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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 |
℞-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 Y |
| ATC code |
D01AE14 G01AX12 |
| PubChem |
CID 2749 |
| DrugBank |
DB01188 |
| 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
- 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 Y
Key:SCKYRAXSEDYPSA-UHFFFAOYSA-N Y
|
| Y (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]
Contents
- 1 Mechanism of action
- 2 Research
- 3 References
- 4 External links
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
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Antifungals (D01 and J02)
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|
Wall/
membrane |
|
Ergosterol
inhibitors
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Azoles
(lanosterol 14
alpha-demethylase inhibitors) |
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Imidazoles
|
- topical: Bifonazole
- Butoconazole
- Clomidazole
- Clotrimazole#, Croconazole
- Econazole
- Fenticonazole
- Ketoconazole
- Isoconazole
- Miconazole#, Neticonazole
- Omoconazole
- Oxiconazole
- Sertaconazole
- Sulconazole
- Tioconazole
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|
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Triazoles
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- topical: (Fluconazole#, Fosfluconazole
- Terconazole)
- systemic: (Fluconazole
- Hexaconazole
- Isavuconazole†, Itraconazole
- Posaconazole
- Voriconazole)
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|
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Thiazoles
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topical: (Abafungin)
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Polyene antimycotics
(ergosterol binding)
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- topical: (Hamycin
- Natamycin
- Nystatin#)
systemic: (Amphotericin B#, Hamycin)
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Allylamines
(squalene monooxygenase
inhibitors) |
- topical: (Amorolfine
- Butenafine
- Naftifine
- Terbinafine)
systemic: (Terbinafine)
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|
|
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β-glucan synthase
inhibitors
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- echinocandins (Anidulafungin
- Caspofungin
- Micafungin)
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| Intracellular |
|
Pyrimidine analogues/
Thymidylate synthase inhibitors
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Mitotic inhibitors
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|
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| Others |
- Bromochlorosalicylanilide
- Methylrosaniline
- Tribromometacresol
- Undecylenic acid
- Polynoxylin
- Chlorophetanol
- Chlorphenesin
- Ticlatone
- Sulbentine
- Ethylparaben
- Haloprogin
- Salicylic acid
- Selenium sulfide#
- Ciclopirox
- Amorolfine
- Dimazole
- Tolnaftate
- Tolciclate
- Sodium thiosulfate#
- Whitfield's ointment#
- Potassium iodide#
- Taurolidine
- Tea tree oil
- citronella oil
- lemon grass
- orange oil
- patchouli
- lemon myrtle
- PCP: Pentamidine
- Dapsone
- Atovaquone
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Gynecological anti-infectives and antiseptics (G01)
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| Antibiotics |
- Candicidin
- Chloramphenicol
- Hachimycin
- Oxytetracycline
- Carfecillin
- Mepartricin
- Clindamycin
- Pentamycin
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| Arsenic compounds |
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| Quinoline derivatives |
- Diiodohydroxyquinoline
- Clioquinol
- Chlorquinaldol
- Dequalinium
- Broxyquinoline
- Oxyquinoline
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| Organic acids |
- Lactic acid
- Acetic acid
- Ascorbic acid
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| Sulfonamides |
|
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| Antifungals |
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Imidazoles
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- Metronidazole
- Clotrimazole
- Miconazole
- Econazole
- Ornidazole
- Isoconazole
- Tioconazole
- Ketoconazole
- Fenticonazole
- Azanidazole
- Propenidazole
- Butoconazole
- Omoconazole
- Oxiconazole
- Flutrimazole
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Triazoles
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Polyenes
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- Nystatin
- Natamycin
- Amphotericin B
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Other
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- Ciclopirox
- Methylrosaniline
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|
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| Other |
- Clodantoin
- Inosine
- Policresulen
- Nifuratel
- Furazolidone
- Povidone-iodine
- Protiofate
- Lactobacillus fermentum
- Copper usnate
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noco/cong/npls, sysi/epon
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proc/asst, drug (G1/G2B/G3CD)
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UpToDate Contents
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English Journal
- In vitro permeation and penetration of ciclopirox olamine from poloxamer 407-based formulations - comparison of isolated human stratum corneum, bovine hoof plates and keratin films.
