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

• ChemBase ID: 998
• Molecular Formular: C18H15Cl3N2O
• Molecular Mass: 381.6835
• Monoisotopic Mass: 380.02499615
• SMILES: Clc1c(C(OCc2ccc(Cl)cc2)Cn2ccnc2)ccc(Cl)c1
• Canonical SMILES: Clc1ccc(cc1)COC(c1ccc(cc1Cl)Cl)Cn1cncc1
• 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
• InChIKey: LEZWWPYKPKIXLL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
• IUPAC Traditional name: econazole
• Brand Name: Econazole Nitrate; Ecostatin; Ecostatin Vaginal Ovules; Ecostatin cream; Gyno-Pevaryl; Gyno-Pevaryl 150; Ifenec; Palavale; Pevaryl; Spectazole; Spectazole cream
• Synonyms: Econazole; 1-(2-((4-chlorophenyl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1h-imidazole

Database IDs

• CAS Number: 27220-47-9
• PubChem SID: 46508881; 160964461
• PubChem CID: 3198

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 4.67
• LOG S: -5.41
• Solubility (Water): 1.48e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 5.5

Product Information

• Purity: 98%

DETAILS

DrugBank - DB01127

• Drug Groups: approved
• Description: A broad spectrum antimycotic with some action against Gram positive bacteria. It is used topically in dermatomycoses also orally and parenterally. [PubChem]
• Indication: For topical application in the treatment of tinea pedis, tinea cruris, and tinea corporis caused by Trichophyton rubrum, Trichophyton mentagrophytes, Trichophyton tonsurans, Microsporum canis, Microsporum audouini, Microsporum gypseum, and Epidermophyton floccosum, in the treatment of cutaneous candidiasis, and in the treatment of tinea versicolor.
• Pharmacology: Econazole is an antifungal medication related to fluconazole (Diflucan), ketoconazole (Nizoral), itraconazole (Sporanox), and clotrimazole (Lotrimin, Mycelex). Econazole prevents fungal organisms from producing vital substances required for growth and function. This medication is effective only for infections caused by fungal organisms. It will not work for bacterial or viral infections.
• Toxicity: Overdosage of econazole in humans has not been reported to date. In mice, rats guinea pigs and dogs, the oral LD 50 values were found to be 462, 668, 272, and > 160 mg/kg, respectively.
• Affected Organisms: Yeast and other fungi
• Biotransformation: Hepatic.
• Absorption: After topical application to the skin of normal subjects, systemic absorption of econazole nitrate is extremely low. Although most of the applied drug remains on the skin surface, drug concentrations were found in the stratum corneum which, by far, exceeded the minimum inhibitory concentration for dermatophytes.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com