Butenafine hydrochloride Chemical Properties

Melting point:

210-214°C

storage temp. 

room temp

solubility 

DMSO: ≥10mg/mL

form 

powder

color 

white to off-white

Merck 

14,1518

InChI

InChI=1S/C23H27N.ClH/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;1H

InChIKey

LJBSAUIFGPSHCN-UHFFFAOYSA-N

SMILES

C12C=CC=CC=1C=CC=C2CN(C)CC1=CC=C(C(C)(C)C)C=C1.Cl

CAS DataBase Reference

101827-46-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

21

Safety Statements 

44

WGK Germany 

nwg

RTECS 

QJ8585000

HS Code 

29214990

Butenafine hydrochloride Usage And Synthesis

Description

Butenafine hydrochloride is a new benzylamine antifungal which appears to block the squalene epoxidation step of sterol synthesis in fungi. Active against a broad spectrum of fungi, butenafine hydrochloride is more effective in a guinea-pig model of tinea pedis than clotrimazole, naftifine and tolnaftate. Its efficacy is partially attributed to its long 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) was dissolved in 50 ml of dry dimethylformamide, and 3.71 g (0.035 mole) of anhydrous sodium carbonate was added, then 2.49 g (0.011 mole) of p-tbutylbenzyl bromide was added by stirring and the mixture was reacted at 30° to 40°C for 5 hours. Ice water was added, and the mixture was extracted with toluene. The organic layer was washed with water, and toluene was evaporated. The residue was chromatographed on silica gel column, and eluated with 5% ethyl acetate/n-hexane. The eluate was concentrated to give 2.98 g (yield 94%) of an oily substance. Hydrochloric acid/ethanol was added to 1 g of this oily product, and the mixture was concentrated. The residue was recrystallized 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 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.

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