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HomeProduct name listButenafine

Butenafine

Butenafine Structural

What is Butenafine?

Absorption

The total amount absorbed through the skin into the systemic circulation has not been quantified.

The Uses of Butenafine

Butenafine (Mentax) is a synthetic benzylamine antifungal agent, related structurally and pharmacologically to terbinafine. It is thought to act by inhibiting the enzyme squalene 2,3-epoxidase, resulting in decreased ergosterol and corresponding increase in squalene, with subsequent cell membrane permeability alteration and cell death. It is active against dermatophytes, yeast, and Sporothrix.
Butenafine (Mentax)

Background

Butenafine hydrochloride is a synthetic benzylamine antifungal agent. Butenafine's mechanism of action is believed to involve the synthesis inhibition of sterols. In particular, butenafine acts to inhibit the activity of the squalene epoxidase enzyme that is essential in the formation of sterols necessary for fungal cell membranes.

Indications

For the topical treatment of the following dermatologic infections: tinea (pityriasis) versicolor due to M. furfur, interdigital tinea pedis (athlete’s foot), tinea corporis (ringworm) and tinea cruris (jock itch) due to E. floccosum, T. mentagrophytes, T. rubrum, and T. tonsurans.

Definition

ChEBI: Trimethylamine in which hydrogen atoms attached to different methyl groups are substituted by 1-naphthyl and 4-tert-butylphenyl groups. It is an inhibitor of squalene epoxidase, an enzyme responsible for the creation of sterols needed in funga cell membranes, and is used as its hydrochloride salt for treatment of dermatological fungal infections.

brand name

Lotrimin (Schering); Mentax (Mylan Bertek).

Pharmacokinetics

Butenafine is a synthetic antifungal agent that is structurally and pharmacologically related to allylamine antifungals. The exact mechanism of action has not been established, but it is suggested that butenafine's antifungal activity is exerted through the alteration of cellular membranes, which results in increased membrane permeability, and growth inhibition. Butenafine is mainly active against dermatophytes and has superior fungicidal activity against this group of fungi when compared to that of terbinafine, naftifine, tolnaftate, clotrimazole, and bifonazole. It is also active against Candida albicans and this activity is superior to that of terbinafine and naftifine. Butenafine also generates low MICs for Cryptococcus neoformans and Aspergillus spp. as well.

Metabolism

The primary metabolite in urine was formed through hydroxylation at the terminal t-butyl side-chain.

Properties of Butenafine

Melting point: 200-202 °C
Boiling point: 426.1±14.0 °C(Predicted)
Density  1.032±0.06 g/cm3(Predicted)
storage temp.  Store at -20°C
solubility  DMSO: 63 mg/mL (198.44 mM);Ethanol: 63 mg/mL (198.44 mM)
pka 7.87±0.50(Predicted)
Water Solubility  Water: Insoluble
CAS DataBase Reference 101828-21-1(CAS DataBase Reference)

Safety information for Butenafine

Computed Descriptors for Butenafine

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