[(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine

• ChemBase编号: 962
• 分子式: C23H27N
• 平均质量: 317.46718
• 单一同位素质量: 317.21434987
• SMILES: N(Cc1ccc(C(C)(C)C)cc1)(Cc1c2c(ccc1)cccc2)C
• Canonical SMILES: CN(Cc1cccc2c1cccc2)Cc1ccc(cc1)C(C)(C)C
• 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
• InChIKey: ABJKWBDEJIDSJZ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: [(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
• IUPAC传统名: butenafine
• 商标名: Lotrimin Ultra; Mentax; Mentax-tc
• 别名: Butenafina [INN-Spanish]; Butenafine HCL; Butenafine hydrochloride; Butenafine [INN]; Butenafinum [INN-Latin]; Butenafine

登记号

• CAS号: 101828-21-1
• PubChem SID: 46506191; 160964425
• PubChem CID: 2484

理论计算性质

JChem

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 2.8725023
• LogD (pH = 7.4): 4.343121
• Log P: 6.173649
• 摩尔折射率: 104.3294 cm^3
• 极化性: 42.022823 Å^3
• 极化表面积: 3.24 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 5.85
• LOG S: -6.62
• 溶解度: 7.56e-05 g/l

分子性质

理化性质

• 溶解度: Slightly soluble (HCl salt)
• 疏水性(logP): 6.6

详细说明

DrugBank - DB01091

• Drug Groups: approved
• Description: 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.
• 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.
• Pharmacology: 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.
• Affected Organisms: Fungi
• Biotransformation: The primary metabolite in urine was formed through hydroxylation at the terminal t-butyl side-chain.
• Absorption: The total amount absorbed through the skin into the systemic circulation has not been quantified.
• 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.
• References: McNeely W, Spencer CM: Butenafine. Drugs. 1998 Mar;55(3):405-12; discussion 413. [Pubmed] ; Singal A: Butenafine and superficial mycoses: current status. Expert Opin Drug Metab Toxicol. 2008 Jul;4(7):999-1005. [Pubmed] ; Gupta AK: Butenafine: an update of its use in superficial mycoses. Skin Therapy Lett. 2002 Sep;7(7):1-2, 5. [Pubmed] ; 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] ; Syed TA, Maibach HI: Butenafine hydrochloride: for the treatment of interdigital tinea pedis. Expert Opin Pharmacother. 2000 Mar;1(3):467-73. [Pubmed] ; 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] ; Iwatani W, Arika T, Yamaguchi H: Two mechanisms of butenafine action in Candida albicans. Antimicrob Agents Chemother. 1993 Apr;37(4):785-8. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• McNeely W, Spencer CM: Butenafine. Drugs. 1998 Mar;55(3):405-12; discussion 413. Pubmed
• Singal A: Butenafine and superficial mycoses: current status. Expert Opin Drug Metab Toxicol. 2008 Jul;4(7):999-1005. Pubmed
• Gupta AK: Butenafine: an update of its use in superficial mycoses. Skin Therapy Lett. 2002 Sep;7(7):1-2, 5. Pubmed
• 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
• Syed TA, Maibach HI: Butenafine hydrochloride: for the treatment of interdigital tinea pedis. Expert Opin Pharmacother. 2000 Mar;1(3):467-73. Pubmed
• 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
• Iwatani W, Arika T, Yamaguchi H: Two mechanisms of butenafine action in Candida albicans. Antimicrob Agents Chemother. 1993 Apr;37(4):785-8. Pubmed