCollection 2018. (PubMed ID 30588073)\" href=\"#reference-A181544\">16</a></sup> It is used to manage symptoms of various types of arthritis pain and in familial adenomatous polyposis (FAP) to reduce precancerous polyps in the colon.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Chen QW, Zhang XM, Zhou JN, Zhou X, Ma GJ, Zhu M, Zhang YY, Yu J, Feng JF, Chen SQ: Analysis of Small Fragment Deletions of the APC gene in Chinese Patients with Familial Adenomatous Polyposis, a Precancerous Condition. Asian Pac J Cancer Prev. 2015;16(12):4915-20. doi: 10.7314/apjcp.2015.16.12.4915. (PubMed ID 26163615)\" href=\"#reference-A181532\">15</a></sup> It is marketed by Pfizer under the brand name Celebrex, and was initially granted FDA approval in 1998.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA approvals, Celebrex\" href=\"#reference-L7604\">27</a></sup> </p><p>Interestingly, selective COX-2 inhibitors (especially celecoxib), have been evaluated as potential cancer chemopreventive and therapeutic drugs in clinical trials for a variety of malignancies.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Gong L, Thorn CF, Bertagnolli MM, Grosser T, Altman RB, Klein TE: Celecoxib pathways: pharmacokinetics and pharmacodynamics. Pharmacogenet Genomics. 2012 Apr;22(4):310-8. doi: 10.1097/FPC.0b013e32834f94cb. (PubMed ID 22336956)\" href=\"#reference-A34124\">7</a></sup></p>','C17H14F3N3O2S','DB00482','Approved, Investigational','Small Molecule','Average: 381.372 Monoisotopic: 381.075882012 ',' , M01AH — Coxibs , M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS , M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS , M — MUSCULO-SKELETAL SYSTEM , G01AE — Sulfonamides , G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS , G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS , G — GENITO URINARY SYSTEM AND SEX HORMONES , L01XX — Other antineoplastic agents , L01X — OTHER ANTINEOPLASTIC AGENTS , L01 — ANTINEOPLASTIC AGENTS , L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS , C08CA — Dihydropyridine derivatives , C08C — SELECTIVE CALCIUM CHANNEL BLOCKERS WITH MAINLY VASCULAR EFFECTS , C08 — CALCIUM CHANNEL BLOCKERS , C — CARDIOVASCULAR SYSTEM','<p>Celecoxib is absorbed rapidly in the gastrointestinal tract.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Gong L, Thorn CF, Bertagnolli MM, Grosser T, Altman RB, Klein TE: Celecoxib pathways: pharmacokinetics and pharmacodynamics. Pharmacogenet Genomics. 2012 Apr;22(4):310-8. doi: 10.1097/FPC.0b013e32834f94cb. (PubMed ID 22336956)\" href=\"#reference-A34124\">7</a></sup> When a single oral dose of 200 mg was given to healthy research subjects, the peak plasma levels of celecoxib occurred within 3 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Gong L, Thorn CF, Bertagnolli MM, Grosser T, Altman RB, Klein TE: Celecoxib pathways: pharmacokinetics and pharmacodynamics. Pharmacogenet Genomics. 2012 Apr;22(4):310-8. doi: 10.1097/FPC.0b013e32834f94cb. (PubMed ID 22336956)\" href=\"#reference-A34124\">7</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CELEBREX (celecoxib) oral capsules\" href=\"#reference-L7646\">31</a></sup> The Cmax is 705 ng/mL.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pfizer Medical Information\" href=\"#reference-L3296\">25</a></sup> When multiple doses are given, steady-state concentrations are reached on or before day 5. When taken with a high-fat meal, peak plasma levels are delayed for about 1 to 2 hours with an increase in total absorption (AUC) of 10% to 20%.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CELEBREX (celecoxib) oral capsules\" href=\"#reference-L7646\">31</a></sup> The AUC of celecoxib has been shown to be significantly lower in patients with chronic renal impairment.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Ahmad SR, Kortepeter C, Brinker A, Chen M, Beitz J: Renal failure associated with the use of celecoxib and rofecoxib. Drug Saf. 2002;25(7):537-44. doi: 10.2165/00002018-200225070-00007. (PubMed ID 12093311)\" href=\"#reference-A4983\">12</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CELEBREX (celecoxib) oral capsules\" href=\"#reference-L7646\">31</a></sup> A meta-analysis of pharmacokinetic studies has suggested an approximately 40% higher AUC (area under the curve) of celecoxib in black patients compared to Caucasians for unknown reasons.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pfizer Medical Information\" href=\"#reference-L3296\">25</a></sup></p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a sulfonamide group that is S-linked to a benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000031\" rel=\"noopener\" target=\"_blank\">Benzenesulfonamides</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=\"Compounds containing a benzene ring which bears a methane group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001091\" rel=\"noopener\" target=\"_blank\">Toluenes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing the sulfonamide functional group, an amide of sulfonic acid with the general structure R1S(=O)2N(R2)R3 (R1=alkyl, aryl; R2,R3=H, alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001585\" rel=\"noopener\" target=\"_blank\">Organosulfonamides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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=\"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=\"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></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 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 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 3 more</a>','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsCytochrome P450 2C9CYP2C9*3(C;C) / (A;C)C AlleleEffect Directly StudiedPatients with this genotype have reduced metabolism of celecoxib.DetailsCytochrome P450 2C9CYP2C9*6Not Available818delAEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*15Not Available485C>AEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*25Not Available353_362delAGAAATGGAAEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*35Not Available374G>T / 430C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*2Not Available430C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*4Not Available1076T>CEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*5Not Available1080C>GEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*8Not Available449G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*11Not Available1003C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*12Not Available1465C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*13Not Available269T>CEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*14Not Available374G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*16Not Available895A>GEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*18Not Available1075A>C / 1190A>C  … show all Effect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*26Not Available389C>GEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*28Not