Butoconazole nitrate CAS 64872-77-1
Introduction：Basic information about Butoconazole nitrate CAS 64872-77-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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 nitrate1-[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 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 |
| InChI | InChI=1S/C19H17Cl3N2S.HNO3/c20-15-7-4-14(5-8-15)6-9-16(12-24-11-10-23-13-24)25-19-17(21)2-1-3-18(19)22;2-1(3)4/h1-5,7-8,10-11,13,16H,6,9,12H2;(H,2,3,4) |
| InChIKey | ZHPWRQIPPNZNML-UHFFFAOYSA-N |
| SMILES | C(CN1C=NC=C1)(SC1C(Cl)=CC=CC=1Cl)CCC1=CC=C(Cl)C=C1.[N+]([O-])(=O)O |
| CAS DataBase Reference | 64872-77-1(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 22 |
| WGK Germany | 3 |
| RTECS | NI4399500 |
| HS Code | 2933290000 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral |
| Toxicity | LD50 in mice, male, female rats (mg/kg): >3200, >3200, 1720 orally; >1600, 940, 940 i.p. (Walker) |
| Description | Butoconazole Nitrate is the nitrate salt form of butaconazole, a synthetic imidazole derivative with fungistatic properties. Butoconazole is an imidazole antifungal agent that completely inhibits the growth of various 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. Butoconazole Nitrate is an antifungal imidazole antimycotics. It is useful in the topical treatment of vulvovaginal candidiasis, being similar in effectiveness to miconazole and clotrimazole. |
| Chemical Properties | Butoconazole nitrate is a white to off-white crystalline powder with a molecular weight of 474.79. It is sparingly soluble in methanol, slightly soluble in chloroform, methylene chloride, acetone, and ethanol, very slightly soluble in ethyl acetate, and practically insoluble in water. It melts at about 159°C with decomposition. |
| Originator | Syntex (USA) |
| Uses | Imidazole derivative with antifungal properties |
| Definition | ChEBI: 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 abicans. |
| Application | Gynazole·1® contains 2% butoconazole nitrate (an imidazole derivative with antifungal activity) in cream of edetate disodium, glyceryl monostearate, methylparaben, mineral oil, polyglycerol-3 oleate, propylene glycol, propylparaben, colloidal silicon dioxide, sorbitol solution, purified water, and microcrystalline wax. Butoconazole nitrate is used locally in the treatment of vulvovaginal candidiasis. It is administered as a 100-mg suppository or 5 g (1 applicatorful) of a 2% cream for three consecutive nights. |
| Manufacturing Process | 1H-Imidazole, 1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-, (+/-)-, mononitrate may be prepared by the same way as described below forenantiomers. To a solution of Li2CuCl4 (0.10 M, 8.8 ml, 0.88 mmol) in dry THF (75 ml) wasadded dropwise a solution of 4-chloromagnesium chloride (17.5 mmol) inether (15 ml) at -35°C. After stirring for 45 min, a pre-cooled (-35°C) solutionof (S)-(+)-glycydil tosylate (2.0 g, 8.8 mmol) in THF (5 ml) was added viasyringe. After 2 h at -35°C, the mixture was quenched with saturated NH4Cland extracted with ether. The organic layer was dried (Na2SO4), evaporated todryness 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 asfollows: to a solution of imidasole (0.52 g, 7.61 mmol) in dry DMF (5 ml) at0°C under N2 was added NaH (60% dispersion in oil, 0.3 g, 7.61 mmol). Thereaction mixture was warmed to room temperature and stirred for 30 min. Asolution of (2S)-1-(p-toluenesulphonyloxy)-4-(4chlorophenyl)butan-2-ol inDMF (15 ml) was then added dropwise over 15 min. The reaction mixture washeated at 75°C for 24 h, cooled poured into water and extracted with ethylacetate. The organic phase was dried and evaporated and was the residuepurified by flash chromatography. Gradient elution (1-5% MeOH/CH2Cl2)afforded (2S)-1-[2-hydroxy-4-(4-chlorophenyl)butyl]-1H-imidazole which wasrecrystallized 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 wasprepared 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 addedtriethylamine (0.28 ml, 2.0 mmol), followed by methanesulfonyl chloride (0,15ml, 2.0 mmol). The reaction mixture was was warmed to room temperatureand stirred for 1 h. The mixture was poured into aq. NaHCO3, extracted withEtOAC, and the organic phase dried and evaporated to dryness. The resultingmesylate 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 mixturewas heated at reflux under N2, cooled to room temperature, evaporated todryness and partionated between water and EtOAc. The organic phase wasdried (Na2SO4), evaporated, and residue purified by flash chromatography (1-2% MeOH/CH2Cl2 gradient elution) to give an oil which was converted tonitrate 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 name | Femstat (Roche);Femstat 3 (Bayer); Gynazole-1 (KV Pharmaceutical). |
| Therapeutic Function | Antifungal |
| Clinical Use | 1-[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 |
