econazole econazole econazole is an antifungal medication of the imidazole class. econazoleclinical datatrade namesspectazole, ecostatin, othersahfs/drugs.commonographmedlineplusa684049license data us dailymed: econazole pregnancycategory au: a routes ofadministrationtopicalatc coded01ac03 (who) g01af05 (who)legal statuslegal status us: ℞-only identifiers iupac name (rs)-1--1h-imidazole cas number27220-47-9 ypubchem cid3198iuphar/bps2446drugbankdb01127 ychemspider3086 yunii6z1y2v4a7mkeggd03936 ychebichebi:4754 ychemblchembl808 ycomptox dashboard (epa)dtxsid2029872 echa infocard100.043.932 chemical and physical dataformulac18h15cl3n2omolar mass381.68 g·mol−13d model (jsmol)interactive imagechiralityracemic mixture smiles clc1ccc(c(cl)c1)c(occ2ccc(cl)cc2)cn3ccnc3 inchi inchi=1s/c18h15cl3n2o/c19-14-3-1-13(2-4-14)11-24-18(10-23-8-7-22-12-23)16-6-5-15(20)9-17(16)21/h1-9,12,18h,10-11h2 ykey:lezwwpykpkixll-uhfffaoysa-n y (verify) it was patented in 1968, and approved for medical use in 1974. medical uses econazole is used as a cream to treat skin infections 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 vaginal thrush. 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 rash. synthesis imidazoles devoid of the nitro group no longer have any antiprotozoal activity, however, such drugs are effective antifungal agents. econazole synthesis: de 1940388 u.s. patent 3,717,655 (1970, 1973 both to janssen). alkylation of imidazole (2) with bromoketone (1) prepared from o,p-dichloroacetophenone 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).