Available641A>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*30Not Available1429G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*33Not Available395G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsCytochrome P450 2C9CYP2C9*3(C;C) / (A;C)C AlleleEffect Directly StudiedPatients with this genotype have reduced metabolism of celecoxib.DetailsCytochrome P450 2C9CYP2C9*6Not Available818delAEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*15Not Available485C>AEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*25Not Available353_362delAGAAATGGAAEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*35Not Available374G>T / 430C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*2Not Available430C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*4Not Available1076T>CEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*5Not Available1080C>GEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*8Not Available449G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*11Not Available1003C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*12Not Available1465C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*13Not Available269T>CEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*14Not Available374G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*16Not Available895A>GEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*18Not Available1075A>C / 1190A>C  … show all Effect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*26Not Available389C>GEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*28Not Available641A>TEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*30Not Available1429G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetailsCytochrome P450 2C9CYP2C9*33Not Available395G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails','11639','169590-42-5','41423','CHEMBL118','2562','<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 phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a ring with least one carbon atom and one non-carbon atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000002\" rel=\"noopener\" target=\"_blank\">Organoheterocyclic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds comprising a five-member nitrogen heterocyclic ring containing at least one other non-carbon atom of either nitrogen, sulfur, or oxygen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000436\" rel=\"noopener\" target=\"_blank\">Azoles</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 pyrazole ring, which is a five-member aromatic ring with two nitrogen atoms (at positions 1 and 2) and three carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000087\" rel=\"noopener\" target=\"_blank\">Pyrazoles</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 phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002019\" rel=\"noopener\" target=\"_blank\">Phenylpyrazoles</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 sulfonamide group that is S-linked to a benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000031\" rel=\"noopener\" target=\"_blank\">Benzenesulfonamides</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=\"Compounds containing a benzene ring which bears a methane group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001091\" rel=\"noopener\" target=\"_blank\">Toluenes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing the sulfonamide functional group, an amide of sulfonic acid with the general structure R1S(=O)2N(R2)R3 (R1=alkyl, aryl; R2,R3=H, alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001585\" rel=\"noopener\" target=\"_blank\">Organosulfonamides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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=\"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=\"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></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 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 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 3 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\">Aminosulfonyl compound</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\">Benzenesulfonamide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenesulfonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</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\">Monocyclic benzene moiety</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic sulfonic acid or derivatives</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\">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\">Phenylpyrazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Sulfonyl</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Toluene</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 15 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic heteromonocyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">organofluorine compound, pyrazoles, sulfonamide (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:41423\" rel=\"noopener\" target=\"_blank\">CHEBI:41423</a>) </span></span></dd></dl>','Azoles','<p>Apparent clearance (CL/F), single oral 200 mg dose, healthy subjects = 27.7 L/hr.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CELEBREX (celecoxib) oral capsules\" href=\"#reference-L7646\">31</a></sup> Clearance may be decreased by about 47% in patients with chronic renal insufficiency, according to a pharmacokinetic study. Studies have not been performed in patients with severe renal impairment.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CELEBREX (celecoxib) oral capsules\" href=\"#reference-L7646\">31</a></sup></p>','This compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.','Phenylpyrazoles','<li>Avoid alcohol. Alcohol increases the risk of gastrointestinal irritation.</li>\n<li>Avoid multivalent ions. Separate the administration of aluminum and magnesium containing drugs by several hours.</li>\n<li>Take with or without food. Doses up to 200 mg can be taken without regard to food, but doses of 400mg or higher should be taken with food.