64872-76-0

Basic information

• Product Name: Butoconazole
• Synonyms: BUTOCONAZOLE;Butooonazole;BUTONAZOLE;1-[4-(4-Chlorophenyl)-2-(2,6-dichlorophenyl)sulfanyl-butyl]imidazole;(±)-1-[4-(4-Chlorophenyl)-2-[(2，6-dichlorophenyl)thio]butyl]-1H-imidazole;1-[2-[(2,6-Dichlorophenyl)thio]-4-(4-chlorophenyl)butyl]-1H-imidazole
• CAS NO: 64872-76-0
• Molecular Formula: C₁₉H₁₇Cl₃N₂S
• Molecular Weight: 411.78
• Product Categories: VIDAZA
• Mol File: 64872-76-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 68-70.5°
• Boiling Point: 566.9 °C at 760 mmHg
• Flash Point: 296.7 °C
• Appearance: /
• Density: 1.32 g/cm³
• Vapor Pressure: 2.76E-12mmHg at 25°C
• Refractive Index: 1.633
• PKA: 6.74±0.12(Predicted)
• CAS DataBase Reference: Butoconazole(CAS DataBase Reference)
• NIST Chemistry Reference: Butoconazole(64872-76-0)
• EPA Substance Registry System: Butoconazole(64872-76-0)

Safety Data

• Hazardous Substances Data: 64872-76-0(Hazardous Substances Data)

Usage

Description

Butoconazole is an imidazole that is pharmacologically quite comparable to clotrimazole. It is a vaginal antifungal agent that increases cell membrane permeability in susceptible fungi. It is indicated for local treatment of vulvovaginal candidiasis (moniliasis).

Uses

Butoconazole 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.

Definition

ChEBI: 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 name

Femstat (Roche);Femstat 3 (Bayer); Gynazole-1 (KV Pharmaceutical).

Synthesis

Butoconazole, 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 inhibitor

This 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.

InChI:InChI=1/C19H17Cl3N2S/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/h1-5,7-8,10-11,13,16H,6,9,12H2

Upstream product

• 67085-11-4 1-[2-hydroxy-4-(4-chlorophenyl)-n-butyl]imidazole 
• 59363-13-2 1-chloro-4-(4-chlorophenyl)-2-butanol 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 67085-12-5 1-[2-chloro-4-(4-chlorophenyl)-n-butyl]imidazole 
• 24966-39-0 2,6-dichlorothiophenol 

Downstream Products

• 67085-13-6 (-)-butoconazole 
• 67085-13-6 (+)-butoconazole 
• 67085-13-6 (2R)-1-<2-(2,6-dichlorophenylthio)-4-(4-chlorophenyl)butyl>-1H-imidazole 
• 67085-13-6 (2S)-1-<2-(2,6-dichlorophenylthio)-4-(4-chlorophenyl)butyl>-1H-imidazole 

Relevant articles and documents

Preparation method of butoconazole nitrate

The invention discloses a preparation method of butoconazole nitrate. The preparation method comprises the following steps: with 4-chlorobenzyl chloride as a starting raw material, synthesizing 1-chloro-4-(4-chlorophenyl)-2-butanol, then synthesizing 1-(4-(4-chlorophenyl)-2-hydroxy-butyl) imidazole, then synthesizing 1-(4-(4-chlorophenyl)-2-chloro-butyl) imidazole, adding the 1-(4-(4-chlorophenyl)-2-chloro-butyl) imidazole, 2, 6-dichlorobenzenethiol and potassium carbonate into acetone, heating for refluxing, adding water and ethyl acetate after the completion of a reaction, performing liquid separation, sequentially washing an ethyl acetate phase by using saturated potassium carbonate and saturated salt water, drying by using anhydrous magnesium sulfate, removing magnesium sulfate, dropwise adding nitric acid with the concentration of 65% in an ice bath until no precipitate is produced, filtering for collecting solid, and recrystallizing by using absolute ethanol to obtain white crystals, namely the butoconazole nitrate. By the preparation method of the butoconazole nitrate, the process is simple, the yield is high, the cost is low, and the purity of the obtained product is high.