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Butoconazole nitrate

CAS No.
64872-77-1
Chemical Name:
Butoconazole nitrate
Synonyms
Gynomy;exelgyn;femstat;gynomyk;rs-35887;Buconazole nitrate;BUTOCONAZOLENITRILE;BUTACONAZOLE NITRATE;BUTOCONAZOLE NITRATE;BOTOCONAZOLE NITRATE
CBNumber:
CB9706745
Molecular Formula:
C19H18Cl3N3O3S
Molecular Weight:
474.79
MDL Number:
MFCD00058159
MOL File:
64872-77-1.mol
MSDS File:
SDS
Last updated:2024-11-19 23:02:33

Butoconazole nitrate 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)
FDA UNII 4805237NP5

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P301+P312+P330
Hazard Codes  Xn
Risk Statements  22
WGK Germany  3
RTECS  NI4399500
HS Code  2933290000
Toxicity LD50 in mice, male, female rats (mg/kg): >3200, >3200, 1720 orally; >1600, 940, 940 i.p. (Walker)
NFPA 704
0
3 0

Butoconazole nitrate price More Price(27)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 1082300 Butoconazole nitrate United States Pharmacopeia (USP) Reference Standard 64872-77-1 200mg $147.2 2024-03-01 Buy
Sigma-Aldrich PHR1621 Butoconazole Nitrate Pharmaceutical Secondary Standard; Certified Reference Material 64872-77-1 1g $82.8 2022-05-15 Buy
TCI Chemical B4801 Butoconazole Nitrate >98.0%(HPLC)(T) 64872-77-1 1g $103 2024-03-01 Buy
Cayman Chemical 23554 Butoconazole (nitrate) ≥98% 64872-77-1 500mg $32 2024-03-01 Buy
Cayman Chemical 23554 Butoconazole (nitrate) ≥98% 64872-77-1 1g $57 2024-03-01 Buy
Product number Packaging Price Buy
1082300 200mg $147.2 Buy
PHR1621 1g $82.8 Buy
B4801 1g $103 Buy
23554 500mg $32 Buy
23554 1g $57 Buy

Butoconazole nitrate Chemical Properties,Uses,Production

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 a bicans.

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 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 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

Global( 263)Suppliers
Supplier Tel Email Country ProdList Advantage
S&Y Biochem Co.,Ltd
+8617774091612 marketing@sybiochem.com China 128 58
Hebei Weibang Biotechnology Co., Ltd
+8615531157085 abby@weibangbio.com China 8807 58
Shaanxi Dideu Medichem Co. Ltd
+86-29-81148696 +86-15536356810 1022@dideu.com China 3882 58
Hebei Mojin Biotechnology Co., Ltd
+86 13288715578 +8613288715578 sales@hbmojin.com China 12834 58
Frapp's ChemicalNFTZ Co., Ltd.
+86 (576) 8169-6106 sales@frappschem.com China 880 50
Capot Chemical Co.,Ltd.
+86-(0)57185586718 +86-13336195806 sales@capot.com China 29791 60
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497 sales01@cooperate-pharm.com CHINA 1803 55
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21634 55
Hangzhou FandaChem Co.,Ltd.
+8615858145714 FandaChem@Gmail.com China 9084 55
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795 ivan@atkchemical.com China 32956 60

View Lastest Price from Butoconazole nitrate manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Butoconazole nitrate pictures 2024-12-16 Butoconazole nitrate
64872-77-1
US $1.00 / kg 1kg 99 1111 S&Y Biochem Co.,Ltd
Butoconazole nitrate pictures 2024-12-13 Butoconazole nitrate
64872-77-1
US $0.00 / Kg/Bag 1KG 98%min 100KGS WUHAN FORTUNA CHEMICAL CO., LTD
Butoconazole nitrate pictures 2024-11-19 Butoconazole nitrate
64872-77-1
US $33.00-77.00 / mg 100% 10g TargetMol Chemicals Inc.

Butoconazole nitrate Spectrum

(+-)-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 BUTOCONAZOLE NITRATE BUTACONAZOLE NITRATE 1-[4-(4-Chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-1H-imidazole Nitrate Gynomy BUTOCONAZOLENITRILE femstat gynomyk rs-35887 BUTOCONAZOLE NITRATE USP(CRM STANDARD) Butoconazole Nitrate (200 mg) 1-[(2R)-4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl]-1H-iMidazole 1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-1H-imidazole,nitrate (1:1) Butoconazole Nitrate > 1-[4-(4-Chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]imidazole Nitrate BOTOCONAZOLE NITRATE Butoconazole nitrate USP/EP/BP Butoconazole Nitrate (1082300) Buconazole nitrate Butoconazole Nitrate (RS35887) 64872-77-1 65872-77-1 C19H18Cl3N3O3S C19H17Cl3N2SHNO3 Intermediates & Fine Chemicals Pharmaceuticals API