</li>','Drugs.com Drug Page',' , Agents causing hyperkalemia , Agents that produce hypertension , Amides , Analgesics , Analgesics, Non-Narcotic , Anti-Inflammatory Agents , Anti-Inflammatory Agents, Non-Steroidal , Antiinflammatory and Antirheumatic Products , Antiinflammatory and Antirheumatic Products, Non-Steroids , Antineoplastic and Immunomodulating Agents , Antirheumatic Agents , BCRP/ABCG2 Substrates , BSEP/ABCB11 Inhibitors , Central Nervous System Agents , COX-2 Inhibitors , Cyclooxygenase Inhibitors , Cyclooxygenase-2 (COX-2) Inhibitors , Cytochrome P-450 CYP2C8 Substrates , Cytochrome P-450 CYP2C9 Substrates , Cytochrome P-450 CYP2D6 Inhibitors , Cytochrome P-450 CYP2D6 Inhibitors (moderate) , Cytochrome P-450 CYP2D6 Inhibitors (strength unknown) , Cytochrome P-450 CYP2D6 Substrates , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Dihydropyridine Derivatives , Drugs causing inadvertant photosensitivity , Enzyme Inhibitors , Genito Urinary System and Sex Hormones , Gynecological Antiinfectives and Antiseptics , Methemoglobinemia Associated Agents , Musculo-Skeletal System , Nephrotoxic agents , P-glycoprotein substrates , Peripheral Nervous System Agents , Photosensitizing Agents , Pyrazoles , Selective Calcium Channel Blockers With Mainly Vascular Effects , Selective Cyclooxygenase 2 Inhibitors (NSAIDs) , Sensory System Agents , Sulfonamides , Sulfones , Sulfur Compounds','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>157-159</td><td>https://www.trc-canada.com/product-detail/?C251000</td></tr><tr><td>boiling point (°C)</td><td>529.0±60.0</td><td>http://www.chemspider.com/Chemical-Structure.2562.html</td></tr><tr><td>water solubility</td><td>Poorly soluble</td><td>https://www.lclabs.com/products/c-1502-celecoxib</td></tr><tr><td>logP</td><td>3.53</td><td>https://s3-us-west-2.amazonaws.com/drugbank/msds/DB00482.pdf?1530223672</td></tr><tr><td>Caco2 permeability</td><td>13</td><td>https://www.tandfonline.com/doi/full/10.3109/10717544.2014.916767</td></tr><tr><td>pKa</td><td>11.1</td><td>https://www.pfizermedicalinformation.com/en-us/celebrex/description</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">organofluorine compound, pyrazoles, sulfonamide (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:41423\" rel=\"noopener\" target=\"_blank\">CHEBI:41423</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/HMDB0005014\" rel=\"noopener\" target=\"_blank\">HMDB0005014</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:D00567\" rel=\"noopener\" target=\"_blank\">D00567</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:C07589\" rel=\"noopener\" target=\"_blank\">C07589</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=2662\" rel=\"noopener\" target=\"_blank\">2662</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=46505596\" rel=\"noopener\" target=\"_blank\">46505596</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.2562.html\" rel=\"noopener\" target=\"_blank\">2562</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=11639\" rel=\"noopener\" target=\"_blank\">11639</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=140587\" rel=\"noopener\" target=\"_blank\">140587</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=41423\" rel=\"noopener\" target=\"_blank\">41423</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/CHEMBL118\" rel=\"noopener\" target=\"_blank\">CHEMBL118</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/ZINC000002570895\" rel=\"noopener\" target=\"_blank\">ZINC000002570895</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=DAP000737\" rel=\"noopener\" target=\"_blank\">DAP000737</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/PA448871\" rel=\"noopener\" target=\"_blank\">PA448871</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/CEL\" rel=\"noopener\" target=\"_blank\">CEL</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/coxib.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/celecoxib.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/Celecoxib\" rel=\"noopener\" target=\"_blank\">Celecoxib</a></dd></dl>','<li>Avoid alcohol. Alcohol increases the risk of gastrointestinal irritation.</li>\n<li>Avoid multivalent ions. Separate the administration of aluminum and magnesium containing drugs by several hours.</li>\n<li>Take with or without food. Doses up to 200 mg can be taken without regard to food, but doses of 400mg or higher should be taken with food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A725\">Malhotra S, Shafiq N, Pandhi P: COX-2 inhibitors: a CLASS act or Just VIGORously promoted. MedGenMed. 2004 Mar 23;6(1):6. [<a href=\"/articles/A725\" target=\"_blank\">Article</a>] </li><li id=\"reference-A726\">Silverstein FE, Faich G, Goldstein JL, Simon LS, Pincus T, Whelton A, Makuch R, Eisen G, Agrawal NM, Stenson WF, Burr AM, Zhao WW, Kent JD, Lefkowith JB, Verburg KM, Geis GS: Gastrointestinal toxicity with celecoxib vs nonsteroidal anti-inflammatory drugs for osteoarthritis and rheumatoid arthritis: the CLASS study: A randomized controlled trial. Celecoxib Long-term Arthritis Safety Study. JAMA. 2000 Sep 13;284(10):1247-55. [<a href=\"/articles/A726\" target=\"_blank\">Article</a>] </li><li id=\"reference-A727\">Solomon SD, McMurray JJ, Pfeffer MA, Wittes J, Fowler R, Finn P, Anderson WF, Zauber A, Hawk E, Bertagnolli M: Cardiovascular risk associated with celecoxib in a clinical trial for colorectal adenoma prevention. N Engl J Med. 2005 Mar 17;352(11):1071-80. Epub 2005 Feb 15. [<a href=\"/articles/A727\" target=\"_blank\">Article</a>] </li><li id=\"reference-A728\">Yelland MJ, Nikles CJ, McNairn N, Del Mar CB, Schluter PJ, Brown RM: Celecoxib compared with sustained-release paracetamol for osteoarthritis: a series of n-of-1 trials. Rheumatology (Oxford). 2007 Jan;46(1):135-40. Epub 2006 Jun 15. [<a href=\"/articles/A728\" target=\"_blank\">Article</a>] </li><li id=\"reference-A729\">Bertagnolli MM, Eagle CJ, Zauber AG, Redston M, Solomon SD, Kim K, Tang J, Rosenstein RB, Wittes J, Corle D, Hess TM, Woloj GM, Boisserie F, Anderson WF, Viner JL, Bagheri D, Burn J, Chung DC, Dewar T, Foley TR, Hoffman N, Macrae F, Pruitt RE, Saltzman JR, Salzberg B, Sylwestrowicz T, Gordon GB, Hawk ET: Celecoxib for the prevention of sporadic colorectal adenomas. N Engl J Med. 2006 Aug 31;355(9):873-84. [<a href=\"/articles/A729\" target=\"_blank\">Article</a>] </li><li id=\"reference-A730\">Sandberg M, Yasar U, Stromberg P, Hoog JO, Eliasson E: Oxidation of celecoxib by polymorphic cytochrome P450 2C9 and alcohol dehydrogenase. Br J Clin Pharmacol. 2002 Oct;54(4):423-9. [<a href=\"/articles/A730\" target=\"_blank\">Article</a>] </li><li id=\"reference-A34124\">Gong L, Thorn CF, Bertagnolli MM, Grosser T, Altman RB, Klein TE: Celecoxib pathways: pharmacokinetics and pharmacodynamics. Pharmacogenet Genomics. 2012 Apr;22(4):310-8. doi: 10.1097/FPC.0b013e32834f94cb. [<a href=\"/articles/A34124\" target=\"_blank\">Article</a>] </li><li id=\"reference-A34152\">Hawkey CJ: COX-1 and COX-2 inhibitors. Best Pract Res Clin Gastroenterol. 2001 Oct;15(5):801-20. doi: 10.1053/bega.2001.0236. [<a href=\"/articles/A34152\" target=\"_blank\">Article</a>] </li><li id=\"reference-A34171\">Gwee KA, Goh V, Lima G, Setia S: Coprescribing proton-pump inhibitors with nonsteroidal anti-inflammatory drugs: risks versus benefits. J Pain Res. 2018 Feb 14;11:361-374. doi: 10.2147/JPR.S156938. eCollection 2018. [<a href=\"/articles/A34171\" target=\"_blank\">Article</a>] </li><li id=\"reference-A34172\">Chan FKL, Ching JYL, Tse YK, Lam K, Wong GLH, Ng SC, Lee V, Au KWL, Cheong PK, Suen BY, Chan H, Kee KM, Lo A, Wong VWS, Wu JCY, Kyaw MH: Gastrointestinal safety of celecoxib versus naproxen in patients with cardiothrombotic diseases and arthritis after upper gastrointestinal bleeding (CONCERN): an industry-independent, double-blind, double-dummy, randomised trial. Lancet. 