Chemical Properties
White or almost white powder.
Originator
Fazol,Fournier,France,1979
Uses
Antibacterial; antifungal.
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.
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.
