ketoconazole   

GtoPdb Ligand ID: 2568

Synonyms: Nizoral® | R-41400
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.
2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
InChI Key XMAYWYJOQHXEEK-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1981), EMA (2014))
IUPAC Name
1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
International Nonproprietary Names
INN number INN
4594 ketoconazole
Synonyms
Nizoral® | R-41400
Database Links
BindingDB Ligand 8610
CAS Registry No. 65277-42-1 (source: Scifinder)
ChEBI CHEBI:48339
ChEMBL Ligand CHEMBL157101
DrugBank Ligand DB01026
DrugCentral Ligand 1527
GtoPdb PubChem SID 135650454
PubChem CID 3823
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Search UniChem for chemical match using the InChIKey XMAYWYJOQHXEEK-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone XMAYWYJOQHXEEK
Wikipedia Ketoconazole