| Description | Butenafine hydrochloride is a new benzylamine antifungal which appears to block thesqualene epoxidation step of sterol synthesis in fungi. Active against a broad spectrumof fungi, butenafine hydrochloride is more effective in a guinea-pig model of tineapedis than clotrimazole, naftifine and tolnaftate. Its efficacy is partially attributed to itslong retention time in the skin. |
| Chemical Properties | White Solid |
| Originator | Kaken (Japan) |
| Uses | Butenafine HCl is a synthetic benzylamine antifungal, works by inhibiting the synthesis of sterols by inhibiting squalene epoxidase. |
| Uses | Butenafine hydrochloride has been used as a standard in high-performance liquid chromatography (HPLC) method to determine butenafine hydrochloride in butenafine-loaded nanosponges. |
| Uses | An antifungal, used to control dermal fungal infections such as athletes foot and ring worm. |
| Definition | ChEBI: The hydrochloride salt of butenafine. An inhibitor of squalene epoxidase, an enzyme responsible for the creation of sterols needed in fungal cell membranes, it is used for treatment of dermatological fungal infections. |
| Manufacturing Process | N-Methyl-1-naphtylmethylamine hydrochloride (2.1 g, 0.01 mole) wasdissolved in 50 ml of dry dimethylformamide, and 3.71 g (0.035 mole) ofanhydrous sodium carbonate was added, then 2.49 g (0.011 mole) of p-tbutylbenzylbromide was added by stirring and the mixture was reacted at30° to 40°C for 5 hours. Ice water was added, and the mixture was extractedwith toluene. The organic layer was washed with water, and toluene wasevaporated. The residue was chromatographed on silica gel column, andeluated with 5% ethyl acetate/n-hexane. The eluate was concentrated to give2.98 g (yield 94%) of an oily substance. Hydrochloric acid/ethanol was addedto 1 g of this oily product, and the mixture was concentrated. The residue wasrecrystallized from methanol/acetic acid to give 0.95 g of desired 1-naphthalenemethanamine, N-((4-(1,1-dimethylethyl)phenyl)methyl)-Nmethyl-,hydrochloride having melting point 200° to 202°C. |
| Brand name | Lotrimin (Schering);Mentax (Mylan Bertek);Volley. |
| Therapeutic Function | Antifungal |
| General Description | Butenafine hydrochloride is chemically known as N-4-tertbutylbenzyl-N-methyl-1-naphthalenemethylamine hydrochloride. Butenafine, a benzylamine derivative, is a new generation antimycotic compound. It is easily soluble in methanol, ethanol, dichloromethane, and chloroform, but not in water. The allyl radical in butenafine hydrochloride is substituted by a butylbenzyl group. |
| Biochem/physiol Actions | Butenafine hydrochloride exhibits fungicidal and antimycotic activity. This fungal squalene epoxidase inhibitor serves as an effective fungicide against T. rubrum, T. mentagrophytes, Microsporum canis, Aspergillus fumigatus, Sporothrix schenckii, Candida parapsilosis, and C. albicans. It is considered more effective and rapid than other antifungal drugs at curing dermatophytosis and preventing recurrences. In humans, it is used topically to treat tinea conditions and superficial candidiasis. Butenafine is considered a promising antimycotic compound to treat tinea pedis due to its efficiency, safety profile, relapse rates, and cost-effectiveness. |
| Side effects | Side Effects:
Blistering, burning, crusting, dryness, or flaking of the skin where the medicine is applied.itching, scaling, severe redness, soreness, or swelling of the skin where the medicine is applied. |
