Ciclopirox

Ciclopirox

Ciclopirox
Systematic (IUPAC) name
6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one
Clinical data
Trade names Loprox
AHFS/Drugs.com
MedlinePlus
Pregnancy
category
  • B
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 Registry Number  Y
ATC code D01 G01
PubChem CID:
DrugBank  Y
ChemSpider  Y
UNII  Y
KEGG  Y
ChEBI  Y
ChEMBL  Y
Chemical data
Formula C12H17NO2
Molecular mass 207.269 g/mol
 Y   

Ciclopirox olamine (used in preparations called Batrafen, Loprox, Rejuvenail, 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 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]

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.[6]

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. ^ "antifung". 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.  
  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.  
  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.  
  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.  
  6. ^ The Cochrane Library: Topical treatments for fungal infections of the skin and nails of the foot, 2009.

External links