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Butenafine

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Butenafine
File:Butenafine structure.svg
Systematic (IUPAC) name
[(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
Clinical data
Trade names Mentax
AHFS/Drugs.com monograph
topical
Pharmacokinetic data
Metabolism Hepatic
Half-life 35-100 hours
Identifiers
101828-21-1 7pxY
D01AE23
PubChem CID 2484
DrugBank DB01091 7pxY
ChemSpider 2390 7pxY
UNII 91Y494NL0X 7pxY
KEGG D07596 7pxY
ChEBI CHEBI:3238 7pxY
ChEMBL CHEMBL990 7pxY
Chemical data
Formula C23H27N
317.47 g/mol
 14pxY (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

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

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

References

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

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