Ciclopirox

Modify Date: 2024-01-02 13:50:39

Ciclopirox Structure
Ciclopirox structure
Common Name Ciclopirox
CAS Number 29342-05-0 Molecular Weight 207.269
Density 1.2±0.1 g/cm3 Boiling Point 350.0±25.0 °C at 760 mmHg
Molecular Formula C12H17NO2 Melting Point 1440C
MSDS N/A Flash Point 165.5±23.2 °C
Symbol GHS07
GHS07
Signal Word Warning

 Use of Ciclopirox


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].

 Names

Name ciclopirox
Synonym More Synonyms

 Ciclopirox 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
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.

 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
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

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Ciclopirox Structure

Ciclopirox

CAS#:29342-05-0

Literature: Hoechst Aktiengesellschaft Patent: US3972888 A1, 1976 ;

~%

Ciclopirox Structure

Ciclopirox

CAS#:29342-05-0

Literature: Hoechst Aktiengesellschaft Patent: US3972888 A1, 1976 ;

~%

Ciclopirox Structure

Ciclopirox

CAS#:29342-05-0

Literature: Hoechst Aktiengesellschaft Patent: US3972888 A1, 1976 ;

~%

Ciclopirox Structure

Ciclopirox

CAS#:29342-05-0

Literature: Lohaus; Dittmar Arzneimittel-Forschung/Drug Research, 1981 , vol. 31, # 8 a p. 1311 - 1316

~%

Ciclopirox Structure

Ciclopirox

CAS#:29342-05-0

Literature: Lohaus; Dittmar Arzneimittel-Forschung/Drug Research, 1981 , vol. 31, # 8 a p. 1311 - 1316

 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.

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 Synonyms

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
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