SML2011
Ciclopirox
≥98% (HPLC)
Sinónimos:
Ciclopirox, 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone, HOE 296b, 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone
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Fórmula empírica (notación de Hill):
C12H17NO2
Número CAS:
Peso molecular:
207.27
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
Servicio técnico
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≥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
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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2
Clase de almacenamiento
11 - Combustible Solids
wgk
WGK 3
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Tao Shen et al.
Current pharmaceutical design, 22(28), 4443-4450 (2016-05-31)
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