SML2011
Ciclopirox
≥98% (HPLC)
Synonym(s):
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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About This Item
Empirical Formula (Hill Notation):
C12H17NO2
CAS Number:
Molecular Weight:
207.27
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
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
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.
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Warning
hcodes
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2
Storage Class
11 - Combustible Solids
wgk
WGK 3
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Tao Shen et al.
Current pharmaceutical design, 22(28), 4443-4450 (2016-05-31)
Ciclopirox (CPX) has been used as an antifungal agent in various formulations to treat superficial fungal infection for decades. Its effectiveness and safety in treatments have been demonstrated by multiple studies. Here we briefly summarize the pharmacological and toxicological properties
Calogero S Messina et al.
Anticancer research, 37(2), 555-559 (2017-02-10)
Prostate cancer is the most common cancer in the Western world. A bi-functional peptide was combined with wingless-related integration site (WNT) inhibitors to determine if there is an additive therapeutic effect when they are used against prostate cancer, since their
Tatiana Arlette M Togue et al.
Planta medica, 86(17), 1298-1303 (2020-07-30)
A phytochemical study of the methanol extract of the leaves of Embelia schimperi resulted in the isolation of three new alkenylresorcinols, 1: - 3: , together with the known analogs 4: - 7: . Their structures were established by a combination of