Chemical Properties
White or almost white powder
Originator
Pevaryl,Cilag Chemie,France,1976
Uses
Econazole (cas# 27220-47-9) is a compound useful in organic synthesis.
Uses
antineoplastic, anti-estrogen.
Econazole (Spectazole) is a synthetic imidazole. Econazole blocks C-14 demethylation of sterols, interfering with the biosynthesis of ergosterol, which results in disorganization of the fungal plasma cell membrane and increased permeability. It is active against dermatophytes, yeast, P. orbiculare, Aspergillus, Cladosporium, and Sporothrix.
Definition
ChEBI: 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole is a member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 4-chlorobenzyl group. It is an ether, a member of imidazoles, a dichlorobenzene and a member of monochlorobenzenes.
Indications
Econazole (Spectazole) is a synthetic imidazole. Econazole blocks C-14
demethylation of sterols, interfering with the biosynthesis of ergosterol,
which results in disorganization of the fungal plasma cell membrane and
increased permeability. It is active against dermatophytes, yeast, P. orbiculare,
Aspergillus, Cladosporium, and Sporothrix.
Indications
Topical treatment of mycoses of the skin induced or sustained by fungi such as dermatophytes and yeasts. In addition, econazole is indicated for therapy of vulvovaginal mycoses caused by Candida species and Candida (Torulopsis) glabrata.
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
Antimicrobial activity
Broad-spectrum imidazole antimycotic with activity against almost all species of pathogenic fungi.
Side effects
Local irritations such as itching and burning sensations and allergic reactions may occur in rare cases after topical therapy and are mainly due to the galenic formulation.
Synthesis
Econazole, 1-[2,4-dichloro-β-[(4-chlorobenzyl)oxy]phenethyl]-imidazole
(35.2.8), is an analog of myconazole. It differs in the presence of a single chlorine atom in
the benzyl part of the molecule, and it is synthesized in the same manner, except that it
uses 4-chlorobenzylchloride in the last stage instead of 2,4-dichlorobenzylbromide.
Solubility in organics
Econazole is soluble in methanol, acetic acid, and PEG 400; less soluble in ethanol, acetone, chloroform, and butanol; and barely soluble in water, ether, cyclohexane, and hexane.
