Econazole

Econazole is an antifungal medication of the imidazole class.^[3]

Econazole

Clinical data
Trade names	Spectazole, Ecostatin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a684049
License data	US DailyMed: Econazole
Pregnancy category	AU: A[1]
Routes of administration	Topical
ATC code	D01AC03 (WHO) G01AF05 (WHO)
Legal status
Legal status	US: ℞-only[2]
Identifiers
IUPAC name (RS)-1-{2-[(4-Chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
CAS Number	27220-47-9 Y
PubChem CID	3198
IUPHAR/BPS	2446
DrugBank	DB01127 Y
ChemSpider	3086 Y
UNII	6Z1Y2V4A7M
KEGG	D03936 Y
ChEBI	CHEBI:4754 Y
ChEMBL	ChEMBL808 Y
CompTox Dashboard (EPA)	DTXSID2029872
ECHA InfoCard	100.043.932
Chemical and physical data
Formula	C18H15Cl3N2O
Molar mass	381.68 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic 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 Y Key:LEZWWPYKPKIXLL-UHFFFAOYSA-N Y
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It was patented in 1968, and approved for medical use in 1974.^[4]

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.^{[citation needed]}

Econazole nitrate exhibits strong anti-feeding properties against the keratin-digesting common clothes moth Tineola bisselliella.^[5]

Econazole is known to bind to tubulin and inhibit its polymerization. ^[6]

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.^[7]

Synthesis

Imidazoles devoid of the nitro group no longer have any antiprotozoal activity, however, such drugs are effective antifungal agents.^{[citation needed]}

Econazole synthesis:^[8] 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^[9] and ECOSONE (econazole/triamcinolone).