Econazole nitrate Chemical Properties

Melting point:

162°C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

chloroform/methanol: soluble25mg/mL (choloroform:methanol (1:1))

form 

powder

color 

white to off-white

Water Solubility 

<0.1 g/100 mL at 19 ºC

Merck 

14,3502

InChIKey

DDXORDQKGIZAME-UHFFFAOYSA-N

CAS DataBase Reference

24169-02-6(CAS DataBase Reference)

EPA Substance Registry System

Econazole mononitrate (24169-02-6)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/38-36/37/38

Safety Statements 

26-36-36/37

WGK Germany 

3

RTECS 

NI4450000

HS Code 

29332900

Toxicity

LD50 in mice, rats (mg/kg): 462.7, 667.7 orally (Thienpont)

MSDS

• Language:English Provider:1-(2,4-Dichloro-beta-((p-chlorobenzyl)oxy)phenethyl)imidazole nitrate
• Language:English Provider:SigmaAldrich

Econazole nitrate Usage And Synthesis

Description

Econazole nitrate is the nitrate salt form of Econazole. It belongs to imidazole-class antifungal medication sold in various places around the world including US, Canada, Western Europe, and Asia. It is usually manufactured into cream form for sale. Econazole nitrate is mainly used for the treatment of skin infections including athlete's foot, tinea, pityriasis versicolor, ringworm, and jock itch caused by fungi such as Trichophyton rubrum, Trichophyton tonsurans and Microsporum audouini. As an imidazole-class drug, Econazole nitrate takes effects through inhibiting the biosynthesis of ergosterol, a key component of fungal cell membrane, thus disrupting the normal permeability of fungal membrane. This causes leakage of essential cellular contents of fungi, further killing them.

References

http://www.rxlist.com/econazole-nitrate-cream-drug/clinical-pharmacology.htm
https://en.wikipedia.org/wiki/Econazole
http://www.pdr.net/drug-summary/Econazole-Nitrate-econazole-nitrate-731

Chemical Properties

White to Off-White Solid

Originator

Pevaryl,Cilag Chemie,France,1976

Uses

Antifungal;Ergosterol synthesis inhibition

Uses

Azole antifungal

Uses

Econazole nitrate is an antifungal agent of the imidazole type used in topical and vaginal preparations to prevent growth of dermatophytes, yeast, and mold.

Manufacturing Process

A suspension of 10.3 parts of α-(2,4-dichlorophenyl)-imidazole-1-ethanol and 2.1 parts of sodium hydride in 50 parts of dry tetrahydrofuran is stirred andrefluxed for 2 hours. After this reaction-time, the evolution of hydrogen is ceased. Then there are added successively 60 parts dimethylformamide and 8 parts of p-chlorobenzylchloride and stirring and refluxing is continued for another two hours. The tetrahydrofuran is removed at atmospheric pressure. The dimethylformamide solution is poured onto water. The product, 1-[2,4- dichloro-β-(p-chlorobenzyloxy)phenethyl]imidazole, is extracted with benzene. The extract is washed with water, dried, filtered and evaporated in vacuo. From the residual oily free base, the nitrate salt is prepared in the usual manner in 2-propanol by treatment with concentrated nitric acid, yielding, after recrystallization of the crude solid salt from a mixture of 2-propanol, methanol and diisopropylether, 1-[2,4-dichloro-β-(pchlorobenzyloxy)phenethyl]imidazole nitrate; MP 162°C.

brand name

Spectazole (Johnson & Johnson).

Therapeutic Function

Antifungal

General Description

White crystalline powder.

Air & Water Reactions

Insoluble in water.

Fire Hazard

Flash point data for Econazole nitrate are not available; however, Econazole nitrate is probably combustible.

Biochem/physiol Actions

Econazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. Inhibition of ergosterol results in increased cellular permeability causing leakage of cellular contents. Econazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and phospholipid biosynthesis.

Econazole nitrate(24169-02-6)Related Product Information

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• NITRATE REDUCTASE
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