Econazole nitrate

Chemical properties

White to Off-White Solid

Originator

Pevaryl,Cilag Chemie,France,1976

The Uses of Econazole nitrate

Antifungal;Ergosterol synthesis inhibition

The Uses of Econazole nitrate

Azole antifungal

The Uses of Econazole nitrate

Econazole nitrate is an antifungal agent of the imidazole type used in topical and vaginal preparations to prevent growth of dermatophytes, yeast, and mold.

What are the applications of Application

Econazole nitrate salt is a ketoconazole-like azole based antifungal agent

Manufacturing Process

A suspension of 10.3 parts of α-(2,4-dichlorophenyl)-imidazole-1-ethanol and 2.1 parts of sodium hydride in 50 parts of dry tetrahydrofuran is stirred andrefluxed for 2 hours. After this reaction-time, the evolution of hydrogen is ceased. Then there are added successively 60 parts dimethylformamide and 8 parts of p-chlorobenzylchloride and stirring and refluxing is continued for another two hours. The tetrahydrofuran is removed at atmospheric pressure. The dimethylformamide solution is poured onto water. The product, 1-[2,4- dichloro-β-(p-chlorobenzyloxy)phenethyl]imidazole, is extracted with benzene. The extract is washed with water, dried, filtered and evaporated in vacuo. From the residual oily free base, the nitrate salt is prepared in the usual manner in 2-propanol by treatment with concentrated nitric acid, yielding, after recrystallization of the crude solid salt from a mixture of 2-propanol, methanol and diisopropylether, 1-[2,4-dichloro-β-(pchlorobenzyloxy)phenethyl]imidazole nitrate; MP 162°C.

brand name

Spectazole (Johnson & Johnson).

Therapeutic Function

Antifungal

General Description

White crystalline powder.

Air & Water Reactions

Insoluble in water.

Fire Hazard

Flash point data for Econazole nitrate are not available; however, Econazole nitrate is probably combustible.

Biochem/physiol Actions

Econazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. Inhibition of ergosterol results in increased cellular permeability causing leakage of cellular contents. Econazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and phospholipid biosynthesis.