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Ciclopirox
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| Systematic (IUPAC) name | |
| 6-cyclohexyl-1-hydroxy-4-methyl-pyridin-2-one | |
| Identifiers | |
| CAS number | |
| ATC code | D01 G01 |
| PubChem | |
| DrugBank | |
| ChemSpider | |
| Chemical data | |
| Formula | C12H17NO2 |
| Mol. mass | 207.269 g/mol |
| Pharmacokinetic data | |
| Bioavailability | <5% with prolonged use |
| Protein binding | 94 to 97% |
| Metabolism | ? |
| Half life | 1.7 hours |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | Topical (applied as a nail lacquer) |
Ciclopirox olamine (also called Batrafen Loprox, Penlac and Stieprox) is a synthetic antifungal agent for topical dermatologic use. Antifungal nail chelation with critical trivalent cations resulting in downstream effects.
It is most useful against Tinea versicolour.[1]
Mechanism
Loss of function of certain catalase and peroxidase enzymes has been implicated 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.[3]. 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.[4]
References
- ^ "antifung". Retrieved on 2008-07-09.
- ^ Leem SH, Park JE, Kim IS, Chae JY, Sugino A, Sunwoo Y (2003). "The possible mechanism of action of ciclopirox olamine in the yeast Saccharomyces cerevisiae". Mol. Cells 15 (1): 55–61. PMID 12661761.
- ^ Niewerth M, Kunze D, Seibold M, Schaller M, Korting HC, Hube B (2003). "Ciclopirox olamine treatment affects the expression pattern of Candida albicans genes encoding virulence factors, iron metabolism proteins, and drug resistance factors". Antimicrob. Agents Chemother. 47 (6): 1805–17. doi:. PMID 12760852.
- ^ Ratnavel RC, Squire RA, Boorman GC (2007). "Clinical efficacies of shampoos containing ciclopirox olamine (1.5%) and ketoconazole (2.0%) in the treatment of seborrhoeic dermatitis". J Dermatolog Treat 18 (2): 88–96. doi:. PMID 17520465.
External links
- Loprox official product website, run by Medicis
- Penlac official product website, run by sanofi-aventis
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Wikipedia content modification information:
- This page was last modified on 1 October 2008, at 02:52.
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