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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1981), EMA (2014))
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
4594 ketoconazole
Synonyms Click here for help
Nizoral® | R-41400
Database Links Click here for help
BindingDB Ligand 8610
CAS Registry No. 65277-42-1 (source: Scifinder)
ChEMBL Ligand CHEMBL157101
DrugBank Ligand DB01026
DrugCentral Ligand 1527
GtoPdb PubChem SID 135650454
PubChem CID 3823
Search Google for chemical match using the InChIKey XMAYWYJOQHXEEK-UHFFFAOYSA-N
Search Google for chemicals with the same backbone XMAYWYJOQHXEEK
Search PubMed clinical trials ketoconazole
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Search PubMed titles/abstracts ketoconazole
UniChem Compound Search for chemical match using the InChIKey XMAYWYJOQHXEEK-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XMAYWYJOQHXEEK-UHFFFAOYSA-N
Wikipedia Ketoconazole