Econazole Chemical Properties

Melting point:

86.8°C

Boiling point:

533.8±50.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Practically insoluble in water, very soluble in ethanol (96 per cent) and in methylene chloride.

pka

6.68±0.12(Predicted)

form 

Solid

color 

White to off-white

Water Solubility 

0.37g/L(ambient temperature)

CAS DataBase Reference

27220-47-9(CAS DataBase Reference)

EPA Substance Registry System

Econazole (27220-47-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36/37/39

Econazole Usage And Synthesis

Chemical Properties

White or almost white powder

Originator

Pevaryl,Cilag Chemie,France,1976

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.

Uses

Econazole (cas# 27220-47-9) is a compound useful in organic synthesis.

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

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.

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.

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.

Econazole(27220-47-9)Related Product Information

• Methoxydiethylborane
• 4,4'-Bis(chloromethyl)-1,1'-biphenyl
• 4-Methoxybenzylchloride
• 1-Vinylimidazole
• 2-Methoxyethanol
• Levamisole
• Sodium dichloroisocyanurate
• Dichloroethane
• Ethyl acrylate
• Ethylparaben
• Ethanol
• Ethyl acetate
• Ethyl maltol
• Imidazole
• Thionyl chloride
• Isoconazole
• Imazalil
• Selank peptide