(61,'Telmisartan','telmisartan','Telmisartan is an ARB used to treat hypertension, diabetic nephropathy, and congestive heart failure.','Actelsar Hct, Micardis, Micardis-hct, Pritor, Twynsta','Telmisartan','<p>Telmisartan is an angiotensin II receptor antagonist (ARB) used in the management of hypertension. Generally, angiotensin II receptor blockers (ARBs) such as telmisartan bind to the angiotensin II type 1 (AT1) receptors with high affinity, causing inhibition of the action of angiotensin II on vascular smooth muscle, ultimately leading to a reduction in arterial blood pressure. Recent studies suggest that telmisartan may also have PPAR-gamma agonistic properties that could potentially confer beneficial metabolic effects.</p>','C33H30N4O2','DB00966','Approved, Investigational','Small Molecule','Average: 514.6169 Monoisotopic: 514.236876224 ',' , C09DB — Angiotensin II receptor blockers (ARBs) and calcium channel blockers , C09D — ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), COMBINATIONS , C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM , C — CARDIOVASCULAR SYSTEM , C09CA — Angiotensin II receptor blockers (ARBs), plain , C09C — ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), PLAIN , C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM , C — CARDIOVASCULAR SYSTEM , C09DA — Angiotensin II receptor blockers (ARBs) and diuretics , C09D — ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), COMBINATIONS , C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM , C — CARDIOVASCULAR SYSTEM','<p>Absolute bioavailability depends on dosage. Food slightly decreases the bioavailability (a decrease of about 6% is seen when the 40-mg dose is administered with 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=\"Organic Compounds containing a benzene ring which bears at least one carboxyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002565\" rel=\"noopener\" target=\"_blank\">Benzoic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000294\" rel=\"noopener\" target=\"_blank\">Benzimidazoles</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=\"Heterocyclic compounds containing an imidazole ring substituted at position 1.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002311\" rel=\"noopener\" target=\"_blank\">N-substituted imidazoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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=\"Compounds containing a carboxylic acid group with the formula -C(=O)OH.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001205\" rel=\"noopener\" target=\"_blank\">Carboxylic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a bond between a carbon atom and an oxygen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000323\" rel=\"noopener\" target=\"_blank\">Organooxygen compounds</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000278\" rel=\"noopener\" target=\"_blank\">Organonitrogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></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','50043280','144701-48-4','9434','CHEMBL1017','59391','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing one or more benzene rings.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002448\" rel=\"noopener\" target=\"_blank\">Benzenoids</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing one monocyclic ring system consisting of benzene.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002279\" rel=\"noopener\" target=\"_blank\">Benzene and substituted derivatives</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing to benzene rings linked together by a C-C bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000041\" rel=\"noopener\" target=\"_blank\">Biphenyls and derivatives</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing to benzene rings linked together by a C-C bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000041\" rel=\"noopener\" target=\"_blank\">Biphenyls and derivatives</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic Compounds containing a benzene ring which bears at least one carboxyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002565\" rel=\"noopener\" target=\"_blank\">Benzoic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000294\" rel=\"noopener\" target=\"_blank\">Benzimidazoles</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=\"Heterocyclic compounds containing an imidazole ring substituted at position 1.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002311\" rel=\"noopener\" target=\"_blank\">N-substituted imidazoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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=\"Compounds containing a carboxylic acid group with the formula -C(=O)OH.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001205\" rel=\"noopener\" target=\"_blank\">Carboxylic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a bond between a carbon atom and an oxygen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000323\" rel=\"noopener\" target=\"_blank\">Organooxygen compounds</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000278\" rel=\"noopener\" target=\"_blank\">Organonitrogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></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\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzimidazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoyl</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Biphenyl</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></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Heteroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidazole</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\">N-substituted imidazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 12 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic 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\">biphenyls, benzimidazoles (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9434\" rel=\"noopener\" target=\"_blank\">CHEBI:9434</a>) </span></span></dd></dl>','Benzene and substituted derivatives','','This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.','Biphenyls and derivatives','<li>Take with or without food. Bioavailability may be slightly reduced by taking telmisartan with food.</li>','Drugs.com Drug Page',' , Agents Acting on the Renin-Angiotensin System , Agents causing angioedema , Agents causing hyperkalemia , Angiotensin 2 Receptor Blocker , Angiotensin II receptor antagonists , Angiotensin II receptor blockers (ARBs) and calcium channel blockers , Angiotensin II receptor blockers (ARBs) and diuretics , Angiotensin II receptor blockers (ARBs), plain , Angiotensin II Type 1 Receptor Blockers , Angiotensin II Type 2 Receptor Blockers , Angiotensin Receptor Antagonists , Antihypertensive Agents , Antihypertensive Agents Indicated for Hypertension , BCRP/ABCG2 Inhibitors , Benzene Derivatives , Benzimidazoles , Biphenyl Compounds , BSEP/ABCB11 Substrates , Cardiovascular Agents , Cytochrome P-450 CYP2C19 Inhibitors , Cytochrome P-450 CYP2C19 inhibitors (strength unknown) , Cytochrome P-450 Enzyme Inhibitors , Heterocyclic Compounds, Fused-Ring , Hypotensive Agents , P-glycoprotein inhibitors , UGT1A3 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>261-263 °C</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>water solubility</td><td>Practically insoluble</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>logP</td><td>7.7</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>Caco2 permeability</td><td>-4.82</td><td>ADME Research, USCD</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">biphenyls, benzimidazoles (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9434\" rel=\"noopener\" target=\"_blank\">CHEBI:9434</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/HMDB0015101\" rel=\"noopener\" target=\"_blank\">HMDB0015101</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:D00627\" rel=\"noopener\" target=\"_blank\">D00627</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:C07710\" rel=\"noopener\" target=\"_blank\">C07710</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=65999\" rel=\"noopener\" target=\"_blank\">65999</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=46505370\" rel=\"noopener\" target=\"_blank\">46505370</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.59391.html\" rel=\"noopener\" target=\"_blank\">59391</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=50043280\" rel=\"noopener\" target=\"_blank\">50043280</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=73494\" rel=\"noopener\" target=\"_blank\">73494</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=9434\" rel=\"noopener\" target=\"_blank\">9434</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/CHEMBL1017\" rel=\"noopener\" target=\"_blank\">CHEMBL1017</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/ZINC000001530886\" rel=\"noopener\" target=\"_blank\">ZINC000001530886</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=DAP000766\" rel=\"noopener\" target=\"_blank\">DAP000766</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/PA451605\" rel=\"noopener\" target=\"_blank\">PA451605</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=592\" 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/TLS\" rel=\"noopener\" target=\"_blank\">TLS</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/telmisartan.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/telmisartan.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/mic1592.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/Telmisartan\" rel=\"noopener\" target=\"_blank\">Telmisartan</a></dd></dl>','<li>Take with or without food. Bioavailability may be slightly reduced by taking telmisartan with food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A1489\">Sharpe M, Jarvis B, Goa KL: Telmisartan: a review of its use in hypertension. Drugs. 2001;61(10):1501-29. [<a href=\"/articles/A1489\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1490\">Smith DH: Treatment of hypertension with an angiotensin II-receptor antagonist compared with an angiotensin-converting enzyme inhibitor: a review of clinical studies of telmisartan and enalapril. Clin Ther. 2002 Oct;24(10):1484-501. [<a href=\"/articles/A1490\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1491\">Kumar AS, Ghosh S, Mehta GN: Efficient and improved synthesis of Telmisartan. Beilstein J Org Chem. 2010 Mar 11;6:25. doi: 10.3762/bjoc.6.25. [<a href=\"/articles/A1491\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1492\">Galzerano D, Capogrosso C, Di Michele S, Galzerano A, Paparello P, Lama D, Gaudio C: New standards in hypertension and cardiovascular risk management: focus on telmisartan. Vasc Health Risk Manag. 2010 Mar 24;6:113-33. [<a href=\"/articles/A1492\" target=\"_blank\">Article</a>] </li></ol>','<p>Bi-exponential decay kinetics with a terminal elimination half-life of approximately 24 hours.</p>','HMDB0015101','4\'-{[4-methyl-6-(1-methyl-1H-1,3-benzodiazol-2-yl)-2-propyl-1H-1,3-benzodiazol-1-yl]methyl}-[1,1\'-biphenyl]-2-carboxylic acid','InChI=1S/C33H30N4O2/c1-4-9-30-35-31-21(2)18-24(32-34-27-12-7-8-13-28(27)36(32)3)19-29(31)37(30)20-22-14-16-23(17-15-22)25-10-5-6-11-26(25)33(38)39/h5-8,10-19H,4,9,20H2,1-3H3,(H,38,39)','RMMXLENWKUUMAY-UHFFFAOYSA-N','<p>Used alone or in combination with other classes of antihypertensives for the treatment of hypertension. Also used in the treatment of diabetic nephropathy in hypertensive patients with type 2 diabetes mellitus, as well as the treatment of congestive heart failure (only in patients who cannot tolerate ACE inhibitors).</p>','C07710','D00627','Organic compounds','<p>Minimally metabolized by conjugation to form a pharmacologically inactive acylglucuronide; the glucuronide of the parent compound is the only metabolite that has been identified in human plasma and urine. The cytochrome P450 isoenzymes are not involved in the metabolism of telmisartan.</p>','Aromatic heteropolycyclic compounds','TLS','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000164?highlight[compounds][]=DB00966&amp;highlight[proteins][]=DB00966\">Telmisartan Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA451605','<p>Highly bound to plasma proteins (&gt;99.5%), mainly albumin and a1-acid glycoprotein. Binding is not dose-dependent.</p>','65999','46505370','<p>Following either intravenous or oral administration of 14C-labeled telmisartan, most of the administered dose (&gt;97%) was eliminated unchanged in feces via biliary excretion; only minute amounts were found in the urine (0.91% and 0.49% of total radioactivity, respectively).</p>','RxList Drug Page','73494','CCCC1=NC2=C(C=C(C=C2C)C2=NC3=CC=CC=C3N2C)N1CC1=CC=C(C=C1)C1=CC=CC=C1C(O)=O','Solid','Biphenyls and derivatives','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzimidazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoyl</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Biphenyl</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></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Heteroaromatic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidazole</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\">N-substituted imidazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 12 more</a>','Benzenoids','<span class=\"citations\"><p>Kumar AS, Ghosh S, Mehta GN: Efficient and improved synthesis of Telmisartan. Beilstein J Org Chem. 2010 Mar 11;6:25. <a href=\"https://www.ncbi.nlm.nih.gov/pubmed/20502601\">Pubmed</a>.</p>\n</span>','DAP000766','<p>Intravenous LD<sub>50</sub> in rats is 150-200 mg/kg in males and 200 to 250 mg/kg in females. Acute oral toxicity is low: no deaths and no changes occurred in rats or dogs at 2000 mg/kg, the highest dose tested. Limited data are available with regard to overdosage in humans. The most likely manifestations of overdosage with telmisartan would be hypotension, dizziness and tachycardia; bradycardia could occur from parasympathetic (vagal) stimulation.</p>','U5SYW473RQ','','Telmisartan','ZINC000001530886'),(62,'Doxorubicin','doxorubicin','Doxorubicin is a medication used to treat various cancers and Kaposi\'s Sarcoma.','Adriamycin, Doxil, Myocet','Doxorubicin','<p>Doxorubicin is a cytotoxic anthracycline antibiotic isolated from cultures of Streptomyces peucetius var. caesius. Doxorubicin binds to nucleic acids, presumably by specific intercalation of the planar anthracycline nucleus with the DNA double helix.</p>','C27H29NO11','DB00997','Approved, Investigational','Small Molecule','Average: 543.5193 Monoisotopic: 543.174060775 ',' , L01DB — Anthracyclines and related substances , L01D — CYTOTOXIC ANTIBIOTICS AND RELATED SUBSTANCES , 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=\"Polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000155\" rel=\"noopener\" target=\"_blank\">Tetracenequinones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Molecules or a portion of a molecule composed of amino-modified sugars.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000282\" rel=\"noopener\" target=\"_blank\">Aminoglycosides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000151\" rel=\"noopener\" target=\"_blank\">Anthraquinones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Monosaccharides in which the sugar unit is a is a six-carbon containing moeity.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001498\" rel=\"noopener\" target=\"_blank\">Hexoses</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002207\" rel=\"noopener\" target=\"_blank\">O-glycosyl compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000048\" rel=\"noopener\" target=\"_blank\">Tetralins</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic 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 aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R\', where R = aryl group and R\'=organyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003670\" rel=\"noopener\" target=\"_blank\">Aryl ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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 an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002012\" rel=\"noopener\" target=\"_blank\">Oxanes</a></span></span></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 in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003889\" rel=\"noopener\" target=\"_blank\">Vinylogous acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carboxylic acid, and an amine group attached to the alpha carbon atom, relative to the C=O group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002912\" rel=\"noopener\" target=\"_blank\">Alpha-hydroxy ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001897\" rel=\"noopener\" target=\"_blank\">1,2-aminoalcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds having the structure R2C(OR\')2 ( R\' not Hydrogen) and thus diethers of geminal diols. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H ). Mixed acetals have different R\' groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001656\" rel=\"noopener\" target=\"_blank\">Acetals</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing more than one hydroxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002286\" rel=\"noopener\" target=\"_blank\">Polyols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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=\"Compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000286\" rel=\"noopener\" target=\"_blank\">Primary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an 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 13 more</a>','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsRetinoic acid receptor gamma---(C;C) / (C;T)C>TADR Directly StudiedPediatric patients who carry this genotype may be at a higher risk of experiencing anthracycline-induced cardiotoxicity when treated with doxorubicin.DetailsSolute carrier family 28 member 3---(A;A) / (A;G)G > AADR Directly StudiedPediatric patients who carry this genotype may be at a higher risk of experiencing anthracycline-induced cardiotoxicity when treated with doxorubicin.DetailsUDP-glucuronosyltransferase 1-6UGT1A6*4(T;T) / (G;T)G > TADR Directly StudiedPediatric patients who carry this genotype may be at a higher risk of experiencing anthracycline-induced cardiotoxicity when treated with doxorubicin.Details','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsRetinoic acid receptor gamma---(C;C) / (C;T)C>TADR Directly StudiedPediatric patients who carry this genotype may be at a higher risk of experiencing anthracycline-induced cardiotoxicity when treated with doxorubicin.DetailsSolute carrier family 28 member 3---(A;A) / (A;G)G > AADR Directly StudiedPediatric patients who carry this genotype may be at a higher risk of experiencing anthracycline-induced cardiotoxicity when treated with doxorubicin.DetailsUDP-glucuronosyltransferase 1-6UGT1A6*4(T;T) / (G;T)G > TADR Directly StudiedPediatric patients who carry this genotype may be at a higher risk of experiencing anthracycline-induced cardiotoxicity when treated with doxorubicin.Details','32022','23214-92-8','28748','CHEMBL53463','29400','<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 anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds that are synthesized either from the amino acid phenylalanine (phenylpropanoids) or the decarboxylative condensation of malonyl-CoA (polyketides). Phenylpropanoids are aromatic compounds based on the phenylpropane skeleton. Polyketides usually consist of alternating carbonyl and methylene groups (beta-polyketones), biogenetically derived from repeated condensation of acetyl coenzyme A (via malonyl coenzyme A), and usually the compounds derived from them by further condensations.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000261\" rel=\"noopener\" target=\"_blank\">Phenylpropanoids and polyketides</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002106\" rel=\"noopener\" target=\"_blank\">Anthracyclines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"not-available\">Not Available</span></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002106\" rel=\"noopener\" target=\"_blank\">Anthracyclines</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=\"Polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000155\" rel=\"noopener\" target=\"_blank\">Tetracenequinones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Molecules or a portion of a molecule composed of amino-modified sugars.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000282\" rel=\"noopener\" target=\"_blank\">Aminoglycosides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000151\" rel=\"noopener\" target=\"_blank\">Anthraquinones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Monosaccharides in which the sugar unit is a is a six-carbon containing moeity.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001498\" rel=\"noopener\" target=\"_blank\">Hexoses</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002207\" rel=\"noopener\" target=\"_blank\">O-glycosyl compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000048\" rel=\"noopener\" target=\"_blank\">Tetralins</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic 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 aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R\', where R = aryl group and R\'=organyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003670\" rel=\"noopener\" target=\"_blank\">Aryl ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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 an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002012\" rel=\"noopener\" target=\"_blank\">Oxanes</a></span></span></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 in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003889\" rel=\"noopener\" target=\"_blank\">Vinylogous acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carboxylic acid, and an amine group attached to the alpha carbon atom, relative to the C=O group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002912\" rel=\"noopener\" target=\"_blank\">Alpha-hydroxy ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001897\" rel=\"noopener\" target=\"_blank\">1,2-aminoalcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds having the structure R2C(OR\')2 ( R\' not Hydrogen) and thus diethers of geminal diols. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H ). Mixed acetals have different R\' groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001656\" rel=\"noopener\" target=\"_blank\">Acetals</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing more than one hydroxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002286\" rel=\"noopener\" target=\"_blank\">Polyols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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=\"Compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000286\" rel=\"noopener\" target=\"_blank\">Primary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an 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 13 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1,2-aminoalcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">1,4-anthraquinone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">9,10-anthraquinone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Acetal</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alpha-hydroxy ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amino saccharide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminoglycoside core</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\">Anisole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anthracene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anthracycline</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anthracyclinone-skeleton</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 ketone</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\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Glycosyl compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hexose monosaccharide</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\">Monosaccharide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">O-glycosyl 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 oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Polyol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetracenequinone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetralin</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous acid</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 33 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\">quinone, anthracycline antibiotic, aminoglycoside, deoxy hexoside, anthracycline (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28748\" rel=\"noopener\" target=\"_blank\">CHEBI:28748</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Other Polyketides, Anthracyclinones (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C01661\" rel=\"noopener\" target=\"_blank\">C01661</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Anthracyclinones (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMPK13050001\" rel=\"noopener\" target=\"_blank\">LMPK13050001</a>) </span></span></dd></dl>','Anthracyclines','','This compound belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.','Anthracyclines','<li>Avoid St. John\'s Wort. This herb induces CYP3A4 metabolism, which may reduce the serum concentration of doxorubicin.</li>\n<li>Exercise caution with grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum concentration of doxorubicin.</li>','Drugs.com Drug Page',' , Anthracycline Topoisomerase Inhibitor , Anthracyclines , Anthracyclines and Related Substances , Antibiotics, Antineoplastic , Antineoplastic Agents , Antineoplastic and Immunomodulating Agents , BCRP/ABCG2 Substrates , BSEP/ABCB11 Substrates , BSEP/ABCB11 Substrates with a Narrow Therapeutic Index , Carbohydrates , Cardiotoxic antineoplastic agents , Cytochrome P-450 CYP2B6 Inhibitors , Cytochrome P-450 CYP2B6 Inhibitors (strength unknown) , Cytochrome P-450 CYP2D6 Inhibitors , Cytochrome P-450 CYP2D6 Inhibitors (strength unknown) , Cytochrome P-450 CYP3A Inhibitors , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Inhibitors , Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Cytotoxic Antibiotics and Related Substances , Drugs causing inadvertant photosensitivity , Enzyme Inhibitors , Glycosides , Immunosuppressive Agents , Myelosuppressive Agents , Naphthacenes , Narrow Therapeutic Index Drugs , P-glycoprotein inducers , P-glycoprotein inhibitors , P-glycoprotein substrates , P-glycoprotein substrates with a Narrow Therapeutic Index , Photosensitizing Agents , Topoisomerase II Inhibitors , Topoisomerase 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>229-231 °C</td><td>PhysProp</td></tr><tr><td>water solubility</td><td>Soluble</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>logP</td><td>1.27</td><td>HANSCH,C ET AL. (1995)</td></tr><tr><td>Caco2 permeability</td><td>-6.8</td><td>ADME Research, USCD</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">quinone, anthracycline antibiotic, aminoglycoside, deoxy hexoside, anthracycline (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28748\" rel=\"noopener\" target=\"_blank\">CHEBI:28748</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Other Polyketides, Anthracyclinones (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C01661\" rel=\"noopener\" target=\"_blank\">C01661</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Anthracyclinones (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMPK13050001\" rel=\"noopener\" target=\"_blank\">LMPK13050001</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/HMDB0015132\" rel=\"noopener\" target=\"_blank\">HMDB0015132</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:D03899\" rel=\"noopener\" target=\"_blank\">D03899</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:C01661\" rel=\"noopener\" target=\"_blank\">C01661</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=31703\" rel=\"noopener\" target=\"_blank\">31703</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=46507641\" rel=\"noopener\" target=\"_blank\">46507641</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.29400.html\" rel=\"noopener\" target=\"_blank\">29400</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=32022\" rel=\"noopener\" target=\"_blank\">32022</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=3639\" rel=\"noopener\" target=\"_blank\">3639</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=28748\" rel=\"noopener\" target=\"_blank\">28748</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/CHEMBL53463\" rel=\"noopener\" target=\"_blank\">CHEMBL53463</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/ZINC000003918087\" rel=\"noopener\" target=\"_blank\">ZINC000003918087</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=DNC000163\" rel=\"noopener\" target=\"_blank\">DNC000163</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/PA449412\" rel=\"noopener\" target=\"_blank\">PA449412</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/DM2\" rel=\"noopener\" target=\"_blank\">DM2</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/doxor.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/doxorubicin.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/Doxorubicin\" rel=\"noopener\" target=\"_blank\">Doxorubicin</a></dd></dl>','<li>Avoid St. John\'s Wort. This herb induces CYP3A4 metabolism, which may reduce the serum concentration of doxorubicin.</li>\n<li>Exercise caution with grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum concentration of doxorubicin.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A1573\">Weiss RB: The anthracyclines: will we ever find a better doxorubicin? Semin Oncol. 1992 Dec;19(6):670-86. [<a href=\"/articles/A1573\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1574\">Tan C, Tasaka H, Yu KP, Murphy ML, Karnofsky DA: Daunomycin, an antitumor antibiotic, in the treatment of neoplastic disease. Clinical evaluation with special reference to childhood leukemia. Cancer. 1967 Mar;20(3):333-53. [<a href=\"/articles/A1574\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1575\">Arcamone F, Cassinelli G, Fantini G, Grein A, Orezzi P, Pol C, Spalla C: Adriamycin, 14-hydroxydaunomycin, a new antitumor antibiotic from S. peucetius var. caesius. Biotechnol Bioeng. 1969 Nov;11(6):1101-10. [<a href=\"/articles/A1575\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1576\">Di Marco A, Gaetani M, Scarpinato B: Adriamycin (NSC-123,127): a new antibiotic with antitumor activity. Cancer Chemother Rep. 1969 Feb;53(1):33-7. [<a href=\"/articles/A1576\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1577\">Lomovskaya N, Otten SL, Doi-Katayama Y, Fonstein L, Liu XC, Takatsu T, Inventi-Solari A, Filippini S, Torti F, Colombo AL, Hutchinson CR: Doxorubicin overproduction in Streptomyces peucetius: cloning and characterization of the dnrU ketoreductase and dnrV genes and the doxA cytochrome P-450 hydroxylase gene. J Bacteriol. 1999 Jan;181(1):305-18. [<a href=\"/articles/A1577\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1578\">Mordente A, Meucci E, Silvestrini A, Martorana GE, Giardina B: New developments in anthracycline-induced cardiotoxicity. Curr Med Chem. 2009;16(13):1656-72. [<a href=\"/articles/A1578\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1579\">Minotti G: Reactions of adriamycin with microsomal iron and lipids. Free Radic Res Commun. 