2017 Jun 17;389(10087):2375-2382. doi: 10.1016/S0140-6736(17)30981-9. Epub 2017 Apr 11. [<a href=\"/articles/A34172\" target=\"_blank\">Article</a>] </li><li id=\"reference-A14814\">Davies NM, McLachlan AJ, Day RO, Williams KM: Clinical pharmacokinetics and pharmacodynamics of celecoxib: a selective cyclo-oxygenase-2 inhibitor. Clin Pharmacokinet. 2000 Mar;38(3):225-42. doi: 10.2165/00003088-200038030-00003. [<a href=\"/articles/A14814\" target=\"_blank\">Article</a>] </li><li id=\"reference-A4983\">Ahmad SR, Kortepeter C, Brinker A, Chen M, Beitz J: Renal failure associated with the use of celecoxib and rofecoxib. Drug Saf. 2002;25(7):537-44. doi: 10.2165/00002018-200225070-00007. [<a href=\"/articles/A4983\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181526\">Daniels S, Robbins J, West CR, Nemeth MA: Celecoxib in the treatment of primary dysmenorrhea: results from two randomized, double-blind, active- and placebo-controlled, crossover studies. Clin Ther. 2009 Jun;31(6):1192-208. doi: 10.1016/j.clinthera.2009.06.003. [<a href=\"/articles/A181526\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181529\">Frampton JE, Keating GM: Celecoxib: a review of its use in the management of arthritis and acute pain. Drugs. 2007;67(16):2433-72. doi: 10.2165/00003495-200767160-00008. [<a href=\"/articles/A181529\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181532\">Chen QW, Zhang XM, Zhou JN, Zhou X, Ma GJ, Zhu M, Zhang YY, Yu J, Feng JF, Chen SQ: Analysis of Small Fragment Deletions of the APC gene in Chinese Patients with Familial Adenomatous Polyposis, a Precancerous Condition. Asian Pac J Cancer Prev. 2015;16(12):4915-20. doi: 10.7314/apjcp.2015.16.12.4915. [<a href=\"/articles/A181532\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181544\">Shin S: Safety of celecoxib versus traditional nonsteroidal anti-inflammatory drugs in older patients with arthritis. J Pain Res. 2018 Dec 14;11:3211-3219. doi: 10.2147/JPR.S186000. eCollection 2018. [<a href=\"/articles/A181544\" target=\"_blank\">Article</a>] </li><li id=\"reference-A11861\">Zhu J, Huang JW, Tseng PH, Yang YT, Fowble J, Shiau CW, Shaw YJ, Kulp SK, Chen CS: From the cyclooxygenase-2 inhibitor celecoxib to a novel class of 3-phosphoinositide-dependent protein kinase-1 inhibitors. Cancer Res. 2004 Jun 15;64(12):4309-18. doi: 10.1158/0008-5472.CAN-03-4063. [<a href=\"/articles/A11861\" target=\"_blank\">Article</a>] </li><li id=\"reference-A28426\">Weber A, Casini A, Heine A, Kuhn D, Supuran CT, Scozzafava A, Klebe G: Unexpected nanomolar inhibition of carbonic anhydrase by COX-2-selective celecoxib: new pharmacological opportunities due to related binding site recognition. J Med Chem. 2004 Jan 29;47(3):550-7. [<a href=\"/articles/A28426\" target=\"_blank\">Article</a>] </li><li id=\"reference-A20066\">Nishimori I, Minakuchi T, Onishi S, Vullo D, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Bioorg Med Chem. 2007 Dec 1;15(23):7229-36. Epub 2007 Aug 25. [<a href=\"/articles/A20066\" target=\"_blank\">Article</a>] </li><li id=\"reference-A38563\">Daily EB, Aquilante CL: Cytochrome P450 2C8 pharmacogenetics: a review of clinical studies. Pharmacogenomics. 2009 Sep;10(9):1489-510. doi: 10.2217/pgs.09.82. [<a href=\"/articles/A38563\" target=\"_blank\">Article</a>] </li><li id=\"reference-A181379\">Siu YA, Hao MH, Dixit V, Lai WG: Celecoxib is a substrate of CYP2D6: Impact on celecoxib metabolism in individuals with CYP2C9*3 variants. Drug Metab Pharmacokinet. 2018 Oct;33(5):219-227. doi: 10.1016/j.dmpk.2018.06.001. Epub 2018 Jun 19. [<a href=\"/articles/A181379\" target=\"_blank\">Article</a>] </li><li id=\"reference-T647\">Brandon Cohen; Charles V. Preuss (2019). Celecoxib, NIH StatPearls. StatPearls. </li><li id=\"reference-L3293\">FDA drug safety, June 28 2018 [<a href=\"https://www.fda.gov/Drugs/DrugSafety/ucm611959.htm\" target=\"_blank\">Link</a>] </li><li id=\"reference-L3294\">Medscape drug reference [<a href=\"https://www.medscape.com/viewarticle/895722\" target=\"_blank\">Link</a>] </li><li id=\"reference-L3296\">Pfizer Medical Information [<a href=\"https://www.pfizermedicalinformation.ca/en-ca/celebrex/action-and-clinical-pharmacology\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7592\">Medicines UK, Celebrex 200mg capsule [<a href=\"https://www.medicines.org.uk/emc/product/2945/smpc\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7604\">FDA approvals, Celebrex [<a href=\"https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&amp;ApplNo=020998\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7607\">Bpac NZ: Celecoxib [<a href=\"https://bpac.org.nz/2018/celecoxib.aspx\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7610\">CaymanChem: Celecoxib MSDS [<a href=\"https://www.caymanchem.com/msdss/10008672m.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7622\">US Pharmacist: Cardiovascular risk associated with NSAIDS and COX2 inhibitors [<a href=\"https://www.uspharmacist.com/article/cardiovascular-risk-associated-with-nsaids-and-cox2-inhibitors\" target=\"_blank\">Link</a>] </li><li id=\"reference-L7646\">FDA Approved Drug Products: CELEBREX (celecoxib) oral capsules [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020998s056lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L35930\">FDA Approved Drug Products: ELYXYB (celecoxib) solution [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/212157s002lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L38949\">FDA Approved Drug Products: SEGLENTIS (celecoxib and tramadol hydrochloride) tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/213426s000lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>The effective half-life of celecoxib is approximately 11 hours when a single 200 mg dose is given to healthy subjects.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pfizer Medical Information\" href=\"#reference-L3296\">25</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CELEBREX (celecoxib) oral capsules\" href=\"#reference-L7646\">31</a></sup> The terminal half-life of celecoxib varies because of its low solubility, which prolongs absorption.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CELEBREX (celecoxib) oral capsules\" href=\"#reference-L7646\">31</a></sup></p>','HMDB0005014','4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide','InChI=1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19)20)22-23(15)13-6-8-14(9-7-13)26(21,24)25/h2-10H,1H3,(H2,21,24,25)','RZEKVGVHFLEQIL-UHFFFAOYSA-N','<p>Celecoxib is indicated for symptomatic treatment of adult osteoarthritis (OA) and adult rheumatoid arthritis (RA).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CELEBREX (celecoxib) oral capsules\" href=\"#reference-L7646\">31</a></sup> Celecoxib is not a substitute for aspirin for cardiovascular event prophylaxis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CELEBREX (celecoxib) oral capsules\" href=\"#reference-L7646\">31</a></sup> </p><p>It may be also be used to treat acute pain from various sources, juvenile rheumatoid arthritis in children over 2, ankylosing spondylitis, and primary dysmenorrhea.