Econazole

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Econazole
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Clinical data
Trade namesSpectazole, Ecostatin, others
AHFS/Drugs.comMonograph
MedlinePlusa684049
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Pregnancy
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Routes of
administration		Topical
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Legal status
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Identifiers
  • (RS)-1-{2-[(4-Chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
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Chemical and physical data
FormulaC18H15Cl3N2O
Molar mass381.68 g·mol−1
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ChiralityRacemic mixture
  • Clc1ccc(c(Cl)c1)C(OCc2ccc(Cl)cc2)Cn3ccnc3
  • 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 checkY
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Econazole is an antifungal medication of the imidazole class.[3]

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]

File:Econazole synthesis.svg
Econazole synthesis:[8] Page Template:Citation/styles.css has no content.DE 1940388  U.S. patent 3717655 (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).

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content."Econazole topical Use During Pregnancy". Drugs.com. 3 September 2018. Retrieved 31 January 2020.
  2. ^ Page Module:Citation/CS1/styles.css has no content."Spectazole (econazole nitrate 1%) Cream". DailyMed. U.S. National Library of Medicine. 30 September 2013. Retrieved 31 July 2021.
  3. ^ Page Module:Citation/CS1/styles.css has no content.Thienpont D, Van Cutsem J, Van Nueten JM, Niemegeers CJ, Marsboom R (February 1975). "Biological and toxicological properties of econazole, a broad-spectrum antimycotic". Arzneimittel-Forschung. 25 (2): 224–230. PMID 1173036.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 502. ISBN 9783527607495.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Sunderland MR, Cruickshank RH, Leighs SJ (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. doi:10.1177/0040517513515312. S2CID 135799368.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Baksheeva VE, La Rocca R, Allegro D, Derviaux C, Pasquier E, Roche P, Morelli X, Devred F, Golovin AV, Tsvetkov PO (2025). "NanoDSF Screening for Anti-tubulin Agents Uncovers New Structure–Activity Insights". Journal of Medicinal Chemistry. doi:10.1021/acs.jmedchem.5c01008.
  7. ^ Page Module:Citation/CS1/styles.css has no content."Econazole nitrate cream". Daily Med. U.S. National Library of Medicine.
  8. ^ Page Module:Citation/CS1/styles.css has no content.Godefroi EF, Heeres J, Van Cutsem J, Janssen PA (September 1969). "The preparation and antimycotic properties of derivatives of 1-phenethylimidazole". Journal of Medicinal Chemistry. 12 (5): 784–791. doi:10.1021/jm00305a014. PMID 4897900.
  9. ^ Page Module:Citation/CS1/styles.css has no content."Product descriptions: Ecoderm Cream". Bangladesh: REPHCO Pharmaceuticals Limited. Archived from the original on 31 August 2011. Retrieved 1 June 2012.

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