Butenafine

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Butenafine
Butenafine structure.svg
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 Registry Number 101828-21-1 YesY
ATC code D01AE23
PubChem CID: 2484
DrugBank DB01091 YesY
ChemSpider 2390 YesY
UNII 91Y494NL0X YesY
KEGG D07596 YesY
ChEBI CHEBI:3238 YesY
ChEMBL CHEMBL990 YesY
Chemical data
Formula C23H27N
Molecular mass 317.47 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.

Medical uses[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.

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.

Typical usage[edit]

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

References[edit]

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