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SML2011 Sigma-Aldrich

Ciclopirox

≥98% (HPLC)

Synonym: 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone, 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone, Ciclopirox, HOE 296b

  • CAS Number 29342-05-0

  • Empirical Formula (Hill Notation) C12H17NO2

  • Molecular Weight 207.27

  •  MDL number MFCD00599441

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, CI-CZ, Cell Biology
assay   ≥98% (HPLC)
form   powder
color   white to beige
solubility   DMSO: 2 mg/mL, clear
shipped in   ambient
storage temp.   2-8°C
SMILES string   ON1C(C2CCCCC2)=CC(C)=CC1=O
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
InChI key   SCKYRAXSEDYPSA-UHFFFAOYSA-N

Description

Biochem/physiol Actions

Ciclopirox is a chemical compound belonging to the class of hydroxypyridones. It is found active against dermatophytes, yeasts, molds, some bacterias and also azole-resistant Candida species. Unlike other antifungal agents that act for ergosterol inhibition, ciclopirox has a different action. It targets metal-dependent enzymes, which degrades fungal cell peroxides. This unique action of ciclopirox provides less chance for resistance in pathogenic fungi. This compound is used in topical formulations specifically for nails and skin.

Ciclopirox is an antifungal and cell-permeable iron-chelating agent. It has been found to inhibit multiple enzymes and signaling pathways including prolyl hydroxylase 2 (PHD2), eukaryotic translation initiation factor 5A (eIF5A), Wnt/β-catenin, hypoxia-inducible factor-1α (HIF-1 α)/vascular endothelial growth factor (VEGF), vascular endothelial growth factor receptor 3 (VEGFR-3), mammalian target of rapamycin (mTOR), and cyclin dependent kinases (CDKs). Ciclopirox has been shown to have anti-viral and anticancer activity in addition to its antifungal activity. Ciclopirox has also been shown to counteract glucotoxicity in diabetic mice in a p21-dependent manner.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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