1989;7(3-6):143-8. [<a href=\"/articles/A1579\" target=\"_blank\">Article</a>] </li></ol>','<p>Terminal half life = 20 - 48 hours. </p>','HMDB0015132','(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione','InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1','AOJJSUZBOXZQNB-TZSSRYMLSA-N','<p>Doxorubicin is used to produce regression in disseminated neoplastic conditions like acute lymphoblastic leukemia, acute myeloblastic leukemia, Wilms’ tumor, neuroblastoma, soft tissue and bone sarcomas, breast carcinoma, ovarian carcinoma, transitional cell bladder carcinoma, thyroid carcinoma, gastric carcinoma, Hodgkin’s disease, malignant lymphoma and bronchogenic carcinoma in which the small cell histologic type is the most responsive compared to other cell types. Doxorubicin is also indicated for use as a component of adjuvant therapy in women with evidence of axillary lymph node involvement following resection of primary breast cancer.</p>','C01661','D03899','Organic compounds','<p>Doxorubicin is capable of undergoing 3 metabolic routes: one-electron reduction, two-electron reduction, and deglycosidation. However, approximately half of the dose is eliminated from the body unchanged. Two electron reduction yields doxorubicinol, a secondary alcohol. This pathway is considered the primary metabolic pathway. The one electron reduction is facilitated by several oxidoreductases to form a doxirubicin-semiquinone radical. These enzymes include mitochondrial and cystolic NADPH dehydrogenates, xanthine oxidase, and nitric oxide synthases. Deglycosidation is a minor metabolic pathway (1-2% of the dose undergoes this pathway). The resultant metabolites are deoxyaglycone or hydroxyaglycone formed via reduction or hydrolysis respectively. Enzymes that may be involved with this pathway include xanthine oxidase, NADPH-cytochrome P450 reductase, and cytosolic NADPH dehydrogenase. </p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteropolycyclic compounds','DM2','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000650?highlight[compounds][]=DB00997&amp;highlight[proteins][]=DB00997\">Doxorubicin Metabolism Pathway</a></td><td>Drug metabolism</td></tr></tbody>','PA449412','<p>Doxorubicin and its major metabolite, doxorubicinol, is 74-76% bound to plasma protein. The extent to binding is independent of plasma concentration up to 1.1 mcg/mL. Doxorubicin does not cross the blood brain barrier. </p>','31703','46507641','<p>40% of the dose appears in bile in 5 days. 5-12% of the drug and its metabolites appears in urine during the same time period. &lt;3% of the dose recovered in urine was doxorubicinol. </p>','RxList Drug Page','3639','COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(=O)CO)C(O)=C1C2=O','Solid','Not Available','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1,2-aminoalcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">1,4-anthraquinone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">9,10-anthraquinone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Acetal</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alpha-hydroxy ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amino saccharide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminoglycoside core</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\">Anisole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anthracene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anthracycline</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anthracyclinone-skeleton</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 ketone</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\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Glycosyl compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hexose monosaccharide</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\">Monosaccharide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">O-glycosyl 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 oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Polyol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetracenequinone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetralin</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous acid</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 33 more</a>','Phenylpropanoids and polyketides','<span class=\"citations\"><p>Gian P. Vicario, Sergio Penco, Federico Arcamone, \"Daunorubicin and doxorubicin labelled with .sup.14 C at the 14-position and processes for their preparation.\" U.S. Patent US4211864, issued March, 1976.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=4211864&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US4211864</a>','DNC000163','<p>LD<sub>50</sub>=21800 ug/kg (rat, subcutaneous)</p>','80168379AG','<p>The distributive half-life is 5 minutes, which suggests that doxorubicin is rapidly taken up by tissue.\nSteady state volume of distribution = 809 to 1214 L/m2</p>','Doxorubicin','ZINC000003918087'),(63,'Minocycline','minocycline','Minocycline is a tetracycline analog used to treat a wide variety of infections in the body.','Amzeeq, Arestin, Dynacin, Minocin, Minolira, Solodyn, Ximino, Zilxi','Minocycline','<p>Minocycline was first described in the literacture in 1966.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Redin GS: Antibacterial activity in mice of minocycline, a new tetracycline. Antimicrob Agents Chemother (Bethesda). 1966;6:371-6. (PubMed ID 5985260)\" href=\"#reference-A190681\">1</a></sup> It is a second generation tetracycline antibiotic that is active against gram-negative and gram-positive bacteria.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Garrido-Mesa N, Zarzuelo A, Galvez J: Minocycline: far beyond an antibiotic. Br J Pharmacol. 2013 May;169(2):337-52. doi: 10.1111/bph.12139. (PubMed ID 23441623)\" href=\"#reference-A190723\">7</a></sup> Like other semisynthetic tetracyclines, minocycline has modifications to carbons 7-9 on the D ring to generate higher efficacy than previous tetracyclines.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Garrido-Mesa N, Zarzuelo A, Galvez J: Minocycline: far beyond an antibiotic. Br J Pharmacol. 2013 May;169(2):337-52. doi: 10.1111/bph.12139. (PubMed ID 23441623)\" href=\"#reference-A190723\">7</a></sup></p><p>Minocycline was granted FDA approval on 30 June 1971.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Minocin Minocycline Oral Capsules (Discontinued)\" href=\"#reference-L11695\">9</a></sup></p>','C23H27N3O7','DB01017','Approved, Investigational','Small Molecule','Average: 457.4764 Monoisotopic: 457.184900233 ',' , J01AA — Tetracyclines , J01A — TETRACYCLINES , J01 — ANTIBACTERIALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , J01AA — Tetracyclines , J01A — TETRACYCLINES , J01 — ANTIBACTERIALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , A01AB — Antiinfectives and antiseptics for local oral treatment , A01A — STOMATOLOGICAL PREPARATIONS , A01 — STOMATOLOGICAL PREPARATIONS , A — ALIMENTARY TRACT AND METABOLISM','<p>100mg of oral minocycline reaches a C<sub>max</sub> of 1.6mg/L, with a T<sub>max</sub> of 1.9h, and an AUC of 31.6mg/L*h.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Saivin S, Houin G: Clinical pharmacokinetics of doxycycline and minocycline. Clin Pharmacokinet. 1988 Dec;15(6):355-66. doi: 10.2165/00003088-198815060-00001. (PubMed ID 3072140)\" href=\"#reference-A190708\">5</a></sup> 200mg of oral minocycline reaches a C<sub>max</sub> of 3.1mg/L, with a T<sub>max</sub> of 2.5h, and an AUC of 48.3mg/L*h.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Saivin S, Houin G: Clinical pharmacokinetics of doxycycline and minocycline. Clin Pharmacokinet. 1988 Dec;15(6):355-66. doi: 10.2165/00003088-198815060-00001. (PubMed ID 3072140)\" href=\"#reference-A190708\">5</a></sup></p>','','Enteric bacteria and other eubacteria\nBacillus anthracis\nTreponema pallidum\nStreptococcus pneumoniae\nNeisseria meningitidis\nListeria monocytogenes\nHaemophilus influenzae\nChlamydia trachomatis\nChlamydophila psittaci\nMycoplasma pneumoniae\nNeisseria gonorrhoeae\nVibrio cholerae\nYersinia pestis\nEscherichia coli\nFrancisella tularensis\nStaphylococcus aureus\nAcinetobacter\nKlebsiella\nShigella\nClostridium\nPropionibacterium acnes\nEnterobacter aerogenes\nFusobacterium nucleatum','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a naphthacene moiety, which is a polyaromatic hydrocarbon made of four linearly fused benzene rings.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000022\" rel=\"noopener\" target=\"_blank\">Naphthacenes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carboxylic acid group (or a derivative thereof) attached to an anthracene ring system.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001911\" rel=\"noopener\" target=\"_blank\">Anthracenecarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000048\" rel=\"noopener\" target=\"_blank\">Tetralins</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R\', where R = aryl group and R\'=organyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003670\" rel=\"noopener\" target=\"_blank\">Aryl ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003901\" rel=\"noopener\" target=\"_blank\">Dialkylarylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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=\"Phenols that a unsubstituted at the 2-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004646\" rel=\"noopener\" target=\"_blank\">1-hydroxy-2-unsubstituted benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003899\" rel=\"noopener\" target=\"_blank\">Aralkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003889\" rel=\"noopener\" target=\"_blank\">Vinylogous acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, a carboxylic acid group (or a derivative thereof), and a side-chain that is specific to each amino acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000347\" rel=\"noopener\" target=\"_blank\">Amino acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds comprising primary carboxylic acid amide functional group, with the general structure RC(=O)NH2.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001662\" rel=\"noopener\" target=\"_blank\">Primary carboxylic acid amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing more than one hydroxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002286\" rel=\"noopener\" target=\"_blank\">Polyols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing the enol functional group, with the structure HO(R)C=CR\'. Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000132\" rel=\"noopener\" target=\"_blank\">Enols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 8 more</a>','Not Available','Not Available','50103599','10118-90-8','50694','CHEMBL1434','16735907','<dl class=\"inner-dl\"><dt class=\"col-md-4 col-sm-5\" id=\"description\">Description</dt><dd class=\"col-md-8 col-sm-7\">This compound belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds that are synthesized either from the amino acid phenylalanine (phenylpropanoids) or the decarboxylative condensation of malonyl-CoA (polyketides). Phenylpropanoids are aromatic compounds based on the phenylpropane skeleton. Polyketides usually consist of alternating carbonyl and methylene groups (beta-polyketones), biogenetically derived from repeated condensation of acetyl coenzyme A (via malonyl coenzyme A), and usually the compounds derived from them by further condensations.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000261\" rel=\"noopener\" target=\"_blank\">Phenylpropanoids and polyketides</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000181\" rel=\"noopener\" target=\"_blank\">Tetracyclines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"not-available\">Not Available</span></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000181\" rel=\"noopener\" target=\"_blank\">Tetracyclines</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a naphthacene moiety, which is a polyaromatic hydrocarbon made of four linearly fused benzene rings.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000022\" rel=\"noopener\" target=\"_blank\">Naphthacenes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carboxylic acid group (or a derivative thereof) attached to an anthracene ring system.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001911\" rel=\"noopener\" target=\"_blank\">Anthracenecarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000048\" rel=\"noopener\" target=\"_blank\">Tetralins</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R\', where R = aryl group and R\'=organyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003670\" rel=\"noopener\" target=\"_blank\">Aryl ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003901\" rel=\"noopener\" target=\"_blank\">Dialkylarylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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=\"Phenols that a unsubstituted at the 2-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004646\" rel=\"noopener\" target=\"_blank\">1-hydroxy-2-unsubstituted benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003899\" rel=\"noopener\" target=\"_blank\">Aralkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003889\" rel=\"noopener\" target=\"_blank\">Vinylogous acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, a carboxylic acid group (or a derivative thereof), and a side-chain that is specific to each amino acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000347\" rel=\"noopener\" target=\"_blank\">Amino acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds comprising primary carboxylic acid amide functional group, with the general structure RC(=O)NH2.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001662\" rel=\"noopener\" target=\"_blank\">Primary carboxylic acid amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing more than one hydroxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002286\" rel=\"noopener\" target=\"_blank\">Polyols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing the enol functional group, with the structure HO(R)C=CR\'. Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000132\" rel=\"noopener\" target=\"_blank\">Enols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 8 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1-hydroxy-2-unsubstituted benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amino acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anthracene carboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aralkylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic homopolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carboxamide group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclohexenone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dialkylarylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Enol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Naphthacene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Polyol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary carboxylic acid amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic/aromatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetracene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetracycline</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetralin</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous acid</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 24 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic homopolycyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">tetracyclines, tetracenomycin (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50694\" rel=\"noopener\" target=\"_blank\">CHEBI:50694</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Linear tetracyclines (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C07225\" rel=\"noopener\" target=\"_blank\">C07225</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Linear tetracyclines (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMPK07000002\" rel=\"noopener\" target=\"_blank\">LMPK07000002</a>) </span></span></dd></dl>','Tetracyclines','<p>Intravenous minocycline has a clearance of 3.36-5.7L/h, while oral minocycline has a clearance of 3.42-4.4L/h.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Saivin S, Houin G: Clinical pharmacokinetics of doxycycline and minocycline. Clin Pharmacokinet. 1988 Dec;15(6):355-66. doi: 10.2165/00003088-198815060-00001. (PubMed ID 3072140)\" href=\"#reference-A190708\">5</a></sup></p>','This compound belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.','Tetracyclines','<li>Avoid multivalent ions. Separate administration of aluminium, calcium, iron and magnesium containing products from medication by at least 2 hours.</li>\n<li>Take with or without food.</li>','Drugs.com Drug Page',' , Agents Causing Muscle Toxicity , Agents that produce neuromuscular block (indirect) , Alimentary Tract and Metabolism , Anti-Bacterial Agents , Anti-Infective Agents , Antibacterials for Systemic Use , Antiinfectives and Antiseptics for Local Oral Treatment , Antiinfectives for Systemic Use , Drugs causing inadvertant photosensitivity , Naphthacenes , OAT1/SLC22A6 inhibitors , OAT3/SLC22A8 Inhibitors , Photosensitizing Agents , Stomatological Preparations , Tetracyclines','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>boiling point (°C)</td><td>753.2</td><td>ChemSpider</td></tr><tr><td>water solubility</td><td>5.2E+004 mg/L (at 25 °C)</td><td>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</td></tr><tr><td>logP</td><td>0.05</td><td>SANGSTER (1993)</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">tetracyclines, tetracenomycin (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50694\" rel=\"noopener\" target=\"_blank\">CHEBI:50694</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Linear tetracyclines (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C07225\" rel=\"noopener\" target=\"_blank\">C07225</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Linear tetracyclines (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMPK07000002\" rel=\"noopener\" target=\"_blank\">LMPK07000002</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/HMDB0015152\" rel=\"noopener\" target=\"_blank\">HMDB0015152</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:D05045\" rel=\"noopener\" target=\"_blank\">D05045</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:C07225\" rel=\"noopener\" target=\"_blank\">C07225</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=54675783\" rel=\"noopener\" target=\"_blank\">54675783</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=46504772\" rel=\"noopener\" target=\"_blank\">46504772</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.16735907.html\" rel=\"noopener\" target=\"_blank\">16735907</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=50103599\" rel=\"noopener\" target=\"_blank\">50103599</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=6980\" rel=\"noopener\" target=\"_blank\">6980</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=50694\" rel=\"noopener\" target=\"_blank\">50694</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/CHEMBL1434\" rel=\"noopener\" target=\"_blank\">CHEMBL1434</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/ZINC000014879992\" rel=\"noopener\" target=\"_blank\">ZINC000014879992</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=DAP000405\" rel=\"noopener\" target=\"_blank\">DAP000405</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/PA450519\" rel=\"noopener\" target=\"_blank\">PA450519</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/MIY\" rel=\"noopener\" target=\"_blank\">MIY</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/minocycline.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/minocycline.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/min1270.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/Minocycline\" rel=\"noopener\" target=\"_blank\">Minocycline</a></dd></dl>','<li>Avoid multivalent ions. Separate administration of aluminium, calcium, iron and magnesium containing products from medication by at least 2 hours.</li>\n<li>Take with or without food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A190681\">Redin GS: Antibacterial activity in mice of minocycline, a new tetracycline. Antimicrob Agents Chemother (Bethesda). 1966;6:371-6. [<a href=\"/articles/A190681\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190696\">Nelis HJ, De Leenheer AP: Metabolism of minocycline in humans. Drug Metab Dispos. 1982 Mar-Apr;10(2):142-6. [<a href=\"/articles/A190696\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190699\">Welling PG, Shaw WR, Uman SJ, Tse FL, Craig WA: Pharmacokinetics of minocycline in renal failure. Antimicrob Agents Chemother. 1975 Nov;8(5):532-7. doi: 10.1128/aac.8.5.532. [<a href=\"/articles/A190699\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190702\">Simon C, Malerczyk V, Preuss I, Schmidt K, Grahmann H: [Activity in vitro and pharmacokinetics of minocycline (author\'s transl)]. Arzneimittelforschung. 1976 Apr;26(4):556-60. [<a href=\"/articles/A190702\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190708\">Saivin S, Houin G: Clinical pharmacokinetics of doxycycline and minocycline. Clin Pharmacokinet. 1988 Dec;15(6):355-66. doi: 10.2165/00003088-198815060-00001. [<a href=\"/articles/A190708\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190714\">Zhou J, Tran BT, Tam VH: The complexity of minocycline serum protein binding. J Antimicrob Chemother. 2017 Jun 1;72(6):1632-1634. doi: 10.1093/jac/dkx039. [<a href=\"/articles/A190714\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190723\">Garrido-Mesa N, Zarzuelo A, Galvez J: Minocycline: far beyond an antibiotic. Br J Pharmacol. 2013 May;169(2):337-52. doi: 10.1111/bph.12139. [<a href=\"/articles/A190723\" target=\"_blank\">Article</a>] </li><li id=\"reference-A19429\">Chopra I, Roberts M: Tetracycline antibiotics: mode of action, applications, molecular biology, and epidemiology of bacterial resistance. Microbiol Mol Biol Rev. 2001 Jun;65(2):232-60 ; second page, table of contents. [<a href=\"/articles/A19429\" target=\"_blank\">Article</a>] </li><li id=\"reference-L11695\">FDA Approved Drug Products: Minocin Minocycline Oral Capsules (Discontinued) [<a href=\"https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&amp;ApplNo=050315\" target=\"_blank\">Link</a>] </li><li id=\"reference-L11701\">FDA Approved Drug Products: Ximino Minocycline Oral Extended Release Capsules [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/201922s002lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L11704\">FDA Approved Drug Products: Solodyn Minocycline Oral Extended Release Tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050808s023lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L11707\">FDA Approved Drug Products: Minocycline Oral Capsules [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/anda/99/65-005_Minocycline%20Hydrochloride_prntlbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L11710\">FDA Approved Drug Products: Minocin Minocycline Oral Pellet-Filled Capsules [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050649s027lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L11713\">FDA Approved Drug Products: Minocin Minocycline Powder for Intravenous Injection [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050444s049lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L11716\">FDA Approved Drug Products: Arestin Minocycline Subgingival Microspheres [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050781s020lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L11719\">FDA Approved Drug Products: Amzeeq Minocycline Topical Foam [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/212379s000lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L11722\">Cayman Chemical: Minocycline MSDS [<a href=\"https://www.caymanchem.com/msdss/14454m.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>The half life of minocycline pellet filled capsules is 11.1-22.1 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Minocin Minocycline Oral Pellet-Filled Capsules\" href=\"#reference-L11710\">13</a></sup> Minocycline intravenous injections have a half live of 15-23 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Simon C, Malerczyk V, Preuss I, Schmidt K, Grahmann H: [Activity in vitro and pharmacokinetics of minocycline (author\'s transl)]. Arzneimittelforschung. 1976 Apr;26(4):556-60. (PubMed ID 782466)\" href=\"#reference-A190702\">4</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Minocin Minocycline Powder for Intravenous Injection\" href=\"#reference-L11713\">14</a></sup></p>','HMDB0015152','(4S,4aS,5aR,12aS)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide','InChI=1S/C23H27N3O7/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28/h5-6,9,11,17,27,29-30,33H,7-8H2,1-4H3,(H2,24,32)/t9-,11-,17-,23-/m0/s1','DYKFCLLONBREIL-KVUCHLLUSA-N','<p>Oral and topical minocycline are indicated to treat inflammatory lesions of acne vulgaris.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ximino Minocycline Oral Extended Release Capsules\" href=\"#reference-L11701\">10</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Solodyn Minocycline Oral Extended Release Tablets\" href=\"#reference-L11704\">11</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Amzeeq Minocycline Topical Foam\" href=\"#reference-L11719\">16</a></sup> Subgingival microspheres are indicated as an adjunct treatment in the reduction of pocket depth in adults with periodontitis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Arestin Minocycline Subgingival Microspheres\" href=\"#reference-L11716\">15</a></sup> Oral and intravenous formulations are indicated to treat infections of susceptible microorganisms.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Minocycline Oral Capsules\" href=\"#reference-L11707\">12</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Minocin Minocycline Oral Pellet-Filled Capsules\" href=\"#reference-L11710\">13</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Minocin Minocycline Powder for Intravenous Injection\" href=\"#reference-L11713\">14</a></sup> These include rickettsiae, <em>Mycoplasma pneumoniae</em>, <em>Chlamydia trachomatis</em>, <em>Chlamydophila psittaci</em>, <em>Chlamydia trachomatis</em>, <em>Ureaplasma urealyticum</em>, <em>Borrelia recurrentis</em>, <em>Haemophilus ducreyi</em>, <em>Yersinia pestis</em>, <em>Francisella tularensis</em>, <em>Vibrio cholerae</em>, <em>Campylobacter fetus</em>, <em>Brucella</em> species, <em>Bartonella bacilliformis</em>, <em>Klebsiella granulomatis</em>, <em>Escherichia coli</em>, <em>Enterobacter aerogenes</em>, <em>Shigella</em> species, <em>Acinetobacter</em> species, <em>Haemophilus influenzae</em>, and <em>Kelbsiella</em> species.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Minocin Minocycline Oral Pellet-Filled Capsules\" href=\"#reference-L11710\">13</a></sup></p>','C07225','D05045','Organic compounds','<p>Minocycline is primarily metabolized to 9-hydroxyminocycline.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Nelis HJ, De Leenheer AP: Metabolism of minocycline in humans. Drug Metab Dispos. 1982 Mar-Apr;10(2):142-6. (PubMed ID 6124399)\" href=\"#reference-A190696\">2</a></sup> It is also metabolized to 2 different N-demethylated metabolites.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Nelis HJ, De Leenheer AP: Metabolism of minocycline in humans. Drug Metab Dispos. 1982 Mar-Apr;10(2):142-6. (PubMed ID 6124399)\" href=\"#reference-A190696\">2</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic homopolycyclic compounds','MIY','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000292?highlight[compounds][]=DB01017&amp;highlight[proteins][]=DB01017\">Minocycline Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA450519','<p>Minocycline is 76% protein bound in serum.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Zhou J, Tran BT, Tam VH: The complexity of minocycline serum protein binding. J Antimicrob Chemother. 2017 Jun 1;72(6):1632-1634. doi: 10.1093/jac/dkx039. (PubMed ID 28333250)\" href=\"#reference-A190714\">6</a></sup></p>','54675783','46504772','<p>Minocycline is predominantly eliminated through the biliary route.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Welling PG, Shaw WR, Uman SJ, Tse FL, Craig WA: Pharmacokinetics of minocycline in renal failure. Antimicrob Agents Chemother. 1975 Nov;8(5):532-7. doi: 10.1128/aac.8.5.532. (PubMed ID 1211910)\" href=\"#reference-A190699\">3</a></sup> 4.5-9% of an intravenous minocycline dose is recovered in the urine.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Simon C, Malerczyk V, Preuss I, Schmidt K, Grahmann H: [Activity in vitro and pharmacokinetics of minocycline (author\'s transl)]. Arzneimittelforschung. 1976 Apr;26(4):556-60. (PubMed ID 782466)\" href=\"#reference-A190702\">4</a>,<a class=\"reference-popover-link\" data-content=\"Saivin S, Houin G: Clinical pharmacokinetics of doxycycline and minocycline. Clin Pharmacokinet. 1988 Dec;15(6):355-66. doi: 10.2165/00003088-198815060-00001. (PubMed ID 3072140)\" href=\"#reference-A190708\">5</a></sup> 10-19.5% of an oral dose is recovered in the urine and 20-34% is recovered in the feces.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Saivin S, Houin G: Clinical pharmacokinetics of doxycycline and minocycline. Clin Pharmacokinet. 1988 Dec;15(6):355-66. doi: 10.2165/00003088-198815060-00001. (PubMed ID 3072140)\" href=\"#reference-A190708\">5</a></sup></p>','RxList Drug Page','6980','[H][C@@]12CC3=C(C(O)=CC=C3N(C)C)C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])C2','Solid','Not Available','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1-hydroxy-2-unsubstituted benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amino acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Anthracene carboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aralkylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic homopolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carboxamide group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclohexenone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dialkylarylamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Enol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Naphthacene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Polyol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary carboxylic acid amide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic/aromatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetracene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetracycline</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetralin</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous acid</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 24 more</a>','Phenylpropanoids and polyketides','<span class=\"citations\"><p>Zita Mendes, Jose Rafael Antunes, Susana Marto, William Heggie, \"Crystalline Minocycline Base and Processes for its Preparation.\" U.S. Patent US20100286417, issued November 11, 2010.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=20100286417&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US20100286417</a>','DAP000405','<p>The oral LD<sub>50</sub> in rats is 2380mg/kg and in mice is 3600mg/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Cayman Chemical: Minocycline MSDS\" href=\"#reference-L11722\">17</a></sup> The intraperitoneal LD<sub>50</sub> in rats is 331mg/kg and in mice is 299mg/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Cayman Chemical: Minocycline MSDS\" href=\"#reference-L11722\">17</a></sup> The subcutaneous LD<sub>50</sub> in rats is 1700mg/kg and in mice is 2290mg/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Cayman Chemical: Minocycline MSDS\" href=\"#reference-L11722\">17</a></sup></p><p>Patients experiencing an overdose may present with dizziness, nausea, and vomiting.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Minocin Minocycline Oral Pellet-Filled Capsules\" href=\"#reference-L11710\">13</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Minocin Minocycline Powder for Intravenous Injection\" href=\"#reference-L11713\">14</a></sup> In the event of an overdose, discontinue minocycline and treat patients with symptomatic and supportive measures.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Ximino Minocycline Oral Extended Release Capsules\" href=\"#reference-L11701\">10</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Solodyn Minocycline Oral Extended Release Tablets\" href=\"#reference-L11704\">11</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Minocycline Oral Capsules\" href=\"#reference-L11707\">12</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Minocin Minocycline Oral Pellet-Filled Capsules\" href=\"#reference-L11710\">13</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Minocin Minocycline Powder for Intravenous Injection\" href=\"#reference-L11713\">14</a></sup></p>','FYY3R43WGO','<p>The volume of distribution of minocycline has been reported as 67.5-115L.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Saivin S, Houin G: Clinical pharmacokinetics of doxycycline and minocycline. Clin Pharmacokinet. 1988 Dec;15(6):355-66. doi: 10.2165/00003088-198815060-00001. (PubMed ID 3072140)\" href=\"#reference-A190708\">5</a></sup></p>','Minocycline','ZINC000014879992');