- Täuber A1, Müller-Goymann CC2.
- International journal of pharmaceutics.Int J Pharm.2015 Jul 15;489(1-2):73-82. doi: 10.1016/j.ijpharm.2015.04.043. Epub 2015 Apr 17.
- Fungal infections of skin and/or nails are common diseases resulting in major challenges in topical treatment. Therefore, the objective of the present study was to develop a dermal formulation targeting both tinea pedis and onychomycosis. The antifungal agent ciclopirox olamine (CPX) was incorporate
- PMID 25895717
- In Vitro Antifungal Activity of ME1111, a New Topical Agent for Onychomycosis, against Clinical Isolates of Dermatophytes.
- Ghannoum M1, Isham N2, Long L2.
- Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2015 Jun 8. pii: AAC.00992-15. [Epub ahead of print]
- BACKGROUND: The treatment of onychomycosis has improved considerably over the past several decades following the introduction of the oral antifungals terbinafine and itraconazole. However, these oral agents suffer from certain disadvantages, including drug interactions and potential liver toxicity.
- PMID 26055386
- [Cutaneous Malassezia infections and Malassezia associated dermatoses : An update].
- Nenoff P1, Krüger C, Mayser P.
- Der Hautarzt; Zeitschrift für Dermatologie, Venerologie, und verwandte Gebiete.Hautarzt.2015 Jun;66(6):465-86. doi: 10.1007/s00105-015-3631-z.
- The lipophilic yeast fungus Malassezia (M.) spp. is the only fungal genus or species which is part of the physiological human microbiome. Today, at least 14 different Malassezia species are known; most of them can only be identified using molecular biological techniques. As a facultative pathogenic
- PMID 25968082
Japanese Journal
- Effects of Antifungal Drugs on Proliferation Signals in Candida albicans(Microbiology)
- , , [他], , ,
- Biological & pharmaceutical bulletin 29(5), 919-922, 2006-05-01
- … Ciclopirox olamine and siccanin were more effective under aerobic than under anaerobic conditions. …
- NAID 110005602214
- Crystal Structure of Ciclopirox Olamine
- ,
- Analytical Sciences: X-ray Structure Analysis Online 19, X21-X22, 2003
- … The crystal structure of ciclopirox was determined. … There are two ciclopirox molecules, of which one is neutral and the other is negatively charged, and one positively charged 2-amino ethanol molecule in an asymmetric unit. …
- NAID 130004442506
- A randomised, single-blind, single-centre clinical trial to evaluate comparative clinical efficacy of shampoos containing ciclopirox olamine (1.5%) and salicylic acid (3%), or ketoconazole (2%, Nizoral) for the treatment of dandruff/seorrhoeic dermatitis
Related Links
- ci·clo·pir·ox ol·a·mine (sī′klō-pîr′ŏks′ ô′lə-mēn′, sĭk′lō-) n. A broad-spectrum antifungal agent used in the treatment of a variety of fungal and yeast infections of the skin. ciclopirox olamine (sik´lōpē´roks) (topical), n brand name: Loprox; ...
- Ciclopirox Olamine reference guide for safe and effective use from the American Society of Health-System Pharmacists (AHFS DI). ... Cautions for Ciclopirox Olamine Contraindications Known hypersensitivity to ciclopirox, ciclopirox ...
Related Pictures
★リンクテーブル★
[★]
- 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
[★]
- 英
- ciclopirox、ciclopirox olamine
- 関
- シクロピロクスオラミン、シクロピロックス
[★]
シクロピロクスオラミン
- 関
- ciclopirox、ciclopirox olamine