1-{2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole; nitric acid

• ChemBase ID: 73070
• Molecular Formular: C18H16Cl3N3O4
• Molecular Mass: 444.69634
• Monoisotopic Mass: 443.02063905
• SMILES: c1c(cc(c(c1)C(Cn1ccnc1)OCc1ccc(cc1)Cl)Cl)Cl.[N+](=O)([O-])O
• Canonical SMILES: Clc1ccc(cc1)COC(c1ccc(cc1Cl)Cl)Cn1cncc1.[O-][N+](=O)O
• InChI: InChI=1S/C18H15Cl3N2O.HNO3/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;2-1(3)4/h1-9,12,18H,10-11H2;(H,2,3,4)
• InChIKey: DDXORDQKGIZAME-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole; nitric acid
• IUPAC Traditional name: econazole; nitric acid; acid, nitric; econazole
• Synonyms: Ecostatin; Epi-Pevaryl; Gyno-Pevaryl; Gynoryl; Econazole nitrate; 1-(2-[(4-Chlorophenyl)methoxy]-2-[2,4-dichlorophenyl]ethyl)-1H-imidazole; Econazole nitrate salt; 1-[2-[(4-Chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole Nitrate; 1-[2-(4-Chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Nitrate; Econazole nitrate; Ecostatin; Epi-Pevaryl; Gyno-Pevaril; Gynoryl; Ifenec; Micofugal; Micogin; Palavale; Pargin; Pevaryl; (+/-)-Econazole Nitrate; NSC 243115; 1-[2-([4-Chlorophenyl]methoxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole nitrate

Database IDs

• CAS Number: 24169-02-6
• EC Number: 246-053-5
• MDL Number: MFCD00058160
• PubChem SID: 24894567; 162037990
• PubChem CID: 68589

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.8221188
• LogD (pH = 7.4): 5.286615
• Log P: 5.3523235
• Molar Refractivity: 98.2628 cm^3
• Polarizability: 38.087494 Å^3
• Polar Surface Area: 27.05 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid
• Melting Point: 162-166°C; 163-165°C (dec.)

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: NI4450000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/38; R:22-36/37/38
• Safety Statements: 26-36; S:25-26-36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Salt Data: nitrate

DETAILS

MP Biomedicals - 02157897

(1-[2-([4-Chlorophenyl]methoxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole nitrate)

Selleck Chemicals - S2535

Research Area: Infection
Biological Activity:
Econazole nitrate (Spectazole) is an imidazole class antifungal medication. Econazole nitrate (Spectazole) is used to treat skin infections such as athlete’s foot, tinea, pityriasis versicolor, ringworm, and jock itch. The in vitro activity spectrum of econazole nitrate (Spectazole) is very broad: the dermatophytes, the yeasts, the dimorphic fungi, the aspergilli, the mycetoma causing agents and the Gram-positive bacteria being most sensitive. Guinea-pigs infected with T. mentagrophytes, M. canis or C. albicans and treated topically or orally with econazole, were cured. In each of these tests the activity of econazole was compared with that of different reference drugs. Vaginal candidiasis in rats was cured after oral administration of econazole. [1][2]

Sigma Aldrich - E4632

Application
Econazole is a broad spectrum antimycotic similar to ketoconazole. It has some action against Gram positive bacteria. It is used topically in dermatomycoses as well as orally and parenterally. It is used for studies on processes such as platelet serotonin uptake, prostanoid biosynthesis, EDHF-mediated relaxation, and Ca2+ transport pathways in thymic lymphocytes1.
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. It Inhibits Ca2+ transport pathways in thymic lymphocytes1.

Toronto Research Chemicals - E326000

Antifungal.

REFERENCES

• http://en.wikipedia.org/wiki/Econazole
• Passerini, N., et al.: J. Pharm. Pharmacol., 61, 559 (2009)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2009)