INSERT INTO `drugs_drugs` VALUES (64,'Abacavir','abacavir','Abacavir is an antiviral nucleoside reverse transcriptase inhibitor used in combination with other antiretrovirals for the treatment of HIV.','Epzicom, Kivexa, Triumeq, Trizivir, Ziagen','Abacavir','<p>Abacavir (ABC) is a powerful nucleoside analog reverse transcriptase inhibitor (NRTI) used to treat HIV and AIDS. Chemically, it is a synthetic carbocyclic nucleoside and is the enantiomer with 1S, 4R absolute configuration on the cyclopentene ring. In vivo, abacavir sulfate dissociates to its free base, abacavir.</p>','C14H18N6O','DB01048','Approved, Investigational','Small Molecule','Average: 286.3323 Monoisotopic: 286.154209228 ',' , J05AR — Antivirals for treatment of HIV infections, combinations , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , J05AR — Antivirals for treatment of HIV infections, combinations , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , J05AR — Antivirals for treatment of HIV infections, combinations , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , J05AF — Nucleoside and nucleotide reverse transcriptase inhibitors , J05A — DIRECT ACTING ANTIVIRALS , J05 — ANTIVIRALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE','<p>Rapid and extensive after oral administration (83% bioavailability, tablet). When a 300 mg tablet is given twice daily to subjects, the peak plasma concentration (Cmax) was 3.0 ± 0.89 mcg/mL and the area under the curve (AUC 0-12 hours) was 6.02 ± 1.73 mcg•hr/mL. </p>','','Human Immunodeficiency Virus','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain an alkylamine group attached at the 6-position of a purine. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003454\" rel=\"noopener\" target=\"_blank\">6-alkylaminopurines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Secondary alkylarylamines with the general formula HN(R)R\' (R = alkyl, R\' = aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002458\" rel=\"noopener\" target=\"_blank\">Secondary alkylarylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amino group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001262\" rel=\"noopener\" target=\"_blank\">Aminopyrimidines and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Heterocyclic compounds containing an imidazole ring substituted at position 1.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002311\" rel=\"noopener\" target=\"_blank\">N-substituted imidazoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Cyclic organooxygen compounds containing the structure RC(=N)N where the central carbon atom and one of the linked nitrogen atoms are part of the same ring( R here is an organyl group). They can also be viewed as analogs of lactams where the oxygen atom is replaced by a nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003886\" rel=\"noopener\" target=\"_blank\">Imidolactams</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Amines having the nitrogen atom linked to exactly one hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002450\" rel=\"noopener\" target=\"_blank\">Primary amines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000286\" rel=\"noopener\" target=\"_blank\">Primary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 1 more</a>','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsHLA class I histocompatibility antigen protein P5HLA-B*5701(G;G)G alleleADR Directly StudiedPatients who carry this SNP are at a higher risk of experiencing a hypersensitivity reaction to abacavir.Details','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsHLA class I histocompatibility antigen protein P5HLA-B*5701(G;G)G alleleADR Directly StudiedPatients who carry this SNP are at a higher risk of experiencing a hypersensitivity reaction to abacavir.Details','50366816','136470-78-5','421707','CHEMBL1380','390063','<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 1,3-substituted cyclopentyl purine nucleosides. These are nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 3-position with either a purine base.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a nucleobase linked to a ribose or deoxyribose sugar via a beta-glycosidic linkage. The ribose or deoxyribose moiety bears at least a phosphate group in case of nucleotides.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000289\" rel=\"noopener\" target=\"_blank\">Nucleosides, nucleotides, and analogues</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003737\" rel=\"noopener\" target=\"_blank\">Nucleoside and nucleotide analogues</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 2- or the 3- position with either a purine or pyrimidine base.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003738\" rel=\"noopener\" target=\"_blank\">Cyclopentyl nucleosides</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"direct-parent\">Direct Parent</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 3-position with either a purine base.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003718\" rel=\"noopener\" target=\"_blank\">1,3-substituted cyclopentyl purine nucleosides</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain an alkylamine group attached at the 6-position of a purine. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003454\" rel=\"noopener\" target=\"_blank\">6-alkylaminopurines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Secondary alkylarylamines with the general formula HN(R)R\' (R = alkyl, R\' = aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002458\" rel=\"noopener\" target=\"_blank\">Secondary alkylarylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amino group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001262\" rel=\"noopener\" target=\"_blank\">Aminopyrimidines and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Heterocyclic compounds containing an imidazole ring substituted at position 1.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002311\" rel=\"noopener\" target=\"_blank\">N-substituted imidazoles</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Cyclic organooxygen compounds containing the structure RC(=N)N where the central carbon atom and one of the linked nitrogen atoms are part of the same ring( R here is an organyl group). They can also be viewed as analogs of lactams where the oxygen atom is replaced by a nitrogen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003886\" rel=\"noopener\" target=\"_blank\">Imidolactams</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004139\" rel=\"noopener\" target=\"_blank\">Azacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Amines having the nitrogen atom linked to exactly one hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002450\" rel=\"noopener\" target=\"_blank\">Primary amines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000286\" rel=\"noopener\" target=\"_blank\">Primary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 1 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1,3-substituted cyclopentyl purine nucleoside</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">6-alkylaminopurine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">6-aminopurine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminopyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Heteroaromatic compound</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidazopyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidolactam</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">N-substituted imidazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Purine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary aliphatic/aromatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary amine</span></span></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 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\">2,6-diaminopurine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:421707\" rel=\"noopener\" target=\"_blank\">CHEBI:421707</a>) </span></span></dd></dl>','Nucleoside and nucleotide analogues','','This compound belongs to the class of organic compounds known as 1,3-substituted cyclopentyl purine nucleosides. These are nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 3-position with either a purine base.','1,3-substituted cyclopentyl purine nucleosides','<li>Avoid alcohol. Alcohol increases the systemic exposure to the drug.</li>\n<li>Take with or without food. The absorption is unaffected by food.</li>','Drugs.com Drug Page',' , Anti-HIV Agents , Anti-Infective Agents , Anti-Retroviral Agents , Antiinfectives for Systemic Use , Antiviral Agents , Antivirals for Systemic Use , Antivirals used in combination for the treatment of HIV infections , Deoxyribonucleosides , Direct Acting Antivirals , Drugs that are Mainly Renally Excreted , Enzyme Inhibitors , Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor , Nucleic Acid Synthesis Inhibitors , Nucleic Acids, Nucleotides, and Nucleosides , Nucleoside and Nucleotide Reverse Transcriptase Inhibitors , Nucleoside Reverse Transcriptase Inhibitors , Nucleosides , Reverse Transcriptase Inhibitors , UGT1A1 Substrates','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>165 °C</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>water solubility</td><td>77 mg/mL (sulfate salt)</td><td>FDA label </td></tr><tr><td>logP</td><td>1.20 </td><td>FDA label</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">2,6-diaminopurine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:421707\" rel=\"noopener\" target=\"_blank\">CHEBI:421707</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/HMDB0015182\" rel=\"noopener\" target=\"_blank\">HMDB0015182</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:D07057\" rel=\"noopener\" target=\"_blank\">D07057</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:C07624\" rel=\"noopener\" target=\"_blank\">C07624</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=441300\" rel=\"noopener\" target=\"_blank\">441300</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=46505718\" rel=\"noopener\" target=\"_blank\">46505718</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.390063.html\" rel=\"noopener\" target=\"_blank\">390063</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=50366816\" rel=\"noopener\" target=\"_blank\">50366816</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=190521\" rel=\"noopener\" target=\"_blank\">190521</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=421707\" rel=\"noopener\" target=\"_blank\">421707</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/CHEMBL1380\" rel=\"noopener\" target=\"_blank\">CHEMBL1380</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/ZINC000002015928\" rel=\"noopener\" target=\"_blank\">ZINC000002015928</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=DAP000704\" rel=\"noopener\" target=\"_blank\">DAP000704</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/PA448004\" rel=\"noopener\" target=\"_blank\">PA448004</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/1KX\" rel=\"noopener\" target=\"_blank\">1KX</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/abavir.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/abacavir.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/cx1527.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/Abacavir\" rel=\"noopener\" target=\"_blank\">Abacavir</a></dd></dl>','<li>Avoid alcohol. Alcohol increases the systemic exposure to the drug.</li>\n<li>Take with or without food. The absorption is unaffected by food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A1650\">Zucman D, Truchis Pd, Majerholc C, Stegman S, Caillat-Zucman S: Prospective screening for human leukocyte antigen-B*5701 avoids abacavir hypersensitivity reaction in the ethnically mixed French HIV population. J Acquir Immune Defic Syndr. 2007 May 1;45(1):1-3. [<a href=\"/articles/A1650\" target=\"_blank\">Article</a>] </li><li id=\"reference-L96\">Link [<a href=\"http://pharmgkb.org/pathway/PA166104634#\" target=\"_blank\">Link</a>] </li></ol>','<p>1.54 ± 0.63 hours</p>','HMDB0015182','[(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl]methanol','InChI=1S/C14H18N6O/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19)/t8-,10+/m1/s1','MCGSCOLBFJQGHM-SCZZXKLOSA-N','<p>For the treatment of HIV-1 infection, in combination with other antiretroviral agents.</p>','C07624','D07057','Organic compounds','<p>Hepatic, by alcohol dehydrogenase and glucuronosyltransferase to a 5′-carboxylic acid metabolite and 5′-glucuronide metabolite, respectively. These metabolites have no antiviral activity. Abacavir is not significantly metabolized by cytochrome P450 enzymes.</p>','Aromatic heteropolycyclic compounds','1KX','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000737?highlight[compounds][]=DB01048&amp;highlight[proteins][]=DB01048\">Abacavir Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA448004','<p>Moderate (approximately 50%). Binding of abacavir to plasma protein was independent of concentration. </p>','441300','46505718','<p>Elimination of abacavir was quantified in a mass balance study following administration of a 600-mg dose of 14C-abacavir: 99% of the radioactivity was recovered, 1.2% was excreted in the urine as abacavir, 30% as the 5′-carboxylic acid metabolite, 36% as the 5′-glucuronide metabolite, and 15% as unidentified minor metabolites in the urine. Fecal elimination accounted for 16% of the dose. Renal excretion of unchanged abacavir is a minor route of elimination in humans.</p>','RxList Drug Page','190521','NC1=NC2=C(N=CN2[C@@H]2C[C@H](CO)C=C2)C(NC2CC2)=N1','Solid','Cyclopentyl nucleosides','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1,3-substituted cyclopentyl purine nucleoside</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">6-alkylaminopurine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">6-aminopurine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminopyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Heteroaromatic compound</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidazopyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Imidolactam</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">N-substituted imidazole</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Primary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Purine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Pyrimidine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary aliphatic/aromatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary amine</span></span></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>','Nucleosides, nucleotides, and analogues','<a href=\"https://www.google.com/?tbm=pts#q=5034394&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5034394</a>','DAP000704','<p>Some myocardial degeneration has been noticed in rats and mice. The most commonly reported adverse reactions of at least moderate intensity (incidence ≥10%) in adult HIV-1 clinical trials were nausea, headache, malaise and fatigue, nausea and vomiting, and dreams/sleep disorders. Serious hypersensitivity reactions have been associated with abacavir which has been strongly linked to the presence of the HLA-B*57:01 allele. This reaction manifests itself in patients within the first 6 weeks of treatment. Patients should be tested for the presence of this allele as recommended by the U.S Food and Drug Administration (FDA). </p>','WR2TIP26VS','','Abacavir','ZINC000002015928'),(65,'Diphenhydramine','diphenhydramine','Diphenhydramine is a H1 receptor antihistamine used in the treatment of seasonal allergies, and various allergic reactions including sneezing, runny nose, itchy/watery eyes, itching of nose or throat, pruritus, urticaria, insect bites/stings, and allergic rashes.','Acetadryl, Advil PM, Aleve PM, Allegra Cooling Relief Anti-itch, Banophen, Benadryl, Benadryl Itch Stopping, Benadryl-D Allergy and Sinus, Calagel, Damylin With Codeine, Dimetapp Nighttime Cold & Congestion, Diphen, Diphenhist, Diphenist, Excedrin PM Triple Action, Goody\'s PM, Legatrin PM, Motrin PM, Nytol, Nytol Quickgels, Percogesic Reformulated Jan 2011, Siladryl, Simply Sleep, Sleepinal, Sominex, Triaminic Night Time Cold & Cough, Tylenol PM, Unisom, Unisom Sleep, Vanamine, Wal-dryl, Wal-som','Diphenhydramine','<p>Diphenhydramine - perhaps known most commonly as its brand name formulation Benadryl - is a first-generation H1 receptor antihistamine that is used extensively for the treatment of seasonal allergies, insect bites and stings, and rashes <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"StatPearls [Internet]: Diphenhydramine\" href=\"#reference-L5263\">9</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Histergan (diphenhydramine hydrochloride) Tablets Patient Information\" href=\"#reference-L5266\">10</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Histergan (diphenhydramine hydrochloride) Cream Monograph\" href=\"#reference-L5269\">11</a>,<a class=\"reference-popover-link\" data-content=\"DIPHENHYDRAMINE- diphenhydramine hcl tablet, coated DailyMed FDA Label\" href=\"#reference-F3379\">17</a></sup>. However, it also has antiemetic, antitussive, hypnotic, and antiparkinson properties <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Histergan (diphenhydramine hydrochloride) Cream Monograph\" href=\"#reference-L5269\">11</a>,<a class=\"reference-popover-link\" data-content=\"Diphenhydramine Hydrochloride Injection, USP FDA Label\" href=\"#reference-F3352\">16</a></sup>. As histamine receptors exist both peripherally and in the central nervous system, diphenhydramine has been shown to cause sedation due to its competitive antagonism of histamine H1 receptors within the central nervous system <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"StatPearls [Internet]: Diphenhydramine\" href=\"#reference-L5263\">9</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Histergan (diphenhydramine hydrochloride) Tablets Patient Information\" href=\"#reference-L5266\">10</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Histergan (diphenhydramine hydrochloride) Cream Monograph\" href=\"#reference-L5269\">11</a>,<a class=\"reference-popover-link\" data-content=\"DIPHENHYDRAMINE- diphenhydramine hcl tablet, coated DailyMed FDA Label\" href=\"#reference-F3379\">17</a>,<a class=\"reference-popover-link\" data-content=\"Flake ZA, Scalley RD, Bailey AG: Practical selection of antiemetics. Am Fam Physician. 2004 Mar 1;69(5):1169-74. (PubMed ID 15023018)\" href=\"#reference-A174541\">5</a></sup>. While its use in allergy therapy can sometimes fall out of favor due to its sedative effect, diphenhydramine has been repurposed for use within many non-prescription over-the-counter sleep aids and cough-and-cold medications that have been marketed for \"night time\" use <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"StatPearls [Internet]: Diphenhydramine\" href=\"#reference-L5263\">9</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Boots Sleepeaze (diphenhydramine hydrochloride) 50mg Tablets Monograph\" href=\"#reference-L5281\">12</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">13</a></sup>. </p><p>Diphenhydramine is also used in combination with <a href=\"https://go.drugbank.com/drugs/DB14132\">8-chlorotheophylline</a> as the anti-nausea drug <a href=\"https://go.drugbank.com/drugs/DB00985\">Dimenhydrinate</a> where it is utilized primarily for its antagonism of H1 histamine receptors within the vestibular system <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Jaju BP, Wang SC: Effects of diphenhydramine and dimenhydrinate on vestibular neuronal activity of cat: a search for the locus of their antimotion sickness action. J Pharmacol Exp Ther. 1971 Mar;176(3):718-24. (PubMed ID 4329456)\" href=\"#reference-A1540\">4</a></sup>.</p><p>Diphenhydramine has also been shown to be implicated in a number of neurotransmitter systems that affect behaviour including dopamine, norepinephrine, serotonin, acetylcholine, and opioid <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Halpert AG, Olmstead MC, Beninger RJ: Mechanisms and abuse liability of the anti-histamine dimenhydrinate. Neurosci Biobehav Rev. 2002 Jan;26(1):61-7. (PubMed ID 11835984)\" href=\"#reference-A1539\">3</a></sup>. As a result, diphenhydramine is being investigated for its anxiolytic and anti-depressant properties.</p>','C17H21NO','DB01075','Approved, Investigational','Small Molecule','Average: 255.3547 Monoisotopic: 255.162314299 ',' , D04AA — Antihistamines for topical use , D04A — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC. , D04 — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC. , D — DERMATOLOGICALS , R06AA — Aminoalkyl ethers , R06A — ANTIHISTAMINES FOR SYSTEMIC USE , R06 — ANTIHISTAMINES FOR SYSTEMIC USE , R — RESPIRATORY SYSTEM , D04AA — Antihistamines for topical use , D04A — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC. , D04 — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC. , D — DERMATOLOGICALS , R06AA — Aminoalkyl ethers , R06A — ANTIHISTAMINES FOR SYSTEMIC USE , R06 — ANTIHISTAMINES FOR SYSTEMIC USE , R — RESPIRATORY SYSTEM','<p>Diphenhydramine is quickly absorbed after oral administration with maximum activity occurring in approximately one hour <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. (PubMed ID 2866055)\" href=\"#reference-A644\">6</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">13</a></sup>. The oral bioavailability of diphenhydramine has been documented in the range of 40% to 60%, and peak plasma concentration occurs about 2 to 3 hours after administration <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. (PubMed ID 2866055)\" href=\"#reference-A644\">6</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">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=\"Aromatic ethers with the general formula ROCR\' (R = alkyl, aryl; R\'=benzene).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002542\" rel=\"noopener\" target=\"_blank\">Benzylethers</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 the dialkyl ether functional group, with the formula ROR\', where R and R\' are alkyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001167\" rel=\"noopener\" target=\"_blank\">Dialkyl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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>','Not Available','Not Available','50017674','58-73-1','4636','CHEMBL657','2989','<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 diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"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 diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000369\" rel=\"noopener\" target=\"_blank\">Diphenylmethanes</a></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 diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000369\" rel=\"noopener\" target=\"_blank\">Diphenylmethanes</a></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 ethers with the general formula ROCR\' (R = alkyl, aryl; R\'=benzene).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002542\" rel=\"noopener\" target=\"_blank\">Benzylethers</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 the dialkyl ether functional group, with the formula ROR\', where R and R\' are alkyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001167\" rel=\"noopener\" target=\"_blank\">Dialkyl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic homomonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzylether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dialkyl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Diphenylmethane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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 homomonocyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">tertiary amino compound, ether (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4636\" rel=\"noopener\" target=\"_blank\">CHEBI:4636</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-10890\" rel=\"noopener\" target=\"_blank\">CPD-10890</a>) </span></span></dd></dl>','Benzene and substituted derivatives','<p>Values for plasma clearance of a 50 mg oral dose of diphenhydramine has been documented as lying in the range of 600-1300 ml/min <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Benylin Chesty Coughs UK MHRA Product Information\" href=\"#reference-F3394\">18</a></sup>.</p>','This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.','Diphenylmethanes','<li>Avoid alcohol.</li>\n<li>Take before a meal. Take 30 minutes before a meal or 30 minutes before departure for motion sickness.</li>','Drugs.com Drug Page',' , Agents producing tachycardia , Amines , Aminoalkyl Ethers , Anesthetics , Anesthetics, Local , Anti-Allergic Agents , Anticholinergic Agents , Antiemetics , Antihistamines for Systemic Use , Antihistamines for Topical Use , Antipruritics, Incl. Antihistamines, Anesthetics, Etc. , Benzene Derivatives , Benzhydryl Compounds , Central Nervous System Agents , Central Nervous System Depressants , Cytochrome P-450 CYP2C19 Substrates , Cytochrome P-450 CYP2C9 Substrates , Cytochrome P-450 CYP2D6 Inhibitors , Cytochrome P-450 CYP2D6 Inhibitors (strength unknown) , Cytochrome P-450 CYP2D6 Substrates , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Dermatologicals , Drugs causing inadvertant photosensitivity , Ethanolamine Derivatives , Ethylamines , First Generation Antihistamines , Gastrointestinal Agents , Histamine Agents , Histamine Antagonists , Histamine H1 Antagonists , Hypnotics and Sedatives , Muscarinic Antagonists , OCT2 Inhibitors , Photosensitizing Agents , Potential QTc-Prolonging Agents , QTc Prolonging Agents , Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome , Sleep Aids, Pharmaceutical','<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>161-162</td><td>Martin, H., Hafliger, F.,Gatzi, K.and Grob, A.; U.S. Patent 2,397,799; April 2,1946; assigned to J.R. Geigy AG, Switzerland.\nRieveschl, G. Jr.; U.S. Patent 2,421,714; June 3,1947; assigned to Parke, Davis &amp; Co. Rieveschl, G. Jr.; U.S. Patent 2,427,878; September 23,1947; assigned to Parke, Davis &amp;\nCompany.</td></tr><tr><td>boiling point (°C)</td><td>150-165 °C at 2.00E+00 mm Hg</td><td>PhysProp</td></tr><tr><td>water solubility</td><td>3060 mg/L (at 37 °C)</td><td>BEILSTEIN</td></tr><tr><td>logP</td><td>3.27</td><td>HANSCH,C ET AL. (1995)</td></tr><tr><td>pKa</td><td>8.98</td><td>SANGSTER (1994)</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">tertiary amino compound, ether (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4636\" rel=\"noopener\" target=\"_blank\">CHEBI:4636</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-10890\" rel=\"noopener\" target=\"_blank\">CPD-10890</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/HMDB0001927\" rel=\"noopener\" target=\"_blank\">HMDB0001927</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:D00300\" rel=\"noopener\" target=\"_blank\">D00300</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:C06960\" rel=\"noopener\" target=\"_blank\">C06960</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=3100\" rel=\"noopener\" target=\"_blank\">3100</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=46505484\" rel=\"noopener\" target=\"_blank\">46505484</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.2989.html\" rel=\"noopener\" target=\"_blank\">2989</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=50017674\" rel=\"noopener\" target=\"_blank\">50017674</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=3498\" rel=\"noopener\" target=\"_blank\">3498</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=4636\" rel=\"noopener\" target=\"_blank\">4636</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/CHEMBL657\" rel=\"noopener\" target=\"_blank\">CHEMBL657</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/ZINC000000020244\" rel=\"noopener\" target=\"_blank\">ZINC000000020244</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=DAP000490\" rel=\"noopener\" target=\"_blank\">DAP000490</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/PA449349\" rel=\"noopener\" target=\"_blank\">PA449349</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=1224\" 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/2PM\" rel=\"noopener\" target=\"_blank\">2PM</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/dihydram.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/diphenhydramine.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/Diphenhydramine\" rel=\"noopener\" target=\"_blank\">Diphenhydramine</a></dd></dl>','<li>Avoid alcohol.</li>\n<li>Take before a meal. Take 30 minutes before a meal or 30 minutes before departure for motion sickness.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A1700\">Raphael GD, Angello JT, Wu MM, Druce HM: Efficacy of diphenhydramine vs desloratadine and placebo in patients with moderate-to-severe seasonal allergic rhinitis. Ann Allergy Asthma Immunol. 2006 Apr;96(4):606-14. [<a href=\"/articles/A1700\" target=\"_blank\">Article</a>] </li><li id=\"reference-A18428\">Abdi A, Rose E, Levine M: Diphenhydramine overdose with intraventricular conduction delay treated with hypertonic sodium bicarbonate and i.v. lipid emulsion. West J Emerg Med. 2014 Nov;15(7):855-8. doi: 10.5811/westjem.2014.8.23407. Epub 2014 Sep 19. [<a href=\"/articles/A18428\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1539\">Halpert AG, Olmstead MC, Beninger RJ: Mechanisms and abuse liability of the anti-histamine dimenhydrinate. Neurosci Biobehav Rev. 2002 Jan;26(1):61-7. [<a href=\"/articles/A1539\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1540\">Jaju BP, Wang SC: Effects of diphenhydramine and dimenhydrinate on vestibular neuronal activity of cat: a search for the locus of their antimotion sickness action. J Pharmacol Exp Ther. 1971 Mar;176(3):718-24. [<a href=\"/articles/A1540\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174541\">Flake ZA, Scalley RD, Bailey AG: Practical selection of antiemetics. Am Fam Physician. 