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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/11/29 03:41:16」(JST)
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Butenafine
|
| Clinical data |
| Trade names |
Mentax, Lotrimin Ultra |
| AHFS/Drugs.com |
Monograph |
Pregnancy
category |
|
Routes of
administration |
Topical (cream) |
| ATC code |
D01AE23 (WHO) |
| Legal status |
| Legal status |
- OTC (Lotrimin Ultra),
℞-only (Mentax)
|
| Pharmacokinetic data |
| Metabolism |
Hepatic |
| Biological half-life |
35–100 hours |
| Identifiers |
|
Systematic (IUPAC) name: [(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
|
| CAS Number |
101828-21-1 Y |
| PubChem (CID) |
2484 |
| DrugBank |
DB01091 Y |
| ChemSpider |
2390 Y |
| UNII |
91Y494NL0X Y |
| KEGG |
D07596 Y |
| ChEBI |
CHEBI:3238 Y |
| ChEMBL |
CHEMBL990 Y |
| Chemical and physical data |
| Formula |
C23H27N |
| Molar mass |
317.47 g/mol |
| 3D model (Jmol) |
Interactive image |
SMILES
-
N(C)(Cc1ccc(cc1)C(C)(C)C)Cc3c2ccccc2ccc3
|
InChI
-
InChI=1S/C23H27N/c1-23(2,3)21-14-12-18(13-15-21)16-24(4)17-20-10-7-9-19-8-5-6-11-22(19)20/h5-15H,16-17H2,1-4H3 Y
-
Key:ABJKWBDEJIDSJZ-UHFFFAOYSA-N Y
|
| (verify) |
Butenafine hydrochloride is a synthetic benzylamine antifungal, marketed under the trade names Mentax, Butop (India) and is the active ingredient in Lotrimin Ultra. It is structurally related to synthetic allylamine antifungals such as terbinafine.
Contents
- 1 Medical uses
- 2 Pharmacology
- 3 Typical usage
- 4 References
Medical uses
Butenafine is indicated for the topical treatment of tinea (pityriasis) versicolor due to Malassezia furfur, as well as athlete's foot (Tinea pedis), ringworm (Tinea corporis) and jock itch (Tinea cruris) due to Epidermophyton floccosum, Trichophyton mentagrophytes, Trichophyton rubrum, and Trichophyton tonsurans.
It also displays superior activity against Candida albicans than terbinafine and naftifine. Butenafine demonstrates low minimum inhibitory concentrations against Cryptococcus and Aspergillus.
There is some evidence that it is effective against dermatophyte infections of the toenails, but needs to be applied daily for prolonged periods (at least one year).[2]
Butenafine is typically available as a 1% topical cream.
Pharmacology
Butenafine hydrochloride is an odorless white crystalline powder that is freely soluble in methanol, ethanol, and chloroform, and slightly soluble in water.
Like the allylamine antifungals, butenafine works by inhibiting the synthesis of ergosterol by inhibiting squalene epoxidase, an enzyme responsible for the creation of sterols needed in fungal cell membranes. Lacking ergosterol, the cell membranes increase in permeability, allowing their contents to leak out.
Typical usage
For 1% cream:
- for adults and children 12 years and older:
- wash the affected skin with soap and water and dry completely before applying
- apply once a day to affected skin for 2 weeks or as directed by a doctor
- wash hands after each use
- children under 12 years: ask a doctor
References
- ^ "Mentax (butenafine hydrochloride) Cream. Human Prescription Drug Label". dailymed.nlm.nih.gov. Mylan Pharmaceuticals Inc. Retrieved 24 August 2016.
- ^ The Cochrane Library: Topical treatments for fungal infections of the skin and nails of the foot, 2009.
