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Ketoconazole

Antifungal chemical compoundPharmaceutical compoundLevoketoconazole (left) and dextroketoconazole (right)Clinical dataPronunciation Trade namesNizoral, othersOther namesR-41400; KW-1414AHFS/Drugs.comMonographMedlinePlusa682816License dataUS DailyMed: KetoconazolePregnancycategoryAU: B3Routes ofadministrationBy mouth (tablets), topical (cream, shampoo, solution)ATC codeJ02AB02 (WHO) D01AC08 (WHO), G01AF11 (WHO), H02CA03 (WHO)Legal statusLegal statusUK: POM (Prescription only)US: ℞-onlyEU: Rx-onlyIn general: ℞ (Prescription only)Pharmacokinetic dataBioavailabilityBy mouth: 37–97%Protein binding84 to 99%MetabolismExtensive liver (predominantly oxidation, O-dealkylation)MetabolitesN-deacetyl ketoconazoleElimination half-lifeBiphasicExcretionBile duct (major) and kidneyIdentifiersIUPAC name1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanoneCAS Number65277-42-1PubChemCID382347576IUPHAR/BPS2568DrugBankDB01026ChemSpider4016953691UNIIR9400W927IKEGGD00351ChEBICHEBI:48336ChEMBLChEMBL75ChEMBL157101PDB ligandKTN (PDBe, RCSB PDB)CompTox Dashboard(EPA)DTXSID20273956ECHA InfoCard100.059.680Chemical and physical dataFormulaC26H28Cl2N4O4Molar mass531.43 g·mol3D model (JSmol)Interactive imageChiralityRacemic mixtureSMILESO=C(N5CCN(c4ccc(OC[C@@H]1O[C@](OC1)(c2ccc(Cl)cc2Cl)Cn3ccnc3)cc4)CC5)CInChIInChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m0/s1Key:XMAYWYJOQHXEEK-OZXSUGGESA-N (verify)StadaKetoconazole, sold under the brand name Nizoral, among others, is an antiandrogen, antifungal, and antiglucocorticoid medication used to treat a number of fungal infections.

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