2004 Mar 1;69(5):1169-74. [<a href=\"/articles/A174541\" target=\"_blank\">Article</a>] </li><li id=\"reference-A644\">Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [<a href=\"/articles/A644\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174574\">Akutsu T, Kobayashi K, Sakurada K, Ikegaya H, Furihata T, Chiba K: Identification of human cytochrome p450 isozymes involved in diphenhydramine N-demethylation. Drug Metab Dispos. 2007 Jan;35(1):72-8. doi: 10.1124/dmd.106.012088. Epub 2006 Oct 4. [<a href=\"/articles/A174574\" target=\"_blank\">Article</a>] </li><li id=\"reference-A174577\">Rodrigues WC, Castro C, Catbagan P, Moore C, Wang G: Immunoassay screening of diphenhydramine (Benadryl(R)) in urine and blood using a newly developed assay. J Anal Toxicol. 2012 Mar;36(2):123-9. doi: 10.1093/jat/bkr015. [<a href=\"/articles/A174577\" target=\"_blank\">Article</a>] </li><li id=\"reference-L5263\">StatPearls [Internet]: Diphenhydramine [<a href=\"https://www.ncbi.nlm.nih.gov/books/NBK526010/#article-20535.s1\" target=\"_blank\">Link</a>] </li><li id=\"reference-L5266\">Electronic Medicines Compendium: Histergan (diphenhydramine hydrochloride) Tablets Patient Information [<a href=\"https://www.medicines.org.uk/emc/product/8071/pil\" target=\"_blank\">Link</a>] </li><li id=\"reference-L5269\">Electronic Medicines Compendium: Histergan (diphenhydramine hydrochloride) Cream Monograph [<a href=\"https://www.medicines.org.uk/emc/product/2303/smpc\" target=\"_blank\">Link</a>] </li><li id=\"reference-L5281\">Electronic Medicines Compendium: Boots Sleepeaze (diphenhydramine hydrochloride) 50mg Tablets Monograph [<a href=\"https://www.medicines.org.uk/emc/product/6568/smpc\" target=\"_blank\">Link</a>] </li><li id=\"reference-L5287\">Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph [<a href=\"https://www.medicines.org.uk/emc/product/340/smpc\" target=\"_blank\">Link</a>] </li><li id=\"reference-L15716\">DailyMed: Ibuprofen PM (ibuprofen/diphenhydramine) product information [<a href=\"https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9c5c1f48-d285-4faa-96d0-b04f435c9c5c\" target=\"_blank\">Link</a>] </li><li id=\"reference-L26506\">BASG Product Information: Multodrin (dexamethasone/diphenhydramine hydrochloride) topical ointment [<a href=\"https://aspregister.basg.gv.at/document/servlet?action=show&amp;zulnr=13232&amp;type=DOTC_FACH_INFO\" target=\"_blank\">Link</a>] </li><li id=\"reference-F3352\">Diphenhydramine Hydrochloride Injection, USP FDA Label [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/003/352/original/091526lbl.pdf?1549410675\" target=\"_blank\">File</a>] </li><li id=\"reference-F3379\">DIPHENHYDRAMINE- diphenhydramine hcl tablet, coated DailyMed FDA Label [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/003/379/original/20180620_70a584ab-9e24-404a-aad7-f9a05c377248.pdf?1549478576\" target=\"_blank\">File</a>] </li><li id=\"reference-F3394\">Benylin Chesty Coughs UK MHRA Product Information [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/003/394/original/con1478238522475.pdf?1549496792\" target=\"_blank\">File</a>] </li></ol>','<p>The elimination half-life ranges from 2.4-9.3 hours in healthy adults <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Benylin Chesty Coughs UK MHRA Product Information\" href=\"#reference-F3394\">18</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">13</a></sup>. The terminal elimination half-life is prolonged in liver cirrhosis <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">13</a></sup>.</p>','HMDB0001927','[2-(diphenylmethoxy)ethyl]dimethylamine','InChI=1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3','ZZVUWRFHKOJYTH-UHFFFAOYSA-N','<p>Diphenhydramine is a first-generation histamine H1 receptor antagonist (H1 antihistamine) that is widely available as a non-prescription, over-the-counter (OTC) medication. As an OTC medication, diphenhydramine is typically formulated as tablets and creams indicated for use in treating sneezing, runny nose, itchy/watery eyes, itching of nose or throat, insomnia, pruritis, urticaria, insect bites/stings, allergic rashes, and nausea <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"StatPearls [Internet]: Diphenhydramine\" href=\"#reference-L5263\">9</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Histergan (diphenhydramine hydrochloride) Tablets Patient Information\" href=\"#reference-L5266\">10</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Histergan (diphenhydramine hydrochloride) Cream Monograph\" href=\"#reference-L5269\">11</a>,<a class=\"reference-popover-link\" data-content=\"DIPHENHYDRAMINE- diphenhydramine hcl tablet, coated DailyMed FDA Label\" href=\"#reference-F3379\">17</a>,<a class=\"reference-popover-link\" data-content=\"Flake ZA, Scalley RD, Bailey AG: Practical selection of antiemetics. Am Fam Physician. 2004 Mar 1;69(5):1169-74. (PubMed ID 15023018)\" href=\"#reference-A174541\">5</a></sup>.</p><p>Additionally, when the use of oral diphenhydramine is impractical, there are also prescription-only formulations such as diphenhydramine injection products that are effective in adults and pediatric patients (other than premature infants and neonates) for:\ni) the amelioration of allergic reactions to blood or plasma, in anaphylaxis as an adjunct to epinephrine and other standard measures after acute allergic reaction symptoms have been controlled, and for other uncomplicated allergic conditions of the immediate type when oral therapy is impossible or contraindicated <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Diphenhydramine Hydrochloride Injection, USP FDA Label\" href=\"#reference-F3352\">16</a></sup>;\nii) the active treatment of motion sickness <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Diphenhydramine Hydrochloride Injection, USP FDA Label\" href=\"#reference-F3352\">16</a></sup>; and\niii) use in parkinsonism when oral therapy is impossible or contraindicated, as follows: parkinsonism in the elderly who are unable to tolerate more potent agents; mild cases of parkinsonism in other age groups, and in other cases of parkinsonism in combination with centrally acting anticholinergic agents <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Diphenhydramine Hydrochloride Injection, USP FDA Label\" href=\"#reference-F3352\">16</a></sup>.</p>','C06960','D00300','Organic compounds','<p>Diphenhydramine undergoes rapid and extensive first-pass metabolism <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Benylin Chesty Coughs UK MHRA Product Information\" href=\"#reference-F3394\">18</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">13</a>,<a class=\"reference-popover-link\" data-content=\"Rodrigues WC, Castro C, Catbagan P, Moore C, Wang G: Immunoassay screening of diphenhydramine (Benadryl(R)) in urine and blood using a newly developed assay. J Anal Toxicol. 2012 Mar;36(2):123-9. doi: 10.1093/jat/bkr015. (PubMed ID 22337782)\" href=\"#reference-A174577\">8</a></sup>. In particular, two successive N-demethylations occur wherein diphenhydramine is demethylated to N-desmethyldiphenhydramine (the N-desmethyl metabolite) and then this metabolite is itself demethylated to N,N-didesmethyldiphenhydramine (the N,N-didesmethyl metabolite) <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Benylin Chesty Coughs UK MHRA Product Information\" href=\"#reference-F3394\">18</a>,<a class=\"reference-popover-link\" data-content=\"Rodrigues WC, Castro C, Catbagan P, Moore C, Wang G: Immunoassay screening of diphenhydramine (Benadryl(R)) in urine and blood using a newly developed assay. J Anal Toxicol. 2012 Mar;36(2):123-9. doi: 10.1093/jat/bkr015. (PubMed ID 22337782)\" href=\"#reference-A174577\">8</a></sup>. Subsequently, acetyl metabolites like N-acetyl-N-desmethyldiphenhydramine are generated via the amine moiety of the N,N-didesmethyl metabolite <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Rodrigues WC, Castro C, Catbagan P, Moore C, Wang G: Immunoassay screening of diphenhydramine (Benadryl(R)) in urine and blood using a newly developed assay. J Anal Toxicol. 2012 Mar;36(2):123-9. doi: 10.1093/jat/bkr015. (PubMed ID 22337782)\" href=\"#reference-A174577\">8</a></sup>. Additionally, the N,N-didesmethyl metabolite also undergoes some oxidation to generate the diphenylmethoxyacetic acid metabolite as well <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Benylin Chesty Coughs UK MHRA Product Information\" href=\"#reference-F3394\">18</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">13</a>,<a class=\"reference-popover-link\" data-content=\"Rodrigues WC, Castro C, Catbagan P, Moore C, Wang G: Immunoassay screening of diphenhydramine (Benadryl(R)) in urine and blood using a newly developed assay. J Anal Toxicol. 2012 Mar;36(2):123-9. doi: 10.1093/jat/bkr015. (PubMed ID 22337782)\" href=\"#reference-A174577\">8</a></sup>. The remaining percentage of a dose of administered diphenhydramine is excreted unchanged <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Benylin Chesty Coughs UK MHRA Product Information\" href=\"#reference-F3394\">18</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">13</a>,<a class=\"reference-popover-link\" data-content=\"Rodrigues WC, Castro C, Catbagan P, Moore C, Wang G: Immunoassay screening of diphenhydramine (Benadryl(R)) in urine and blood using a newly developed assay. J Anal Toxicol. 2012 Mar;36(2):123-9. doi: 10.1093/jat/bkr015. (PubMed ID 22337782)\" href=\"#reference-A174577\">8</a></sup>. The metabolites are further conjugated with glycine and glutamine and excreted in urine <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">13</a></sup>.</p><p>Moreover, studies have determined that a variety of cytochrome P450 isoenzymes are involved in the N-demethylation that characterizes the primary metabolic pathway of diphenhydramine, including CYP2D6, CYP1A2, CYP2C9, and CYP2C19 <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Akutsu T, Kobayashi K, Sakurada K, Ikegaya H, Furihata T, Chiba K: Identification of human cytochrome p450 isozymes involved in diphenhydramine N-demethylation. Drug Metab Dispos. 2007 Jan;35(1):72-8. doi: 10.1124/dmd.106.012088. Epub 2006 Oct 4. (PubMed ID 17020955)\" href=\"#reference-A174574\">7</a></sup>. In particular, CYP2D6 demonstrates higher affinity catalysis with the diphenhydramine substrate than the other isoenzymes identified <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Akutsu T, Kobayashi K, Sakurada K, Ikegaya H, Furihata T, Chiba K: Identification of human cytochrome p450 isozymes involved in diphenhydramine N-demethylation. Drug Metab Dispos. 2007 Jan;35(1):72-8. doi: 10.1124/dmd.106.012088. Epub 2006 Oct 4. (PubMed ID 17020955)\" href=\"#reference-A174574\">7</a></sup>. Consequently, inducers or inhibitors of these such CYP enzymes may potentially affect the serum concentration and incidence and/or severity of adverse effects associated with exposure to diphenhydramine <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Akutsu T, Kobayashi K, Sakurada K, Ikegaya H, Furihata T, Chiba K: Identification of human cytochrome p450 isozymes involved in diphenhydramine N-demethylation. Drug Metab Dispos. 2007 Jan;35(1):72-8. doi: 10.1124/dmd.106.012088. Epub 2006 Oct 4. (PubMed ID 17020955)\" href=\"#reference-A174574\">7</a></sup>.</p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic homomonocyclic compounds','2PM','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0058785?highlight[compounds][]=DB01075&amp;highlight[proteins][]=DB01075\">Diphenhydramine H1-Antihistamine Action</a></td><td>Drug action</td></tr></tbody>','PA449349','<p>Some prescribing information records the protein binding of diphenhydramine as approximately 78% <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Benylin Chesty Coughs UK MHRA Product Information\" href=\"#reference-F3394\">18</a></sup> while others have suggested the medication is about 80 to 85% <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">13</a></sup> bound to plasma proteins.</p>','3100','46505484','<p>The metabolites of diphenhydramine are conjugated with glycine and glutamine and excreted in urine <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Boots Sleepeaze (diphenhydramine hydrochloride) 50mg Tablets Monograph\" href=\"#reference-L5281\">12</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">13</a></sup>. Only about 1% of a single dose is excreted unchanged in urine <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Boots Sleepeaze (diphenhydramine hydrochloride) 50mg Tablets Monograph\" href=\"#reference-L5281\">12</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">13</a></sup>. The medication is ultimately eliminated by the kidneys slowly, mainly as inactive metabolites <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Boots Sleepeaze (diphenhydramine hydrochloride) 50mg Tablets Monograph\" href=\"#reference-L5281\">12</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">13</a></sup>.</p>','RxList Drug Page','3498','CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1','Solid','Diphenylmethanes','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic homomonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzylether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dialkyl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Diphenylmethane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span></span></span>','Benzenoids','<span class=\"citations\"><p>Alison B. Lukacsko, Joseph J. Piala, \"Effect of a combination of a terbutaline, diphenhydramine and ranitidine composition on gastrointestinal injury produced by nonsteroidal anti-inflammatory compositions.\" U.S. Patent US5260333, issued December, 1983.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=5260333&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5260333</a>','DAP000490','<p>Overdose is expected to result in effects similar to the adverse effects that are ordinarily associated with the use of diphenhydramine, including drowsiness, hyperpyrexia, and anticholinergic effects, among others <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Histergan (diphenhydramine hydrochloride) Tablets Patient Information\" href=\"#reference-L5266\">10</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Histergan (diphenhydramine hydrochloride) Cream Monograph\" href=\"#reference-L5269\">11</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Boots Sleepeaze (diphenhydramine hydrochloride) 50mg Tablets Monograph\" href=\"#reference-L5281\">12</a>,<a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">13</a>,<a class=\"reference-popover-link\" data-content=\"Benylin Chesty Coughs UK MHRA Product Information\" href=\"#reference-F3394\">18</a></sup>. Additional symptoms during overdose may include mydriasis, fever, flushing, agitation, tremor, dystonic reactions, hallucinations and ECG changes <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">13</a></sup>. Large overdose may cause rhabdomyolysis, convulsions, delirium, toxic psychosis, arrhythmias, coma and cardiovascular collapse <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">13</a></sup>. Moreover, with higher doses, and particularly in children, symptoms of CNS excitation including hallucinations and convulsions may appear; with massive doses, coma or cardiovascular collapse may follow <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Benylin Chesty Coughs UK MHRA Product Information\" href=\"#reference-F3394\">18</a></sup>.</p><p>Although diphenhydramine has been in widespread use for many years without ill consequence, it is known to cross the placenta and has been detected in breast milk <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Benylin Chesty Coughs UK MHRA Product Information\" href=\"#reference-F3394\">18</a></sup>. This medication should therefore only be used when the potential benefit of treatment to the mother exceeds any possible hazards to the developing fetus or suckling infant <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Benylin Chesty Coughs UK MHRA Product Information\" href=\"#reference-F3394\">18</a></sup>.</p><p>Pharmacokinetic studies indicate no major differences in the distribution or elimination of diphenhydramine compared to younger adults <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Benylin Chesty Coughs UK MHRA Product Information\" href=\"#reference-F3394\">18</a></sup>. Nevertheless, diphenhydramine should be used with caution in the elderly, who are more likely to experience adverse effects <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">13</a></sup>. Avoid use in elderly patients with confusion <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph\" href=\"#reference-L5287\">13</a></sup>.</p><p>The results of a review on the use of diphenhydramine in renal failure suggest that in moderate to severe renal failure, the dose interval should be extended by a period dependent on Glomerular filtration rate (GFR) <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Benylin Chesty Coughs UK MHRA Product Information\" href=\"#reference-F3394\">18</a></sup>.</p><p>After intravenous administration of 0.8 mg/kg diphenhydramine, a prolonged half-life was noted in patients with chronic liver disease which correlated with the severity of the disease <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Benylin Chesty Coughs UK MHRA Product Information\" href=\"#reference-F3394\">18</a></sup>. However, the mean plasma clearance and apparent volume of distribution were not significantly affected <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Benylin Chesty Coughs UK MHRA Product Information\" href=\"#reference-F3394\">18</a></sup>.</p><p>LD<sub>50</sub>=500 mg/kg (orally in rats). Considerable overdosage can lead to myocardial infarction (heart attack), serious ventricular dysrhythmias, coma and death.</p>','8GTS82S83M','<p>Diphenhydramine is widely distributed throughout the body, including the CNS <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Benylin Chesty Coughs UK MHRA Product Information\" href=\"#reference-F3394\">18</a></sup>. Following a 50 mg oral dose of diphenhydramine, the volume of distribution is in the range of 3.3 - 6.8 l/kg <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Benylin Chesty Coughs UK MHRA Product Information\" href=\"#reference-F3394\">18</a></sup>.</p>','Diphenhydramine','ZINC000000020244'),(66,'Nifedipine','nifedipine','Nifedipine is a dihydropyridine calcium channel blocker indicated for the management of several subtypes of angina pectoris, and hypertension.','Adalat, Afeditab CR, Nifediac, Nifedical, Procardia','Nifedipine','<p>Nifedipine, or BAY a 1040, is a first generation dihydropyridine L-type calcium channel blocker, similar to <a href=\"https://go.drugbank.com/drugs/DB00622\">nicardipine</a>.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Chung M, Reitberg DP, Gaffney M, Singleton W: Clinical pharmacokinetics of nifedipine gastrointestinal therapeutic system. A controlled-release formulation of nifedipine. Am J Med. 1987 Dec 21;83(6B):10-4. doi: 10.1016/0002-9343(87)90630-9. (PubMed ID 3503594)\" href=\"#reference-A190210\">3</a>,<a class=\"reference-popover-link\" data-content=\"Wang AL, Iadecola C, Wang G: New generations of dihydropyridines for treatment of hypertension. J Geriatr Cardiol. 2017 Jan;14(1):67-72. doi: 10.11909/j.issn.1671-5411.2017.01.006. (PubMed ID 28270844)\" href=\"#reference-A190273\">10</a>,<a class=\"reference-popover-link\" data-content=\"Godfraind T: Discovery and Development of Calcium Channel Blockers. Front Pharmacol. 2017 May 29;8:286. doi: 10.3389/fphar.2017.00286. eCollection 2017. (PubMed ID 28611661)\" href=\"#reference-A175390\">11</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Procardia Nifedipine Oral Capsules\" href=\"#reference-L11383\">13</a></sup> Nifedipine was developed by Bayer and first described in the literature, along with other dihydropyridines, in 1972.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Godfraind T: Discovery and Development of Calcium Channel Blockers. Front Pharmacol. 2017 May 29;8:286. doi: 10.3389/fphar.2017.00286. eCollection 2017. (PubMed ID 28611661)\" href=\"#reference-A175390\">11</a>,<a class=\"reference-popover-link\" data-content=\"Vater W, Kroneberg G, Hoffmeister F, Saller H, Meng K, Oberdorf A, Puls W, Schlossmann K, Stoepel K: [Pharmacology of 4-(2\'-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester (Nifedipine, BAY a 1040)]. Arzneimittelforschung. 1972 Jan;22(1):1-14. (PubMed ID 4622472)\" href=\"#reference-A190276\">12</a></sup> Since nifedipine\'s development, second and third generation dihydropyridines have been developed with slower onsets and longer durations of action.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Wang AL, Iadecola C, Wang G: New generations of dihydropyridines for treatment of hypertension. J Geriatr Cardiol. 2017 Jan;14(1):67-72. doi: 10.11909/j.issn.1671-5411.2017.01.006. (PubMed ID 28270844)\" href=\"#reference-A190273\">10</a></sup> The most popular of the third generation dihydropyridines is <a href=\"https://go.drugbank.com/drugs/DB00381\">amlodipine</a>.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Wang AL, Iadecola C, Wang G: New generations of dihydropyridines for treatment of hypertension. J Geriatr Cardiol. 2017 Jan;14(1):67-72. doi: 10.11909/j.issn.1671-5411.2017.01.006. (PubMed ID 28270844)\" href=\"#reference-A190273\">10</a></sup></p><p>Nifedipine was granted FDA approval on 31 December 1981.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Procardia Nifedipine Oral Capsules\" href=\"#reference-L11383\">13</a></sup></p>','C17H18N2O6','DB01115','Approved','Small Molecule','Average: 346.3346 Monoisotopic: 346.116486318 ',' , C08CA — Dihydropyridine derivatives , C08C — SELECTIVE CALCIUM CHANNEL BLOCKERS WITH MAINLY VASCULAR EFFECTS , C08 — CALCIUM CHANNEL BLOCKERS , C — CARDIOVASCULAR SYSTEM , C08GA — Calcium channel blockers and diuretics , C08G — CALCIUM CHANNEL BLOCKERS AND DIURETICS , C08 — CALCIUM CHANNEL BLOCKERS , C — CARDIOVASCULAR SYSTEM , C08CA — Dihydropyridine derivatives , C08C — SELECTIVE CALCIUM CHANNEL BLOCKERS WITH MAINLY VASCULAR EFFECTS , C08 — CALCIUM CHANNEL BLOCKERS , C — CARDIOVASCULAR SYSTEM , C07FB — Beta blocking agents and calcium channel blockers , C07F — BETA BLOCKING AGENTS, OTHER COMBINATIONS , C07 — BETA BLOCKING AGENTS , C — CARDIOVASCULAR SYSTEM','<p>Sublingual dosing leads to a C<sub>max</sub> of 10ng/mL, with a T<sub>max</sub> of 50min, and an AUC of 25ng*h/mL.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"van Harten J, Burggraaf K, Danhof M, van Brummelen P, Breimer DD: Negligible sublingual absorption of nifedipine. Lancet. 1987 Dec 12;2(8572):1363-5. doi: 10.1016/s0140-6736(87)91258-x. (PubMed ID 2890954)\" href=\"#reference-A190264\">9</a></sup> Oral dosing leads to a C<sub>max</sub> of 82ng/mL, with a T<sub>max</sub> of 28min, and an AUC of 152ng*h/mL.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"van Harten J, Burggraaf K, Danhof M, van Brummelen P, Breimer DD: Negligible sublingual absorption of nifedipine. Lancet. 1987 Dec 12;2(8572):1363-5. doi: 10.1016/s0140-6736(87)91258-x. (PubMed ID 2890954)\" href=\"#reference-A190264\">9</a></sup></p><p>Nifedipine is a Biopharmaceutics Classification System Class II drug, meaning it has low solubility and high intestinal permeability.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Nader AM, Quinney SK, Fadda HM, Foster DR: Effect of Gastric Fluid Volume on the In Vitro Dissolution and In Vivo Absorption of BCS Class II Drugs: a Case Study with Nifedipine. AAPS J. 2016 Jul;18(4):981-8. doi: 10.1208/s12248-016-9918-x. Epub 2016 Apr 22. (PubMed ID 27106837)\" href=\"#reference-A190261\">8</a></sup> It is almost completely absorbed in the gastrointestinal tract but has a bioavilability of 45-68%, partly due to first pass metabolism.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Chung M, Reitberg DP, Gaffney M, Singleton W: Clinical pharmacokinetics of nifedipine gastrointestinal therapeutic system. A controlled-release formulation of nifedipine. Am J Med. 1987 Dec 21;83(6B):10-4. doi: 10.1016/0002-9343(87)90630-9. (PubMed ID 3503594)\" href=\"#reference-A190210\">3</a>,<a class=\"reference-popover-link\" data-content=\"Nader AM, Quinney SK, Fadda HM, Foster DR: Effect of Gastric Fluid Volume on the In Vitro Dissolution and In Vivo Absorption of BCS Class II Drugs: a Case Study with Nifedipine. AAPS J. 2016 Jul;18(4):981-8. doi: 10.1208/s12248-016-9918-x. Epub 2016 Apr 22. (PubMed ID 27106837)\" href=\"#reference-A190261\">8</a></sup></p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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></span><span class=\"list-separator\"> / </span><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=\"Organic compounds containing exactly two carboxylic acid groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000346\" rel=\"noopener\" target=\"_blank\">Dicarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003890\" rel=\"noopener\" target=\"_blank\">Vinylogous amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"An alpha,beta-unsaturated carboxylic ester of general formula R1C(R2)=C(R3)C(=O)OR4 (R4= organyl compound) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003626\" rel=\"noopener\" target=\"_blank\">Enoate esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR\', where R=H or organyl group and R\'=methyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003416\" rel=\"noopener\" target=\"_blank\">Methyl esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, a carboxylic acid group (or a derivative thereof), and a side-chain that is specific to each amino acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000347\" rel=\"noopener\" target=\"_blank\">Amino acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic 1,3-dipolar compounds with the general structure  X#N+-Z- &lt;-&gt; X-=N+=Z &lt;-&gt; X-=N-Z+ &lt;-&gt; X-N=Z (X = C or O, Z = C, N, or O).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003633\" rel=\"noopener\" target=\"_blank\">Propargyl-type 1,3-dipolar organic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one 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 the enamine functional group with the general structure R1N(R2)CR=C(R3)R4.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000470\" rel=\"noopener\" target=\"_blank\">Enamines</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002228\" rel=\"noopener\" target=\"_blank\">Dialkylamines</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 compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span 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></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>','Not Available','Not Available','50101817','21829-25-4','7565','CHEMBL193','4330','<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 dihydropyridinecarboxylic acids and derivatives. These are compounds containing a dihydropyridine moiety bearing a carboxylic acid group.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a ring with least one carbon atom and one non-carbon atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000002\" rel=\"noopener\" target=\"_blank\">Organoheterocyclic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"class\">Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000089\" rel=\"noopener\" target=\"_blank\">Pyridines and derivatives</a></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 hydrogenated pyridine ring (i.e. containing less than the maximum number of double bonds.).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002224\" rel=\"noopener\" target=\"_blank\">Hydropyridines</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 dihydropyridine moiety bearing a carboxylic acid group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001562\" rel=\"noopener\" target=\"_blank\">Dihydropyridinecarboxylic acids and derivatives</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a 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></span><span class=\"list-separator\"> / </span><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=\"Organic compounds containing exactly two carboxylic acid groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000346\" rel=\"noopener\" target=\"_blank\">Dicarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, which is indirectly attached to a carbonyl via an intervening vinyl (&gt;C=C&lt;) moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003890\" rel=\"noopener\" target=\"_blank\">Vinylogous amides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"An alpha,beta-unsaturated carboxylic ester of general formula R1C(R2)=C(R3)C(=O)OR4 (R4= organyl compound) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003626\" rel=\"noopener\" target=\"_blank\">Enoate esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR\', where R=H or organyl group and R\'=methyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003416\" rel=\"noopener\" target=\"_blank\">Methyl esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, a carboxylic acid group (or a derivative thereof), and a side-chain that is specific to each amino acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000347\" rel=\"noopener\" target=\"_blank\">Amino acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic 1,3-dipolar compounds with the general structure  X#N+-Z- &lt;-&gt; X-=N+=Z &lt;-&gt; X-=N-Z+ &lt;-&gt; X-N=Z (X = C or O, Z = C, N, or O).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003633\" rel=\"noopener\" target=\"_blank\">Propargyl-type 1,3-dipolar organic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one 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 the enamine functional group with the general structure R1N(R2)CR=C(R3)R4.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000470\" rel=\"noopener\" target=\"_blank\">Enamines</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002228\" rel=\"noopener\" target=\"_blank\">Dialkylamines</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 compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span 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></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\">Allyl-type 1,3-dipolar organic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alpha,beta-unsaturated carboxylic ester</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\">Aromatic heteromonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">C-nitro compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carboxylic acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dicarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dihydropyridinecarboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Enamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Enoate ester</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 ester</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\">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\">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\">Propargyl-type 1,3-dipolar organic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous amide</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 23 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic heteromonocyclic compounds</dd><dt class=\"col-md-4 col-sm-5\" id=\"external-descriptors\">External Descriptors</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">dihydropyridine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7565\" rel=\"noopener\" target=\"_blank\">CHEBI:7565</a>) </span></span></dd></dl>','Pyridines and derivatives','<p>The total body clearance of nifedipine is 450-700mL/min.