Butenafine hydrochloride

Butenafine hydrochloride Basic information
Product Name:Butenafine hydrochloride
Synonyms:kp-363;n-((4-(1,1-dimethylethyl)phenyl)methyl)-n-methyl-1-naphthalenemethanaminehyd;n-((4-(1,1-dimethylethyl)phenyl)methyl)-n-methyl-1-naphthalenemethanaminhy;n-(4-tert-butylbenzyl)-n-methyl-1-naphthalenemethylamine hydrochloride;BUTENAFINE HCL;BUTENAFINE HYDROCHLORIDE;Butenafine hydrochloide;N-(4-t-Butylbenzyl)-N-Methyl-1-naphthalenemethylamine hydrochloride
CAS:101827-46-7
MF:C23H27N.ClH
MW:353.93
EINECS:642-354-4
Product Categories:Active Pharmaceutical Ingredients;API;Antifungals for Research and Experimental Use;Biochemistry;Butenafine;Amines;Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;101827-46-7
Mol File:101827-46-7.mol
Butenafine hydrochloride Structure
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
InChIKeyLJBSAUIFGPSHCN-UHFFFAOYSA-N
CAS DataBase Reference101827-46-7(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 21
Safety Statements 44
WGK Germany nwg
RTECS QJ8585000
HS Code 29214990
MSDS Information
Butenafine hydrochloride Usage And Synthesis
DescriptionButenafine 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 PropertiesWhite Solid
OriginatorKaken (Japan)
UsesButenafine HCl is a synthetic benzylamine antifungal, works by inhibiting the synthesis of sterols by inhibiting squalene epoxidase.
UsesButenafine hydrochloride has been used as a standard in high-performance liquid chromatography (HPLC) method to determine butenafine hydrochloride in butenafine-loaded nanosponges.
UsesAn antifungal, used to control dermal fungal infections such as athletes foot and ring worm.
DefinitionChEBI: 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 ProcessN-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 nameLotrimin (Schering); Mentax (Mylan Bertek);Volley.
Therapeutic FunctionAntifungal
General DescriptionButenafine 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 ActionsButenafine 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.
Butenafine hydrochloride Preparation Products And Raw materials
Raw materialsBenzyl bromide-->1-Methyl-aminomethyl naphthalene
Butenafine Topotecan hydrochloride Sibutramine hydrochloride 1-[(2-Chlorophenyl)-N-(methylimino)methyl]cyclopentanol hydrochloride Tramadol hydrochloride Methylamine Benzylamine Tribenuron methyl Trimethylamine Meglumine Methylamine hydrochloride 1-AdaMantanethylaMine 1-Methyl-aminomethyl naphthalene Methyl salicylate Trimethylamine hydrochloride Methyl acetate Methyl bromide METSULFURON METHYL

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