Ciclopirox

Ciclopirox
Systematic (IUPAC) name
6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one
Clinical data
Trade names Loprox
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a604021
Pregnancy cat.  ?
Legal status ℞-only (US) Rx-only (CA)
Routes Topical (applied as a nail lacquer or shampoo)
Pharmacokinetic data
Bioavailability <5% with prolonged use
Protein binding 94 to 97%
Half-life 1.7 hours
Identifiers
CAS number 29342-05-0
ATC code D01AE14 G01AX12
PubChem CID 2749
DrugBank APRD00871
ChemSpider 2647 Y
UNII 19W019ZDRJ Y
KEGG D03488 Y
ChEBI CHEBI:453011 Y
ChEMBL CHEMBL1413 Y
Chemical data
Formula C12H17NO2 
Mol. mass 207.269 g/mol
SMILES eMolecules & PubChem
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Ciclopirox olamine (also called Batrafen, Loprox, Mycoster, Penlac and Stieprox) is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. It is most useful against Tinea versicolor.[1]

Mechanism of action

In contrast to the azoles and other antimycotic drugs, the mechanism of action of ciclopirox is only poorly understood.[2] 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. [3]

It acts by inhibiting the membrane transfer system by interrupting the Na+ K+ ATPase.[4] 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.[5]

References

  1. ^ "antifung". http://faculty.swosu.edu/scott.long/phcl/antifung.htm. Retrieved 2008-07-09. 
  2. ^ 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=155814. 
  3. ^ 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. http://www.molcells.org/home/journal/article_read.asp?volume=15&number=1&startpage=55. 
  4. ^ 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=155814. 
  5. ^ 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. 

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