Sertaconazole nitrate Chemical Properties

Melting point:

146-147°

Boiling point:

614.1±55.0 °C(Predicted)

Density 

1.43±0.1 g/cm3(Predicted)

storage temp. 

Refrigerator

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

6.68±0.12(Predicted)

color 

White to Pale Yellow

CAS DataBase Reference

99592-32-2(CAS DataBase Reference)

Sertaconazole nitrate Usage And Synthesis

Description

Sertaconazole has been developed and launched for the treatment of dermatological fungal infections by Ferrer Internacional S. A. Mylan received FDA approval for sertaconazole nitrate cream for the treatment of athlete's foot (tinea pedis) at the end of 2003.

Uses

An imidazole antifungal agent, inhibits the synthesis of ergosterol, an essential cell wall component of fungi.

Definition

ChEBI: 1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole is a member of the class of imidazoles that carries a 2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl group at position 1. It is a dichlorobenzene, an ether, a member of imidazoles and a member of 1-benzothiophenes.

Indications

Topical treatment of mycoses of the skin induced or sustained by fungi such as yeasts and dermatophytes. New formulations for the treatment of vaginal mycoses are in development.

Antimicrobial activity

Sertaconazole is a rather new broad-spectrum imidazole antimycotic with activity against almost all species of pathogenic fungi. It also has excellent activity against pathogenic yeasts.

Synthesis

2,4-Dichloro acetophenone 169 was brominated at low temperature to give bromide intermediate 170, which was used without isolation. To the same pot, five-fold excess of imidazole was added to give imidazolylacetophenone 171 in 71% yield from 169. Sodium borohydride was employed to reduce ketone 171 to alcohol 172 in 78% yield. Racemic alcohol 172 was resolved with (-)-DIP-chloride to give its corresponding chiral R-alcohol 173 in 80% yield. Compound 173 was then alkylated with 3-bromomethyl-7-chlorobenzo[b]thiophene (174) in dry DMF in the presence of potassium t-butoxide to give the alkylation product in 68% yield. Finally, 60% nitric acid was used to make sertaconazole mononitrate (XXI) in 89% yield.

Solubility in organics

Fairly soluble in ethanol (1.7 %), chloroform (1.5 %); slightly soluble in acetone (0.95 %); very slightly soluble in noctanol (0.069 %). Practically insoluble in water (< 0.01 %).

Sertaconazole nitrate(99592-32-2)Related Product Information

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