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Merck
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SML2011

Sigma-Aldrich

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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About This Item

Fórmula empírica (notación de Hill):
C12H17NO2
Número de CAS:
29342-05-0
Peso molecular:
207.27
Número MDL:
MFCD00599441
Código UNSPSC:
12352200
NACRES:
NA.77

Análisis

≥98% (HPLC)

formulario

powder

color

white to beige

solubilidad

DMSO: 2 mg/mL, clear

Condiciones de envío

ambient

temp. de almacenamiento

2-8°C

cadena 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

Clave InChI

SCKYRAXSEDYPSA-UHFFFAOYSA-N

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Acciones bioquímicas o fisiológicas

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.

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H302 + H312 + H332,H319

Clasificaciones de peligro

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Certificados de análisis (COA)

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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
Alessandro Subissi et al.
Drugs, 70(16), 2133-2152 (2010-10-23)
Ciclopirox is a topical antimycotic agent belonging to the chemical class of hydroxypyridones and not related to azoles or any other class of antifungal agents. Its antimicrobial profile includes nearly all of the clinically relevant dermatophytes, yeasts and moulds, and
Chrysovalantou Mihailidou et al.
Pflugers Archiv : European journal of physiology, 468(11-12), 1957-1968 (2016-10-21)
Pancreatic dysfunction during diabetes is linked to the induction of endoplasmic reticulum (ER) stress on pancreatic beta (β) cells. Our laboratory recently discovered that p21 protects from diabetes by modifying the outcome of ER stress response. In the present study
Federica Riccio et al.
Cell death discovery, 8(1), 16-16 (2022-01-12)
Repurposing of drugs for new therapeutic use has received considerable attention for its potential to limit time and cost of drug development. Here we present a new strategy to identify chemicals that are likely to promote a desired phenotype. We
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