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CELEBREX (celecoxib) oral capsules\" href=\"#reference-L7646\">31</a></sup></p><p>Celecoxib, in combination with <a href=\"https://go.drugbank.com/drugs/DB00193\">tramadol</a>, is indicated for the management of acute pain in adults severe enough to require an opioid analgesic and in whom alternative treatments are inadequate.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: SEGLENTIS (celecoxib and tramadol hydrochloride) tablets\" href=\"#reference-L38949\">33</a></sup></p>','C07589','D00567','Organic compounds','<p>A large part of celecoxib metabolism is mediated by cytochrome P450 2C9 in the liver with some contribution from CYP3A4 and CYP2C8 and possible contributions from CYP2D6.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Gong L, Thorn CF, Bertagnolli MM, Grosser T, Altman RB, Klein TE: Celecoxib pathways: pharmacokinetics and pharmacodynamics. Pharmacogenet Genomics. 2012 Apr;22(4):310-8. doi: 10.1097/FPC.0b013e32834f94cb. (PubMed ID 22336956)\" href=\"#reference-A34124\">7</a>,<a class=\"reference-popover-link\" data-content=\"Siu YA, Hao MH, Dixit V, Lai WG: Celecoxib is a substrate of CYP2D6: Impact on celecoxib metabolism in individuals with CYP2C9*3 variants. Drug Metab Pharmacokinet. 2018 Oct;33(5):219-227. doi: 10.1016/j.dmpk.2018.06.001. Epub 2018 Jun 19. (PubMed ID 30219715)\" href=\"#reference-A181379\">21</a>,<a class=\"reference-popover-link\" data-content=\"Daily EB, Aquilante CL: Cytochrome P450 2C8 pharmacogenetics: a review of clinical studies. Pharmacogenomics. 2009 Sep;10(9):1489-510. doi: 10.2217/pgs.09.82. (PubMed ID 19761371)\" href=\"#reference-A38563\">20</a>,<a class=\"reference-popover-link\" data-content=\"Brandon Cohen; Charles V. Preuss (2019). Celecoxib, NIH StatPearls. StatPearls.\" href=\"#reference-T647\">22</a></sup> It is metabolized by biotransformation to carboxylic acid and glucuronide metabolites.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Ahmad SR, Kortepeter C, Brinker A, Chen M, Beitz J: Renal failure associated with the use of celecoxib and rofecoxib. Drug Saf. 2002;25(7):537-44. doi: 10.2165/00002018-200225070-00007. (PubMed ID 12093311)\" href=\"#reference-A4983\">12</a></sup> Three metabolites, a primary alcohol, a carboxylic acid, and a glucuronide conjugate, have been found in human plasma after celecoxib administration.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Gong L, Thorn CF, Bertagnolli MM, Grosser T, Altman RB, Klein TE: Celecoxib pathways: pharmacokinetics and pharmacodynamics. Pharmacogenet Genomics. 2012 Apr;22(4):310-8. doi: 10.1097/FPC.0b013e32834f94cb. (PubMed ID 22336956)\" href=\"#reference-A34124\">7</a></sup> These are considered inactive metabolites in regards to COX enzyme inhibition. Patients who are known or suspected to have decreased cytochrome P450 2C9 activity or function, based on their previous history, should be administered celecoxib with caution as they may have abnormally high serum concentrations resulting from decreased metabolism celecoxib.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CELEBREX (celecoxib) oral capsules\" href=\"#reference-L7646\">31</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteromonocyclic compounds','CEL','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000096?highlight[compounds][]=DB00482&amp;highlight[proteins][]=DB00482\">Celecoxib Action Pathway</a></td><td>Drug action</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000644?highlight[compounds][]=DB00482&amp;highlight[proteins][]=DB00482\">Celecoxib Metabolism Pathway</a></td><td>Drug metabolism</td></tr></tbody>','PA448871','<p>The protein binding of celecoxib is 97%, and it is primarily bound to albumin.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Ahmad SR, Kortepeter C, Brinker A, Chen M, Beitz J: Renal failure associated with the use of celecoxib and rofecoxib. Drug Saf. 2002;25(7):537-44. doi: 10.2165/00002018-200225070-00007. (PubMed ID 12093311)\" href=\"#reference-A4983\">12</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CELEBREX (celecoxib) oral capsules\" href=\"#reference-L7646\">31</a></sup></p>','2662','46505596','<p>Celecoxib is primarily eliminated by hepatic metabolism with small amounts (&lt;3%) of the unchanged drug found in both the urine and feces.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Ahmad SR, Kortepeter C, Brinker A, Chen M, Beitz J: Renal failure associated with the use of celecoxib and rofecoxib. Drug Saf. 2002;25(7):537-44. doi: 10.2165/00002018-200225070-00007. (PubMed ID 12093311)\" href=\"#reference-A4983\">12</a></sup> About 57% of an oral dose of celecoxib is excreted in the feces and 27% is found to be excreted into the urine in the form of metabolites. The main metabolite in urine and feces is identified as the carboxylic acid metabolite (73%). The amount of glucuronide in the urine is reported to be low.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CELEBREX (celecoxib) oral capsules\" href=\"#reference-L7646\">31</a></sup></p>','RxList Drug Page','140587','CC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F','Solid','Pyrazoles','<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\">Aminosulfonyl compound</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\">Benzenesulfonamide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenesulfonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</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\">Monocyclic benzene moiety</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic sulfonic acid or derivatives</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\">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\">Phenylpyrazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Sulfonyl</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Toluene</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>','Organoheterocyclic compounds','<a href=\"https://www.google.com/?tbm=pts#q=5466823&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5466823</a>','DAP000737','<p>The oral TDLo in humans 5.71 mg/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"CaymanChem: Celecoxib MSDS\" href=\"#reference-L7610\">29</a></sup></p><p>It is not advisable to administer celecoxib in patients with renal impairment or advanced hepatic impairment, as this may lead to increased serum concentrations, causing toxicity.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CELEBREX (celecoxib) oral capsules\" href=\"#reference-L7646\">31</a></sup> Symptoms of overdose may include breathing difficulties, coma, drowsiness, gastrointestinal bleeding, high blood pressure, kidney failure, nausea, sluggishness, stomach pain, and vomiting.