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Butoconazole nitrate

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CAS:64872-77-1
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Products Intro: Product Name:Butoconazole nitrate
CAS:64872-77-1
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Products Intro: Product Name:Butoconazole nitrate
CAS:64872-77-1
Purity:99% Package:25KG;5KG;1KG

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  • Butoconazole nitrate
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  • $0.00 / 25KG
  • 2023-07-04
  • CAS:64872-77-1
  • Min. Order: 1KG
  • Purity: 99%
  • Supply Ability: 50000KG/month
  • Butoconazole nitrate
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  • $50.00 / 1kg
  • 2023-04-20
  • CAS:64872-77-1
  • Min. Order: 1kg
  • Purity: 99%
  • Supply Ability: 50 tons
  • Butoconazole nitrate
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  • $0.00 / 1Kg/Bag
  • 2021-09-29
  • CAS:64872-77-1
  • Min. Order: 1KG
  • Purity: 98%min
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Butoconazole nitrate Basic information
Product Name:Butoconazole nitrate
Synonyms:(+-)-1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-1h-imidazolem;1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-1h-imidazol(+-)-1h-imidazol;exelgyn;Butoconazole nitrate 1-[4-(4-Chlorophenyl)-2-(2,6-dichlorophenyl)sulfanyl-butyl]imidazole nitrate;1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]imidazole;(+-)-1-(4-(p-Chlorophenyl)-2-(;1-(4-(4-Chlorophenyl)-2-(2,6-dichlorophenylthio)-n-butyl)imidazole nitrate;1-[4-(4-chlorophenyl)-2-(2,6-dichlorophenyl)sulfanyl-butyl]imidazole nitrate
CAS:64872-77-1
MF:C19H18Cl3N3O3S
MW:474.79
EINECS:613-721-6
Product Categories:Intermediates & Fine Chemicals;Pharmaceuticals;API
Mol File:64872-77-1.mol
Butoconazole nitrate Structure
Butoconazole nitrate Chemical Properties
Melting point 159°C (dec.)
storage temp. Sealed in dry,2-8°C
solubility DMSO or DMF: soluble
form powder
color White to Off-White
Merck 14,1529
InChIKeyZHPWRQIPPNZNML-UHFFFAOYSA-N
CAS DataBase Reference64872-77-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 22
WGK Germany 3
RTECS NI4399500
HS Code 2933290000
ToxicityLD50 in mice, male, female rats (mg/kg): >3200, >3200, 1720 orally; >1600, 940, 940 i.p. (Walker)
MSDS Information
Butoconazole nitrate Usage And Synthesis
DescriptionButoconazole Nitrate is an antifungal imidazole antimycotics. It is useful in the topical treatment of vulvovaginal candidiasis, being similar in effectiveness to miconazole and clotrimazole.
DescriptionButoconazole is an imidazole antifungal agent that completely inhibits growth of a variety of fungi in vitro when used at concentrations of 0.05-30 μg/ml. It is active against vaginal infections of pure and mixed strains of C. albicans in mice when used vaginally at concentrations of 0.25-2% and 0.1-1%, respectively. Formulations containing butoconazole have been used in the treatment of vaginal yeast infections.
Chemical PropertiesWhite Solid
OriginatorSyntex (USA)
UsesImidazole derivative with antifungal properties
DefinitionChEBI: An organic nitrate salt obtained by reaction of equimolar amounts of butaconazole and nitric acid. An antifungal agent, it is used in gynaecology for treatment of vulvovaginal infections caused by Candida species, particularly Candida a bicans.
Manufacturing Process1H-Imidazole, 1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-, (+/- )-, mononitrate may be prepared by the same way as described below for enantiomers.
