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Ciclopirox
|
| Systematic (IUPAC) name |
|
6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one
|
| Clinical data |
| Trade names |
Many brand names worldwide[1] |
| Drugs.com |
Micromedex Detailed Consumer Information |
| MedlinePlus |
a604021 |
Pregnancy
category |
|
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 Y |
| ATC code |
D01AE14 (WHO) G01AX12 (WHO) |
| PubChem |
CID 2749 |
| DrugBank |
DB01188 Y |
| ChemSpider |
2647 Y |
| UNII |
19W019ZDRJ Y |
| KEGG |
D03488 Y |
| ChEBI |
CHEBI:453011 Y |
| ChEMBL |
CHEMBL1413 Y |
| Chemical data |
| Formula |
C12H17NO2 |
| Molar 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
|
| (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]
Contents
- 1 Indications for use
- 2 Mechanism of action
- 3 Efficacy in treating nail infections
- 4 References
- 5 External links
Indications for use
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
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
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]
References
- ^ a b Drugs.com International brand names for ciclopirox Page accessed January 201, 2016
- ^ "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.
External links
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Antifungals (D01 and J02)
|
|
Wall/
membrane |
Ergosterol
inhibitors |
Azoles
(lanosterol 14
alpha-demethylase inhibitors) |
| Imidazoles |
- Topical: bifonazole‡
- chlormidazole‡
- croconazole‡
- fenticonazole‡
- isoconazole‡
- luliconazole
- neticonazole‡
- omoconazole‡
- butoconazole
- clotrimazole#
- econazole
- ketoconazole
- miconazole#
- oxiconazole
- sertaconazole
- sulconazole
- tioconazole
|
|
| Triazoles |
- Topical: fluconazole#, fosfluconazole
- efinaconazole
- terconazole
- Systemic: hexaconazole‡
- isavuconazole
- fluconazole#
- itraconazole
- posaconazole
- voriconazole
|
|
| Thiazoles |
|
|
|
Polyene antimycotics
(ergosterol binding) |
- Topical: hamycin‡
- natamycin
- nystatin#
Systemic: amphotericin B#, hamycin‡
|
|
Allylamines
(squalene monooxygenase
inhibitors) |
- Topical: amorolfine‡
- butenafine
- naftifine
- terbinafine
Systemic: terbinafine
|
|
|
β-glucan synthase
inhibitors |
- echinocandins (anidulafungin
- caspofungin
- micafungin)
|
|
|
| Intracellular |
Pyrimidine analogues/
thymidylate synthase inhibitors |
|
|
| Mitotic inhibitors |
|
|
| Aminoacyl tRNA synthetase inhibitors |
|
|
|
| Others |
- bromochlorosalicylanilide
- methylrosaniline
- tribromometacresol
- undecylenic acid
- polynoxylin
- chlorophetanol
- chlorphenesin
- ticlatone
- sulbentine
- ethylparaben
- haloprogin
- salicylic acid
- selenium disulfide#
- 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
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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|
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Gynecological anti-infectives and antiseptics (G01)
|
|
| Antibiotics |
- Candicidin
- Chloramphenicol
- Hachimycin
- Oxytetracycline
- Carfecillin
- Mepartricin
- Clindamycin
- Pentamycin
|
|
| Arsenic compounds |
|
|
| Quinoline derivatives |
- Diiodohydroxyquinoline
- Clioquinol
- Chlorquinaldol
- Dequalinium
- Broxyquinoline
- Oxyquinoline
|
|
| Organic acids |
- Lactic acid
- Acetic acid
- Ascorbic acid
|
|
| Sulfonamides |
|
|
| Antifungals |
| Imidazoles |
- Metronidazole
- Clotrimazole
- Miconazole
- Econazole
- Ornidazole
- Isoconazole
- Tioconazole
- Ketoconazole
- Fenticonazole
- Azanidazole
- Propenidazole
- Butoconazole
- Omoconazole
- Oxiconazole
- Flutrimazole
|
|
| Triazoles |
|
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| Polyenes |
- Nystatin
- Natamycin
- Amphotericin B
|
|
| Other |
- Ciclopirox
- Methylrosaniline
|
|
|
| Other |
- Clodantoin
- Inosine
- Policresulen
- Nifuratel
- Furazolidone
- Povidone-iodine
- Protiofate
- Lactobacillus fermentum
- Copper usnate
|
|
UpToDate Contents
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English Journal
- Application of Hansen Solubility Parameters to predict drug-nail interactions, which can assist the design of nail medicines.
- Hossin B1, Rizi K1, Murdan S2.
- European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V.Eur J Pharm Biopharm.2016 Feb 23. pii: S0939-6411(16)30011-X. doi: 10.1016/j.ejpb.2016.02.009. [Epub ahead of print]
- We hypothesised that Hansen Solubility Parameters (HSPs) can be used to predict drug-nail affinities. Our aims were to: (i) determine the HSPs (δD, δP, δH) of the nail plate, the hoof membrane (a model for the nail plate), and of the drugs terbinafine HCl, amorolfine HCl, ciclopirox olamine and e
- PMID 26924329
- Efinaconazole and Tavaborole: Emerging Antifungal Alternatives for the Topical Treatment of Onychomycosis.
- Poulakos M1, Grace Y2, Machin JD1, Dorval E1.
- Journal of pharmacy practice.J Pharm Pract.2016 Feb 11. pii: 0897190016630904. [Epub ahead of print]
- PURPOSE: The purpose of this article is to review the safety, efficacy, and role of efinaconazole and tavaborole in the treatment of onychomycosis.SUMMARY: Onychomycosis is a fungal infection of the nail caused by dermatophytes, yeasts, and nondermatophyte fungi. Distal and lateral subungual onychom
- PMID 26873506
- Evaluation of the Efficacy of ME1111 in the Topical Treatment of Dermatophytosis in a Guinea Pig Model.
- Long L1, Hager C1, Ghannoum M2.
- Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2016 Feb 1. pii: AAC.03073-15. [Epub ahead of print]
- The treatment of dermatophytosis including onychomycosis has come a long way over the past few decades with the introduction of oral antifungals (e.g. terbinafine and itraconazole). However, with these advancements in oral therapies come several undesirable effects such as kidney and liver toxicity,
- PMID 26833160
Japanese Journal
- Ciclopirox nail lacquer for the treatment of onychomycosis : An open non-comparative study
- SHEMER Avner,NATHANSOHN Nir,TRAU Henri,AMICHAI Boaz,GRUNWALD Marcelo H.
- Journal of dermatology 37(2), 137-139, 2010-02-01
- NAID 10027065700
- Effects of Antifungal Drugs on Proliferation Signals in Candida albicans(Microbiology)
- MATSUKI Mitsuo,KANATSU Hatsuki,WATANABE Toshihiko,OGASAWARA Ayako,MIKAMI Takeshi,MATSUMOTO Tatsuji
- 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
- 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
- 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.
Related Pictures
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[★]
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- ciclopirox、ciclopirox olamine
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- 英
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[★]
シクロピロクスオラミン
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