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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key XMAYWYJOQHXEEK-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1981), EMA (2014))
IUPAC Name Click here for help
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 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)
ChEBI CHEBI:48339
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
Search PubMed titles ketoconazole
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