To a solution of Li2CuCl4 (0.10 M, 8.8 ml, 0.88 mmol) in dry THF (75 ml) was added dropwise a solution of 4-chloromagnesium chloride (17.5 mmol) in ether (15 ml) at -35°C. After stirring for 45 min, a pre-cooled (-35°C) solution of (S)-(+)-glycydil tosylate (2.0 g, 8.8 mmol) in THF (5 ml) was added via syringe. After 2 h at -35°C, the mixture was quenched with saturated NH4Cl and extracted with ether. The organic layer was dried (Na2SO4), evaporated to dryness and purificated by flash chromatography affording (2S)-1-(p-toluenesulphonyloxy)-4-(4-chlorophenyl)butan-2-ol, as a white solid (1.9 g, 77%), m.p. 72.7-74°C.
(2S)-1-[2-Hydroxy-4-(4-chlorophenyl)butyl]-1H-imidazole was prepared as follows: to a solution of imidasole (0.52 g, 7.61 mmol) in dry DMF (5 ml) at 0°C under N2 was added NaH (60% dispersion in oil, 0.3 g, 7.61 mmol). The reaction mixture was warmed to room temperature and stirred for 30 min. A solution of (2S)-1-(p-toluenesulphonyloxy)-4-(4chlorophenyl)butan-2-ol in DMF (15 ml) was then added dropwise over 15 min. The reaction mixture was heated at 75°C for 24 h, cooled poured into water and extracted with ethyl acetate. The organic phase was dried and evaporated and was the residue purified by flash chromatography. Gradient elution (1-5% MeOH/CH2Cl2) afforded (2S)-1-[2-hydroxy-4-(4-chlorophenyl)butyl]-1H-imidazole which was recrystallized from EtOAc/Et2O (236 mg, 67%), m.p. 128°-131°C; [α]D25- 23.23 (c 0.4, CHCl3).
(2S)-1-[2-Hydroxy-4-(4-chlorophenyl)butyl]-1H-imidazole nitrate was prepared as follows. To a solution of (2S)-1-(p-toluenesulphonyloxy)-4-(4- chlorophenyl)butan-2-ol (250 mg, 1 mmol) in THF (5 ml) at 0°C was added triethylamine (0.28 ml, 2.0 mmol), followed by methanesulfonyl chloride (0,15 ml, 2.0 mmol). The reaction mixture was was warmed to room temperature and stirred for 1 h. The mixture was poured into aq. NaHCO3, extracted with EtOAC, and the organic phase dried and evaporated to dryness. The resulting mesylate was dissolved in acetone (50 ml), then 2,6-dichlorobenzenethiol(464 mg, 2.6 mmol) and K2CO3 (568 mg, 4.1 mmol) were added. The mixture was heated at reflux under N2, cooled to room temperature, evaporated to dryness and partionated between water and EtOAc. The organic phase was dried (Na2SO4), evaporated, and residue purified by flash chromatography (1- 2% MeOH/CH2Cl2 gradient elution) to give an oil which was converted to nitrate salt. Recrystallization from EtOAc/Et2O gave 260 mg (55%) (2S)-1-[2- hydroxy-4-(4-chlorophenyl)butyl]-1H-imidazole nitrate, m.p. 120°-124°C; [α]D25+22.68 (c 0.4, EtOH).
The R enantiomer was prepared the same way from (-)-glycidyl tosylate.
Brand nameFemstat (Roche);Femstat 3 (Bayer); Gynazole-1 (KV Pharmaceutical).
Therapeutic FunctionAntifungal
Clinical Use1-[4-(4-Chlorophenyl)-2-[(2,6-dichlorophenyl)-thio]butyl]-1H-imidazole (Femstat) is an extremely broad-spectrum antifungaldrug that is specifically effective against C. albicans.It is supplied as a vaginal cream containing 2% of thesalt. It is intended for the treatment of vaginal candidiasis.
Butoconazole nitrate Preparation Products And Raw materials
Raw materials(2S)-(+)-Glycidyl tosylate-->LITHIUM TETRACHLOROCUPRATE-->Imidazole-->Methanesulfonyl chloride-->Triethylamine-->Sodium hydride
Tag:Butoconazole nitrate(64872-77-1) Related Product Information
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