Butenafine

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Butenafine
Systematic (IUPAC) name
[(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
Clinical data
Trade namesMentax
AHFS/Drugs.commonograph
Legal status ?
Routestopical
Pharmacokinetic data
MetabolismHepatic
Half-life35-100 hours
Identifiers
CAS number101828-21-1 YesY
ATC codeD01AE23
PubChemCID 2484
DrugBankDB01091
ChemSpider2390 YesY
UNII91Y494NL0X YesY
KEGGD07596 YesY
ChEBICHEBI:3238 YesY
ChEMBLCHEMBL990 YesY
Chemical data
FormulaC23H27N 
Mol. mass317.47 g/mol
 YesY (what is this?)  (verify)
 
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Butenafine
Systematic (IUPAC) name
[(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
Clinical data
Trade namesMentax
AHFS/Drugs.commonograph
Legal status ?
Routestopical
Pharmacokinetic data
MetabolismHepatic
Half-life35-100 hours
Identifiers
CAS number101828-21-1 YesY
ATC codeD01AE23
PubChemCID 2484
DrugBankDB01091
ChemSpider2390 YesY
UNII91Y494NL0X YesY
KEGGD07596 YesY
ChEBICHEBI:3238 YesY
ChEMBLCHEMBL990 YesY
Chemical data
FormulaC23H27N 
Mol. mass317.47 g/mol
 YesY (what is this?)  (verify)

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.

Pharmacology[edit]

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.

Indications[edit]

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).[1]

Butenafine is typically available as a 1% topical cream.

Typical usage[edit]

For 1% cream

References[edit]

  1. ^ The Cochrane Library: Topical treatments for fungal infections of the skin and nails of the foot, 2009.