Ciclopirox

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Ciclopirox
Ciclopirox.svg
Systematic (IUPAC) name
6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one
Clinical data
Trade namesLoprox
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa604021
Pregnancy cat.B
Legal status-only (US) Rx-only (CA)
RoutesTopical (applied as a nail lacquer or shampoo)
Pharmacokinetic data
Bioavailability<5% with prolonged use
Protein binding94 to 97%
Half-life1.7 hours
Identifiers
CAS number29342-05-0 YesY
ATC codeD01AE14 G01AX12
PubChemCID 2749
DrugBankDB01188
ChemSpider2647 YesY
UNII19W019ZDRJ YesY
KEGGD03488 YesY
ChEBICHEBI:453011 YesY
ChEMBLCHEMBL1413 YesY
Chemical data
FormulaC12H17NO2 
Mol. mass207.269 g/mol
 YesY (what is this?)  (verify)
 
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Ciclopirox
Ciclopirox.svg
Systematic (IUPAC) name
6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one
Clinical data
Trade namesLoprox
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa604021
Pregnancy cat.B
Legal status-only (US) Rx-only (CA)
RoutesTopical (applied as a nail lacquer or shampoo)
Pharmacokinetic data
Bioavailability<5% with prolonged use
Protein binding94 to 97%
Half-life1.7 hours
Identifiers
CAS number29342-05-0 YesY
ATC codeD01AE14 G01AX12
PubChemCID 2749
DrugBankDB01188
ChemSpider2647 YesY
UNII19W019ZDRJ YesY
KEGGD03488 YesY
ChEBICHEBI:453011 YesY
ChEMBLCHEMBL1413 YesY
Chemical data
FormulaC12H17NO2 
Mol. mass207.269 g/mol
 YesY (what is this?)  (verify)

Ciclopirox olamine (used in preparations 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[edit]

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/or 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).

Research[edit]

Ciclopirox has been found to permanently eradicate HIV in cell cultures. It is hoped that it may do the same in the human body, although trials are yet to begin. [7] [8] It also has shown activity against Acinetobacter baumannii. [9]

References[edit]

  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. doi:10.1128/AAC.47.6.1805-1817.2003. PMC 155814. PMID 12760852. 
  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. 
  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. 
  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. 
  6. ^ The Cochrane Library: Topical treatments for fungal infections of the skin and nails of the foot, 2009.
  7. ^ http://news.cnet.com/8301-11386_3-57604460-76/foot-cream-kills-hiv-by-tricking-cells-to-commit-suicide/
  8. ^ Hanauske-Abel HM, Saxena D, Palumbo PE, Hanauske A-R, Luchessi AD, et al. (2013) Drug-Induced Reactivation of Apoptosis Abrogates HIV-1 Infection. PLoS ONE 8(9): e74414. doi:10.1371/journal.pone.0074414 http://www.plosone.org/article/info%3Adoi%2F10.1371%2Fjournal.pone.0074414
  9. ^ http://www.ncbi.nlm.nih.gov/pubmed/23936064/

External links[edit]