Ciclopirox

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Ciclopirox
Ciclopirox.svg
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[edit]

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[edit]

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[edit]

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]

New Developments in treatment of HIV/AIDS[edit]

"...(S)cientists have discovered that an anti-fungal drug known as Ciclopirox causes HIV to commit suicide. The cells have a natural suicide mechanism in it that activates if the cell is damaged or impacted by things like a virus, making it easier for the healthy specimens to procreate. This drug can trick the cells into turning off the mechanism that keeps it from killing itself, eradicating the HIV infected cells without harming the healthy cells. Essentially, the Ciclopirox impacts the HIV by jamming up the mitochondria in the cell. So this new drug combats HIV in two ways: It inhibits the expression of HIV genes, and (this is the kicker) it blocks the function of the mitochondria. This block reactivates the cell’s suicide pathway. Notably, the healthy, uninfected cells that were a part of the culture were not impacted or destroyed. Amazingly, the virus did not bounce back when Ciclopirox was removed.

And unlike current anti-HIV drugs, Ciclopirox completely eradicates infectious HIV from cell cultures, with no rebound of virus when the drug is stopped."[8][9]

References[edit]

  1. ^ a b 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 155814free to read. 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 155814free to read. 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.
  8. ^ "Scientist Find Possible Cure for HIV in an Unusual Place". 2014-02-20. Retrieved 2016-08-09. 
  9. ^ Hoque, Mainul; Hanauske-Abel, Hartmut M; Palumbo, Paul; Saxena, Deepti; D'Alliessi Gandolfi, Darlene; Park, Myung Hee; Pe'ery, Tsafi; Mathews, Michael B (2009-10-13). "Inhibition of HIV-1 gene expression by Ciclopirox and Deferiprone, drugs that prevent hypusination of eukaryotic initiation factor 5A". Retrovirology. 6: 90. doi:10.1186/1742-4690-6-90. ISSN 1742-4690. PMC 2770518free to read. PMID 19825182. 

External links[edit]