Ciclopirox

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
  • B
Routes of
administration		 Topical (applied as a nail lacquer or shampoo)
Legal status
Legal status
Pharmacokinetic data
Bioavailability <5% with prolonged use
Protein binding 94 to 97%
Biological half-life 1.7 hours
Identifiers
CAS Number 29342-05-0 YesY
ATC code D01AE14 (WHO) G01AX12 (WHO)
PubChem CID 2749
DrugBank DB01188 YesY
ChemSpider 2647 YesY
UNII 19W019ZDRJ YesY
KEGG D03488 YesY
ChEBI CHEBI:453011 YesY
ChEMBL CHEMBL1413 YesY
Chemical data
Formula C12H17NO2
Molar mass 207.269 g/mol
  (verify)

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]

Indications for use

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).

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).

Efficacy in treating nail infections

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.

"Combining data from 2 trials of ciclopiroxolamine versus placebo found treatments failure rates of 61% and 64% for ciclopiroxolamine. These outcomes followed long treatment times (48 weeks) and this makes ciclopiroxolamine a poor choice for nail infections. Better results were observed with the use of amorolfine lacquer; 6% treatment failure rates were found after 1 month of treatment but these data were collected on a very small sample of people and these high rates of success might be unreliable."[7]


References

  1. 1 2 Drugs.com International brand names for ciclopirox Page accessed January 201, 2016
  2. ↑ "antifung". Retrieved 2008-07-09.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ The Cochrane Library: Topical treatments for fungal infections of the skin and nails of the foot, 2009.

External links

This article is issued from Wikipedia - version of the Wednesday, April 20, 2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.