Butenafine (Molecule of the Month for April 2017)
Athlete's Foot
Butenafine hydrochloride is a synthetic benzylamine antifungal, marketed under the trade names Mentax, Butop and is the active ingredient in Lotrimin Ultra. It is structurally related to synthetic allylamine antifungals such as terbinafine.
Butenafine is indicated for the topical treatment of tinea (pityriasis) versicolor due to Malassezia furfur, as well as athlete's foot (Tinea pedis), ringworm (Tinea corporis) and jock itch (Tinea cruris) due to Epidermophyton floccosum, Trichophyton mentagrophytes, Trichophyton rubrum, and Trichophyton tonsurans.
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.
Formal Chemical Name (IUPAC)
N-(4-(tert-butyl)benzyl)-N-methyl-1-(naphthalen-1-yl)methanamine
References
click on the picture of Butenafine above to interact
with the 3D model of the
Butenafine structure
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C23 H27 N
Update by Karl Harrison
(Molecule of the Month for
April 2017
)
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