Econazole nitrate

Econazole nitrate Basic information
Description References
Product Name:Econazole nitrate
Synonyms:(RS)-1-[2,4-DICHLORO-BETA-(P-CHLOROBENZYLOXY)PHENETHYL]-IMIDAZOLE NITRATE;1-[2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazolium nitrate;ECONAZOLE NITRATE 99%-101%;ECONAZOLE NITRATE;ECONAZOLE NITRATE SALT;ECONAZOL NITRATE;1-(2,4-dichloro-beta-((p-chlorobenzyl)oxy)phenethyl)imidazole nitrate;1-[2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)-ethyl]-1h-imidazole mononitrate
CAS:24169-02-6
MF:C18H16Cl3N3O4
MW:444.7
EINECS:246-053-5
Product Categories:Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Spectazole;Pyridines;Aromatic Nitriles;Organics;ACTIVE PHARMACEUTICAL INGREDIENTS;24169-02-6
Mol File:24169-02-6.mol
Econazole nitrate Structure
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
InChIKeyDDXORDQKGIZAME-UHFFFAOYSA-N
CAS DataBase Reference24169-02-6(CAS DataBase Reference)
EPA Substance Registry SystemEconazole 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
ToxicityLD50 in mice, rats (mg/kg): 462.7, 667.7 orally (Thienpont)
Econazole nitrate Usage And Synthesis
DescriptionEconazole 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.
Referenceshttp://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 PropertiesWhite to Off-White Solid
OriginatorPevaryl,Cilag Chemie,France,1976
UsesAzole antifungal
UsesAntifungal;Ergosterol synthesis inhibition
UsesEconazole nitrate is an antifungal agent of the imidazole type used in topical and vaginal preparations to prevent growth of dermatophytes, yeast, and mold.
Manufacturing ProcessA 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 nameSpectazole (Johnson & Johnson).
Therapeutic FunctionAntifungal
General DescriptionWhite crystalline powder.
Air & Water ReactionsInsoluble in water.
Fire HazardFlash point data for Econazole nitrate are not available; however, Econazole nitrate is probably combustible.
Biochem/physiol ActionsEconazole 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 Preparation Products And Raw materials
Raw materials4-Chlorobenzyl chloride-->Nitric acid-->Sodium hydride
Preparation ProductsEconazole
2-Chlorophenethylamine Phenethyl phenylacetate Methoxy ECONAZOLE NITRATE EPE(CRM STANDARD) Nitrite ECONAZOLE NITRATE IMP. A (EP): (1RS)-1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YL)ETHANOL ECONAZOLE NITRATE BP STANDARD(CRM STANDARD) ECONAZOLE NITRATE USP(CRM STANDARD) ECONAZOLE NITRATE ASSAY STANDARD BP(CRM STANDARD) ECONAZOLE NITRATE REFERENCE SPECTRUM EPY(CRM STANDARD) Econazole Nitrate USP ECONAZOLE NITRATE - REFERENCE SPECTRUM ECONAZOLE NITRATE--N/H MICONAZOLE NITRATE ECONAZOLE NITRATE MM(CRM STANDARD) ECONAZOLE NITRATE IMP. B (EP) AS NITRATE: (2RS)-2-[(4-CHLOROBENZYL)OXY]-2-(2,4-DICHLOROPHENYL)ETHANAMINE NITRATE ECONAZOLE NITRATE IMP. B (EP) AS NITRATE: (2RS)-2-[(4-CHLOROBENZYL)OXY]-2-(2,4-DICHLOROPHENYL)ETHANAMINE NITRATE MM(CRM STANDARD) ECONAZOLE NITRATE IMP. A (EP): (1RS)-1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YL)ETHANOL MM(CRM STANDARD)

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