関: ciclopirox、ciclopirox olamine

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/11/02 10:31:10」(JST)

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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).

Research

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

^ "antifung". Retrieved 2008-07-09.
^ 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.
^ 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.
^ 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.
^ 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.
^ The Cochrane Library: Topical treatments for fungal infections of the skin and nails of the foot, 2009.
^ http://news.cnet.com/8301-11386_3-57604460-76/foot-cream-kills-hiv-by-tricking-cells-to-commit-suicide/
^ 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
^ http://www.ncbi.nlm.nih.gov/pubmed/23936064/

External links

English Journal

Interaction between ciclopirox and acenocoumarol.

Morales-Molina JA, Pérez-Moyano R, Fayet-Pérez A, Urquízar-Rodríguez O, Gíménez-López MJ.SourcePharmacy Department, Hospital de Poniente, 04700, El Ejido, Almería, Spain, joseantonio.morales@ephpo.es.
European journal of clinical pharmacology.Eur J Clin Pharmacol.2013 Mar;69(3):727-8. doi: 10.1007/s00228-012-1347-x. Epub 2012 Jul 12.
PMID 22791274

Nail penetration and predicted mycological efficacy of an innovative hydrosoluble ciclopirox nail lacquer vs. a standard amorolfine lacquer in healthy subjects.

Monti D, Herranz U, Dal Bo L, Subissi A.SourceDepartment of Pharmaceutical Sciences, University of Pisa, Pisa, Italy Cross Research S.A., Arzo, and IPAS Institute for Pharmacokinetic and Analytical Studies, Ligornetto, Switzerland.
Journal of the European Academy of Dermatology and Venereology : JEADV.J Eur Acad Dermatol Venereol.2013 Feb;27(2):e153-8. doi: 10.1111/j.1468-3083.2012.04529.x. Epub 2012 Mar 26.
Background In a previous study a new hydrosoluble nail lacquer (P-3051) containing 8% ciclopirox (CPX) showed higher nail penetration compared to a water-insoluble 5% amorolfine (MRF) lacquer. To our knowledge, in vivo human data on a similar topic are not available. Objectives To compare fing
PMID 22449201

Japanese Journal

2重盲検法によるCiclopirox Olamine液の白癬にたいする効果判定

日本皮膚科学会CiclopiroxOlamine研究班
西日本皮膚科 39(2), p247-253, 1977-04
NAID 40002795352

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リンク元	「シクロピロクスオラミン」

「シクロピロクスオラミン」

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.	B;
Legal status	US: ℞-only; 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	DB01188
ChemSpider	2647
UNII	19W019ZDRJ
KEGG	D03488
ChEBI	CHEBI:453011
ChEMBL	CHEMBL1413
Chemical data
Formula	C12H17NO2
Mol. mass	207.269 g/mol
	SMILES O=C1/C=C(\C=C(/N1O)C2CCCCC2)C;
	InChI InChI=1S/C12H17NO2/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10/h7-8,10,15H,2-6H2,1H3 ; Key:SCKYRAXSEDYPSA-UHFFFAOYSA-N ;
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英: ciclopirox olamine、ciclopiroxolamine
関: シクロピロクス
商: バトラフェン、オーラミンシクロピロックス

[urlantifung-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.

[pmid12760852-4] 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] ttp://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] ttp://www.ncbi.nlm.nih.gov/pubmed/23936064/

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案内

ciclopiroxolamine