Econazole is an antifungal medication of the imidazole class.
It was patented in 1968, and approved for medical use in 1974.
Medical uses
Econazole is used as a cream to treat
such as athlete's foot,
tinea, pityriasis versicolor,
ringworm, and
jock itch. It is also sold in Canada under the brand name Ecostatin as vaginal ovules to treat
candidiasis.
Econazole nitrate exhibits strong anti-feeding properties against the keratin-digesting common clothes moth Tineola bisselliella.
Adverse effects
About 3% of patients treated with econazole nitrate cream reported side effects. The most common symptoms were burning, itching, redness (
erythema), and one outbreak of a
pruritic.
Synthesis
Imidazoles devoid of the
nitro group no longer have any
antiprotozoal activity, however, such drugs are effective antifungal agents.
Alkylation of
imidazole (
2) with bromoketone (
1) prepared from
o,p-dichloro
acetophenone affords the displacement product (
3). Reduction of the ketone with sodium borohydride gives the corresponding alcohol (
4). Alkylation of the
alkoxide from that alcohol with
p-chlorobenzyl chloride leads to econazole (
5); alkylation with
o,p-dichlorobenzyl chloride gives
miconazole.
Society and culture
Brand names
It is sold under the brand names Spectrazole (
United States) and Ecostatin (
Canada), among others. It is a component of Pevisone, Ecoderm-TA
and ECOSONE (econazole/triamcinolone).
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