SML2011

Ciclopirox

≥98% (HPLC)

• Synonyme(s) : Ciclopirox, 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone, HOE 296b, 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone
• Formule empirique (notation de Hill) : C₁₂H₁₇NO₂
• CAS Number: 29342-05-0
• Poids moléculaire : 207.27
• Numéro MDL: MFCD00599441
• Code UNSPSC : 12352200
• Nomenclature NACRES : NA.77

Propriétés

• Essai: ≥98% (HPLC)
• Forme: powder
• Couleur: white to beige
• Solubilité: DMSO: 2 mg/mL, clear
• Conditions d'expédition: ambient
• Température de stockage: 2-8°C
• Chaîne SMILES: 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
• Clé InChI: SCKYRAXSEDYPSA-UHFFFAOYSA-N

Description

Actions biochimiques/physiologiques

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.

Informations sur la sécurité

• Pictogrammes: GHS07
• Mention d'avertissement: Warning
• Mentions de danger: H302 + H312 + H332,H319
• Conseils de prudence: P261 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P305 + P351 + P338
• Classification des risques: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2
• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3