Butenafine

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Butenafine
Systematic (IUPAC) name
N-methyl-1-naphthalen-1-yl-N-[(4-tert-butylphenyl)methyl]methanamine
Identifiers
CAS number	101828-21-1
ATC code	D01AE23
PubChem	2484
DrugBank	APRD00833
Chemical data
Formula	C₂₃H₂₇N
Mol. mass	317.47 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Half life	35-100 hours
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	topical

Butenafine hydrochloride is a synthetic benzylamine antifungal, marketed under the trade names Mentax, Butop(India) and is the active ingredient in Schering-Plough's Lotrimin® Ultra. It is structurally related to synthetic allylamine antifungals such as terbinafine.

[edit] Pharmacology

Butenafine hydrochloride is an odorless white crystalline powder that is freely soluble in methanol, ethanol, and chloroform, and slightly soluble in water.

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.

[edit] Indications

Butenafine is indicated for the topical treatment of tinea (pityriasis) versicolor due to M. furfur, as well as athlete’s foot (Tinea pedis), ringworm (Tinea corporis) and jock itch (Tinea cruris) due to E. floccosum, T. mentagrophytes, T. rubrum, and T. tonsurans. It has superior fungicidal activity against this group of fungi when compared to that of terbinafine, naftifine, clotrimazole, and tolnaftate.

It also displays superior activity against Candida albicans when compared against terbinafine and naftifine. Butenafine demonstrates low minimum inhibitory concentrations against cryptococcus and aspergillus.

Butenafine is typically available as a 1% topical cream.