- 関
- butenafine
WordNet
- a complex consisting of an organic base in association with hydrogen chloride
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/05/16 00:08:21」(JST)
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Butenafine
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| Systematic (IUPAC) name |
| [(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine |
| Clinical data |
| Trade names |
Mentax |
| AHFS/Drugs.com |
monograph |
|
Routes of
administration
|
topical |
| Pharmacokinetic data |
| Metabolism |
Hepatic |
| Half-life |
35-100 hours |
| Identifiers |
|
CAS Registry Number
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101828-21-1 Y |
|
ATC code
|
D01AE23 |
| PubChem |
CID 2484 |
| DrugBank |
DB01091 Y |
| ChemSpider |
2390 Y |
| UNII |
91Y494NL0X Y |
| KEGG |
D07596 Y |
| ChEBI |
CHEBI:3238 Y |
| ChEMBL |
CHEMBL990 Y |
| Chemical data |
| Formula |
C23H27N |
|
Molecular mass
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317.47 g/mol |
SMILES
- N(C)(Cc1ccc(cc1)C(C)(C)C)Cc3c2ccccc2ccc3
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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
|
| Y (what is this?) (verify) |
Butenafine hydrochloride is a synthetic benzylamine antifungal, marketed under the trade names Mentax, Butop (India) and is the active ingredient in Schering-Plough's 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 M. furfur, as well as athlete’s foot (Tinea pedis), ringworm (Tinea corporis) and jock itch (Tinea cruris) due to E. floccosum, T. mentagrophytes, T. rubrum, and T. 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).[1]
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
- ^ The Cochrane Library: Topical treatments for fungal infections of the skin and nails of the foot, 2009.
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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
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- 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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|
|
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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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β-glucan synthase
inhibitors
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- echinocandins (anidulafungin
- caspofungin
- micafungin)
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|
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| Intracellular |
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Pyrimidine analogues/
thymidylate synthase inhibitors
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|
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Mitotic inhibitors
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|
|
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Aminoacyl tRNA synthetase 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 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
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|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Index of fungal disease
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| Description |
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| Disease |
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| Treatment |
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UpToDate Contents
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English Journal
- 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
- Boron-Catalyzed N-Alkylation of Amines using Carboxylic Acids.
- Fu MC1, Shang R2, Cheng WM1, Fu Y3.
- Angewandte Chemie (International ed. in English).Angew Chem Int Ed Engl.2015 Jul 27;54(31):9042-6. doi: 10.1002/anie.201503879. Epub 2015 Jul 6.
- A boron-based catalyst was found to catalyze the straightforward alkylation of amines with readily available carboxylic acids in the presence of silane as the reducing agent. Various types of primary and secondary amines can be smoothly alkylated with good selectivity and good functional-group compa
- PMID 26150397
- HPLC-DAD for the determination of three different classes of antifungals: method characterization, statistical approach, and application to a permeation study.
- Miron D1, Lange A, Zimmer AR, Mayorga P, Schapoval EE.
- Biomedical chromatography : BMC.Biomed Chromatogr.2014 Dec;28(12):1728-37. doi: 10.1002/bmc.3213. Epub 2014 May 2.
- This study describes and characterizes methods for high-performance liquid chromatography diode array detection (HPLC-DAD) analysis of formulations containing molecules with antifungal activity of three different classes: terbinafine and butenafine (allylamines), miconazole and fluconazole (azoles),
- PMID 24788676
Japanese Journal
- 外用坑真菌剤を用いた爪白癬の治療における歯科用ドリル併用の効果
- 新規ベンジルアミン系抗真菌剤塩酸ブテナフィン(KP-363)の合成と抗真菌活性
- 前田 鉄也 [他],高瀬 三夫,石橋 明彦,山本 俊之,佐々木 和也,有可 正,横尾 守,雨宮 功治
- 藥學雜誌 111(2), 126-137, 1991-02-25
- … Among them, butenafine hydrochloride (N-p-tert-butylbenzyl-N-methyl-1-naphthalenemethylamine hydrochloride, KP-363) has proved to show the strongest activity. …
- NAID 110003649213
- Butenafine hydrochloride の抗真菌作用メカニズムに関する研究II. Sporothrix schenckii のtolciclate 耐性変異株を用いた解析
Related Links
- [Butenafine Hydrochloride] [101827-46-7] | 価格や在庫、物性値などの詳細情報ページです。 ... ・川口の在庫は即日，つくばの在庫は2〜3日以内の出荷となります。・詳細につきましては，お手数ですが営業部までお問い合わせください。
- butenafine [bu-ten´ah-fēn] a topical antifungal agent used as the hydrochloride salt in the treatment of athlete's foot, jock itch, and ringworm. butenafine (byoo-ten-a-feen) , Lotrimin Ultra (trade name), Mentax (trade name) Classification
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