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药品详细

Butenafine(布替萘芬)

化学结构式图
中文名
布替萘芬
英文名
Butenafine
分子式
C23H27N
化学名
[(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
分子量
Average: 317.4672
Monoisotopic: 317.214349869
CAS号
101828-21-1
ATC分类
D01A 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

Butenafine hydrochloride is a synthetic benzylamine antifungal agent. Butenafine works by inhibiting the synthesis of sterols by inhibiting squalene epoxidase, an enzyme responsible for the creation of sterols needed in fungal cell membranes.

生产厂家
  • Mylan pharmaceuticals inc
  • Schering plough healthcare products inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. McNeely W, Spencer CM: Butenafine. Drugs. 1998 Mar;55(3):405-12; discussion 413. Pubmed
  2. Singal A: Butenafine and superficial mycoses: current status. Expert Opin Drug Metab Toxicol. 2008 Jul;4(7):999-1005. Pubmed
  3. Gupta AK: Butenafine: an update of its use in superficial mycoses. Skin Therapy Lett. 2002 Sep;7(7):1-2, 5. Pubmed
  4. Mingeot-Leclercq MP, Gallet X, Flore C, Van Bambeke F, Peuvot J, Brasseur R: Experimental and conformational analyses of interactions between butenafine and lipids. Antimicrob Agents Chemother. 2001 Dec;45(12):3347-54. Pubmed
  5. Syed TA, Maibach HI: Butenafine hydrochloride: for the treatment of interdigital tinea pedis. Expert Opin Pharmacother. 2000 Mar;1(3):467-73. Pubmed
  6. Reyes BA, Beutner KR, Cullen SI, Rosen T, Shupack JL, Weinstein MB: Butenafine, a fungicidal benzylamine derivative, used once daily for the treatment of interdigital tinea pedis. Int J Dermatol. 1998 Jun;37(6):450-3. Pubmed
  7. Iwatani W, Arika T, Yamaguchi H: Two mechanisms of butenafine action in Candida albicans. Antimicrob Agents Chemother. 1993 Apr;37(4):785-8. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Naphthalenes
  • Cumenes and Derivatives
Substructures
  • Naphthalenes
  • Benzene and Derivatives
  • Cumenes and Derivatives
  • Aliphatic and Aryl Amines
  • Aromatic compounds
适应症
药理
Indication For the topical treatment of the following dermatologic infections: tinea (pityriasis) versicolor due to M. furfur, interdigital tinea pedis (athlete’s foot), tinea corporis (ringworm) and tinea cruris (jock itch) due to E. floccosum, T. mentagrophytes, T. rubrum, and T. tonsurans.
Pharmacodynamics Butenafine is a synthetic antifungal agent that is structurally and pharmacologically related to allylamine antifungals. The exact mechanism of action has not been established, but it is suggested that butenafine's antifungal activity is exerted through the alteration of cellular membranes, which results in increased membrane permeability, and growth inhibition. Butenafine is mainly active against dermatophytes and has superior fungicidal activity against this group of fungi when compared to that of terbinafine, naftifine, tolnaftate, clotrimazole, and bifonazole. It is also active against Candida albicans and this activity is superior to that of terbinafine and naftifine. Butenafine also generates low MICs for Cryptococcus neoformans and Aspergillus spp. as well.
Mechanism of action Although the mechanism of action has not been fully established, it has been suggested that butenafine, like allylamines, interferes with sterol biosynthesis (especially ergosterol) by inhibiting squalene monooxygenase, an enzyme responsible for converting squalene to 2,3-oxydo squalene. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Blockage of squalene monooxygenase also leads to a subsequent accumulation of squalene. When a high concentration of squalene is reached, it is thought to have an effect of directly kill fungal cells.
Absorption The total amount absorbed through the skin into the systemic circulation has not been quantified.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
The primary metabolite in urine was formed through hydroxylation at the terminal t-butyl side-chain.
Route of elimination Not Available
Half life Following topical application, a biphasic decline of plasma butenafine concentrations was observed with the half-lives estimated to be 35 hours initial and over 150 hours terminal.
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Fungi
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
water solubility Slightly soluble (HCl salt) Not Available
logP 6.6 Not Available
Predicted Properties
Property Value Source
water solubility 7.56e-05 g/l ALOGPS
logP 5.85 ALOGPS
logP 6.17 ChemAxon
logS -6.6 ALOGPS
pKa (strongest basic) 9.23 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 3.24 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 104.33 ChemAxon
polarizability 38.41 ChemAxon
药物相互作用
食物相互作用
Not Available

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