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Butenafine hydrochloride

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Butenafine hydrochloride Basic information
Butenafine hydrochloride Chemical Properties
  • Melting point:210-214°C
  • storage temp. Refrigerator, Under Inert Atmosphere
  • 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
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.
  • 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
Butenafine hydrochloride Preparation Products And Raw materials
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