Ciclopirox
 | |
| Systematic (IUPAC) name | |
|---|---|
|
6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one | |
| Clinical data | |
| Trade names | Many brand names worldwide[1] |
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| MedlinePlus | a604021 |
| Pregnancy category |
|
| Legal status | |
| Routes of administration | Topical (applied as a nail lacquer or shampoo) |
| Pharmacokinetic data | |
| Bioavailability | <5% with prolonged use |
| Protein binding | 94 to 97% |
| Biological half-life | 1.7 hours |
| Identifiers | |
| CAS Number |
29342-05-0  |
| ATC code | D01AE14 G01AX12 |
| PubChem | CID 2749 |
| DrugBank |
DB01188 |
| ChemSpider |
2647 |
| UNII |
19W019ZDRJ |
| KEGG |
D03488 |
| ChEBI |
CHEBI:453011 |
| ChEMBL |
CHEMBL1413 |
| Chemical data | |
| Formula | C12H17NO2 |
| Molar mass | 207.269 g/mol |
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Ciclopirox olamine is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. It is most useful against Tinea versicolor.[2] It is sold under many brand names worldwide.[1]
Mechanism of action
In contrast to the azoles and other antimycotic drugs, the mechanism of action of ciclopirox is poorly understood.[3] 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.[4] It acts by inhibiting the membrane transfer system by interrupting the Na+ K+ ATPase.[5] 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.[6]
Ciclopirox is a considered a hydroxypyrimidine antifungal agent (Paddock Laboratories, Inc., Oct. 2009).
In addition to other formulations, ciclopirox is used in lacquers for topical treatment of onychomycosis (fungal infections of the nails). A meta-analysis of the six trials of nail infections available in 2009 concluded that they provided evidence that topical ciclopiroxolamine had poor cure rates and that amorolfine might be substantially more effective, but more research was required.[7]
Ciclopirox is indicated for the treatment of tinea pedis and tinea corporis due to Trichophyton rubrum, Trichophyton mentagrophytes and Epidermophyton floccosum, as well as seborrheic dermatitis. It is not to be used in the eyes or vagina, and nursing women should consult their doctors before use, since it is not known whether ciclopirox passes into human milk. A burning sensation may be felt when first applying ciclopirox (Paddock Laboratories, Inc., Oct. 2009).
References
- 1 2 Drugs.com International brand names for ciclopirox Page accessed January 201, 2016
- ↑ "antifung". Retrieved 2008-07-09.
- ↑ Niewerth M, Kunze D, Seibold M, Schaller M, Korting HC, Hube B. (June 2003). "Ciclopirox Olamine Treatment Affects the Expression Pattern of Candida albicans Genes Encoding Virulence Factors, Iron Metabolism Proteins, and Drug Resistance Factors". Antimicrobial Agents and Chemotherapy 47 (6): 1805–17. doi:10.1128/AAC.47.6.1805-1817.2003. PMC 155814. PMID 12760852.
- ↑ 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:10.1128/AAC.47.6.1805-1817.2003. PMC 155814. 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:10.1080/16537150601092944. PMID 17520465.
- ↑ The Cochrane Library: Topical treatments for fungal infections of the skin and nails of the foot, 2009.
External links
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