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA drug safety, June 28 2018\" href=\"#reference-L3293\">23</a></sup> Because serious gastrointestinal tract ulceration and bleeding can occur without preceding symptoms, patients should be monitored for signs/symptoms of gastrointestinal bleeding. Symptomatic and supportive measures should be taken in a celecoxib overdose. The induction of emesis or administration of active charcoal should take place if the patient is seen within 4 hours of celecoxib ingestion. Diuresis, urinary alkalinization, hemodialysis, or hemoperfusion may not be useful in a celecoxib overdose due to its high level of protein binding.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CELEBREX (celecoxib) oral capsules\" href=\"#reference-L7646\">31</a></sup> </p>','JCX84Q7J1L','<p>The apparent volume of distribution of celecoxib at steady state (Vss/F) is about 429 L<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Pfizer Medical Information\" href=\"#reference-L3296\">25</a></sup>, which suggests wide distribution into various tissues. Celecoxib is not preferentially bound to red blood cells.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CELEBREX (celecoxib) oral capsules\" href=\"#reference-L7646\">31</a></sup> Another resource reports a volume of distribution of 455 ± 166L.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Ahmad SR, Kortepeter C, Brinker A, Chen M, Beitz J: Renal failure associated with the use of celecoxib and rofecoxib. Drug Saf. 2002;25(7):537-44. doi: 10.2165/00002018-200225070-00007. (PubMed ID 12093311)\" href=\"#reference-A4983\">12</a></sup></p>','Celecoxib','ZINC000002570895'),(35,'Aminocaproic acid','aminocaproic-acid','Aminocaproic acid is an antifibrinolytic agent used to induce clotting postoperatively.','Amicar','Aminocaproic acid','<p>An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties.</p>','C6H13NO2','DB00513','Approved, Investigational','Small Molecule','Average: 131.1729 Monoisotopic: 131.094628665 ',' , B02AA — Amino acids , B02A — ANTIFIBRINOLYTICS , B02 — ANTIHEMORRHAGICS , B — BLOOD AND BLOOD FORMING ORGANS','<p>Absorbed rapidly following oral administration. In adults, oral absorption appears to be a zero-order process with an absorption rate of 5.2 g/hr. The mean lag time in absorption is 10 minutes. After a single oral dose of 5 g, absorption was complete (F=1).</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=\"Fatty acids containing an amine group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000489\" rel=\"noopener\" target=\"_blank\">Amino fatty acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Fatty acids with a straight aliphatic chain.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000333\" rel=\"noopener\" target=\"_blank\">Straight chain fatty acids</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=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an primary aliphatic amine group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000469\" rel=\"noopener\" target=\"_blank\">Monoalkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span></span></span>','Not Available','Not Available','50357211','60-32-2','57826','CHEMBL1046','548','<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 medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"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=\"Organic molecules synthesized by chain elongation of an acetyl-CoA primer with malonyl-CoA (or methylmalonyl-CoA) groups that might contain a cyclic functionality and/or are substituted with heteroatoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003909\" rel=\"noopener\" target=\"_blank\">Fatty Acyls</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=\"Aliphatic monocarboxylic acids with a saturated or unsaturated aliphatic tail (with at least 4 Carbon atoms).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000262\" rel=\"noopener\" target=\"_blank\">Fatty acids and conjugates</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=\"Fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003086\" rel=\"noopener\" target=\"_blank\">Medium-chain fatty acids</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Fatty acids containing an amine group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000489\" rel=\"noopener\" target=\"_blank\">Amino fatty acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Fatty acids with a straight aliphatic chain.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000333\" rel=\"noopener\" target=\"_blank\">Straight chain fatty acids</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=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an primary aliphatic amine group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000469\" rel=\"noopener\" target=\"_blank\">Monoalkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span 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\">Aliphatic acyclic compound</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\">Amino fatty acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Medium-chain fatty acid</span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aliphatic acyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">omega-amino fatty acid, epsilon-amino acid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16586\" rel=\"noopener\" target=\"_blank\">CHEBI:16586</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Amino fatty acids (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C02378\" rel=\"noopener\" target=\"_blank\">C02378</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Amino fatty acids (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMFA01100035\" rel=\"noopener\" target=\"_blank\">LMFA01100035</a>) </span></span></dd></dl>','Fatty Acyls','','This compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.','Medium-chain fatty acids','<li>Take with or without food. The absorption is unaffected by food.</li>','Drugs.com Drug Page',' , Acids, Acyclic , Amino Acids , Amino Acids, Peptides, and Proteins , Aminocaproates , Antifibrinolytic Agents , Blood and Blood Forming Organs , Caproates , Coagulants , Decreased Fibrinolysis , Fibrin Modulating Agents , Hematologic Agents , Hemostatics','<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>205 °C</td><td>PhysProp</td></tr><tr><td>water solubility</td><td>5.05E+005 mg/L (at 25 °C)</td><td>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</td></tr><tr><td>logP</td><td>-2.95</td><td>HANSCH,C ET AL. (1995)</td></tr><tr><td>pKa</td><td>4.43 (at 25 °C)</td><td>KORTUM,G ET AL (1961)</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">omega-amino fatty acid, epsilon-amino acid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16586\" rel=\"noopener\" target=\"_blank\">CHEBI:16586</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Amino fatty acids (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C02378\" rel=\"noopener\" target=\"_blank\">C02378</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Amino fatty acids (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMFA01100035\" rel=\"noopener\" target=\"_blank\">LMFA01100035</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/HMDB0001901\" rel=\"noopener\" target=\"_blank\">HMDB0001901</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:D00160\" rel=\"noopener\" target=\"_blank\">D00160</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:C02378\" rel=\"noopener\" target=\"_blank\">C02378</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=564\" rel=\"noopener\" target=\"_blank\">564</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=46506934\" rel=\"noopener\" target=\"_blank\">46506934</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.548.html\" rel=\"noopener\" target=\"_blank\">548</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=50357211\" rel=\"noopener\" target=\"_blank\">50357211</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=99\" rel=\"noopener\" target=\"_blank\">99</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=57826\" rel=\"noopener\" target=\"_blank\">57826</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/CHEMBL1046\" rel=\"noopener\" target=\"_blank\">CHEMBL1046</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/ZINC000001529425\" rel=\"noopener\" target=\"_blank\">ZINC000001529425</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=DAP000200\" rel=\"noopener\" target=\"_blank\">DAP000200</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/PA164774947\" rel=\"noopener\" target=\"_blank\">PA164774947</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/ACA\" rel=\"noopener\" target=\"_blank\">ACA</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/amicarpre.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/aminocaproic-acid.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/Aminocaproic_acid\" rel=\"noopener\" target=\"_blank\">Aminocaproic_acid</a></dd></dl>','<li>Take with or without food. The absorption is unaffected by food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-L11154\">FDA Approved Drug Products: Amicar (aminocaproic acid) oral tablets/solution [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/015197s043,015230s035lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>The terminal elimination half-life is approximately 2 hours.</p>','HMDB0001901','6-aminohexanoic acid','InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)','SLXKOJJOQWFEFD-UHFFFAOYSA-N','<p>For use in the treatment of excessive postoperative bleeding.</p>','C02378','D00160','Organic compounds','<p>Sixty-five percent of the dose is recovered in the urine as unchanged drug and 11% of the dose appears as the metabolite adipic acid.</p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aliphatic acyclic compounds','ACA','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000286?highlight[compounds][]=DB00513&amp;highlight[proteins][]=DB00513\">Aminocaproic Acid Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA164774947','<p><span class=\"not-available\">Not Available</span></p>','564','46506934','<p>Renal excretion is the primary route of elimination, whether aminocaproic acid is administered orally or intravenously.</p>','RxList Drug Page','99','NCCCCCC(O)=O','Solid','Fatty acids and conjugates','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Aliphatic acyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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\">Amino fatty acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Medium-chain fatty acid</span></span></span>','Lipids and lipid-like molecules','<span class=\"citations\"><p>Frantisek Mares, \"Process for producing caprolactam from 6-aminocaproic acid.\" U.S. Patent US3988319, issued August, 1955.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=3988319&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US3988319</a>','DAP000200','<p>A few cases of acute overdosage with intravenous administration have been reported. The effects have ranged from no reaction to transient hypotension to severe acute renal failure leading to death. The intravenous and oral LD<sub>50</sub> were 3.0 and 12.0 g/kg respectively in the mouse and 3.2 and 16.4 g/kg respectively in the rat. An intravenous infusion dose of 2.3 g/kg was lethal in the dog.</p>','U6F3787206','','Aminocaproic_acid','ZINC000001529425'),(36,'Alitretinoin','alitretinoin','Alitretinoin is a vitamin A derivative used to treat Kaposi\'s sarcoma and used off label to treat chronic hand eczema and psoriasis.','Panretin, Toctino','Alitretinoin','<p>An important regulator of gene expression during growth and development, and in neoplasms. Tretinoin, also known as retinoic acid and derived from maternal vitamin A, is essential for normal growth; and embryonic development. An excess of tretinoin can be teratogenic. It is used in the treatment of psoriasis; acne vulgaris; and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute).</p>','C20H28O2','DB00523','Approved, Investigational','Small Molecule','Average: 300.4351 Monoisotopic: 300.20893014 ',' , D11AH — Agents for dermatitis, excluding corticosteroids , D11A — OTHER DERMATOLOGICAL PREPARATIONS , D11 — OTHER DERMATOLOGICAL PREPARATIONS , D — DERMATOLOGICALS , L01XX — Other antineoplastic agents , L01X — OTHER ANTINEOPLASTIC AGENTS , 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=\"Terpene compounds formed by four isoprene units.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001551\" rel=\"noopener\" target=\"_blank\">Diterpenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003086\" rel=\"noopener\" target=\"_blank\">Medium-chain fatty acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003544\" rel=\"noopener\" target=\"_blank\">Methyl-branched fatty acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Fatty acids with a chain that contains at least one CC double bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000339\" rel=\"noopener\" target=\"_blank\">Unsaturated fatty 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 oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span></span></span>','Not Available','Not Available','31892','5300-03-8','50648','CHEMBL705','395778','<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 retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.</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=\"Lipids synthesized from the five-carbon-unit precursors isopentenyl diphosphate and dimethylallyl diphosphate.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000259\" rel=\"noopener\" target=\"_blank\">Prenol lipids</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=\"Oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001606\" rel=\"noopener\" target=\"_blank\">Retinoids</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=\"Oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001606\" rel=\"noopener\" target=\"_blank\">Retinoids</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=\"Terpene compounds formed by four isoprene units.