Butenafine

Names

[ Name ]:
Butenafine

[Synonym ]:
1-[4-(1,1-diméthyléthyl)phényl]-N-méthyl-N-(naphtalén-1-ylméthyl)méthanamine chlorhydrate
Butenafine hydrochloride
1-(4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanamine,hydrochloride
Butenafine HCl
Butenafina
1-(4-tert-Butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanaminhydrochlorid
1-Naphthalenemethanamine, N-[[4-(1,1-dimethylethyl)phenyl]methyl]-N-methyl-
Butenafinum
Butenafina [INN-Spanish]
1-(4-tert-Butylphenyl)-N-methyl-N-(1-naphthylmethyl)methanamine
1-(4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanamine
MFCD00865577
Mentax
Butenafine
1-Naphthalenemethanamine, N-[[4-(1,1-dimethylethyl)phenyl]methyl]-N-methyl-, hydrochloride (1:1)
N-((4-(1,1-Dimethylethyl)phenyl)methyl)-N-methyl-1-naphthalenemethanamine hydrochloride
1-naphthalenemethanamine, N-[[4-(1,1-dimethylethyl)phenyl]methyl]-N-methyl-, hydrochloride
N-Methyl-1-[4-(2-methyl-2-propanyl)phenyl]-N-(1-naphthylmethyl)methanamine
1-(4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanamine hydrochloride (1:1)
1-Naphthalenemethanamine, N-((4-(1,1-dimethylethyl)phenyl)methyl)-N-methyl-, hydrochloride
N-(p-tert-Butylbenzyl)-N-methyl-1-naphthalenemethylamine hydrochloride
1-(4-tert-Butylphenyl)-N-methyl-N-(1-naphthylmethyl)methanamine hydrochloride (1:1)
N-Methyl-1-[4-(2-methyl-2-propanyl)phenyl]-N-(1-naphthylmethyl)methanamine hydrochloride (1:1)
Butenafine [INN]
1-(4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanamine hydrochloride
N-[[4-(1,1-Dimethylethyl)phenyl]methyl]-N-methyl-1-naphthalene methanamine
Butenafinum [INN-Latin]

Biological Activity

[Description]:

Butenafine is a potent and broad spectrum benzylamine antifungal agent[1]. Butenafine inhibits fungal ergosterol biosynthesis at the point of squalene epoxidation, leading to a deficiency of the fungal cell membranes. Butenafine is effective against dermatophytes infections, such as tinea pedis, tinea cruris, tinea versicolor[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

[Target]

IC50: antifungal[1]

[In Vitro]

Butenafine demonstrates comparable activity against the dermatophytes with a MIC range of 0.03-0.25 μg/ml. It displays limited activity against the yeast Candida albicans and no activity against Malassezia furfur[1]. Butenafine (25; 50 or 100 μM) eliminates the promastigote forms of L. amazonensis and L. braziliensis in a dose-dependent manner, and shows EC50 values of 34.10±3.76 μM and 81.25±10.24 μM, respectively, in peritoneal macrophages from BALB/c mice. Butenafine induces mild cytotoxicity in peritoneal macrophages from BALB/c mice with a CC50 of 97.88 μM[1].

[In Vivo]

Butenafine (subcutaneous administration; 1-100 mg/kg) to mice has no effect on the central and autonomic nervous systems. Topical administration of 0.3-3.0% butenafine solutions to guinea pigs also has no effect on the somatic nervous system[1]. In primary therapeutic studies on guinea pigs, Butenafine (1% topical application; 4-10 days; day 3 and 4 post-infection) exhibits a complete cure after 10 days in vivo-effect on dermatophytosis, T. mentagrophytes[1]. Butenafine (0.125, 0.25, 0.5 and 1.0% topical application; q.d. or b.i.d. for 10 days; day 4 post-infection) exhibits a 100% cure after 0.5% or 1% application and has no difference in efficacy between 1% q.d. and b.i.d. in vivo-effect on dermatophytosis, T. mentagrophytes[1].

[References]

[1]. Katrina Kokjohn, et al. Evaluation of in vitro activity of ciclopirox olamine, butenafine HCl and econazole nitrate against dermatophytes, yeasts and bacteria.Int J Dermatol. 2003 Sep;42 Suppl 1:11-7.

[2]. Adriana Bezerra-Souza, et al. The antifungal compound butenafine eliminates promastigote and amastigote forms of Leishmania (Leishmania) amazonensis and Leishmania (Viannia) braziliensis. 2016 Dec;65(6 Pt A):702-707.

[3]. Topical Antifungal Agent. Butenafine

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
426.1±14.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₃H₂₇N

[ Molecular Weight ]:
317.467

[ Flash Point ]:
187.7±17.0 °C

[ Exact Mass ]:
317.214355

[ PSA ]:
3.24000

[ LogP ]:
6.77

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.598

Safety Information

[ HS Code ]:
2921199090

Customs

[ HS Code ]: 2921199090

[ Summary ]:
2921199090 other acyclic monoamines and their derivatives; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%