Butenafine

Butenafine

Clinical data
Trade names	Mentax, Lotrimin Ultra
AHFS/Drugs.com	Monograph
Pregnancy category	US: C[1]
Routes of administration	Topical (cream)
ATC code	D01AE23 (WHO)
Legal status
Legal status	OTC (Lotrimin Ultra), ℞-only (Mentax)
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	35–100 hours
Identifiers
IUPAC name [(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
CAS Number	101828-21-1
PubChem (CID)	2484
DrugBank	DB01091
ChemSpider	2390
UNII	91Y494NL0X
KEGG	D07596
ChEBI	CHEBI:3238
ChEMBL	CHEMBL990
Chemical and physical data
Formula	C23H27N
Molar mass	317.47 g/mol
3D model (Jmol)	Interactive image
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 Key:ABJKWBDEJIDSJZ-UHFFFAOYSA-N
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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 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 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

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. "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.