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Chung M, Reitberg DP, Gaffney M, Singleton W: Clinical pharmacokinetics of nifedipine gastrointestinal therapeutic system. A controlled-release formulation of nifedipine. Am J Med. 1987 Dec 21;83(6B):10-4. doi: 10.1016/0002-9343(87)90630-9. (PubMed ID 3503594)\" href=\"#reference-A190210\">3</a></sup></p>','This compound belongs to the class of organic compounds known as dihydropyridinecarboxylic acids and derivatives. These are compounds containing a dihydropyridine moiety bearing a carboxylic acid group.','Dihydropyridinecarboxylic acids and derivatives','<li>Avoid excessive or chronic alcohol consumption.</li>\n<li>Avoid grapefruit products. Grapefruit down-regulates post-translational expression of CYP3A4, the major metabolizing enzyme of nifedipine. Grapefruit, in all forms (e.g. whole fruit, juice and rind), can significantly increase serum levels of nifedipine and may cause toxicity. Avoid grapefruit products while on this medication.</li>\n<li>Avoid natural licorice.</li>\n<li>Take with or without food.</li>','Drugs.com Drug Page',' , Agents causing hyperkalemia , Antiarrhythmic agents , Antihypertensive Agents , Antihypertensive Agents Indicated for Hypertension , Beta blocking agents and calcium channel blockers , Bradycardia-Causing Agents , BSEP/ABCB11 Inhibitors , BSEP/ABCB11 Substrates , Calcium Channel Blockers , Calcium Channel Blockers (Dihydropyridine) , Calcium Channel Blockers and Diuretics , Calcium-Regulating Hormones and Agents , Cardiovascular Agents , Cytochrome P-450 CYP1A2 Inhibitors , Cytochrome P-450 CYP1A2 Inhibitors (strength unknown) , Cytochrome P-450 CYP1A2 Substrates , Cytochrome P-450 CYP2A6 Substrates , Cytochrome P-450 CYP2B6 Inducers , Cytochrome P-450 CYP2B6 Inducers (strength unknown) , Cytochrome P-450 CYP2C8 Inhibitors , Cytochrome P-450 CYP2C8 Inhibitors (strength unknown) , Cytochrome P-450 CYP2C9 Inducers , Cytochrome P-450 CYP2C9 Inducers (strength unknown) , Cytochrome P-450 CYP2C9 Inhibitors , Cytochrome P-450 CYP2C9 Inhibitors (strength unknown) , Cytochrome P-450 CYP2D6 Inhibitors , Cytochrome P-450 CYP2D6 Inhibitors (strength unknown) , Cytochrome P-450 CYP2D6 Substrates , Cytochrome P-450 CYP2E1 Inhibitors , Cytochrome P-450 CYP2E1 Inhibitors (strength unknown) , Cytochrome P-450 CYP3A Inducers , Cytochrome P-450 CYP3A Inhibitors , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Inducers , Cytochrome P-450 CYP3A4 Inducers (strength unknown) , Cytochrome P-450 CYP3A4 Inhibitors , Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A5 Substrates , Cytochrome P-450 CYP3A7 Substrates , Cytochrome P-450 Enzyme Inducers , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Dihydropyridine Derivatives , Dihydropyridines , Drugs that are Mainly Renally Excreted , Hypotensive Agents , Membrane Transport Modulators , Moderate Risk QTc-Prolonging Agents , OATP1B1/SLCO1B1 Inhibitors , P-glycoprotein inducers , P-glycoprotein inhibitors , P-glycoprotein substrates , Pyridines , QTc Prolonging Agents , Reproductive Control Agents , Selective Calcium Channel Blockers With Mainly Vascular Effects , Tocolytic Agents , Vasodilating Agents','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>172-174 °C</td><td>PhysProp</td></tr><tr><td>water solubility</td><td>Insoluble</td><td>FDA Label</td></tr><tr><td>logP</td><td>2.20</td><td>MASUMOTO,K ET AL. (1995)</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">dihydropyridine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7565\" rel=\"noopener\" target=\"_blank\">CHEBI:7565</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/HMDB0015247\" rel=\"noopener\" target=\"_blank\">HMDB0015247</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:D00437\" rel=\"noopener\" target=\"_blank\">D00437</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:C07266\" rel=\"noopener\" target=\"_blank\">C07266</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=4485\" rel=\"noopener\" target=\"_blank\">4485</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=46505103\" rel=\"noopener\" target=\"_blank\">46505103</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.4330.html\" rel=\"noopener\" target=\"_blank\">4330</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=50101817\" rel=\"noopener\" target=\"_blank\">50101817</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=7417\" rel=\"noopener\" target=\"_blank\">7417</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=7565\" rel=\"noopener\" target=\"_blank\">7565</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/CHEMBL193\" rel=\"noopener\" target=\"_blank\">CHEMBL193</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/ZINC000085205448\" rel=\"noopener\" target=\"_blank\">ZINC000085205448</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=DAP000529\" rel=\"noopener\" target=\"_blank\">DAP000529</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/PA450631\" rel=\"noopener\" target=\"_blank\">PA450631</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=2514\" 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/C5U\" rel=\"noopener\" target=\"_blank\">C5U</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/nifedip.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/nifedipine.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/Nifedipine\" rel=\"noopener\" target=\"_blank\">Nifedipine</a></dd></dl>','<li>Avoid excessive or chronic alcohol consumption.</li>\n<li>Avoid grapefruit products. Grapefruit down-regulates post-translational expression of CYP3A4, the major metabolizing enzyme of nifedipine. Grapefruit, in all forms (e.g. whole fruit, juice and rind), can significantly increase serum levels of nifedipine and may cause toxicity. Avoid grapefruit products while on this medication.</li>\n<li>Avoid natural licorice.</li>\n<li>Take with or without food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A190204\">Khan KM, Patel J, Schaefer TJ: Nifedipine . [<a href=\"/articles/A190204\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190207\">Otto J, Lesko LJ: Protein binding of nifedipine. J Pharm Pharmacol. 1986 May;38(5):399-400. doi: 10.1111/j.2042-7158.1986.tb04598.x. [<a href=\"/articles/A190207\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190210\">Chung M, Reitberg DP, Gaffney M, Singleton W: Clinical pharmacokinetics of nifedipine gastrointestinal therapeutic system. A controlled-release formulation of nifedipine. Am J Med. 1987 Dec 21;83(6B):10-4. doi: 10.1016/0002-9343(87)90630-9. [<a href=\"/articles/A190210\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190219\">Herrington DM, Insley BM, Weinmann GG: Nifedipine overdose. Am J Med. 1986 Aug;81(2):344-6. doi: 10.1016/0002-9343(86)90276-7. [<a href=\"/articles/A190219\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190222\">Whitebloom D, Fitzharris J: Nifedipine overdose. Clin Cardiol. 1988 Jul;11(7):505-6. doi: 10.1002/clc.4960110714. [<a href=\"/articles/A190222\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190228\">Raemsch KD, Sommer J: Pharmacokinetics and metabolism of nifedipine. Hypertension. 1983 Jul-Aug;5(4 Pt 2):II18-24. doi: 10.1161/01.hyp.5.4_pt_2.ii18. [<a href=\"/articles/A190228\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190225\">Waller DG, Renwick AG, Gruchy BS, George CF: The first pass metabolism of nifedipine in man. Br J Clin Pharmacol. 1984 Dec;18(6):951-4. doi: 10.1111/j.1365-2125.1984.tb02569.x. [<a href=\"/articles/A190225\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190261\">Nader AM, Quinney SK, Fadda HM, Foster DR: Effect of Gastric Fluid Volume on the In Vitro Dissolution and In Vivo Absorption of BCS Class II Drugs: a Case Study with Nifedipine. AAPS J. 2016 Jul;18(4):981-8. doi: 10.1208/s12248-016-9918-x. Epub 2016 Apr 22. [<a href=\"/articles/A190261\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190264\">van Harten J, Burggraaf K, Danhof M, van Brummelen P, Breimer DD: Negligible sublingual absorption of nifedipine. Lancet. 1987 Dec 12;2(8572):1363-5. doi: 10.1016/s0140-6736(87)91258-x. [<a href=\"/articles/A190264\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190273\">Wang AL, Iadecola C, Wang G: New generations of dihydropyridines for treatment of hypertension. J Geriatr Cardiol. 2017 Jan;14(1):67-72. doi: 10.11909/j.issn.1671-5411.2017.01.006. [<a href=\"/articles/A190273\" target=\"_blank\">Article</a>] </li><li id=\"reference-A175390\">Godfraind T: Discovery and Development of Calcium Channel Blockers. Front Pharmacol. 2017 May 29;8:286. doi: 10.3389/fphar.2017.00286. eCollection 2017. [<a href=\"/articles/A175390\" target=\"_blank\">Article</a>] </li><li id=\"reference-A190276\">Vater W, Kroneberg G, Hoffmeister F, Saller H, Meng K, Oberdorf A, Puls W, Schlossmann K, Stoepel K: [Pharmacology of 4-(2\'-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester (Nifedipine, BAY a 1040)]. Arzneimittelforschung. 1972 Jan;22(1):1-14. [<a href=\"/articles/A190276\" target=\"_blank\">Article</a>] </li><li id=\"reference-L11383\">FDA Approved Drug Products: Procardia Nifedipine Oral Capsules [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/018482s052lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L11389\">FDA Approved Drug Products: Procardia XL Nifedipine Oral Extended Release Tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019684s029lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L1245\">FDA Approved Drug Products: Adalat CC Nifedipine Oral Extended Release Tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020198s023lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L11428\">Cayman Chemical: Nifedipine MSDS [<a href=\"https://www.caymanchem.com/msdss/11106m.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>The terminal elimination half life of nifedipine is approximately 2 hours.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Chung M, Reitberg DP, Gaffney M, Singleton W: Clinical pharmacokinetics of nifedipine gastrointestinal therapeutic system. A controlled-release formulation of nifedipine. Am J Med. 1987 Dec 21;83(6B):10-4. doi: 10.1016/0002-9343(87)90630-9. (PubMed ID 3503594)\" href=\"#reference-A190210\">3</a>,<a class=\"reference-popover-link\" data-content=\"Nader AM, Quinney SK, Fadda HM, Foster DR: Effect of Gastric Fluid Volume on the In Vitro Dissolution and In Vivo Absorption of BCS Class II Drugs: a Case Study with Nifedipine. AAPS J. 2016 Jul;18(4):981-8. doi: 10.1208/s12248-016-9918-x. Epub 2016 Apr 22. (PubMed ID 27106837)\" href=\"#reference-A190261\">8</a></sup></p>','HMDB0015247','3,5-dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate','InChI=1S/C17H18N2O6/c1-9-13(16(20)24-3)15(14(10(2)18-9)17(21)25-4)11-7-5-6-8-12(11)19(22)23/h5-8,15,18H,1-4H3','HYIMSNHJOBLJNT-UHFFFAOYSA-N','<p>Nifedipine capsules are indicated to treat vasospastic angina and chronic stable angina.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Procardia Nifedipine Oral Capsules\" href=\"#reference-L11383\">13</a></sup> Extended release tablets are indicated to treat vasospastic angina, chronic stable angina, and hypertension.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Procardia XL Nifedipine Oral Extended Release Tablets\" href=\"#reference-L11389\">14</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Adalat CC Nifedipine Oral Extended Release Tablets\" href=\"#reference-L1245\">15</a></sup></p>','C07266','D00437','Organic compounds','<p>Nifedipine is predominantly metabolized by CYP3A4.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Khan KM, Patel J, Schaefer TJ: Nifedipine . (PubMed ID 30725737)\" href=\"#reference-A190204\">1</a>,<a class=\"reference-popover-link\" data-content=\"Nader AM, Quinney SK, Fadda HM, Foster DR: Effect of Gastric Fluid Volume on the In Vitro Dissolution and In Vivo Absorption of BCS Class II Drugs: a Case Study with Nifedipine. AAPS J. 2016 Jul;18(4):981-8. doi: 10.1208/s12248-016-9918-x. Epub 2016 Apr 22. (PubMed ID 27106837)\" href=\"#reference-A190261\">8</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Procardia Nifedipine Oral Capsules\" href=\"#reference-L11383\">13</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Procardia XL Nifedipine Oral Extended Release Tablets\" href=\"#reference-L11389\">14</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Adalat CC Nifedipine Oral Extended Release Tablets\" href=\"#reference-L1245\">15</a></sup> Nifedipine is predominantly metabolized to 2,6-dimethyl-4-(2-nitrophenyl)-5-methoxycarbonyl-pyridine-3-carboxylic acid, and then further metabolized to 2-hydroxymethyl-pyridine carboxylic acid.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Raemsch KD, Sommer J: Pharmacokinetics and metabolism of nifedipine. Hypertension. 1983 Jul-Aug;5(4 Pt 2):II18-24. doi: 10.1161/01.hyp.5.4_pt_2.ii18. (PubMed ID 6862586)\" href=\"#reference-A190228\">6</a></sup> Nifedipine is also minorly metabolized to dehydronifedipine.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Waller DG, Renwick AG, Gruchy BS, George CF: The first pass metabolism of nifedipine in man. Br J Clin Pharmacol. 1984 Dec;18(6):951-4. doi: 10.1111/j.1365-2125.1984.tb02569.x. (PubMed ID 6529535)\" href=\"#reference-A190225\">7</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteromonocyclic compounds','C5U','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000379?highlight[compounds][]=DB01115&amp;highlight[proteins][]=DB01115\">Nifedipine Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA450631','<p>Nifedipine is 92-98% protein bound in serum.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Procardia Nifedipine Oral Capsules\" href=\"#reference-L11383\">13</a></sup> Nifedipine is 97±12% bound in a 40g/L solution of pure albumin.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Otto J, Lesko LJ: Protein binding of nifedipine. J Pharm Pharmacol. 1986 May;38(5):399-400. doi: 10.1111/j.2042-7158.1986.tb04598.x. (PubMed ID 2872322)\" href=\"#reference-A190207\">2</a></sup> Nifedipine is 51.4±5.9% protein bound in a 50mg/100mL solution of alpha-1-acid glycoprotein, and 75.5±3.5% protein bound in a 150mg/mL solution.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Otto J, Lesko LJ: Protein binding of nifedipine. J Pharm Pharmacol. 1986 May;38(5):399-400. doi: 10.1111/j.2042-7158.1986.tb04598.x. (PubMed ID 2872322)\" href=\"#reference-A190207\">2</a></sup></p>','4485','46505103','<p>Nifedipine is 60-80% recovered in the urine as inactive water soluble metabolites, and the rest is eliminated in the feces as metabolites.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Procardia XL Nifedipine Oral Extended Release Tablets\" href=\"#reference-L11389\">14</a></sup></p>','RxList Drug Page','7417','COC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC=C1[N+]([O-])=O)C(=O)OC','Solid','Hydropyridines','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Allyl-type 1,3-dipolar organic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alpha,beta-unsaturated carboxylic ester</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\">Aromatic heteromonocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Azacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">C-nitro compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carboxylic acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dicarboxylic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dihydropyridinecarboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Enamine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Enoate ester</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 ester</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\">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\">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\">Propargyl-type 1,3-dipolar organic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Vinylogous amide</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 23 more</a>','Organoheterocyclic compounds','<span class=\"citations\"><p>Hiroitsu Kawata, Tadayoshi Ohmura, Katsuhiko Yano, Mikio Matsumura, Saburo Higuchi, Yoshiaki Soeishi, \"Nifedipine-containing solid preparation composition.\" U.S. Patent US4412986, issued November, 1976.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=4412986&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US4412986</a>','DAP000529','<p>The oral LD<sub>50</sub> in rats is 1022mg/kg and in mice is 202mg/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Cayman Chemical: Nifedipine MSDS\" href=\"#reference-L11428\">16</a></sup></p><p>Patients experiencing an overdose may present with hypotension, sinus node dysfunction, atrioventricular node dysfunction, and reflex tachycardia.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Herrington DM, Insley BM, Weinmann GG: Nifedipine overdose. Am J Med. 1986 Aug;81(2):344-6. doi: 10.1016/0002-9343(86)90276-7. (PubMed ID 3740090)\" href=\"#reference-A190219\">4</a>,<a class=\"reference-popover-link\" data-content=\"Whitebloom D, Fitzharris J: Nifedipine overdose. Clin Cardiol. 1988 Jul;11(7):505-6. doi: 10.1002/clc.4960110714. (PubMed ID 3416517)\" href=\"#reference-A190222\">5</a></sup> Overdose may be managed by monitoring cardiovascular and respiratory function; elevating extremities; and administering vasopressors, fluids, and calcium infusions.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Procardia Nifedipine Oral Capsules\" href=\"#reference-L11383\">13</a></sup></p>','I9ZF7L6G2L','<p>The steady state volume of distribution of nifedipine is 0.62-0.77L/kg and the volume of distribution of the central compartment is 0.25-0.29L/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Chung M, Reitberg DP, Gaffney M, Singleton W: Clinical pharmacokinetics of nifedipine gastrointestinal therapeutic system. A controlled-release formulation of nifedipine. Am J Med. 1987 Dec 21;83(6B):10-4. doi: 10.1016/0002-9343(87)90630-9. (PubMed ID 3503594)\" href=\"#reference-A190210\">3</a></sup></p>','Nifedipine','ZINC000085205448'),(67,'Amiodarone','amiodarone','Amiodarone is a class III antiarrhythmic indicated for the treatment of recurrent hemodynamically unstable ventricular tachycardia and recurrent ventricular fibrillation.','Nexterone, Pacerone','Amiodarone','<p>Amiodarone is a benzofuran derivative, anti-arrhythmic drug used commonly in a variety of settings.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Latini R, Tognoni G, Kates RE: Clinical pharmacokinetics of amiodarone. Clin Pharmacokinet. 1984 Mar-Apr;9(2):136-56. doi: 10.2165/00003088-198409020-00002. (PubMed ID 6370540)\" href=\"#reference-A36817\">4</a></sup> Most known for its approved indication in life-threatening ventricular arrhythmias, it is also used off-label in the outpatient and inpatient setting for atrial fibrillation. Because of its ability to cause serious toxicity and possibly death, amiodarone use should be reserved for its approved indications, according to prescribing information.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CORDARONE (amiodarone HCl) tablets\" href=\"#reference-L3561\">18</a>,<a class=\"reference-popover-link\" data-content=\"NIH StatPearls: Amiodarone\" href=\"#reference-L11265\">19</a>,<a class=\"reference-popover-link\" data-content=\"AAFP: Medication Guide for Amiodarone\" href=\"#reference-L11286\">20</a></sup></p>','C25H29I2NO3','DB01118','Approved, Investigational','Small Molecule','Average: 645.3116 Monoisotopic: 645.023680639 ',' , C01BD — Antiarrhythmics, class III , C01B — ANTIARRHYTHMICS, CLASS I AND III , C01 — CARDIAC THERAPY , C — CARDIOVASCULAR SYSTEM','<p>The Cmax of amiodarone in the plasma is achieved about 3 to 7 hours after administration.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CORDARONE (amiodarone HCl) tablets\" href=\"#reference-L3561\">18</a></sup> The general time to onset of action of amiodarone after one dose given by the intravenous route is between 1 and 30 minutes, with therapeutic effects lasting from 1-3 hours. Steady-state concentrations of amiodarone in the plasma ranges between 0.4 to 11.99 μg/ml; it is advisable that steady-state levels are generally maintained between 1.0 and 2.5 μg/ml in patients with arrhythmias.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Latini R, Tognoni G, Kates RE: Clinical pharmacokinetics of amiodarone. Clin Pharmacokinet. 1984 Mar-Apr;9(2):136-56. doi: 10.2165/00003088-198409020-00002. (PubMed ID 6370540)\" href=\"#reference-A36817\">4</a>,<a class=\"reference-popover-link\" data-content=\"Zipes DP, Prystowsky EN, Heger JJ: Amiodarone: electrophysiologic actions, pharmacokinetics and clinical effects. J Am Coll Cardiol. 1984 Apr;3(4):1059-71. doi: 10.1016/s0735-1097(84)80367-8. (PubMed ID 6368644)\" href=\"#reference-A183137\">5</a></sup></p><p>Interestingly, its onset of action may sometimes begin after 2 to 3 days, but frequently takes 1 to 3 weeks, despite the administration of higher loading doses.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CORDARONE (amiodarone HCl) tablets\" href=\"#reference-L3561\">18</a></sup> The bioavailability of amiodarone varies in clinical studies, averaging between 35 and 65%.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CORDARONE (amiodarone HCl) tablets\" href=\"#reference-L3561\">18</a></sup></p><p>Effect of food</p><p>In healthy subjects who were given a single 600-mg dose immediately after consuming a meal high in fat, the AUC of amiodarone increased by 2.3 and the Cmax by 3.8 times.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CORDARONE (amiodarone HCl) tablets\" href=\"#reference-L3561\">18</a></sup> Food also enhances absorption, reducing the Tmax by about 37%.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CORDARONE (amiodarone HCl) tablets\" href=\"#reference-L3561\">18</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 benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000301\" rel=\"noopener\" target=\"_blank\">Benzofurans</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds contaning a phenoxy group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004742\" rel=\"noopener\" target=\"_blank\">Phenoxy compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing an ether group substituted with a benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002341\" rel=\"noopener\" target=\"_blank\">Phenol ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing 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=\"Compounds containing a furan moiety which is acylated at the 3-position with an aromatic moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003218\" rel=\"noopener\" target=\"_blank\">3-aroylfurans</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 class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R\' , where R is an alkyl group and R\' is an aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000128\" rel=\"noopener\" target=\"_blank\">Alkyl aryl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing 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=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a chemical bond between a carbon atom and 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 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 5 more</a>','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsPotassium voltage-gated channel subfamily H member 2MiRP1Not AvailableKCNE2ADR Directly StudiedThe presence of polymorphisms in KCNH2 and KCNE2 may potentially be associated with increased susceptibility to long Q-T syndrome or cardiac arrhytmia when treated with amiodarone.Details','Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetailsPotassium voltage-gated channel subfamily H member 2MiRP1Not AvailableKCNE2ADR Directly StudiedThe presence of polymorphisms in KCNH2 and KCNE2 may potentially be associated with increased susceptibility to long Q-T syndrome or cardiac arrhytmia when treated with amiodarone.Details','18957','1951-25-3','2663','CHEMBL633','2072','<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 aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and 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=\"Organic compounds that contain one or more oxygen atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004603\" rel=\"noopener\" target=\"_blank\">Organic oxygen 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 bond between a carbon atom and an oxygen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000323\" rel=\"noopener\" target=\"_blank\">Organooxygen compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"sub-class\">Sub Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a 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></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=\"Aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004297\" rel=\"noopener\" target=\"_blank\">Aryl-phenylketones</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 benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000301\" rel=\"noopener\" target=\"_blank\">Benzofurans</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds contaning a phenoxy group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004742\" rel=\"noopener\" target=\"_blank\">Phenoxy compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Aromatic compounds containing an ether group substituted with a benzene ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002341\" rel=\"noopener\" target=\"_blank\">Phenol ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing 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=\"Compounds containing a furan moiety which is acylated at the 3-position with an aromatic moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003218\" rel=\"noopener\" target=\"_blank\">3-aroylfurans</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 class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R\' , where R is an alkyl group and R\' is an aryl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000128\" rel=\"noopener\" target=\"_blank\">Alkyl aryl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing 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=\"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004144\" rel=\"noopener\" target=\"_blank\">Heteroaromatic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a chemical bond between a carbon atom and 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 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 5 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">3-aroylfuran</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl halide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl iodide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl-phenylketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzofuran</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoyl</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\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Furan</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Halobenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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\">Iodobenzene</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\">Organohalogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 19 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic 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\">tertiary amino compound, organoiodine compound, 1-benzofurans, aromatic ketone (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2663\" rel=\"noopener\" target=\"_blank\">CHEBI:2663</a>) </span></span></dd></dl>','Organooxygen compounds','<p>The clearance of amiodarone after intravenous administration in patients with ventricular fibrillation and ventricular tachycardia ranged from 220 to 440 ml/hr/kg in one clinically study.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CORDARONE (amiodarone HCl) tablets\" href=\"#reference-L3561\">18</a></sup> Another study determined that the total body clearance of amiodarone varies from 0.10 to 0.77 L/min after one intravenous dose.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Latini R, Tognoni G, Kates RE: Clinical pharmacokinetics of amiodarone. Clin Pharmacokinet. 1984 Mar-Apr;9(2):136-56. doi: 10.2165/00003088-198409020-00002. (PubMed ID 6370540)\" href=\"#reference-A36817\">4</a></sup> Renal impairment does not appear to affect the clearance of amiodarone, but hepatic impairment may reduce clearance. Patients with liver cirrhosis exhibited significantly lower Cmax and mean amiodarone concentration for DEA, but not for amiodarone. Severe left ventricular dysfunction prolongs the half-life of DEA.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CORDARONE (amiodarone HCl) tablets\" href=\"#reference-L3561\">18</a></sup></p><p>A note on monitoring </p><p>No guidelines have been developed for adjusting the dose of amiodarone in renal, hepatic, or cardiac abnormalities. In patients on chronic amiodarone treatment, close clinical monitoring is advisable, especially for elderly patients and those with severe left ventricular dysfunction.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CORDARONE (amiodarone HCl) tablets\" href=\"#reference-L3561\">18</a></sup></p>','This compound belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.','Aryl-phenylketones','<li>Avoid grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum concentration of amiodarone.</li>\n<li>Avoid St. John\'s Wort. This herb induces the CYP3A4 metabolism of amiodarone. Therefore it may reduce the serum concentration and effectiveness of amiodarone.</li>\n<li>Take with or without food. The absorption is unaffected by food.</li>','Drugs.com Drug Page',' , Agents causing hyperkalemia , Agents Causing Muscle Toxicity , alpha-Galactosidase, antagonists & inhibitors , Antiarrhythmic agents , Antiarrhythmics, Class III , Benzofurans , Bradycardia-Causing Agents , BSEP/ABCB11 Inhibitors , BSEP/ABCB11 Substrates , BSEP/ABCB11 Substrates with a Narrow Therapeutic Index , Calcium Channel Blockers , Cardiac Therapy , Cardiovascular Agents , Cytochrome P-450 CYP1A2 Inhibitors , Cytochrome P-450 CYP1A2 Inhibitors (strength unknown) , Cytochrome P-450 CYP1A2 Inhibitors (strong) , Cytochrome P-450 CYP2A6 Inhibitors , Cytochrome P-450 CYP2A6 Inhibitors (moderate) , Cytochrome P-450 CYP2C19 Inhibitors , Cytochrome P-450 CYP2C19 inhibitors (strength unknown) , 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 Substrates , Cytochrome P-450 CYP2C8 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP2C9 Inhibitors , Cytochrome P-450 CYP2C9 Inhibitors (moderate) , Cytochrome P-450 CYP2D6 Inhibitors , Cytochrome P-450 CYP2D6 Inhibitors (weak) , Cytochrome P-450 CYP3A Inhibitors , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Inhibitors , Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) , Cytochrome P-450 CYP3A4 Inhibitors (strong) , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A4 Substrates (strength unknown) , Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Drugs causing inadvertant photosensitivity , Enzyme Inhibitors , Heterocyclic Compounds, Fused-Ring , Highest Risk QTc-Prolonging Agents , Hypotensive Agents , Membrane Transport Modulators , Narrow Therapeutic Index Drugs , OCT2 Inhibitors , P-glycoprotein inducers , P-glycoprotein inhibitors , Photosensitizing Agents , Potassium Channel Blockers , QTc Prolonging Agents , Sodium Channel Blockers , Vasodilating Agents','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>156</td><td>O\'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 85. Marly, SA, Belgium.