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001551\" rel=\"noopener\" target=\"_blank\">Diterpenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003086\" rel=\"noopener\" target=\"_blank\">Medium-chain fatty acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003544\" rel=\"noopener\" target=\"_blank\">Methyl-branched fatty acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Fatty acids with a chain that contains at least one CC double bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000339\" rel=\"noopener\" target=\"_blank\">Unsaturated fatty 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 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\">Aliphatic homomonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Branched fatty acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Diterpenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Fatty acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Fatty acyl</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Medium-chain fatty acid</span></span></span></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aliphatic 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\">retinoic acid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50648\" rel=\"noopener\" target=\"_blank\">CHEBI:50648</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Retinoids (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C15493\" rel=\"noopener\" target=\"_blank\">C15493</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Retinoids (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMPR01090022\" rel=\"noopener\" target=\"_blank\">LMPR01090022</a>) </span></span></dd></dl>','Prenol lipids','<p><span class=\"not-available\">Not Available</span></p>','This compound belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.','Retinoids','<li>Take at the same time every day.</li>\n<li>Take with food. Food increases the bioavailability of alitretinoin capsules.</li>','Drugs.com Drug Page',' , Agents for Dermatitis, Excluding Corticosteroids , Alkenes , Antineoplastic Agents , Antineoplastic and Immunomodulating Agents , Biological Factors , Carotenoids , Cyclohexanes , Cyclohexenes , Cycloparaffins , Dermatologicals , Diterpenes , Hydrocarbons, Acyclic , Misc. Skin and Mucous Membrane Agents , P-glycoprotein substrates , Pigments, Biological , Polyenes , Retinoids , Terpenes , Vitamin A , Vitamins , Vitamins (Fat Soluble)','<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>189-190 °C</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>water solubility</td><td>0.6 mg/L</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>logP</td><td>4.2</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\">retinoic acid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50648\" rel=\"noopener\" target=\"_blank\">CHEBI:50648</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Retinoids (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C15493\" rel=\"noopener\" target=\"_blank\">C15493</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Retinoids (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMPR01090022\" rel=\"noopener\" target=\"_blank\">LMPR01090022</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/HMDB0002369\" rel=\"noopener\" target=\"_blank\">HMDB0002369</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:D02815\" rel=\"noopener\" target=\"_blank\">D02815</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:C15493\" rel=\"noopener\" target=\"_blank\">C15493</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=449171\" rel=\"noopener\" target=\"_blank\">449171</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=46507356\" rel=\"noopener\" target=\"_blank\">46507356</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.395778.html\" rel=\"noopener\" target=\"_blank\">395778</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=31892\" rel=\"noopener\" target=\"_blank\">31892</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=81864\" rel=\"noopener\" target=\"_blank\">81864</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=50648\" rel=\"noopener\" target=\"_blank\">50648</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/CHEMBL705\" rel=\"noopener\" target=\"_blank\">CHEMBL705</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/ZINC000012661824\" rel=\"noopener\" target=\"_blank\">ZINC000012661824</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=DAP000275\" rel=\"noopener\" target=\"_blank\">DAP000275</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/PA164746900\" rel=\"noopener\" target=\"_blank\">PA164746900</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/9CR\" rel=\"noopener\" target=\"_blank\">9CR</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/alitre.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/alitretinoin.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/Alitretinoin\" rel=\"noopener\" target=\"_blank\">Alitretinoin</a></dd></dl>','<li>Take at the same time every day.</li>\n<li>Take with food. Food increases the bioavailability of alitretinoin capsules.</li>','<span class=\"not-available\">Not Available</span>','<p><span class=\"not-available\">Not Available</span></p>','HMDB0002369','(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid','InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+','SHGAZHPCJJPHSC-ZVCIMWCZSA-N','<p>For topical treatment of cutaneous lesions in patients with AIDS-related Kaposi\'s sarcoma.</p>','C15493','D02815','Organic compounds','','Aliphatic homomonocyclic compounds','9CR','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000074?highlight[compounds][]=DB00523&amp;highlight[proteins][]=DB00523\">Retinol Metabolism</a></td><td>Metabolic</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000336?highlight[compounds][]=DB00523&amp;highlight[proteins][]=DB00523\">Vitamin A Deficiency</a></td><td>Disease</td></tr></tbody>','PA164746900','<p><span class=\"not-available\">Not Available</span></p>','449171','46507356','<p><span class=\"not-available\">Not Available</span></p>','RxList Drug Page','81864','C\\C(\\C=C\\C1=C(C)CCCC1(C)C)=C\\C=C\\C(\\C)=C\\C(O)=O','Solid','Retinoids','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Aliphatic homomonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Branched fatty acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Diterpenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Fatty acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Fatty acyl</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Medium-chain fatty acid</span></span></span>','Lipids and lipid-like molecules','<span class=\"citations\"><p>Hector F. DeLuca, Praveen K. Tadikonda, \"Method of synthesis of retinoic acid.\" U.S. Patent US5808120, issued December, 1975.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=5808120&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5808120</a>','DAP000275','<p><span class=\"not-available\">Not Available</span></p>','1UA8E65KDZ','<p><span class=\"not-available\">Not Available</span></p>','Alitretinoin','ZINC000012661824'),