Butenafine

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Butenafine
Butenafine.svg
Systematic (IUPAC) name
[(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
Clinical data
Trade names Mentax, Lotrimin Ultra
AHFS/Drugs.com Monograph
Pregnancy
category
Routes of
administration
Topical (cream)
Legal status
Legal status
  • OTC (Lotrimin Ultra),
    ℞-only (Mentax)
Pharmacokinetic data
Metabolism Hepatic
Biological half-life 35–100 hours
Identifiers
CAS Number 101828-21-1 YesY
ATC code D01AE23 (WHO)
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
Molar mass 317.47 g/mol
  (verify)

Butenafine hydrochloride is a synthetic benzylamine antifungal, marketed under the trade names Mentax, Butop (India) and is the active ingredient in 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 Malassezia furfur, as well as athlete's foot (Tinea pedis), ringworm (Tinea corporis) and jock itch (Tinea cruris) due to Epidermophyton floccosum, Trichophyton mentagrophytes, Trichophyton rubrum, and Trichophyton 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).[2]

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. ^ "Mentax (butenafine hydrochloride) Cream. Human Prescription Drug Label". dailymed.nlm.nih.gov. Mylan Pharmaceuticals Inc. Retrieved 24 August 2016. 
  2. ^ The Cochrane Library: Topical treatments for fungal infections of the skin and nails of the foot, 2009.