29342-05-0

29342-05-0 structure

Name: Ciclopirox
Chemical Name: ciclopirox
CAS Number: 29342-05-0
Molecular Formula: C₁₂H₁₇NO₂
Molecular Weight: 207.269
Catalog: API Synthetic anti-infective drugs Antifungal drugs
Create Date: 2018-02-20 08:00:00
Modify Date: 2024-01-02 13:50:39
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].

Name	ciclopirox
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

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.

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

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

504-29-0

14818-35-0

29342-05-0

Literature: Hoechst Aktiengesellschaft Patent: US3972888 A1, 1976 ;

288-32-4

14818-35-0

29342-05-0

Literature: Hoechst Aktiengesellschaft Patent: US3972888 A1, 1976 ;

504-29-0

1824-81-3

14818-35-0

29342-05-0

Literature: Hoechst Aktiengesellschaft Patent: US3972888 A1, 1976 ;

14818-35-0

29342-05-0

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

924-50-5

2719-27-9

29342-05-0

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

Precursor 6
504-29-0 14818-35-0 288-32-4 1824-81-3
924-50-5 2719-27-9
DownStream 0

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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1279033-13-4