| Identification | More | [Name]
Econazole | [CAS]
27220-47-9 | [Synonyms]
1-[2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1h-imidazole
ECONAZOLE
ECONAZOLUM
1-(2-((4-chlorophenyl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1h-imidazol
1-(2,4-dichloro-beta-((p-chlorobenzyl)oxy)phenethyl)-imidazol
1-[2,4-Dichloro-β-[(p-chlorobenzyl)oxy]phenethyl]imidazole
1H-Imidazole, 1-[2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-
Imidazole, 1-[2,4-dichloro-β-[(p-chlorobenzyl)oxy]phenethyl]-(8CI)
NSC 187789
Econazole (base and/or unspecified salts)
1-(1H-Imidazole-1-yl)-2-(2,4-dichlorophenyl)-2-(4-chlorobenzyloxy)ethane
1-[2,4-Dichloro-β-(p-chlorobenzyloxy)phenethyl]-1H-imidazole
1-[β-[(4-Chlorobenzyl)oxy]-2,4-dichlorophenethyl]-1H-imidazole | [EINECS(EC#)]
248-341-6 | [Molecular Formula]
C18H15Cl3N2O | [MDL Number]
MFCD00800993 | [Molecular Weight]
381.68 | [MOL File]
27220-47-9.mol |
| Chemical Properties | Back Directory | [Appearance]
White or almost white powder | [Melting point ]
86.8°C | [Boiling point ]
533.8±50.0 °C(Predicted) | [density ]
1.33±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Practically insoluble in water, very soluble in ethanol (96 per cent) and in methylene chloride. | [form ]
neat | [pka]
6.68±0.12(Predicted) | [color ]
White to off-white | [Water Solubility ]
0.37g/L(ambient temperature) | [Major Application]
pharmaceutical small molecule | [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 | [InChIKey]
LEZWWPYKPKIXLL-UHFFFAOYSA-N | [SMILES]
Clc1c(ccc(c1)Cl)C(OCc3ccc(cc3)Cl)C[n]2cncc2 | [CAS DataBase Reference]
27220-47-9(CAS DataBase Reference) | [EPA Substance Registry System]
27220-47-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
WGK 3 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Chemical Properties]
White or almost white powder | [Originator]
Pevaryl,Cilag Chemie,France,1976 | [Uses]
antineoplastic, anti-estrogen.
Econazole (Spectazole) is a synthetic imidazole. Econazole blocks C-14 demethylation of sterols, interfering with the biosynthesis of ergosterol, which results in disorganization of the fungal plasma cell membrane and increased permeability. It is active against dermatophytes, yeast, P. orbiculare, Aspergillus, Cladosporium, and Sporothrix. | [Uses]
Econazole (cas# 27220-47-9) is a compound useful in organic synthesis. | [Definition]
ChEBI: 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole is a member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 4-chlorobenzyl group. It is an ether, a member of imidazoles, a dichlorobenzene and a member of monochlorobenzenes. | [Indications]
Econazole (Spectazole) is a synthetic imidazole. Econazole blocks C-14
demethylation of sterols, interfering with the biosynthesis of ergosterol,
which results in disorganization of the fungal plasma cell membrane and
increased permeability. It is active against dermatophytes, yeast, P. orbiculare,
Aspergillus, Cladosporium, and Sporothrix. | [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 | [Antimicrobial activity]
Broad-spectrum imidazole antimycotic with activity against almost all species of pathogenic fungi. | [Side effects]
Local irritations such as itching and burning sensations and allergic reactions may occur in rare cases after topical therapy and are mainly due to the galenic formulation. | [Synthesis]
Econazole, 1-[2,4-dichloro-β-[(4-chlorobenzyl)oxy]phenethyl]-imidazole
(35.2.8), is an analog of myconazole. It differs in the presence of a single chlorine atom in
the benzyl part of the molecule, and it is synthesized in the same manner, except that it
uses 4-chlorobenzylchloride in the last stage instead of 2,4-dichlorobenzylbromide. | [Solubility in organics]
Econazole is soluble in methanol, acetic acid, and PEG 400; less soluble in ethanol, acetone, chloroform, and butanol; and barely soluble in water, ether, cyclohexane, and hexane. |
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