Ciclopirox: Difference between revisions
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| IUPAC_name = 6-cyclohexyl-1-hydroxy-4-methyl- |
| IUPAC_name = 6-cyclohexyl-1-hydroxy-4-methyl-1,2-dihydropyridin-2-one |
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| image = Ciclopirox.svg |
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Revision as of 10:25, 21 December 2008
 | This article may require copy editing for grammar, style, cohesion, tone, or spelling. (June 2008) |
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| Clinical data | |
|---|---|
| Routes of administration | Topical (applied as a nail lacquer) |
| ATC code | |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Bioavailability | <5% with prolonged use |
| Protein binding | 94 to 97% |
| Elimination half-life | 1.7 hours |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.045.056 |
| Chemical and physical data | |
| Formula | C12H17NO2 |
| Molar mass | 207.269 g/mol g·mol−1 |
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 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.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ 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:10.1128/AAC.47.6.1805-1817.2003. PMID 12760852.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ 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:10.1080/16537150601092944. PMID 17520465.
{{cite journal}}: CS1 maint: multiple names: authors list (link)
External links
- Loprox official product website, run by Medicis
- Penlac official product website, run by sanofi-aventis