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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/11/05 18:08:24」(JST)

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Econazole (commonly used as the nitrate salt) is an antifungal medication of the imidazole class.^[1] It is used as a cream under the brand names Spectazole (United States), Ecostatin (Canada), Pevaryl (Western Europe), and Pevisone (the latter consisting of the combination econazole/triamcinolone) 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. In Asia, it is sold under the brand name Endix-G (by Dongkwang, Korea), while in Thailand, it is sold as Ecosone by Qualimed. In Taiwan, it is sold as Vivicome Cream, manufactured by Yong Chang Pharmaceuticals. In Egypt, it is sold as a foam spray by ATM. In Bangladesh, it is sold under the brand name Ecoderm by Rephco Pharmaceuticals Ltd. The combination of econazole nitrate with triamcinolone acetonide is also available under the brand name Ecoderm-TA.^[2] 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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English Journal

Design and synthesis of 1H-1,2,3-triazoles derived from econazole as antitubercular agents.

Kim S, Cho SN, Oh T, Kim P.SourceCancer & Infectious Diseases Therapeutics Research Group, Korea Research Institute of Chemical Technology, Daejeon, Republic of Korea; College of Pharmacy, Kyung Hee University, Seoul, Republic of Korea.
Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2012 Nov 15;22(22):6844-7. doi: 10.1016/j.bmcl.2012.09.041. Epub 2012 Sep 23.
Econazole has been known to be active against Mycobacterium tuberculosis. We have designed and synthesized 1H-1,2,3-triazoles derived from econazole as antitubercular agents. The majority of triazole derivatives have been prepared by microwave-assisted click chemistry. It turned out that all of the
PMID 23058885

Pharmacological comparison of novel synthetic fenamate analogues with econazole and 2-APB on the inhibition of TRPM2 channels.

Chen GL, Zeng B, Eastmond S, Elsenussi SE, Boa AN, Xu SZ.SourceCentre for Cardiovascular and Metabolic Research, Hull York Medical School, University of Hull, Hull, UK Department of Chemistry, University of Hull, Hull, UK.
British journal of pharmacology.Br J Pharmacol.2012 Nov;167(6):1232-43. doi: 10.1111/j.1476-5381.2012.02058.x.
BACKGROUND AND PURPOSE Fenamate analogues, econazole and 2-aminoethoxydiphenyl borate (2-APB) are inhibitors of transient receptor potential melastatin 2 (TRPM2) channels and are used as research tools. However, these compounds have different chemical structures and therapeutic applications. Here we
PMID 22646516

Japanese Journal

TRPM4 Channels Mediate Hypertonicity-induced, Ca2+-impermeable, Non-selective Cation Currents in a Cervical Cancer Cell Line, HeLa Cells

, , , ,
信州医学雑誌 62(1), 33-44, 2014
… Ion channels mediating these currents were Ca2+-impermeable and sensitive to flufenamic acid (FFA) and econazole but not to amiloride or ruthenium red. …
NAID 130004551913

In Vitro Evaluation of Mucoadhesive Vaginal Tablets of Antifungal Drugs Prepared with Thiolated Polymer and Development of a New Dissolution Technique for Vaginal Formulations

, , [他], , , , ,
Chemical and Pharmaceutical Bulletin 59(8), 952-958, 2011
… Econazole nitrate (EN) and miconazole nitrate (MN) were used as antifungal drugs to prepare the vaginal tablet formulations. …
NAID 130000960925

Synthesis and Evaluation of Different Fatty Acid Esters Formulated into Precirol ATO-Based Lipid Nanoparticles as Vehicles for Topical Delivery

, , [他],
Chemical and Pharmaceutical Bulletin 57(7), 680-684, 2009
… Moreover, drug loading and skin permeation of Econazole nitrate, chosen as a lipophilic model drug, were evaluated as well. … The maximum flux of drug was observed for the nanoparticles containing esters with 17 and 19 carbon atoms, suggesting that these formulations may constitute a potential carrier for topical delivery of econazole nitrate. …
NAID 130000124366

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リンク元	「エコナゾール」
拡張検索	「econazole nitrate」

「エコナゾール」

Econazole
Systematic (IUPAC) name
	(RS)-1-{2-[(4-Chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a684049
Identifiers
CAS Number	27220-47-9
ATC code	D01AC03 (WHO) G01AF05 (WHO)
PubChem	CID 3198
IUPHAR/BPS	2446
DrugBank	DB01127
ChemSpider	3086
UNII	6Z1Y2V4A7M
KEGG	D03936
ChEBI	CHEBI:4754
ChEMBL	CHEMBL808
Chemical data
Formula	C18H15Cl3N2O
Molar mass	381.683 g/mol
Chirality	Racemic mixture
3D model (Jmol)	Interactive image
	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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英: econazole
化: 硝酸エコナゾール econazole nitrate
商: パラベール

「econazole nitrate」

　　[★] エコナゾール econazole。硝酸エコナゾール

[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.

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econazole