Econazole

Econazole
Clinical data
Trade names	Spectazole, Ecostatin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a684049
ATC code	D01AC03 (WHO) G01AF05 (WHO);
Identifiers
	IUPAC name (RS)-1-{2-[(4-Chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole;
CAS Number	27220-47-9 ;
PubChem CID	3198;
IUPHAR/BPS	2446;
DrugBank	DB01127 ;
ChemSpider	3086 ;
UNII	6Z1Y2V4A7M;
KEGG	D03936 ;
ChEBI	CHEBI:4754 ;
ChEMBL	CHEMBL808 ;
ECHA InfoCard	100.043.932
Chemical and physical data
Formula	C18H15Cl3N2O
Molar mass	381.683 g/mol
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 ; Key:LEZWWPYKPKIXLL-UHFFFAOYSA-N ;
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Econazole (commonly used as the nitrate salt) is an antifungal medication of the imidazole class.^[1] It is sold under the brand names Spectrazole (United States) and Ecostatin (Canada), among others. It is a component of Pevisone and Ecoderm-TA^[2] (econazole/triamcinolone).

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.^[3]

Adverse effects

About 3% of patients treated with econazole nitrate cream reported side effects. The most common symptoms were burning, itching, erythema, and one outbreak of a pruritic rash.^[4]

Synthesis

Imidazoles devoid of the nitro group no longer have any antiprotozoal activity, however, such drugs are effective antifungal agents.

Econazole synthesis:^[5] 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.

References

↑ Thienpont, D; Van Cutsem, J; Van Nueten, JM; Niemegeers, CJ; Marsboom, R (1975). "Bilogical and toxicological properties of econazole, a broad-spectrum antimycotic". Arzneimittel-Forschung. 25 (2): 224–30. PMID 1173036.
↑ Product descriptions at REPHCO Pharmaceuticals Limited, Bangladesh. Retrieved June 2012
↑ Sunderland, M. R.; Cruickshank, R. H.; Leighs, S. J. (2014). “The efficacy of antifungal azole and antiprotozoal compounds in protection of wool from keratin-digesting insect larvae”. Textile Research Journal 84 (9): 924–931. http://trj.sagepub.com/content/84/9/924
↑ Perrigo Econazole Nitrate Cream Product Description. 2012.
↑ Godefroi, E. F.; Heeres, J.; Van Cutsem, J.; Janssen, P. A. J. (1969). "Preparation and antimycotic properties of derivatives of 1-phenethylimidazole". Journal of Medicinal Chemistry. 12 (5): 784. doi:10.1021/jm00305a014.

External links

Description and details at Drugs.com

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[1] Thienpont, D; Van Cutsem, J; Van Nueten, JM; Niemegeers, CJ; Marsboom, R (1975). "Bilogical and toxicological properties of econazole, a broad-spectrum antimycotic". Arzneimittel-Forschung. 25 (2): 224–30. PMID 1173036.

[2] Product descriptions at REPHCO Pharmaceuticals Limited, Bangladesh. Retrieved June 2012

[3] Sunderland, M. R.; Cruickshank, R. H.; Leighs, S. J. (2014). “The efficacy of antifungal azole and antiprotozoal compounds in protection of wool from keratin-digesting insect larvae”. Textile Research Journal 84 (9): 924–931. http://trj.sagepub.com/content/84/9/924

[4] Perrigo Econazole Nitrate Cream Product Description. 2012.

[5] Godefroi, E. F.; Heeres, J.; Van Cutsem, J.; Janssen, P. A. J. (1969). "Preparation and antimycotic properties of derivatives of 1-phenethylimidazole". Journal of Medicinal Chemistry. 12 (5): 784. doi:10.1021/jm00305a014.