64872-76-0 Usage
Description
Butoconazole is an imidazole antifungal agent that is pharmacologically comparable to clotrimazole. It is used for the local treatment of vulvovaginal candidiasis (moniliasis) by increasing cell membrane permeability in susceptible fungi.
Uses
Used in Pharmaceutical Industry:
Butoconazole is used as a vaginal antifungal agent for the treatment of vulvovaginal candidiasis caused by various types of candida. It is believed to inhibit the biosynthesis of ergosterol in the cytoplasmic membrane of fungi, although this may not be the only mechanism of its action.
Used as a Topical Treatment:
Butoconazole is used only externally and vaginally, making it suitable for localized treatment of fungal infections without the need for systemic administration.
Synonyms:
Femstat, Listomin, and others.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 64872-76-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,4,8,7 and 2 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 64872-76:
(7*6)+(6*4)+(5*8)+(4*7)+(3*2)+(2*7)+(1*6)=160
160 % 10 = 0
So 64872-76-0 is a valid CAS Registry Number.
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
64872-76-0Relevant articles and documents
Preparation method of butoconazole nitrate
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, (2018/01/11)
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.