</td></tr><tr><td>boiling point (°C)</td><td>100</td><td>https://auromedics.com/wordpress/wp-content/uploads/Amiodarone-Hydrochloride-Injection-USP-SDS-US-11-28-17.pdf</td></tr><tr><td>water solubility</td><td>Low</td><td>https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018972s042lbl.pdf</td></tr><tr><td>logP</td><td>7.2</td><td>https://journals.lww.com/md-journal/fulltext/2018/09140/comedication_with_interacting_drugs_predisposes.46.aspx</td></tr><tr><td>pKa</td><td> 6.56 ± 0.06</td><td>https://www.chemicalbook.com/ChemicalProductProperty_US_CB7131332.aspx</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">tertiary amino compound, organoiodine compound, 1-benzofurans, aromatic ketone (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2663\" rel=\"noopener\" target=\"_blank\">CHEBI:2663</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/HMDB0015250\" rel=\"noopener\" target=\"_blank\">HMDB0015250</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:D02910\" rel=\"noopener\" target=\"_blank\">D02910</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:C06823\" rel=\"noopener\" target=\"_blank\">C06823</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=2157\" rel=\"noopener\" target=\"_blank\">2157</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=46507387\" rel=\"noopener\" target=\"_blank\">46507387</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.2072.html\" rel=\"noopener\" target=\"_blank\">2072</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=18957\" rel=\"noopener\" target=\"_blank\">18957</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=703\" rel=\"noopener\" target=\"_blank\">703</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=2663\" rel=\"noopener\" target=\"_blank\">2663</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/CHEMBL633\" rel=\"noopener\" target=\"_blank\">CHEMBL633</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/ZINC000003830212\" rel=\"noopener\" target=\"_blank\">ZINC000003830212</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=DAP000496\" rel=\"noopener\" target=\"_blank\">DAP000496</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/PA448383\" rel=\"noopener\" target=\"_blank\">PA448383</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=2566\" 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/BBI\" rel=\"noopener\" target=\"_blank\">BBI</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/amiodarone.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/amiodarone.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/Amiodarone\" rel=\"noopener\" target=\"_blank\">Amiodarone</a></dd></dl>','<li>Avoid grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum concentration of amiodarone.</li>\n<li>Avoid St. John\'s Wort. This herb induces the CYP3A4 metabolism of amiodarone. Therefore it may reduce the serum concentration and effectiveness of amiodarone.</li>\n<li>Take with or without food. The absorption is unaffected by food.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A1899\">Singh BN, Vaughan Williams EM: The effect of amiodarone, a new anti-anginal drug, on cardiac muscle. Br J Pharmacol. 1970 Aug;39(4):657-67. [<a href=\"/articles/A1899\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1901\">Rosenbaum MB, Chiale PA, Halpern MS, Nau GJ, Przybylski J, Levi RJ, Lazzari JO, Elizari MV: Clinical efficacy of amiodarone as an antiarrhythmic agent. Am J Cardiol. 1976 Dec;38(7):934-44. [<a href=\"/articles/A1901\" target=\"_blank\">Article</a>] </li><li id=\"reference-A1903\">Rosenbaum MB, Chiale PA, Haedo A, Lazzari JO, Elizari MV: Ten years of experience with amiodarone. Am Heart J. 1983 Oct;106(4 Pt 2):957-64. [<a href=\"/articles/A1903\" target=\"_blank\">Article</a>] </li><li id=\"reference-A36817\">Latini R, Tognoni G, Kates RE: Clinical pharmacokinetics of amiodarone. Clin Pharmacokinet. 1984 Mar-Apr;9(2):136-56. doi: 10.2165/00003088-198409020-00002. [<a href=\"/articles/A36817\" target=\"_blank\">Article</a>] </li><li id=\"reference-A183137\">Zipes DP, Prystowsky EN, Heger JJ: Amiodarone: electrophysiologic actions, pharmacokinetics and clinical effects. J Am Coll Cardiol. 1984 Apr;3(4):1059-71. doi: 10.1016/s0735-1097(84)80367-8. [<a href=\"/articles/A183137\" target=\"_blank\">Article</a>] </li><li id=\"reference-A183140\">Riva E, Gerna M, Latini R, Giani P, Volpi A, Maggioni A: Pharmacokinetics of amiodarone in man. J Cardiovasc Pharmacol. 1982 Mar-Apr;4(2):264-9. doi: 10.1097/00005344-198203000-00015. [<a href=\"/articles/A183140\" target=\"_blank\">Article</a>] </li><li id=\"reference-A189666\">Freedman MD, Somberg JC: Pharmacology and pharmacokinetics of amiodarone. J Clin Pharmacol. 1991 Nov;31(11):1061-9. doi: 10.1002/j.1552-4604.1991.tb03673.x. [<a href=\"/articles/A189666\" target=\"_blank\">Article</a>] </li><li id=\"reference-A189720\">Rowland E, Krikler DM: Electrophysiological assessment of amiodarone in treatment of resistant supraventricular arrhythmias. Br Heart J. 1980 Jul;44(1):82-90. doi: 10.1136/hrt.44.1.82. [<a href=\"/articles/A189720\" target=\"_blank\">Article</a>] </li><li id=\"reference-A189723\">Soult JA, Munoz M, Lopez JD, Romero A, Santos J, Tovaruela A: Efficacy and safety of intravenous amiodarone for short-term treatment of paroxysmal supraventricular tachycardia in children. Pediatr Cardiol. 1995 Jan-Feb;16(1):16-9. doi: 10.1007/BF02310328. [<a href=\"/articles/A189723\" target=\"_blank\">Article</a>] </li><li id=\"reference-A189747\">Honjo H, Kodama I, Kamiya K, Toyama J: Block of cardiac sodium channels by amiodarone studied by using Vmax of action potential in single ventricular myocytes. Br J Pharmacol. 1991 Mar;102(3):651-6. doi: 10.1111/j.1476-5381.1991.tb12228.x. [<a href=\"/articles/A189747\" target=\"_blank\">Article</a>] </li><li id=\"reference-A182168\">Narayana SK, Woods DR, Boos CJ: Management of amiodarone-related thyroid problems. Ther Adv Endocrinol Metab. 2011 Jun;2(3):115-26. doi: 10.1177/2042018811398516. [<a href=\"/articles/A182168\" target=\"_blank\">Article</a>] </li><li id=\"reference-A189829\">Ha HR, Bigler L, Binder M, Kozlik P, Stieger B, Hesse M, Altorfer HR, Follath F: Metabolism of amiodarone (part I): identification of a new hydroxylated metabolite of amiodarone. Drug Metab Dispos. 2001 Feb;29(2):152-8. [<a href=\"/articles/A189829\" target=\"_blank\">Article</a>] </li><li id=\"reference-A189832\">Deng P, You T, Chen X, Yuan T, Huang H, Zhong D: Identification of amiodarone metabolites in human bile by ultraperformance liquid chromatography/quadrupole time-of-flight mass spectrometry. Drug Metab Dispos. 2011 Jun;39(6):1058-69. doi: 10.1124/dmd.110.037671. Epub 2011 Mar 11. [<a href=\"/articles/A189832\" target=\"_blank\">Article</a>] </li><li id=\"reference-A20227\">Szalowska E, van der Burg B, Man HY, Hendriksen PJ, Peijnenburg AA: Model steatogenic compounds (amiodarone, valproic acid, and tetracycline) alter lipid metabolism by different mechanisms in mouse liver slices. PLoS One. 2014 Jan 29;9(1):e86795. doi: 10.1371/journal.pone.0086795. eCollection 2014. [<a href=\"/articles/A20227\" target=\"_blank\">Article</a>] </li><li id=\"reference-A20650\">Song M, Kim YJ, Ryu JC: Phospholipidosis induced by PPARgamma signaling in human bronchial epithelial (BEAS-2B) cells exposed to amiodarone. Toxicol Sci. 2011 Mar;120(1):98-108. doi: 10.1093/toxsci/kfq361. Epub 2010 Dec 1. [<a href=\"/articles/A20650\" target=\"_blank\">Article</a>] </li><li id=\"reference-L2908\">Electronic Medicines Compendium Amiodarone 100mg Tablets [<a href=\"https://www.medicines.org.uk/emc/product/6019/smpc\" target=\"_blank\">Link</a>] </li><li id=\"reference-L8087\">Nexterone FDA label [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022325lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L3561\">FDA Approved Drug Products: CORDARONE (amiodarone HCl) tablets [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/018972s054lbl.pdf\" target=\"_blank\">Link</a>] </li><li id=\"reference-L11265\">NIH StatPearls: Amiodarone [<a href=\"https://www.ncbi.nlm.nih.gov/books/NBK482154/\" target=\"_blank\">Link</a>] </li><li id=\"reference-L11286\">AAFP: Medication Guide for Amiodarone [<a href=\"https://www.aafp.org/afp/2005/0401/p1434.html\" target=\"_blank\">Link</a>] </li><li id=\"reference-L6994\">FDA Approved Drug Products: NEXTERONE (amiodarone HCl) injection [<a href=\"https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/022325s013lbl.pdf\" target=\"_blank\">Link</a>] </li></ol>','<p>The terminal half-life of amiodarone varies according to the patient, but is long nonetheless, and ranges from about 9-100 days. The half-life duration varies according to different sources. <sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Rosenbaum MB, Chiale PA, Haedo A, Lazzari JO, Elizari MV: Ten years of experience with amiodarone. Am Heart J. 1983 Oct;106(4 Pt 2):957-64. (PubMed ID 6613843)\" href=\"#reference-A1903\">3</a>,<a class=\"reference-popover-link\" data-content=\"Freedman MD, Somberg JC: Pharmacology and pharmacokinetics of amiodarone. J Clin Pharmacol. 1991 Nov;31(11):1061-9. doi: 10.1002/j.1552-4604.1991.tb03673.x. (PubMed ID 1753010)\" href=\"#reference-A189666\">7</a></sup> According to the prescribing information for amiodarone, the average apparent plasma terminal elimination half-life of amiodarone is of 58 days (ranging from 15 to 142 days). The terminal half-life range was between 14 to 75 days for the active metabolite, (DEA).<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CORDARONE (amiodarone HCl) tablets\" href=\"#reference-L3561\">18</a></sup> The plasma half-life of amiodarone after one dose ranges from 3.2 to 79.7 hours, according to one source.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Latini R, Tognoni G, Kates RE: Clinical pharmacokinetics of amiodarone. Clin Pharmacokinet. 1984 Mar-Apr;9(2):136-56. doi: 10.2165/00003088-198409020-00002. (PubMed ID 6370540)\" href=\"#reference-A36817\">4</a></sup></p>','HMDB0015250','{2-[4-(2-butyl-1-benzofuran-3-carbonyl)-2,6-diiodophenoxy]ethyl}diethylamine','InChI=1S/C25H29I2NO3/c1-4-7-11-22-23(18-10-8-9-12-21(18)31-22)24(29)17-15-19(26)25(20(27)16-17)30-14-13-28(5-2)6-3/h8-10,12,15-16H,4-7,11,13-14H2,1-3H3','IYIKLHRQXLHMJQ-UHFFFAOYSA-N','<p>The FDA approved indications for amiodarone are recurrent ventricular fibrillation (VF)\nand recurrent hemodynamically unstable ventricular tachycardia (VT). The FDA emphasizes that this drug should only be given in these conditions when they are clinically documented and have not responded to normal therapeutic doses of other antiarrhythmic agents, or when other drugs are not tolerated by the patient.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CORDARONE (amiodarone HCl) tablets\" href=\"#reference-L3561\">18</a></sup></p><p>Off-label indications include atrial fibrillation and supraventricular tachycardia.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Freedman MD, Somberg JC: Pharmacology and pharmacokinetics of amiodarone. J Clin Pharmacol. 1991 Nov;31(11):1061-9. doi: 10.1002/j.1552-4604.1991.tb03673.x. (PubMed ID 1753010)\" href=\"#reference-A189666\">7</a>,<a class=\"reference-popover-link\" data-content=\"Rowland E, Krikler DM: Electrophysiological assessment of amiodarone in treatment of resistant supraventricular arrhythmias. Br Heart J. 1980 Jul;44(1):82-90. doi: 10.1136/hrt.44.1.82. (PubMed ID 7426165)\" href=\"#reference-A189720\">8</a>,<a class=\"reference-popover-link\" data-content=\"Soult JA, Munoz M, Lopez JD, Romero A, Santos J, Tovaruela A: Efficacy and safety of intravenous amiodarone for short-term treatment of paroxysmal supraventricular tachycardia in children. Pediatr Cardiol. 1995 Jan-Feb;16(1):16-9. doi: 10.1007/BF02310328. (PubMed ID 7753695)\" href=\"#reference-A189723\">9</a>,<a class=\"reference-popover-link\" data-content=\"AAFP: Medication Guide for Amiodarone\" href=\"#reference-L11286\">20</a></sup></p>','C06823','D02910','Organic compounds','<p>This drug is metabolized to the main metabolite desethylamiodarone (DEA)<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Latini R, Tognoni G, Kates RE: Clinical pharmacokinetics of amiodarone. Clin Pharmacokinet. 1984 Mar-Apr;9(2):136-56. doi: 10.2165/00003088-198409020-00002. (PubMed ID 6370540)\" href=\"#reference-A36817\">4</a></sup> by the CYP3A4 and CYP2C8 enzymes. The CYP3A4 enzyme is found in the liver and intestines.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CORDARONE (amiodarone HCl) tablets\" href=\"#reference-L3561\">18</a></sup> A hydroxyl metabolite of DEA has been identified in mammals, but its clinical significance is unknown.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Ha HR, Bigler L, Binder M, Kozlik P, Stieger B, Hesse M, Altorfer HR, Follath F: Metabolism of amiodarone (part I): identification of a new hydroxylated metabolite of amiodarone. Drug Metab Dispos. 2001 Feb;29(2):152-8. (PubMed ID 11159805)\" href=\"#reference-A189829\">12</a></sup></p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteropolycyclic compounds','BBI','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000665?highlight[compounds][]=DB01118&amp;highlight[proteins][]=DB01118\">Amiodarone Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA448383','<p>The protein binding of amiodarone is about 96%.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Latini R, Tognoni G, Kates RE: Clinical pharmacokinetics of amiodarone. Clin Pharmacokinet. 1984 Mar-Apr;9(2):136-56. doi: 10.2165/00003088-198409020-00002. (PubMed ID 6370540)\" href=\"#reference-A36817\">4</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CORDARONE (amiodarone HCl) tablets\" href=\"#reference-L3561\">18</a></sup></p>','2157','46507387','<p>Amiodarone is eliminated primarily by hepatic metabolism and biliary excretion.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Latini R, Tognoni G, Kates RE: Clinical pharmacokinetics of amiodarone. Clin Pharmacokinet. 1984 Mar-Apr;9(2):136-56. doi: 10.2165/00003088-198409020-00002. (PubMed ID 6370540)\" href=\"#reference-A36817\">4</a></sup> A small amount of desethylamiodarone (DEA) is found in the urine.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CORDARONE (amiodarone HCl) tablets\" href=\"#reference-L3561\">18</a></sup></p>','RxList Drug Page','703','CCCCC1=C(C(=O)C2=CC(I)=C(OCCN(CC)CC)C(I)=C2)C2=C(O1)C=CC=C2','Solid','Carbonyl compounds','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">3-aroylfuran</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alkyl aryl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl halide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl iodide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aryl-phenylketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzofuran</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoyl</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\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Furan</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Halobenzene</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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\">Iodobenzene</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\">Organohalogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 19 more</a>','Organic oxygen compounds','<span class=\"citations\"><p>M.J.A. Walker, P.P.S. Therapeutic Areas I: Central Nervous System, Pain, Metabolic Syndrome, Urology, Gastrointestinal and Cardiovascular: Amiodarone. Comprehensive Medicinal Chemistry II, 2007</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=3248401&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US3248401</a>','DAP000496','<p>The LD50 of oral amiodarone in mice and rats exceeds 3,000 mg/kg.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CORDARONE (amiodarone HCl) tablets\" href=\"#reference-L3561\">18</a></sup>\nAn overdose with amiodarone can have a fatal outcome due to its potential to cause arrhythmia. Signs or symptoms of an overdose may include, hypotension, shock, bradycardia, AV block, and liver toxicity. In cases of an overdose, initiate supportive treatment and, if needed, use fluids, vasopressors, or positive inotropic agents. Temporary pacing may be required for heart block. Ensure to monitor liver function regularly. Amiodarone and its main metabolite, DEA, are not removable by dialysis.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Nexterone FDA label\" href=\"#reference-L8087\">17</a></sup></p>','N3RQ532IUT','<p>In a pharmacokinetic study of 3 healthy individuals and 3 patients diagnosed with supraventricular tachycardia (SVT), the volume of distribution was found to be 9.26-17.17 L/kg in healthy volunteers and 6.88-21.05 L/kg in the SVT patients.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Riva E, Gerna M, Latini R, Giani P, Volpi A, Maggioni A: Pharmacokinetics of amiodarone in man. J Cardiovasc Pharmacol. 1982 Mar-Apr;4(2):264-9. doi: 10.1097/00005344-198203000-00015. (PubMed ID 6175810)\" href=\"#reference-A183140\">6</a></sup> Prescribing information mentions that the volume of distribution of amiodarone varies greatly, with a mean distribution of approximately 60 L/kg. It accumulates throughout the body, especially in adipose tissue<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Latini R, Tognoni G, Kates RE: Clinical pharmacokinetics of amiodarone. Clin Pharmacokinet. 1984 Mar-Apr;9(2):136-56. doi: 10.2165/00003088-198409020-00002. (PubMed ID 6370540)\" href=\"#reference-A36817\">4</a></sup> and highly vascular organs including the lung, liver, and spleen. One major metabolite of amiodarone, desethylamiodarone (DEA), is found in even higher proportions in the same tissues as amiodarone.<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: CORDARONE (amiodarone HCl) tablets\" href=\"#reference-L3561\">18</a></sup> </p>','Amiodarone','ZINC000003830212'),(68,'Desipramine','desipramine','Desipramine is a tricyclic antidepressant used in the treatment of depression.','Norpramin','Desipramine','<p>Desipramine hydrochloride is a dibenzazepine-derivative tricyclic antidepressant (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, desipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, desipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Secondary amine TCAs, such as desipramine and nortriptyline, are more potent inhibitors of norepinephrine reuptake than tertiary amine TCAs, such as amitriptyline and doxepine. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. 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. See toxicity section below for a complete listing of side effects. Desipramine exerts less anticholinergic and sedative side effects compared to tertiary amine TCAs, such as amitriptyline and clomipramine. Desipramine may be used to treat depression, neuropathic pain (unlabeled use), agitation and insomnia (unlabeled use) and attention-deficit hyperactivity disorder (unlabeled use).</p>','C18H22N2','DB01151','Approved, Investigational','Small Molecule','Average: 266.3807 Monoisotopic: 266.178298714 ',' , N06AA — Non-selective monoamine reuptake inhibitors , N06A — ANTIDEPRESSANTS , N06 — PSYCHOANALEPTICS , N — NERVOUS SYSTEM','<p>Desipramine hydrochloride is rapidly and almost completely absorbed from the gastrointestinal tract. It undergoes extensive first-pass metabolism. Peak plasma concentrations are attained 4 - 6 hours following oral administration. </p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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 dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002228\" rel=\"noopener\" target=\"_blank\">Dialkylamines</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 desipramine.DetailsCytochrome P450 2D6CYP2D6*3Not Available2549delAEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of desipramine.DetailsCytochrome P450 2D6CYP2D6*4Not AvailableA alleleEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of desipramine.DetailsCytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of desipramine.DetailsCytochrome P450 2D6CYP2D6*6Not Available1707delTEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of desipramine.DetailsCytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or 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, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or 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, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or 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, alternative drug or 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, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or 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, alternative drug or 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, alternative drug or 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 reduced or poor metabolism of desipramine.DetailsCytochrome P450 2D6CYP2D6*4Not Available3877G>AEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of desipramine.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 desipramine.DetailsCytochrome P450 2D6CYP2D6*3Not Available2549delAEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of desipramine.DetailsCytochrome P450 2D6CYP2D6*4Not AvailableA alleleEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of desipramine.DetailsCytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of desipramine.DetailsCytochrome P450 2D6CYP2D6*6Not Available1707delTEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of desipramine.DetailsCytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or 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, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or 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, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or 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, alternative drug or 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, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.DetailsCytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or 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, alternative drug or 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, alternative drug or 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 reduced or poor metabolism of desipramine.DetailsCytochrome P450 2D6CYP2D6*4Not Available3877G>AEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of desipramine.Details','35229','50-47-5','47781','CHEMBL72','2888','<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 dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002228\" rel=\"noopener\" target=\"_blank\">Dialkylamines</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\">secondary amino compound, dibenzoazepine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:47781\" rel=\"noopener\" target=\"_blank\">CHEBI:47781</a>) </span></span></dd></dl>','Benzazepines','<p><span class=\"not-available\">Not Available</span></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>Limit caffeine intake.</li>\n<li>Take with food. Food reduces irritation.</li>','Drugs.com Drug Page',' , Adrenergic Agents , 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 CYP2B6 Inhibitors , Cytochrome P-450 CYP2B6 Inhibitors (strength unknown) , 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 CYP2E1 Inhibitors (weak) , Cytochrome P-450 CYP3A Inhibitors , Cytochrome P-450 CYP3A4 Inhibitors , Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Dibenzazepines , Drugs that are Mainly Renally Excreted , Enzyme Inhibitors , Heterocyclic Compounds, Fused-Ring , Histamine Antagonists , Histamine H1 Antagonists , Membrane Transport Modulators , Muscarinic Antagonists , Narrow Therapeutic Index Drugs , Nervous System , Neurotoxic agents , Neurotransmitter Agents , Neurotransmitter Uptake Inhibitors , Non-Selective Monoamine Reuptake Inhibitors , OCT1 inhibitors , OCT2 Inhibitors , P-glycoprotein inhibitors , Potential QTc-Prolonging Agents , 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 Agents , Serotonin Modulators , Serotonin Receptor Antagonists , 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>214-218 °C</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>water solubility</td><td>58.6 mg/L (at 24 °C)</td><td>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</td></tr><tr><td>logP</td><td>4.90</td><td>HANSCH,C ET AL. (1995)</td></tr><tr><td>logS</td><td>-3.66</td><td>ADME Research, USCD</td></tr><tr><td>Caco2 permeability</td><td>-4.67</td><td>ADME Research, USCD</td></tr><tr><td>pKa</td><td>10.4</td><td>SANGSTER (1994)</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">secondary amino compound, dibenzoazepine (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:47781\" rel=\"noopener\" target=\"_blank\">CHEBI:47781</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/HMDB0015282\" rel=\"noopener\" target=\"_blank\">HMDB0015282</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:D07791\" rel=\"noopener\" target=\"_blank\">D07791</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:C06943\" rel=\"noopener\" target=\"_blank\">C06943</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=2995\" rel=\"noopener\" target=\"_blank\">2995</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=46504624\" rel=\"noopener\" target=\"_blank\">46504624</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.2888.html\" rel=\"noopener\" target=\"_blank\">2888</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=35229\" rel=\"noopener\" target=\"_blank\">35229</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=3247\" rel=\"noopener\" target=\"_blank\">3247</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=47781\" rel=\"noopener\" target=\"_blank\">47781</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/CHEMBL72\" rel=\"noopener\" target=\"_blank\">CHEMBL72</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/ZINC000001530611\" rel=\"noopener\" target=\"_blank\">ZINC000001530611</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=DAP001151\" rel=\"noopener\" target=\"_blank\">DAP001151</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/PA449233\" rel=\"noopener\" target=\"_blank\">PA449233</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=2399\" 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/DSM\" rel=\"noopener\" target=\"_blank\">DSM</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/desipram.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/desipramine.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/Desipramine\" rel=\"noopener\" target=\"_blank\">Desipramine</a></dd></dl>','<li>Avoid alcohol.</li>\n<li>Limit caffeine intake.</li>\n<li>Take with food. Food reduces irritation.</li>','<span class=\"not-available\">Not Available</span>','<p>7-60+ hours; 70% eliminated renally</p>','HMDB0015282','(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amine','InChI=1S/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3','HCYAFALTSJYZDH-UHFFFAOYSA-N','<p>For relief of symptoms in various depressive syndromes, especially endogenous depression. It has also been used to manage chronic peripheral neuropathic pain, as a second line agent for the management of anxiety disorders (e.g. panic disorder, generalized anxiety disorder), and as a second or third line agent in the ADHD management. </p>','C06943','D07791','Organic compounds','<p>Desipramine is extensively metabolized in the liver by CYP2D6 (major) and CYP1A2 (minor) to 2-hydroxydesipramine, an active metabolite. 2-hydroxydesipramine is thought to retain some amine reuptake inhibition and may possess cardiac depressant activity. The 2-hydroxylation metabolic pathway of desipramine is under genetic control.</p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteropolycyclic compounds','DSM','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000422?highlight[compounds][]=DB01151&amp;highlight[proteins][]=DB01151\">Imipramine Action Pathway</a></td><td>Drug action</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000423?highlight[compounds][]=DB01151&amp;highlight[proteins][]=DB01151\">Desipramine Action Pathway</a></td><td>Drug action</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000625?highlight[compounds][]=DB01151&amp;highlight[proteins][]=DB01151\">Imipramine Metabolism Pathway</a></td><td>Drug metabolism</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000626?highlight[compounds][]=DB01151&amp;highlight[proteins][]=DB01151\">Desipramine Metabolism Pathway</a></td><td>Drug metabolism</td></tr></tbody>','PA449233','<p>73-92% bound to plasma proteins</p>','2995','46504624','<p>Desipramine is metabolized in the liver, and approximately 70% is excreted in the urine.</p>','RxList Drug Page','3247','CNCCCN1C2=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>Biel, J.H.and Judd, C.I.; US. Patent 3,454,554; July 8,1969; assigned to Colgate Palmolive Co.</p>\n</span>','DAP001151','<p>Male mice: LD50 = 290 mg/kg, female rats: LD50 = 320 mg/kg. Antagonism of the histamine H<sub>1</sub> and α<sub>1</sub> receptors can lead to sedation and hypotension. Antimuscarinic activity confers anticholinergic side effects such as blurred vision, dry mouth, constipation and urine retention may occur. Cardiotoxicity may occur with high doses of desipramine. Cardiovascular side effects in postural hypotension, tachycardia, hypertension, ECG changes and congestive heart failure. Psychotoxic effects include impaired memory and delirium. Induction of hypomanic or manic episodes may occur in patients with a history of bipolar disorder. Withdrawal symptoms include GI disturbances (e.g. nausea, vomiting, abdominal pain, diarrhea), anxiety, insomnia, nervousness, headache and malaise.</p>','TG537D343B','<p><span class=\"not-available\">Not Available</span></p>','Desipramine','ZINC000001530611'),(69,'Clarithromycin','clarithromycin','Clarithromycin is a macrolide antibiotic used for the treatment of a wide variety of bacterial infections such as acute otitis, pharyngitis, tonsillitis, respiratory tract infections, uncomplicated skin infections, and helicobacter pylori infection.','Biaxin, Biaxin Bid, Omeclamox, Prevpac','Clarithromycin','<p>Clarithromycin, a semisynthetic macrolide antibiotic derived from erythromycin, inhibits bacterial protein synthesis by binding to the bacterial 50S ribosomal subunit. Binding inhibits peptidyl transferase activity and interferes with amino acid translocation during the translation and protein assembly process. Clarithromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration.