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Butoconazole

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Butoconazole Basic information
Butoconazole Chemical Properties
  • Melting point:68-70.5°
  • Boiling point:566.9±50.0 °C(Predicted)
  • Density 1.32±0.1 g/cm3(Predicted)
  • pka6.74±0.12(Predicted)
  • CAS DataBase Reference64872-76-0(CAS DataBase Reference)
Butoconazole Usage And Synthesis
  • Usesantineoplastic, pyrimidine antimetabolite
  • UsesButoconazole is a fungostatic drug, and it is formally classified as an imidazole, but only because of the presence of an imidazole ring in the structure. It is believed that butoconazole, like miconazole, econazole, and other “pure” representatives of the imidazole class, also inhibits the biosynthesis of estrosterin in the cytoplasmatic membrane of fungi; however, it is very possible that this is not the only mechanism of its action. It is effective for vaginal infections caused by various types of candida. It is also used only externally and vaginally. Synonyms of this drug are femstat, listomin, and others.
  • DefinitionChEBI: A member of the class of imidazoles that is 1H-imidazole in which the hydrogen attached to the nitrogen is substituted by a 4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl group. An antifungal agent, it is used as its nitrate sa t in gynaecology for treatment of vulvovaginal infections caused by Candida species, particularly Candida albicans.
  • brand nameFemstat (Roche);Femstat 3 (Bayer); Gynazole-1 (KV Pharmaceutical).
  • Chemical SynthesisButoconazole, 1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]- 1H-imidazole (35.2.12), is synthesized from 4-chlorobenzylmagnesium bromide, which is reacted with epichloridrine to make 4-(4-chlorophenyl)-1-chlorobutan-2-ol (35.2.10), which is reacted with imidazole in the presence of sodium to make 4-(4-chlorophenyl)- 1-(1H-imidazolyl)butanol-2 (35.2.11). The hydroxyl group in the last is replaced with a chlorine atom upon reaction with thionyl chloride, which is then by the reaction with 2,6- dichlorothiophenol butoconazole, is obtained.

  • Enzyme inhibitorThis fungicide (FW = 411.78 g/mol; CAS 64872-77-1), also known as Femstat?, Femstat-3?, Gynazole-1?, and systematically as 1-[4- (4- chlorophenyl) -2-[ (2,6-dichlorophenyl) -sulfanyl]butyl]-1H-imidazole (* = chiral center), is believed to inhibit steroid synthesis, targeting the conversion of lanosterol to ergosterol and modifying membrane composition/function. At 80 μM, butoconazole was strictly fungistatic against early stationary-phase Candida albicans cells. During early log- phase growth, butoconazole were highly lethal at 20 μM. In 1995, butoconazole was approved for treatment of vaginal yeast infections.
Butoconazole Preparation Products And Raw materials
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