Butenafine hydrochloride is a synthetic benzylamine

Benzylamine

Benzylamine is the chemical compound with the formula C6H5CH2NH2. It consists of a benzyl group, C6H5CH2, attached to an amine functional group...

 antifungal

Antifungal

* Antifungal medication, a medication used to treat fungal infection s such as athlete's foot , ringworm, candidiasis, etc.* Antifungal protein, a protein family* an adjective referring to a fungicide compound...

, 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

Allylamine

Allylamine is an organic compound with the formula C3H5NH2. This colorless liquid is the simplest stable unsaturated amine.-Production:All three allylamines, mono-, di-, and triallylamine, are produced by the treating allyl chloride with ammonia followed by distillation. Pure samples can be...

 antifungals such as terbinafine

Terbinafine

Terbinafine hydrochloride is a...

.

Pharmacology

Butenafine hydrochloride

Hydrochloride

In chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base . This is also known as muriate, derived from hydrochloric acid's other name: muriatic acid....

 is an odorless white crystalline powder that is freely soluble in methanol

Methanol

Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...

, ethanol

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...

, and chloroform

Chloroform

Chloroform is an organic compound with formula CHCl3. It is one of the four chloromethanes. The colorless, sweet-smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous...

, and slightly soluble in water.

Like the allylamine antifungals, butenafine works by inhibiting the synthesis of ergosterol

Ergosterol

Ergosterol is a sterol found in fungi, and named for ergot, a common name for the members of the fungal genus Claviceps from which ergosterol was first isolated. Ergosterol does not occur in plant or animal cells...

 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

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

Jock itch

Tinea cruris, also known as crotch itch, crotch rot, Dhobie itch, eczema marginatum, gym itch, jock itch, and ringworm of the groin in American English is a dermatophyte fungal infection of the groin region in either sex, though more often seen in males...

 (Tinea cruris) due to E. floccosum, T. mentagrophytes, T. rubrum, and T. tonsurans. It has superior fungicidal activity against this group of fungi when compared to that of terbinafine

Terbinafine

Terbinafine hydrochloride is a...

, naftifine

Naftifine

Naftifine is an allylamine antifungal drug for the topical treatment of tinea pedis, tinea cruris, and tinea corporis ....

, clotrimazole

Clotrimazole

Clotrimazole is an antifungal medication commonly used in the treatment of fungal infections such as vaginal yeast infections, oral thrush, and ringworm...

, and tolnaftate

Tolnaftate

Tolnaftate is a synthetic over-the-counter anti-fungal agent. It may come as a cream, powder, spray, or liquid aerosol, and is used to treat jock itch, athlete's foot and ringworm. It is sold under several brand names, most notably Tinactin and Odor Eaters . Other brands are Absorbine, Aftate,...

.

It also displays superior activity against Candida albicans when compared against terbinafine and naftifine. Butenafine demonstrates low minimum inhibitory concentrations against cryptococcus

Cryptococcus

Cryptococcus is a genus of fungus. Species grow in culture as yeasts. The perfect forms or teleomorphs of Cryptococcus species are filamentous fungi in the genus Filobasidiella...

 and aspergillus

Aspergillus

Aspergillus is a genus consisting of several hundred mold species found in various climates worldwide. Aspergillus was first catalogued in 1729 by the Italian priest and biologist Pier Antonio Micheli...

.

Butenafine is typically available as a 1% topical cream.

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