WordNet

any compound containing the nitrate group (such as a salt or ester of nitric acid)
treat with nitric acid, so as to change an organic compound into a nitrate; "nitroglycerin is obtained by nitrating glycerol"

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硝酸塩 / 硝酸塩類化学肥料

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/04/02 13:24:01」(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

Ca²⁺ Movement Induced by Deltamethrin in PC3 Human Prostate Cancer Cells.

Lee HH1, Chou CT2,3, Liang WZ4, Chen WC5, Wang JL6, Yeh JH7, Kuo CC8, Shieh P9, Kuo DH9, Chen FA9, Jan CR4.
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This study explored the effect of deltamethrin, a pesticide, on [Ca²⁺]i in PC3 human prostate cancer cells. Deltamethrin at concentrations between 5 μM and 20 μM evoked [Ca²⁺]i rises in a concentration-dependent manner. This Ca²⁺ signal was inhibited by 22% by removal of extracellular Ca�
PMID 27188467

Effect of 2,5-dimethylphenol on Ca2+ movement and viability in PC3 human prostate cancer cells.

Wang JL1, Chou CT2,3, Liang WZ4, Yeh JH5, Kuo CC6, Lee CY7, Shieh P8, Kuo DH8, Chen FA8, Jan CR4.
Toxicology mechanisms and methods.Toxicol Mech Methods.2016 Jun 16:1-7. [Epub ahead of print]
The phenolic compound 2,5-dimethylphenol is a natural product. 2,5-Dimethylphenol has been shown to affect rat hepatic and pulmonary microsomal metabolism. However, the effect of 2,5-dimethylphenol on Ca2+ signaling and cyotoxicity has never been explored in any culture cells. This study explored
PMID 27310574

The effect of the phenol compound ellagic acid on Ca(2+) homeostasis and cytotoxicity in liver cells.

Liang WZ1, Chou CT2, Cheng JS3, Wang JL4, Chang HT5, Chen IS5, Lu T6, Yeh JH7, Kuo DH8, Shieh P8, Chen FA8, Kuo CC9, Jan CR10.
European journal of pharmacology.Eur J Pharmacol.2016 Jun 5;780:243-51. doi: 10.1016/j.ejphar.2016.03.057. Epub 2016 Mar 30.
Ellagic acid, a natural phenol compound found in numerous fruits and vegetables, causes various physiological effects in different cell models. However, the effect of this compound on Ca(2+) homeostasis in liver cells is unknown. This study examined the effect of ellagic acid on intracellular Ca(2+)
PMID 27038520

Japanese Journal

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

Baloglu Esra,Ay Senyigit Zeynep,Karavana Sinem Yaprak [他],Vetter Anja,Metın Dilek Yesim,Hilmioglu Polat Suleyha,Guneri Tamer,Bernkop-Schnurch Andreas
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

Sanna Vanna,Mariani Alberto,Caria Giuseppe [他],Sechi Mario
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

(6) レタス根腐病菌株間における硝酸エコナゾール感受性差異(平成20年度日本植物病理学会大会講演要旨)

山内智史,白川隆
日本植物病理學會報 74(3), 168, 2008-08-25
NAID 110006965643

「エコナゾール」

Econazole
Clinical data
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 (Jmol)	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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