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Butoconazole nitrate

Product Name
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
Formula Weight
474.79
MOL File
64872-77-1.mol
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Butoconazole nitrate Property

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)
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

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N-Bromosuccinimide Price

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

Raw materials

Preparation Products

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Butoconazole nitrate Suppliers

Jinan Londi Medical Technology Co., LTD
Tel
0531-88996911 15628983711
Fax
0531-88996911
Email
3305202763@qq.com
Country
China
ProdList
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58
Jinan Shengqi Pharmaceutical Co., Ltd
Tel
0531-88892685 18660160628
Email
2153390475@qq.com
Country
China
ProdList
216
Advantage
58
Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
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Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
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61
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
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81
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
chenyj@titansci.com
Country
China
ProdList
14103
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59
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Shanghai Longsheng chemical Co.,Ltd.
Tel
021-58099652-8005 13585536065
Fax
021-58099609
Email
bin.wu@shlschem.com
Country
China
ProdList
9809
Advantage
59
Nanjing Chemlin Chemical Co., Ltd
Tel
025-83697070
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
19179
Advantage
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View Lastest Price from Butoconazole nitrate manufacturers

S&Y Biochem Co.,Ltd
Product
Butoconazole nitrate 64872-77-1
Price
US $1.00/kg
Min. Order
1kg
Purity
99
Supply Ability
1111
Release date
2024-10-11
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Butoconazole nitrate 64872-77-1
Price
US $0.00/Kg/Bag
Min. Order
1KG
Purity
98%min
Supply Ability
100KGS
Release date
2021-09-13
Hebei Weibang Biotechnology Co., Ltd
Product
Butoconazole nitrate 64872-77-1
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-15

64872-77-1, Butoconazole nitrateRelated Search:


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