</p>','C38H69NO13','DB01211','Approved','Small Molecule','Average: 747.9534 Monoisotopic: 747.476891299 ',' , A02BD — Combinations for eradication of Helicobacter pylori , A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) , A02 — DRUGS FOR ACID RELATED DISORDERS , A — ALIMENTARY TRACT AND METABOLISM , A02BD — Combinations for eradication of Helicobacter pylori , A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) , A02 — DRUGS FOR ACID RELATED DISORDERS , A — ALIMENTARY TRACT AND METABOLISM , A02BD — Combinations for eradication of Helicobacter pylori , A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) , A02 — DRUGS FOR ACID RELATED DISORDERS , A — ALIMENTARY TRACT AND METABOLISM , A02BD — Combinations for eradication of Helicobacter pylori , A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) , A02 — DRUGS FOR ACID RELATED DISORDERS , A — ALIMENTARY TRACT AND METABOLISM , A02BD — Combinations for eradication of Helicobacter pylori , A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) , A02 — DRUGS FOR ACID RELATED DISORDERS , A — ALIMENTARY TRACT AND METABOLISM , A02BD — Combinations for eradication of Helicobacter pylori , A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) , A02 — DRUGS FOR ACID RELATED DISORDERS , A — ALIMENTARY TRACT AND METABOLISM , J01FA — Macrolides , J01F — MACROLIDES, LINCOSAMIDES AND STREPTOGRAMINS , J01 — ANTIBACTERIALS FOR SYSTEMIC USE , J — ANTIINFECTIVES FOR SYSTEMIC USE , A02BD — Combinations for eradication of Helicobacter pylori , A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) , A02 — DRUGS FOR ACID RELATED DISORDERS , A — ALIMENTARY TRACT AND METABOLISM , A02BD — Combinations for eradication of Helicobacter pylori , A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) , A02 — DRUGS FOR ACID RELATED DISORDERS , A — ALIMENTARY TRACT AND METABOLISM','<p>Clarithromycin is well-absorbed, acid stable and may be taken with food. </p>','','Enteric bacteria and other eubacteria\nMycobacterium\nStreptococcus pyogenes\nStreptococcus pneumoniae\nHaemophilus influenzae\nHelicobacter pylori\nMycobacterium leprae\nMycobacterium avium','<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 lactone ring of at least twelve members.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000147\" rel=\"noopener\" target=\"_blank\">Macrolides and analogues</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002207\" rel=\"noopener\" target=\"_blank\">O-glycosyl compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002012\" rel=\"noopener\" target=\"_blank\">Oxanes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001540\" rel=\"noopener\" target=\"_blank\">Monosaccharides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001897\" rel=\"noopener\" target=\"_blank\">1,2-aminoalcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, a carboxylic acid group (or a derivative thereof), and a side-chain that is specific to each amino acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000347\" rel=\"noopener\" target=\"_blank\">Amino acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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=\"Organic compounds containing a ketone that is conjugated to a cyclic moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003487\" rel=\"noopener\" target=\"_blank\">Cyclic ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000050\" rel=\"noopener\" target=\"_blank\">Lactones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds having the structure R2C(OR\')2 ( R\' not Hydrogen) and thus diethers of geminal diols. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H ). Mixed acetals have different R\' groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001656\" rel=\"noopener\" target=\"_blank\">Acetals</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the dialkyl ether functional group, with the formula ROR\', where R and R\' are alkyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001167\" rel=\"noopener\" target=\"_blank\">Dialkyl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 9 more</a>','Not Available','Not Available','50404044','81103-11-9','3732','CHEMBL1741','10342604','<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 aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.</dd><dt class=\"col-md-4 col-sm-5\" id=\"kingdom\">Kingdom</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000000\" rel=\"noopener\" target=\"_blank\">Organic compounds</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"super-class\">Super Class</dt><dd class=\"col-md-8 col-sm-7\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds that contain one or more oxygen atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004603\" rel=\"noopener\" target=\"_blank\">Organic oxygen 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 bond between a carbon atom and an oxygen atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000323\" rel=\"noopener\" target=\"_blank\">Organooxygen compounds</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=\"Monosaccharides, disaccharides, oligosaccharides, polysaccharides, and their derivatives.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000011\" rel=\"noopener\" target=\"_blank\">Carbohydrates and carbohydrate 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=\"Molecules or a portion of a molecule composed of amino-modified sugars.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000282\" rel=\"noopener\" target=\"_blank\">Aminoglycosides</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 lactone ring of at least twelve members.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000147\" rel=\"noopener\" target=\"_blank\">Macrolides and analogues</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002207\" rel=\"noopener\" target=\"_blank\">O-glycosyl compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002012\" rel=\"noopener\" target=\"_blank\">Oxanes</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001540\" rel=\"noopener\" target=\"_blank\">Monosaccharides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002239\" rel=\"noopener\" target=\"_blank\">Trialkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R\') (R,R\'=alkyl, aryl).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001661\" rel=\"noopener\" target=\"_blank\">Secondary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001897\" rel=\"noopener\" target=\"_blank\">1,2-aminoalcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an amine group, a carboxylic acid group (or a derivative thereof), and a side-chain that is specific to each amino acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000347\" rel=\"noopener\" target=\"_blank\">Amino acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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=\"Organic compounds containing a ketone that is conjugated to a cyclic moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003487\" rel=\"noopener\" target=\"_blank\">Cyclic ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000050\" rel=\"noopener\" target=\"_blank\">Lactones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds having the structure R2C(OR\')2 ( R\' not Hydrogen) and thus diethers of geminal diols. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H ). Mixed acetals have different R\' groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001656\" rel=\"noopener\" target=\"_blank\">Acetals</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic acids containing exactly one carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001137\" rel=\"noopener\" target=\"_blank\">Monocarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the dialkyl ether functional group, with the formula ROR\', where R and R\' are alkyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001167\" rel=\"noopener\" target=\"_blank\">Dialkyl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 9 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"substituents\">Substituents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1,2-aminoalcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Acetal</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aliphatic heteromonocyclic 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 or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminoglycoside core</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</span></span></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\">Cyclic ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dialkyl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Glycosyl 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\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Lactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Macrolide</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\">Monosaccharide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">O-glycosyl 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\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary amine</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 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\">Aliphatic 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\">macrolide antibiotic (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3732\" rel=\"noopener\" target=\"_blank\">CHEBI:3732</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Macrolides and lactone polyketides (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C06912\" rel=\"noopener\" target=\"_blank\">C06912</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Macrolides and lactone polyketides (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMPK04000014\" rel=\"noopener\" target=\"_blank\">LMPK04000014</a>) </span></span></dd></dl>','Organooxygen compounds','<p><span class=\"not-available\">Not Available</span></p>','This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.','Aminoglycosides','<li>Take with food. Food increases absorption.</li>','Drugs.com Drug Page',' , Alimentary Tract and Metabolism , Anti-Bacterial Agents , Anti-Infective Agents , Antibacterials for Systemic Use , Antiinfectives for Systemic Use , BSEP/ABCB11 Substrates , Cytochrome P-450 CYP3A Inhibitors , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Inhibitors , Cytochrome P-450 CYP3A4 Inhibitors (strong) , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A5 Inhibitors , Cytochrome P-450 CYP3A5 Inhibitors (strong) , Cytochrome P-450 CYP3A5 Substrates , Cytochrome P-450 CYP3A7 Substrates , Cytochrome P-450 Enzyme Inhibitors , Cytochrome P-450 Substrates , Drugs for Acid Related Disorders , Drugs for Peptic Ulcer and Gastro-Oesophageal Reflux Disease (Gord) , Enzyme Inhibitors , Erythromycin and similars , Lactones , Macrolide Antimicrobial , Macrolides , Macrolides, Lincosamides and Streptogramins , Moderate Risk QTc-Prolonging Agents , OATP1B1/SLCO1B1 Inhibitors , OATP1B3 inhibitors , Other Macrolides , P-glycoprotein inhibitors , P-glycoprotein substrates , Polyketides , Protein Synthesis Inhibitors , QTc Prolonging Agents','<table class=\"table table-sm table-bordered\" id=\"experimental-properties\"><thead><tr><th class=\"head-medium\">Property</th><th class=\"head-large\">Value</th><th>Source</th></tr></thead><tbody><tr><td>melting point (°C)</td><td>220 dec °C</td><td>PhysProp</td></tr><tr><td>water solubility</td><td>0.33 mg/L</td><td><span class=\"not-available\">Not Available</span></td></tr><tr><td>logP</td><td>3.16</td><td>MCFARLAND,JW ET AL. (1997)</td></tr><tr><td>pKa</td><td>8.99 (at 25 °C)</td><td>MCFARLAND,JW ET AL. (1997)</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">macrolide antibiotic (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3732\" rel=\"noopener\" target=\"_blank\">CHEBI:3732</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Macrolides and lactone polyketides (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C06912\" rel=\"noopener\" target=\"_blank\">C06912</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Macrolides and lactone polyketides (<a href=\"http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMPK04000014\" rel=\"noopener\" target=\"_blank\">LMPK04000014</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/HMDB0015342\" rel=\"noopener\" target=\"_blank\">HMDB0015342</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:D00276\" rel=\"noopener\" target=\"_blank\">D00276</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:C06912\" rel=\"noopener\" target=\"_blank\">C06912</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=84029\" rel=\"noopener\" target=\"_blank\">84029</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=46506489\" rel=\"noopener\" target=\"_blank\">46506489</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.10342604.html\" rel=\"noopener\" target=\"_blank\">10342604</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=50404044\" rel=\"noopener\" target=\"_blank\">50404044</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=21212\" rel=\"noopener\" target=\"_blank\">21212</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=3732\" rel=\"noopener\" target=\"_blank\">3732</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/CHEMBL1741\" rel=\"noopener\" target=\"_blank\">CHEMBL1741</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/ZINC000085534098\" rel=\"noopener\" target=\"_blank\">ZINC000085534098</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=DAP000410\" rel=\"noopener\" target=\"_blank\">DAP000410</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/PA449028\" rel=\"noopener\" target=\"_blank\">PA449028</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/CTY\" rel=\"noopener\" target=\"_blank\">CTY</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/clarith.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/clarithromycin.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/Clarithromycin\" rel=\"noopener\" target=\"_blank\">Clarithromycin</a></dd></dl>','<li>Take with food. Food increases absorption.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A2117\">Malhotra-Kumar S, Lammens C, Coenen S, Van Herck K, Goossens H: Effect of azithromycin and clarithromycin therapy on pharyngeal carriage of macrolide-resistant streptococci in healthy volunteers: a randomised, double-blind, placebo-controlled study. Lancet. 2007 Feb 10;369(9560):482-90. [<a href=\"/articles/A2117\" target=\"_blank\">Article</a>] </li><li id=\"reference-A2118\">Zuckerman JM, Qamar F, Bono BR: Macrolides, ketolides, and glycylcyclines: azithromycin, clarithromycin, telithromycin, tigecycline. Infect Dis Clin North Am. 2009 Dec;23(4):997-1026, ix-x. doi: 10.1016/j.idc.2009.06.013. [<a href=\"/articles/A2118\" target=\"_blank\">Article</a>] </li><li id=\"reference-A2121\">Piscitelli SC, Danziger LH, Rodvold KA: Clarithromycin and azithromycin: new macrolide antibiotics. Clin Pharm. 1992 Feb;11(2):137-52. [<a href=\"/articles/A2121\" target=\"_blank\">Article</a>] </li><li id=\"reference-A2122\">Peters DH, Clissold SP: Clarithromycin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic potential. Drugs. 1992 Jul;44(1):117-64. [<a href=\"/articles/A2122\" target=\"_blank\">Article</a>] </li><li id=\"reference-A2124\">Authors unspecified: Clarithromycin. Tuberculosis (Edinb). 2008 Mar;88(2):92-5. doi: 10.1016/S1472-9792(08)70005-2. [<a href=\"/articles/A2124\" target=\"_blank\">Article</a>] </li><li id=\"reference-A2127\">Stephenson GA, Stowell JG, Toma PH, Pfeiffer RR, Byrn SR: Solid-state investigations of erythromycin A dihydrate: structure, NMR spectroscopy, and hygroscopicity. J Pharm Sci. 1997 Nov;86(11):1239-44. [<a href=\"/articles/A2127\" target=\"_blank\">Article</a>] </li></ol>','<p>3-4 hours</p>','HMDB0015342','(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione','InChI=1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1','AGOYDEPGAOXOCK-KCBOHYOISA-N','<p>An alternative medication for the treatment of acute otitis media caused by <i>H. influenzae, M. catarrhalis, or S. pneumoniae</i> in patients with a history of type I penicillin hypersensitivity. Also for the treatment of pharyngitis and tonsillitis caused by susceptible <i>Streptococcus pyogenes</i>, as well as respiratory tract infections including acute maxillary sinusitis, acute bacterial exacerbations of chronic bronchitis, mild to moderate community-acquired pneuomia, Legionnaires\' disease, and pertussis. Other indications include treatment of uncomplicated skin or skin structure infections, helicobacter pylori infection, duodenal ulcer disease, bartonella infections, early Lyme disease, and encephalitis caused by <i>Toxoplasma gondii</i> (in HIV infected patients in conjunction with pyrimethamine). Clarithromycin may also decrease the incidence of cryptosporidiosis, prevent the occurence of α-hemolytic (viridans group) streptococcal endocarditis, as well as serve as a primary prevention for <i>Mycobacterium avium</i> complex (MAC) bacteremia or disseminated infections (in adults, adolescents, and children with advanced HIV infection).</p>','C06912','D00276','Organic compounds','<p>Hepatic - predominantly metabolized by CYP3A4 resulting in numerous drug interactions.</p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aliphatic heteromonocyclic compounds','CTY','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000248?highlight[compounds][]=DB01211&amp;highlight[proteins][]=DB01211\">Clarithromycin Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA449028','<p>~ 70% protein bound</p>','84029','46506489','<p>After a 250 mg tablet every 12 hours, approximately 20% of the dose is excreted in the urine as clarithromycin, while after a 500 mg tablet every 12 hours, the urinary excretion of clarithromycin is somewhat greater, approximately 30%.</p>','RxList Drug Page','21212','[H][C@@]1(C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)O[C@H]1[C@H](C)[C@@H](O[C@]2([H])O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@@](C)(C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@@H]1C)OC','Solid','Carbohydrates and carbohydrate conjugates','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">1,2-aminoalcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Acetal</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aliphatic heteromonocyclic 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 or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aminoglycoside core</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</span></span></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\">Cyclic ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dialkyl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Glycosyl 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\">Ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Lactone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Macrolide</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\">Monosaccharide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">O-glycosyl 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\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxane</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Secondary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary aliphatic amine</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary amine</span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 22 more</a>','Organic oxygen compounds','<span class=\"citations\"><p>Jih-Hua Liu, David A. Riley, \"Preparation of crystal form II of clarithromycin.\" U.S. Patent US5844105, issued May, 1997.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=5844105&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5844105</a>','DAP000410','<p>Symptoms of toxicity include diarrhea, nausea, abnormal taste, dyspepsia, and abdominal discomfort. Transient hearing loss with high doses has been observed. Pseudomembraneous colitis has been reported with clarithromycin use. Allergic reactions ranging from urticaria and mild skin eruptions to rare cases of anaphylaxis and Stevens-Johnson syndrome have also occurred. Rare cases of severe hepatic dysfunctions also have been reported. Hepatic failure is usually reversible, but fatalities have been reported. Clarithromycin may also cause tooth decolouration which may be removed by dental cleaning. Fetal abnormalities, such as cardiovascular defects, cleft palate and fetal growth retardation, have been observed in animals. Clarithromycin may cause QT prolongation.</p>','H1250JIK0A','<p><span class=\"not-available\">Not Available</span></p>','Clarithromycin','ZINC000085534098'),(70,'Paclitaxel','paclitaxel','Paclitaxel is a taxoid chemotherapeutic agent used as first-line and subsequent therapy for the treatment of advanced carcinoma of the ovary, and other various cancers including breast and lung cancer.','Abraxane, Taxol','Paclitaxel','<p>Paclitaxel is a chemotherapeutic agent marketed under the brand name Taxol among others. Used as a treatment for various cancers, paclitaxel is a mitotic inhibitor that was first isolated in 1971 from the bark of the Pacific yew tree which contains endophytic fungi that synthesize paclitaxel. It is available as an intravenous solution for injection and the newer formulation contains albumin-bound paclitaxel marketed under the brand name Abraxane.</p>','C47H51NO14','DB01229','Approved, Vet approved','Small Molecule','Average: 853.9061 Monoisotopic: 853.330955345 ',' , L01CD — Taxanes , L01C — PLANT ALKALOIDS AND OTHER NATURAL PRODUCTS , L01 — ANTINEOPLASTIC AGENTS , L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS','<p>When a 24 hour infusion of 135 mg/m^2 is given to ovarian cancer patients, the maximum plasma concentration (Cmax) is 195 ng/mL, while the AUC is 6300 ng•h/mL. </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 four carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002966\" rel=\"noopener\" target=\"_blank\">Tetracarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Ester derivatives of benzoic acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001350\" rel=\"noopener\" target=\"_blank\">Benzoic acid esters</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=\"Ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003420\" rel=\"noopener\" target=\"_blank\">Alpha-acyloxy ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic ester derivatives of a fatty acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000324\" rel=\"noopener\" target=\"_blank\">Fatty acid esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing 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=\"Compounds containing an oxetane ring, which is a four-member saturated aliphatic ring with an oxygen, and three carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000070\" rel=\"noopener\" target=\"_blank\">Oxetanes</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=\"Organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001292\" rel=\"noopener\" target=\"_blank\">Cyclic alcohols and derivatives</a></span></span></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  in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000118\" rel=\"noopener\" target=\"_blank\">Ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the dialkyl ether functional group, with the formula ROR\', where R and R\' are alkyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001167\" rel=\"noopener\" target=\"_blank\">Dialkyl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic 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=\"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=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 9 more</a>','Not Available','Not Available','50001839','33069-62-4','45863','CHEMBL428647','10368587','<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 taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3-&gt;20)-abeotaxane, 3,11-cyclotaxane, 11(15-&gt;1),11(10-&gt;9)-abeotaxane, 3,8-seco-taxane, and 11(15-&gt;1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] propellane ring system.</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=\"Terpene compounds formed by four isoprene units.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001551\" rel=\"noopener\" target=\"_blank\">Diterpenoids</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=\"Diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3-&gt;20)-abeotaxane, 3,11-cyclotaxane, 11(15-&gt;1),11(10-&gt;9)-abeotaxane, 3,8-seco-taxane, and 11(15-&gt;1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] propellane ring system.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000676\" rel=\"noopener\" target=\"_blank\">Taxanes 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=\"Carboxylic acids containing exactly four carboxyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0002966\" rel=\"noopener\" target=\"_blank\">Tetracarboxylic acids and derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Ester derivatives of benzoic acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001350\" rel=\"noopener\" target=\"_blank\">Benzoic acid esters</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=\"Ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003420\" rel=\"noopener\" target=\"_blank\">Alpha-acyloxy ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Carboxylic ester derivatives of a fatty acid.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000324\" rel=\"noopener\" target=\"_blank\">Fatty acid esters</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001670\" rel=\"noopener\" target=\"_blank\">Tertiary alcohols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing 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=\"Compounds containing an oxetane ring, which is a four-member saturated aliphatic ring with an oxygen, and three carbon atoms.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000070\" rel=\"noopener\" target=\"_blank\">Oxetanes</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=\"Organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001292\" rel=\"noopener\" target=\"_blank\">Cyclic alcohols and derivatives</a></span></span></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  in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000118\" rel=\"noopener\" target=\"_blank\">Ketones</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004140\" rel=\"noopener\" target=\"_blank\">Oxacyclic compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing the dialkyl ether functional group, with the formula ROR\', where R and R\' are alkyl groups.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001167\" rel=\"noopener\" target=\"_blank\">Dialkyl ethers</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic 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=\"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=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 9 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"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\">Alpha-acyloxy ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoate ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoyl</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboximidic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboximidic acid derivative</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclic alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dialkyl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Fatty acid ester</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\">Ketone</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 1,3-dipolar compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxetane</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 class=\"list-separator\"> / </span><span class=\"separated-list-item\">Taxane diterpenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetracarboxylic 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 25 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\">taxane diterpenoid, tetracyclic diterpenoid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:45863\" rel=\"noopener\" target=\"_blank\">CHEBI:45863</a>) </span></span></dd></dl>','Prenol lipids','','This compound belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] propellane ring system.','Taxanes and derivatives','<li>Avoid echinacea. Co-administration may decrease the effectiveness of immunosuppressants, and echinacea may induce CYP3A4 increasing paclitaxel metabolism.</li>\n<li>Exercise caution with grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum concentration of paclitaxel.</li>\n<li>Exercise caution with St. John\'s Wort. This herb induces the CYP3A4 metabolism of paclitaxel and may reduce its serum concentration.</li>','Drugs.com Drug Page',' , Agents Causing Muscle Toxicity , Albumins , Amino Acids, Peptides, and Proteins , Antimitotic Agents , Antineoplastic Agents , Antineoplastic Agents, Phytogenic , Antineoplastic and Immunomodulating Agents , BSEP/ABCB11 Inhibitors , BSEP/ABCB11 Substrates , BSEP/ABCB11 Substrates with a Narrow Therapeutic Index , Cardiotoxic antineoplastic agents , Cyclodecanes , Cycloparaffins , Cytochrome P-450 CYP2C8 Substrates , Cytochrome P-450 CYP2C8 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP3A Inducers , Cytochrome P-450 CYP3A Substrates , Cytochrome P-450 CYP3A4 Inducers , Cytochrome P-450 CYP3A4 Inducers (strength unknown) , Cytochrome P-450 CYP3A4 Substrates , Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP3A5 Substrates , Cytochrome P-450 CYP3A5 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 CYP3A7 Substrates , Cytochrome P-450 CYP3A7 Substrates with a Narrow Therapeutic Index , Cytochrome P-450 Enzyme Inducers , Cytochrome P-450 Substrates , Diterpenes , Hypotensive Agents , Immunosuppressive Agents , Microtubule Inhibition , Microtubule Inhibitors , Mitosis Modulators , Myelosuppressive Agents , Narrow Therapeutic Index Drugs , Neurotoxic agents , OATP1B3 substrates , P-glycoprotein inhibitors , P-glycoprotein substrates , P-glycoprotein substrates with a Narrow Therapeutic Index , Proteins , Taxane Derivatives , Taxoids , Terpenes , Tubulin Modulators','<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>216-217 °C</td><td>FDA label </td></tr><tr><td>water solubility</td><td>Insoluble</td><td>FDA label </td></tr><tr><td>logP</td><td>3</td><td><span class=\"not-available\">Not Available</span></td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">taxane diterpenoid, tetracyclic diterpenoid (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:45863\" rel=\"noopener\" target=\"_blank\">CHEBI:45863</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/HMDB0015360\" rel=\"noopener\" target=\"_blank\">HMDB0015360</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:D00491\" rel=\"noopener\" target=\"_blank\">D00491</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:C07394\" rel=\"noopener\" target=\"_blank\">C07394</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=36314\" rel=\"noopener\" target=\"_blank\">36314</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=46506910\" rel=\"noopener\" target=\"_blank\">46506910</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.10368587.html\" rel=\"noopener\" target=\"_blank\">10368587</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=50001839\" rel=\"noopener\" target=\"_blank\">50001839</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=56946\" rel=\"noopener\" target=\"_blank\">56946</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=45863\" rel=\"noopener\" target=\"_blank\">45863</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/CHEMBL428647\" rel=\"noopener\" target=\"_blank\">CHEMBL428647</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/ZINC000096006020\" rel=\"noopener\" target=\"_blank\">ZINC000096006020</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=DNC001411\" rel=\"noopener\" target=\"_blank\">DNC001411</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/PA450761\" rel=\"noopener\" target=\"_blank\">PA450761</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=2770\" 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/TA1\" rel=\"noopener\" target=\"_blank\">TA1</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/paclitaxel.