|
Antifungals (D01 and J02)
|
|
Wall/
membrane |
Ergosterol
inhibitors |
Azoles
(lanosterol 14
alpha-demethylase inhibitors) |
| Imidazoles |
- Topical: bifonazole‡
- butoconazole
- chlormidazole‡
- clotrimazole#
- croconazole‡
- econazole
- fenticonazole‡
- flutrimazole
- isoconazole‡
- ketoconazole
- luliconazole
- miconazole#
- neticonazole‡
- omoconazole‡
- oxiconazole
- sertaconazole
- sulconazole
- tioconazole
|
|
| Triazoles |
- Topical: efinaconazole
- fluconazole#
- fosfluconazole
- terconazole
- Systemic: fluconazole#
- hexaconazole‡
- isavuconazole
- itraconazole
- posaconazole
- voriconazole
- Unknown: albaconazole‡
- ravuconazole†
|
|
| Thiazoles |
|
|
|
Polyene antimycotics
(ergosterol binding) |
- Topical: hamycin‡
- natamycin
- nystatin#
Systemic: amphotericin B#, hamycin‡
|
|
Squalene monooxygenase
inhibitors |
| Allylamines |
- Topical: naftifine
- terbinafine
Systemic: terbinafine
|
|
| Benzylamines |
|
|
|
| Others |
|
|
|
β-glucan synthase
inhibitors |
- echinocandins (anidulafungin
- biafungin
- caspofungin
- cilofungin
- micafungin)
|
|
|
| Intracellular |
Pyrimidine analogues/
thymidylate synthase inhibitors |
|
|
| Mitotic inhibitors |
|
|
| Aminoacyl tRNA synthetase inhibitors |
|
|
|
| Others |
- bromochlorosalicylanilide
- chlorophetanol
- chlorphenesin
- ciclopirox
- crystal violet
- dimazole
- ethylparaben
- haloprogin
- polynoxylin
- potassium iodide#
- salicylic acid
- selenium disulfide#
- sodium thiosulfate#
- sulbentine
- taurolidine
- ticlatone
- tolciclate
- tolnaftate
- tribromometacresol
- undecylenic acid
- Whitfield's ointment#
- citronella oil
- lemon grass
- lemon myrtle
- orange oil
- patchouli
- tea tree oil
- PCP: atovaquone
- dapsone
- pentamidine
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
UpToDate Contents
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English Journal
- In vitro activity of new azoles luliconazole and lanoconazole compared with ten other antifungal drugs against clinical dermatophyte isolates.
- Baghi N1, Shokohi T2, Badali H2, Makimura K3, Rezaei-Matehkolaei A4, Abdollahi M5, Didehdar M1, Haghani I2, Abastabar M6.
- Medical mycology.Med Mycol.2016 Apr 26. pii: myw016. [Epub ahead of print]
- In vitro susceptibilities of 100 clinical dermatophyte isolates belonging to five species from Iran toward lanoconazole and luliconazole were compared with ten other antifungal agents including econazole, itraconazole, miconazole, fluconazole, griseofulvin, butenafine, terbinafine, caspofungin, anid
- PMID 27118804
- Depth-dependent stratum corneum permeability in human skin in vitro.
- Cadavona JJ1, Zhu H2, Hui X2, Jung EC2, Maibach HI2.
- Journal of applied toxicology : JAT.J Appl Toxicol.2016 Feb 3. doi: 10.1002/jat.3289. [Epub ahead of print]
- The stratum corneum (SC), a permeable membrane, limits percutaneous penetration. As SC chemical and structural properties responsible for skin barrier function appear depth-related, we conducted an in vitro dermatopharmacokinetic study on intact and adhesive tape-stripped skin samples to clarify whe
- PMID 26843137
- Microemulsion-loaded hydrogel formulation of butenafine hydrochloride for improved topical delivery.
- Pillai AB1, Nair JV, Gupta NK, Gupta S.
- Archives of dermatological research.Arch Dermatol Res.2015 Sep;307(7):625-33. doi: 10.1007/s00403-015-1573-z. Epub 2015 May 26.
- Topical microemulsion systems for the antifungal drug, butenafine hydrochloride (BTF) were designed and developed to overcome the problems associated with the cutaneous delivery due to poor water solubility. The solubility of BTF in oils, surfactants and co-surfactants was evaluated to screen the co
- PMID 26006164
Japanese Journal
- 臨床研究 角質増殖型足白癬に対する経口抗真菌剤テルビナフィン内服後の塩酸ブテナフィンクリーム外用の有用性
- 各種外用抗真菌薬の<i> in vitro </i>抗真菌活性の測定
- In Vitro Antifungal Activity of ZJ-522, a New Triazole Restructured from Fluconazole and Butenafine, against Clinically Important Fungi in Comparison with Fluconazole and Butenafine(Pharmacology)
- Biological & pharmaceutical bulletin 28(8), 1414-1417, 2005-08-01
- NAID 10016666696
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