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Details

Stereochemistry ACHIRAL
Molecular Formula C23H27N.ClH
Molecular Weight 353.928
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTENAFINE HYDROCHLORIDE

SMILES

Cl.CN(CC1=CC=C(C=C1)C(C)(C)C)CC2=CC=CC3=CC=CC=C23

InChI

InChIKey=LJBSAUIFGPSHCN-UHFFFAOYSA-N
InChI=1S/C23H27N.ClH/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;1H

HIDE SMILES / InChI

Description

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. Butenafine hydrochloride is marketed under the trade names Mentax, Butop (India) and is the active ingredient in Lotrimin Ultra. MENTAX Cream, 1%, is indicated for the topical treatment of tinea (pityriasis) versicolor due to Malassezia furfur (formerly Pityrosporum orbiculare). 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. Butenafine cream 1% is indicated in treatment of tinea pedis, tinea corporis and tinea cruris. In tinea pedis it is recommended twice daily for 7 days or once daily for 4 weeks. In tinea cruris and tinea corporis it is recommended once daily for two weeks.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MENTAX
Primary
Butenafine

Cmax

ValueDoseCo-administeredAnalytePopulation
1.4 ng/mL
6 g 1 times / day multiple, topical
BUTENAFINE blood
Homo sapiens
5 ng/mL
20 g 1 times / day multiple, topical
BUTENAFINE blood
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
23.9 ng × h/mL
6 g 1 times / day multiple, topical
BUTENAFINE blood
Homo sapiens
87.8 ng × h/mL
20 g 1 times / day multiple, topical
BUTENAFINE blood
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
35 h
20 g 1 times / day multiple, topical
BUTENAFINE blood
Homo sapiens

Doses

PubMed

Sample Use Guides

In Vivo Use Guide
Patients with tinea (pityriasis) versicolor should apply MENTAX-TC Cream, 1% (Butenafine), once daily for seven days. Sufficient MENTAX-TC Cream, 1%, should be applied to cover affected areas and extending 4 inches (10.2 cm) onto normal skin immediately surrounding the affected area.
Route of Administration: Topical
In Vitro Use Guide
Butenafine HCl shows minimum inhibitory concentrations ranging from 0.03–1.0 ug/mL against 30 isolates representing different dermatophyte species.