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SML2011

Sigma-Aldrich

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

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About This Item

Formule empirique (notation de Hill):
C12H17NO2
Numéro CAS:
29342-05-0
Poids moléculaire :
207.27
Numéro MDL:
MFCD00599441
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Pureté

≥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

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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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302 + H312 + H332,H319

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

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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
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
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
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
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