CHEBI:453011 - ciclopirox

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ChEBI Name ciclopirox
ChEBI ID CHEBI:453011
Definition A cyclic hydroxamic acid that is 1-hydroxypyridin-2(1H)-one in which the hydrogens at positions 4 and 6 are substituted by methyl and cyclohexyl groups, repectively. A broad spectrum antigfungal agent, it also exhibits antibacterial activity against many Gram-positive and Gram-negative bacteria, and has anti-inflammatory properties. It is used a a topical treatment of fungal skin and nail infections.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C12H17NO2
Net Charge 0
Average Mass 207.26890
Monoisotopic Mass 207.126
InChI InChI=1S/C12H17NO2/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10/h7-8,10,15H,2-6H2,1H3
InChIKey SCKYRAXSEDYPSA-UHFFFAOYSA-N
SMILES Cc1cc(C2CCCCC2)n(O)c(=O)c1
Roles Classification
Biological Role(s): antibacterial agent
A substance that kills or slows the growth of bacteria.
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via hydroxypyridone antifungal drug )
Application(s): antiseborrheic
A drug or agent applied to the skin to control seborrhea or seborrheic dermatitis.
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via hydroxypyridone antifungal drug )
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ChEBI Ontology
Outgoing ciclopirox (CHEBI:453011) has role antibacterial agent (CHEBI:33282)
ciclopirox (CHEBI:453011) has role antiseborrheic (CHEBI:59010)
ciclopirox (CHEBI:453011) is a cyclic hydroxamic acid (CHEBI:23445)
ciclopirox (CHEBI:453011) is a hydroxypyridone antifungal drug (CHEBI:87130)
ciclopirox (CHEBI:453011) is a pyridone (CHEBI:38183)
Incoming ciclopirox olamine (CHEBI:31398) has part ciclopirox (CHEBI:453011)
IUPAC Name
6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one
INNs Sources
ciclopirox ChemIDplus
ciclopirox WHO MedNet
ciclopirox WHO MedNet
ciclopiroxum ChemIDplus
Synonym Source
6-cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone ChEBI
Manual Xrefs Databases
636 DrugCentral
Ciclopirox Wikipedia
D03488 KEGG DRUG
DB01188 DrugBank
LSM-5307 LINCS
US3883545 Patent
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Registry Numbers Types Sources
1533423 Beilstein Registry Number Beilstein
29342-05-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16854048 PubMed citation ChEMBL
17253868 PubMed citation ChEMBL
Last Modified
22 February 2017