Chemistry:Econazole
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| Trade names | Spectazole, Ecostatin, others |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a684049 |
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| Routes of administration | Topical |
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| Formula | C18H15Cl3N2O |
| Molar mass | 381.68 g·mol−1 |
| 3D model (JSmol) | |
| Chirality | Racemic mixture |
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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]
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.[6]
Synthesis
Imidazoles devoid of the nitro group no longer have any antiprotozoal activity, however, such drugs are effective antifungal agents.[citation needed]
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[8] and ECOSONE (econazole/triamcinolone).
References
- ↑ "Econazole topical Use During Pregnancy". 3 September 2018. https://www.drugs.com/pregnancy/econazole-topical.html.
- ↑ "Spectazole (econazole nitrate 1%) Cream". DailyMed. U.S. National Library of Medicine. 30 September 2013. https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=121775.
- ↑ "Bilogical and toxicological properties of econazole, a broad-spectrum antimycotic". Arzneimittel-Forschung 25 (2): 224–230. February 1975. PMID 1173036.
- ↑ Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 502. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA502.
- ↑ "The efficacy of antifungal azole and antiprotozoal compounds in protection of wool from keratin-digesting insect larvae". Textile Research Journal 84 (9): 924–931. 2014. doi:10.1177/0040517513515312.
- ↑ "Econazole nitrate cream". Daily Med. U.S. National Library of Medicine. https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=3acc5e03-0339-4b23-945d-641746e81923.
- ↑ "The preparation and antimycotic properties of derivatives of 1-phenethylimidazole". Journal of Medicinal Chemistry 12 (5): 784–791. September 1969. doi:10.1021/jm00305a014. PMID 4897900.
- ↑ "Product descriptions: Ecoderm Cream". Bangladesh: REPHCO Pharmaceuticals Limited. http://www.rephco-bd.com/index.php?option=com_content&view=article&id=22&Itemid=48.
External links
- "Econazole". Drug Information Portal. U.S. National Library of Medicine. https://druginfo.nlm.nih.gov/drugportal/name/econazole.
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