ketoconazole   Click here for help

GtoPdb Ligand ID: 2568

Synonyms: Nizoral® | R-41400
Approved drug
ketoconazole is an approved drug (FDA (1981), EMA (2014))
Compound class: Synthetic organic
Comment: The approved drug ketoconazole is a racemic mixture of two enantiomers. The structure shown here does not specify stereochemistry and represents the mixture. The non-isomeric structure is also represented in the PubChem and ChEBI entries in the Database Links table, while the two enantiomers forming the racemate are represented by CID 456201 and CID 47576. The ChEMBL entry represents the 2S,4R enantiomer.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 0
Rotatable bonds 8
Topological polar surface area 69.06
Molecular weight 530.15
XLogP 4.08
No. Lipinski's rules broken 0
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Canonical SMILES Clc1ccc(c(c1)Cl)C1(OCC(O1)COc1ccc(cc1)N1CCN(CC1)C(=O)C)Cn1cncc1
Isomeric SMILES Clc1ccc(c(c1)Cl)C1(OCC(O1)COc1ccc(cc1)N1CCN(CC1)C(=O)C)Cn1cncc1
InChI InChI=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
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Summary of Clinical Use Click here for help
Used in the treatment of systemic fungal conditions, namely candidiasis, chronic mucocutaneous candidiasis, oral thrush, candiduria, blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis. The 2014 EMA approval authorises the use of Ketoconazole HRA to treat patients with Cushing's Syndrome.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Inhibitor of fungal enzyme 14-α demethylase. This inhibits the conversion of lanosterol to ergosterol, leading to increased fungal cell permeability. In humans ketoconozole inhibits P450 enzymes in the adrenal gland that are involved in cortosol production, thus reducing the cortisol load and decreasing disease symptoms.
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