Butenafine

Butenafine

Systematic (IUPAC) name
[(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
Clinical data
Trade names	Mentax
AHFS/Drugs.com	monograph
Routes of administration	topical
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	35-100 hours
Identifiers
CAS Number	101828-21-1 Y
ATC code	D01AE23 (WHO)
PubChem	CID: 2484
DrugBank	DB01091 Y
ChemSpider	2390 Y
UNII	91Y494NL0X Y
KEGG	D07596 Y
ChEBI	CHEBI:3238 Y
ChEMBL	CHEMBL990 Y
Chemical data
Formula	C23H27N
Molecular mass	317.47 g/mol
SMILES N(C)(Cc1ccc(cc1)C(C)(C)C)Cc3c2ccccc2ccc3
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 Y Key:ABJKWBDEJIDSJZ-UHFFFAOYSA-N Y
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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.

Medical uses

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 also displays superior activity against Candida albicans than terbinafine and naftifine. Butenafine demonstrates low minimum inhibitory concentrations against Cryptococcus and Aspergillus.

There is some evidence that it is effective against dermatophyte infections of the toenails, but needs to be applied daily for prolonged periods (at least one year).

Butenafine is typically available as a 1% topical cream.

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.

Typical usage

For 1% cream

• for adults and children 12 years and older
• wash the affected skin with soap and water and dry completely before applying
• apply once a day to affected skin for 2 weeks or as directed by a doctor
• wash hands after each use
• children under 12 years: ask a doctor