Ciclopirox

Names

[ Name ]:
Ciclopirox

[Synonym ]:
Ciclopirox Olamine
6-cyclohexyl-1-hydroxy-4-méthylpyridin-2(1H)-one
Terit
6-cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone
MFCD00599441
Ciclopirox
6-Cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one
Ciclopirox (USP)
Mycoster
cyclopirox
EINECS 249-577-2
6-Cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-on
Stieprox
Loprox
Ciclopiroxum
1-Hydroxy-4-methyl-6-cyclohexyl-2-pyridone
Penlac
(6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone)
6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone
2(1H)-Pyridinone, 6-cyclohexyl-1-hydroxy-4-methyl-
6-cyclohexyl-1-hydroxy-4-methyl-1,2-dihydropyridin-2-one
Batrafen
6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one

Biological Activity

[Description]:

Ciclopirox (Penlac) is a synthetic antifungal agent.Target: AntifungalCiclopirox is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. It is most useful against Tinea versicolor. The mechanism of action of ciclopirox is poorly understood [1]. However, loss of function of certain catalase and peroxidase enzymes has been implicated as the mechanism of action, as well as various other components of cellular metabolism. In a study conducted to further elucidate ciclopirox's mechanism, several Saccharomyces cerevisiae mutants were screened and tested. Results from interpretation of the effects of both the drug treatment and mutation suggested that ciclopirox may exert its effect by disrupting DNA repair, cell division signals and structures (mitotic spindles) as well as some elements of intracellular transport [2]. It acts by inhibiting the membrane transfer system by interrupting the Na+ K+ ATPase [1]. It is currently being investigated as an alternative treatment to ketoconazole for seborrhoeic dermatitis as it suppresses growth of the yeast Malassezia furfur. Initial results show similar efficacy to ketoconazole with a relative increase in subjective symptom relief due to its inherent anti-inflammatory properties [3].

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Anti-infection >> Fungal

Research Areas >> Infection

[References]

[1]. Niewerth, M., et al., Ciclopirox olamine treatment affects the expression pattern of Candida albicans genes encoding virulence factors, iron metabolism proteins, and drug resistance factors. Antimicrob Agents Chemother, 2003. 47(6): p. 1805-17.

[2]. Leem, S.H., et al., The possible mechanism of action of ciclopirox olamine in the yeast Saccharomyces cerevisiae. Mol Cells, 2003. 15(1): p. 55-61.

[3]. Ratnavel, R.C., R.A. Squire, and G.C. Boorman, Clinical efficacies of shampoos containing ciclopirox olamine (1.5%) and ketoconazole (2.0%) in the treatment of seborrhoeic dermatitis. J Dermatolog Treat, 2007. 18(2): p. 88-96.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
350.0±25.0 °C at 760 mmHg

[ Melting Point ]:
1440C

[ Molecular Formula ]:
C₁₂H₁₇NO₂

[ Molecular Weight ]:
207.269

[ Flash Point ]:
165.5±23.2 °C

[ Exact Mass ]:
207.125931

[ PSA ]:
42.23000

[ LogP ]:
2.59

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.582

[ Storage condition ]:
-20°C Freezer

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Hazard Codes ]:
C,O

[ Risk Phrases ]:
R8:Contact with combustible material may cause fire. R35:Causes severe burns. R34:Causes burns. R20:Harmful by inhalation.

[ Safety Phrases ]:
S23-S26-S36-S45

[ RIDADR ]:
UN 3264 8/PG 3

[ WGK Germany ]:
1

[ RTECS ]:
QU5900000

[ Packaging Group ]:
II

[ Hazard Class ]:
8

[ HS Code ]:
2933790090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933399090

[ Summary ]:
2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Thermogelling hydrogels of cyclodextrin/poloxamer polypseudorotaxanes as aqueous-based nail lacquers: application to the delivery of triamcinolone acetonide and ciclopirox olamine.

Eur. J. Pharm. Biopharm. 83(3) , 370-7, (2013)

This work investigated the use of in situ gelling hydrogels based on polypseudorotaxanes of Pluronic F-127 and partially methylated β-cyclodextrin as aqueous nail lacquers. N-acetylcysteine and urea w...