Isoconazole

Chemical properties

White or almost white powder.

Originator

Fazol,Fournier,France,1979

The Uses of Isoconazole

Antibacterial; antifungal.

Background

Isoconazole is an azole antifungal drug that has similar effectiveness to clotrimazole in the treatment of foot and vaginal infections.

Definition

ChEBI: 1-{2-[(2,6-dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl}imidazole is a member of the class of imidazoles that carries a 2-[(2,6-dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl group at position 1. It is a dichlorobenzene, an ether and a member of imidazoles.

Indications

Topical treatment of mycoses of the skin induced or sustained by fungi such as dermatophytes and yeasts. In addition, isoconazole is indicated for therapy of vulvovaginal mycoses causes by Candida species and Candida (Torulopsis) glabrata.

Manufacturing Process

To a stirred and refluxing solution of 40 parts of benzene and 35 parts of dimethylformamide (both solvents previously dried azeotropically) are added successively 1.6 parts of sodium hydride and 7.7 parts of α-(2,4- dichlorophenyl)imidazole-1-ethanol, (cooling on ice is necessary). After the addition is complete, stirring and refluxing is continued for 30 minutes. Then there are added 7.8 parts of 2.6-dichlorobenzyl chloride and the whole is stirred at reflux for another 3 hours. The reaction mixture is poured onto water and the product 1-[2,4-dichloro-b-(2,6-dichlorobenzyloxy)phenethyl] imidazole, is extracted with benzene. The extract is washed twice with water, dried, filtered and evaporated in vacuo. The base residue is dissolved in a mixture of acetone and diisopropyl ether and to this solution is added an excess of concentrated nitric acid solution. The precipitated nitrate salt is filtered off and recrystallized from a mixture of methanol and diisopropyl ether, yielding 1-[2,4-dichloro-b-(2,6-dichlorobenzyloxy)phenethyl]imidazole nitrate; melting point 179°C.

Therapeutic Function

Antibacterial, Antifungal

Antimicrobial activity

Broad-spectrum azole antimycotic with activity against almost all species of pathogenic fungi.

Pharmacokinetics

After topical application, isoconazole remains practically unabsorbed. Application in an ethanol/propyleneglycol vehicle increases penetration into the stratum corneum of the skin significantly.

Side Effects

Local irritations such as itching and burning sensations and allergic reactions may occur in rare cases and are mainly due to the galenic formulation.

Metabolism

Not Available

Solubility in organics

Isoconazole is soluble in methanol, acetic acid, and PEG 400; less soluble in ethanol, acetone, chloroform, and butanol; and barely soluble in water, diethyl ether, cyclohexane, and hexane.