Ciclopirox

Name: Ciclopirox
Brand: SIGMA

≥98% (HPLC)

Synonym(e):

Ciclopirox, 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridon

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Über diesen Artikel

Empirische Formel (Hill-System):

C₁₂H₁₇NO₂

CAS-Nummer:

29342-05-0

Molekulargewicht:

207.27

UNSPSC Code:

12352200

NACRES:

NA.77

MDL number:

MFCD00599441

Assay:

≥98% (HPLC)

Form:

powder

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Eigenschaften

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

Beschreibung

Biochem/physiol Actions

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.

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.