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/paclitaxel.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/Paclitaxel\" rel=\"noopener\" target=\"_blank\">Paclitaxel</a></dd></dl>','<li>Avoid echinacea. Co-administration may decrease the effectiveness of immunosuppressants, and echinacea may induce CYP3A4 increasing paclitaxel metabolism.</li>\n<li>Exercise caution with grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum concentration of paclitaxel.</li>\n<li>Exercise caution with St. John\'s Wort. This herb induces the CYP3A4 metabolism of paclitaxel and may reduce its serum concentration.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A2194\">Wall ME, Wani MC: Camptothecin and taxol: discovery to clinic--thirteenth Bruce F. Cain Memorial Award Lecture. Cancer Res. 1995 Feb 15;55(4):753-60. [<a href=\"/articles/A2194\" target=\"_blank\">Article</a>] </li><li id=\"reference-A2196\">Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT: Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc. 1971 May 5;93(9):2325-7. [<a href=\"/articles/A2196\" target=\"_blank\">Article</a>] </li><li id=\"reference-A2198\">Fuchs DA, Johnson RK: Cytologic evidence that taxol, an antineoplastic agent from Taxus brevifolia, acts as a mitotic spindle poison. Cancer Treat Rep. 1978 Aug;62(8):1219-22. [<a href=\"/articles/A2198\" target=\"_blank\">Article</a>] </li><li id=\"reference-A2199\">Saville MW, Lietzau J, Pluda JM, Feuerstein I, Odom J, Wilson WH, Humphrey RW, Feigal E, Steinberg SM, Broder S, et al.: Treatment of HIV-associated Kaposi\'s sarcoma with paclitaxel. Lancet. 1995 Jul 1;346(8966):26-8. [<a href=\"/articles/A2199\" target=\"_blank\">Article</a>] </li><li id=\"reference-A2201\">Authors unspecified: ABI 007. Drugs R D. 2004;5(3):155-9. [<a href=\"/articles/A2201\" target=\"_blank\">Article</a>] </li><li id=\"reference-A2203\">Gaitanis A, Staal S: Liposomal doxorubicin and nab-paclitaxel: nanoparticle cancer chemotherapy in current clinical use. Methods Mol Biol. 2010;624:385-92. doi: 10.1007/978-1-60761-609-2_26. [<a href=\"/articles/A2203\" target=\"_blank\">Article</a>] </li></ol>','<p>When a 24 hour infusion of 135 mg/m^2 is given to ovarian cancer patients, the elimination half=life is 52.7 hours. </p>','HMDB0015360','(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate','InChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,3','RCINICONZNJXQF-MZXODVADSA-N','<p>Used in the treatment of Kaposi\'s sarcoma and cancer of the lung, ovarian, and breast. Abraxane® is specfically indicated for the treatment of metastatic breast cancer and locally advanced or metastatic non-small cell lung cancer.</p>','C07394','D00491','Organic compounds','<p>Hepatic. In vitro studies with human liver microsomes and tissue slices showed that paclitaxel was metabolized primarily to 6a-hydrox-ypaclitaxel by the cytochrome P450 isozyme CYP2C8; and to two minor metabolites, 3’-p-hydroxypaclitaxel and 6a, 3’-p-dihydroxypaclitaxel, by CYP3A4.</p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic heteropolycyclic compounds','TA1','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000434?highlight[compounds][]=DB01229&amp;highlight[proteins][]=DB01229\">Paclitaxel Action Pathway</a></td><td>Drug action</td></tr></tbody>','PA450761','<p>89%-98% bound to plasma protein. The presence of cimetidine, ranitidine, dexamethasone, or diphenhydramine did not affect protein binding of paclitaxel.</p>','36314','46506910','<p>In 5 patients administered a 225 or 250 mg/m2 dose of radiolabeled paclitaxel as a 3-hour infusion, a mean of 71% of the radioactivity was excreted in the feces in 120 hours, and 14% was recovered in the urine.</p>','RxList Drug Page','56946','[H][C@]12[C@H](OC(=O)C3=CC=CC=C3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)C4=CC=CC=C4)C4=CC=CC=C4)C(C)=C([C@@H](OC(C)=O)C(=O)[C@]1(C)[C@@H](O)C[C@H]1OC[C@@]21OC(C)=O)C3(C)C','Solid','Diterpenoids','<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\">Alpha-acyloxy ketone</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Aromatic heteropolycyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoate ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoic acid or derivatives</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Benzoyl</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboximidic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboximidic acid derivative</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carboxylic acid derivative</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid ester</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Cyclic alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Dialkyl ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Ether</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Fatty acid ester</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\">Ketone</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 1,3-dipolar compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic nitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxide</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organic oxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organoheterocyclic compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organonitrogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organooxygen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Organopnictogen compound</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxacycle</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Oxetane</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 class=\"list-separator\"> / </span><span class=\"separated-list-item\">Taxane diterpenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tertiary alcohol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tetracarboxylic 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 25 more</a>','Lipids and lipid-like molecules','<span class=\"citations\"><p>Hendricus B. A. de Bont, Ruben G. G. Leenders, Johan W. Scheeren, Hidde J. Haisma, Dick de Vos, \"Paclitaxel prodrugs, method for preparation as well as their use in selective chemotherapy.\" U.S. Patent US5760072, issued September, 1989.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=5760072&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US5760072</a>','DNC001411','<p>Rat (ipr) LD<sub>50</sub>=32530 µg/kg. Symptoms of overdose include bone marrow suppression, peripheral neurotoxicity, and mucositis. Overdoses in pediatric patients may be associated with acute ethanol toxicity.</p>','P88XT4IS4D','','Paclitaxel','ZINC000096006020'),(71,'Levodopa','levodopa','Levodopa is a dopamine precursor used in the management of Parkinson\'s disease, often in combination with carbidopa, as well as other conditions associated with parkinsonism.','Dhivy, Duodopa, Duopa, Inbrija, Parcopa, Prolopa, Rytary, Sinemet, Stalevo','Levodopa','<p>Levodopa is a prodrug of dopamine that is administered to patients with Parkinson\'s due to its ability to cross the blood-brain barrier<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. Levodopa can be metabolised to dopamine on either side of the blood-brain barrier and so it is generally administered with a dopa decarboxylase inhibitor like carbidopa to prevent metabolism until after it has crossed the blood-brain barrier<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=\"Djamshidian A, Poewe W: Apomorphine and levodopa in Parkinson\'s disease: Two revolutionary drugs from the 1950\'s. Parkinsonism Relat Disord. 2016 Dec;33 Suppl 1:S9-S12. doi: 10.1016/j.parkreldis.2016.12.004. Epub 2016 Dec 22. (PubMed ID 28012951)\" href=\"#reference-A177781\">1</a></sup>. Once past the blood-brain barrier, levodopa is metabolized to dopamine and supplements the low endogenous levels of dopamine to treat symptoms of Parkinson\'s<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. The first developed drug product that was approved by the FDA was a levodopa and carbidopa combined product called Sinemet that was approved on May 2, 1975<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Djamshidian A, Poewe W: Apomorphine and levodopa in Parkinson\'s disease: Two revolutionary drugs from the 1950\'s. Parkinsonism Relat Disord. 2016 Dec;33 Suppl 1:S9-S12. doi: 10.1016/j.parkreldis.2016.12.004. Epub 2016 Dec 22. (PubMed ID 28012951)\" href=\"#reference-A177781\">1</a>,<a class=\"reference-popover-link\" data-content=\"FDA Approved Drug Products: Sinemet\" href=\"#reference-L6133\">7</a></sup>.</p>','C9H11NO4','DB01235','Approved','Small Molecule','Average: 197.1879 Monoisotopic: 197.068807845 ',' , N04BA — Dopa and dopa derivatives , N04B — DOPAMINERGIC AGENTS , N04 — ANTI-PARKINSON DRUGS , N — NERVOUS SYSTEM , N04BA — Dopa and dopa derivatives , N04B — DOPAMINERGIC AGENTS , N04 — ANTI-PARKINSON DRUGS , N — NERVOUS SYSTEM , N04BA — Dopa and dopa derivatives , N04B — DOPAMINERGIC AGENTS , N04 — ANTI-PARKINSON DRUGS , N — NERVOUS SYSTEM','<p>Orally inhaled levodopa reaches a peak concentration in 0.5 hours with a bioavailability than is 70% that of the immediate release levodopa tablets with a peripheral dopa decarboxylase inhibitor like carbidopa or benserazide<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=\"Djamshidian A, Poewe W: Apomorphine and levodopa in Parkinson\'s disease: Two revolutionary drugs from the 1950\'s. Parkinsonism Relat Disord. 2016 Dec;33 Suppl 1:S9-S12. doi: 10.1016/j.parkreldis.2016.12.004. Epub 2016 Dec 22. (PubMed ID 28012951)\" href=\"#reference-A177781\">1</a></sup>.</p>','','Humans and other mammals','<span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing 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></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=\"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=\"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=\"Compounds containing a 1,2-benzenediol moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000135\" rel=\"noopener\" target=\"_blank\">Catechols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Phenols that a unsubstituted at the 2-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004646\" rel=\"noopener\" target=\"_blank\">1-hydroxy-2-unsubstituted benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Phenols that are unsubstituted at the 4-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004647\" rel=\"noopener\" target=\"_blank\">1-hydroxy-4-unsubstituted benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003899\" rel=\"noopener\" target=\"_blank\">Aralkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a carboxylic acid group with the formula -C(=O)OH.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001205\" rel=\"noopener\" target=\"_blank\">Carboxylic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span 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=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 6 more</a>','Not Available','Not Available','60928','59-92-7','15765','CHEMBL1009','5824','<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 tyrosine and derivatives. These are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine 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 tyrosine or a derivative thereof resulting from reaction of tyrosine 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/C0004319\" rel=\"noopener\" target=\"_blank\">Tyrosine and derivatives</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"alternative-parents\">Alternative Parents</dt><dd class=\"col-md-8 col-sm-7\"><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing 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></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=\"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=\"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=\"Compounds containing a 1,2-benzenediol moiety.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0000135\" rel=\"noopener\" target=\"_blank\">Catechols</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Phenols that a unsubstituted at the 2-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004646\" rel=\"noopener\" target=\"_blank\">1-hydroxy-2-unsubstituted benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Phenols that are unsubstituted at the 4-position.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004647\" rel=\"noopener\" target=\"_blank\">1-hydroxy-4-unsubstituted benzenoids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003899\" rel=\"noopener\" target=\"_blank\">Aralkylamines</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"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></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a carboxylic acid group with the formula -C(=O)OH.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001205\" rel=\"noopener\" target=\"_blank\">Carboxylic acids</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Organic compounds containing a carbonyl group, with the general structure RC(=O)R\', where R=organyl, R\'=H, N, O, organyl group or halide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0001831\" rel=\"noopener\" target=\"_blank\">Carbonyl compounds</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004150\" rel=\"noopener\" target=\"_blank\">Hydrocarbon derivatives</a></span><span 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=\"Organic compounds containing an oxide group.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0003940\" rel=\"noopener\" target=\"_blank\">Organic oxides</a></span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\"><a class=\"classyfire-taxnode\" data-content=\"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table.\" href=\"http://classyfire.wishartlab.com/tax_nodes/C0004557\" rel=\"noopener\" target=\"_blank\">Organopnictogen compounds</a></span></span></span></span><a class=\"taxonomy-toggler\" href=\"javascript:void();\"><div class=\"drugbank-icon icon-expand\"><svg class=\"icon\" role=\"img\" title=\"expand\">\n<use xlink:href=\"/assets/icons-539be351b538129271b9ee92cb0ebbd16efad4fccf6e2fe95aa6234f1e7417fa.svg#expand\"></use>\n</svg>\n</div> show 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\">1-hydroxy-2-unsubstituted benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">1-hydroxy-4-unsubstituted benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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\">Benzenoid</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Catechol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</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\">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\">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 class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tyrosine 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 18 more</a></dd><dt class=\"col-md-4 col-sm-5\" id=\"molecular-framework\">Molecular Framework</dt><dd class=\"col-md-8 col-sm-7\">Aromatic 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-tyrosine derivative, dopa (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15765\" rel=\"noopener\" target=\"_blank\">CHEBI:15765</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Other amino acids, Biogenic amines (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C00355\" rel=\"noopener\" target=\"_blank\">C00355</a>) </span></span></dd></dl>','Carboxylic acids and derivatives','<p>Intravenously administered levodopa is cleared at a rate of 14.2mL/min/kg in elderly patients and 23.4mL/min/kg in younger patients<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Robertson DR, Wood ND, Everest H, Monks K, Waller DG, Renwick AG, George CF: The effect of age on the pharmacokinetics of levodopa administered alone and in the presence of carbidopa. Br J Clin Pharmacol. 1989 Jul;28(1):61-9. (PubMed ID 2775615)\" href=\"#reference-A177802\">4</a></sup>. When given carbidopa, the clearance of levodopa was 5.8mL/min/kg in elderyly patients and 9.3mL/min/kg in younger patients<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Robertson DR, Wood ND, Everest H, Monks K, Waller DG, Renwick AG, George CF: The effect of age on the pharmacokinetics of levodopa administered alone and in the presence of carbidopa. Br J Clin Pharmacol. 1989 Jul;28(1):61-9. (PubMed ID 2775615)\" href=\"#reference-A177802\">4</a></sup>.</p>','This compound belongs to the class of organic compounds known as tyrosine and derivatives. These are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.','Tyrosine and derivatives','<li>Avoid multivalent ions. Iron salts may reduce levodopa absorption.</li>\n<li>Take with or without food. A diet high in protein may delay absorption and AUC of levodopa.</li>','Drugs.com Drug Page',' , Amines , Amino Acids , Amino Acids, Aromatic , Amino Acids, Cyclic , Amino Acids, Peptides, and Proteins , Anti-Dyskinesia Agents , Anti-Parkinson Agents (Dopamine Agonist) , Anti-Parkinson Drugs , Benzene Derivatives , Biogenic Amines , Biogenic Monoamines , Catecholamines , Catechols , Central Nervous System Agents , Central Nervous System Depressants , Dihydroxyphenylalanine , Dopa and Dopa Derivatives , Dopamine Agents , Hypotensive Agents , Levodopa, antagonists & inhibitors , Nervous System , Neurotransmitter Agents , Phenols , Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome','<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>295</td><td>MSDS</td></tr><tr><td>boiling point (°C)</td><td>448.4</td><td>ChemSpider</td></tr><tr><td>water solubility</td><td>5mM</td><td>ChemSpider</td></tr><tr><td>logP</td><td>0.05</td><td>https://www.chemeo.com/cid/46-030-7/Levodopa.pdf</td></tr></tbody></table>','<span class=\"inline-separated-list-container\"><span class=\"simple-separated-list-item\">non-proteinogenic L-alpha-amino acid, L-tyrosine derivative, dopa (<a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15765\" rel=\"noopener\" target=\"_blank\">CHEBI:15765</a>) </span><span class=\"list-separator\"> / </span><span class=\"simple-separated-list-item\">Other amino acids, Biogenic amines (<a href=\"http://www.genome.jp/dbget-bin/www_bget?cpd:C00355\" rel=\"noopener\" target=\"_blank\">C00355</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/HMDB0000181\" rel=\"noopener\" target=\"_blank\">HMDB0000181</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:D00059\" rel=\"noopener\" target=\"_blank\">D00059</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:C00355\" rel=\"noopener\" target=\"_blank\">C00355</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=6047\" rel=\"noopener\" target=\"_blank\">6047</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=46508120\" rel=\"noopener\" target=\"_blank\">46508120</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.5824.html\" rel=\"noopener\" target=\"_blank\">5824</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=60928\" rel=\"noopener\" target=\"_blank\">60928</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=6375\" rel=\"noopener\" target=\"_blank\">6375</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=15765\" rel=\"noopener\" target=\"_blank\">15765</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/CHEMBL1009\" rel=\"noopener\" target=\"_blank\">CHEMBL1009</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/ZINC000000895199\" rel=\"noopener\" target=\"_blank\">ZINC000000895199</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=DAP000209\" rel=\"noopener\" target=\"_blank\">DAP000209</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/PA450213\" rel=\"noopener\" target=\"_blank\">PA450213</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=3639\" 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/DAH\" rel=\"noopener\" target=\"_blank\">DAH</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/stalevo.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/levodopa.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/Levodopa\" rel=\"noopener\" target=\"_blank\">Levodopa</a></dd></dl>','<li>Avoid multivalent ions. Iron salts may reduce levodopa absorption.</li>\n<li>Take with or without food. A diet high in protein may delay absorption and AUC of levodopa.</li>','<ol class=\"cite-this-references\"><li id=\"reference-A177781\">Djamshidian A, Poewe W: Apomorphine and levodopa in Parkinson\'s disease: Two revolutionary drugs from the 1950\'s. Parkinsonism Relat Disord. 2016 Dec;33 Suppl 1:S9-S12. doi: 10.1016/j.parkreldis.2016.12.004. Epub 2016 Dec 22. [<a href=\"/articles/A177781\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177745\">Meiser J, Weindl D, Hiller K: Complexity of dopamine metabolism. Cell Commun Signal. 2013 May 17;11(1):34. doi: 10.1186/1478-811X-11-34. [<a href=\"/articles/A177745\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177733\">Elroby SA, Makki MS, Sobahi TR, Hilal RH: Toward the understanding of the metabolism of levodopa I. DFT investigation of the equilibrium geometries, acid-base properties and levodopa-water complexes. Int J Mol Sci. 2012;13(4):4321-39. doi: 10.3390/ijms13044321. Epub 2012 Apr 2. [<a href=\"/articles/A177733\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177802\">Robertson DR, Wood ND, Everest H, Monks K, Waller DG, Renwick AG, George CF: The effect of age on the pharmacokinetics of levodopa administered alone and in the presence of carbidopa. Br J Clin Pharmacol. 1989 Jul;28(1):61-9. [<a href=\"/articles/A177802\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177805\">Abrams WB, Coutinho CB, Leon AS, Spiegel HE: Absorption and metabolism of levodopa. JAMA. 1971 Dec 27;218(13):1912-4. [<a href=\"/articles/A177805\" target=\"_blank\">Article</a>] </li><li id=\"reference-A177817\">Fanali G, Rampoldi V, di Masi A, Bolli A, Lopiano L, Ascenzi P, Fasano M: Binding of anti-Parkinson\'s disease drugs to human serum albumin is allosterically modulated. IUBMB Life. 2010 May;62(5):371-6. doi: 10.1002/iub.317. [<a href=\"/articles/A177817\" target=\"_blank\">Article</a>] </li><li id=\"reference-L6133\">FDA Approved Drug Products: Sinemet [<a href=\"https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&amp;ApplNo=017555\" target=\"_blank\">Link</a>] </li><li id=\"reference-F4579\">Sinemet FDA Label [<a href=\"//s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/004/579/original/Sinemet_FDA_Label.pdf?1556654841\" target=\"_blank\">File</a>] </li></ol>','<p>2.3 hours for orally inhaled levodopa<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. Oral levodopa has a half life of 50 minutes but when combined with a peripheral dopa decarboxylase inhibitor, the half life is increased to 1.5 hours<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sinemet FDA Label\" href=\"#reference-F4579\">8</a></sup>.</p>','HMDB0000181','(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid','InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1','WTDRDQBEARUVNC-LURJTMIESA-N','<p>Levodopa on its own is formulated as an oral inhalation powder indicated for intermittent treatment of off episodes in Parkinson\'s patients who are already being treated with carbidopa and levodopa<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. Levodopa is most commonly formulated as an oral tablet with a peripheral dopa decarboxylase inhibitor indicated for treatment of Parkinson\'s disease, post-encephalitic parkinsonism, and symptomatic parkinsonism following carbon monoxide intoxication or manganese intoxication<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Sinemet FDA Label\" href=\"#reference-F4579\">8</a></sup>.</p>','C00355','D00059','Organic compounds','<p>Levodopa is either converted to dopamine by aromatic-L-amino-acid decarboxylase or O-methylated to 3-O-methyldopa by catechol-O-methyltransferase<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=\"Meiser J, Weindl D, Hiller K: Complexity of dopamine metabolism. Cell Commun Signal. 2013 May 17;11(1):34. doi: 10.1186/1478-811X-11-34. (PubMed ID 23683503)\" href=\"#reference-A177745\">2</a>,<a class=\"reference-popover-link\" data-content=\"Elroby SA, Makki MS, Sobahi TR, Hilal RH: Toward the understanding of the metabolism of levodopa I. DFT investigation of the equilibrium geometries, acid-base properties and levodopa-water complexes. Int J Mol Sci. 2012;13(4):4321-39. doi: 10.3390/ijms13044321. Epub 2012 Apr 2. (PubMed ID 22605980)\" href=\"#reference-A177733\">3</a></sup>. 3-O-methyldopa cannot be metabolized to dopamine<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Elroby SA, Makki MS, Sobahi TR, Hilal RH: Toward the understanding of the metabolism of levodopa I. DFT investigation of the equilibrium geometries, acid-base properties and levodopa-water complexes. Int J Mol Sci. 2012;13(4):4321-39. doi: 10.3390/ijms13044321. Epub 2012 Apr 2. (PubMed ID 22605980)\" href=\"#reference-A177733\">3</a></sup>. Once levodopa is converted to dopamine, it is converted to sulfated or glucuronidated metabolites, epinephrine E, or homovanillic acid through various metabolic processes<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Meiser J, Weindl D, Hiller K: Complexity of dopamine metabolism. Cell Commun Signal. 2013 May 17;11(1):34. doi: 10.1186/1478-811X-11-34. (PubMed ID 23683503)\" href=\"#reference-A177745\">2</a></sup>. The primary metabolites are 3,4-dihydroxyphenylacetic acid (13-47%) and homovanillic acid (23-39%)<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Elroby SA, Makki MS, Sobahi TR, Hilal RH: Toward the understanding of the metabolism of levodopa I. DFT investigation of the equilibrium geometries, acid-base properties and levodopa-water complexes. Int J Mol Sci. 2012;13(4):4321-39. doi: 10.3390/ijms13044321. Epub 2012 Apr 2. (PubMed ID 22605980)\" href=\"#reference-A177733\">3</a>,<a class=\"reference-popover-link\" data-content=\"Abrams WB, Coutinho CB, Leon AS, Spiegel HE: Absorption and metabolism of levodopa. JAMA. 1971 Dec 27;218(13):1912-4. (PubMed ID 5171067)\" href=\"#reference-A177805\">5</a></sup>.</p><p class=\"d-none d-sm-block\"><strong>Hover over products below to view reaction partners</strong></p>','Aromatic homomonocyclic compounds','DAH','<thead><tr><th>Pathway</th><th>Category</th></tr></thead><tbody><tr><td><a href=\"http://smpdb.ca/view/SMP0000170?highlight[compounds][]=DB01235&amp;highlight[proteins][]=DB01235\">Aromatic L-Aminoacid Decarboxylase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000006?highlight[compounds][]=DB01235&amp;highlight[proteins][]=DB01235\">Tyrosine Metabolism</a></td><td>Metabolic</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000012?highlight[compounds][]=DB01235&amp;highlight[proteins][]=DB01235\">Catecholamine Biosynthesis</a></td><td>Metabolic</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000218?highlight[compounds][]=DB01235&amp;highlight[proteins][]=DB01235\">Tyrosinemia Type I</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000429?highlight[compounds][]=DB01235&amp;highlight[proteins][]=DB01235\">Disulfiram Action Pathway</a></td><td>Drug action</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000169?highlight[compounds][]=DB01235&amp;highlight[proteins][]=DB01235\">Alkaptonuria</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000190?highlight[compounds][]=DB01235&amp;highlight[proteins][]=DB01235\">Hawkinsinuria</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000494?highlight[compounds][]=DB01235&amp;highlight[proteins][]=DB01235\">Tyrosinemia, Transient, of the Newborn</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000497?highlight[compounds][]=DB01235&amp;highlight[proteins][]=DB01235\">Tyrosine Hydroxylase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000498?highlight[compounds][]=DB01235&amp;highlight[proteins][]=DB01235\">Dopamine beta-Hydroxylase Deficiency</a></td><td>Disease</td></tr><tr><td><a href=\"http://smpdb.ca/view/SMP0000533?highlight[compounds][]=DB01235&amp;highlight[proteins][]=DB01235\">Monoamine Oxidase-A Deficiency (MAO-A)</a></td><td>Disease</td></tr></tbody>','PA450213','<p>Levodopa binding to plasma proteins is negligible<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Fanali G, Rampoldi V, di Masi A, Bolli A, Lopiano L, Ascenzi P, Fasano M: Binding of anti-Parkinson\'s disease drugs to human serum albumin is allosterically modulated. IUBMB Life. 2010 May;62(5):371-6. doi: 10.1002/iub.317. (PubMed ID 20225277)\" href=\"#reference-A177817\">6</a></sup>.</p>','6047','46508120','<p>After 48 hours, 0.17% of an orally administered dose is recovered in stool, 0.28% is exhaled, and 78.4% is recovered in urine<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Abrams WB, Coutinho CB, Leon AS, Spiegel HE: Absorption and metabolism of levodopa. JAMA. 1971 Dec 27;218(13):1912-4. (PubMed ID 5171067)\" href=\"#reference-A177805\">5</a></sup></p>','RxList Drug Page','6375','N[C@@H](CC1=CC(O)=C(O)C=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\">1-hydroxy-2-unsubstituted benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">1-hydroxy-4-unsubstituted benzenoid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">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\">Benzenoid</span></span></span><span class=\"hidden-taxonomy\" style=\"display: none\"><span class=\"list-separator\"> / </span><span class=\"separated-list-container\"><span class=\"separated-list col-lg-12 col-xl-6\"><span class=\"separated-list-item\">Carbonyl group</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Carboxylic acid</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Catechol</span><span class=\"list-separator\"> / </span><span class=\"separated-list-item\">Hydrocarbon derivative</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\">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\">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 class=\"list-separator\"> / </span><span class=\"separated-list-item\">Tyrosine 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 18 more</a>','Organic acids and derivatives','<span class=\"citations\"><p>Vincenzo Cannata, Giancarlo Tamerlani, Mauro Morotti, \"Process for the synthesis of the levodopa.\" U.S. Patent US4962223, issued December, 1986.</p>\n</span><a href=\"https://www.google.com/?tbm=pts#q=4962223&amp;tbm=pts\" rel=\"noopener\" target=\"_blank\">US4962223</a>','DAP000209','<p>There is no readily available data for the use of levodopa in pregnancy<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. Rabbits treated with levodopa and carbidopa produced smaller litters and their offspring developed visceral and skeletal deformities<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. Levodopa may lower prolactin and interfere with lactation but there is limited human data to demonstrate this effect<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. Levodopa is present in human breast milk and so the potential effects of nursing while taking levodopa should be considered before prescribing levodopa to nursing mothers<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. There is currently a lack of data on the safety and effectiveness of using levodopa in pediatric patients<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>. Patients over 65 years of age are more likely to experience adverse effects associated with taking levodopa, however this generally is not sufficient to exclude this patient group from treatment<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','46627O600J','<p>168L for orally inhaled levodopa<sup class=\"text-reference-group\"><a class=\"reference-popover-link\" data-content=\"Official drug label\" href=\"#label-reference\">Label</a></sup>.</p>','Levodopa','ZINC000000895199'),