1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole

• ChemBase ID: 1024
• Molecular Formular: C20H15Cl3N2OS
• Molecular Mass: 437.7699
• Monoisotopic Mass: 435.99706715
• SMILES: Clc1c(C(OCc2c3c(sc2)c(Cl)ccc3)Cn2ccnc2)ccc(Cl)c1
• Canonical SMILES: Clc1ccc(c(c1)Cl)C(Cn1ccnc1)OCc1csc2c1cccc2Cl
• InChI: InChI=1S/C20H15Cl3N2OS/c21-14-4-5-16(18(23)8-14)19(9-25-7-6-24-12-25)26-10-13-11-27-20-15(13)2-1-3-17(20)22/h1-8,11-12,19H,9-10H2
• InChIKey: JLGKQTAYUIMGRK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
• IUPAC Traditional name: sertaconazole
• Brand Name: Ertaczo
• Synonyms: Sertaconazol [Spanish]; Sertaconazolum [Latin]; Sertaconazole

Database IDs

• CAS Number: 99592-32-2
• PubChem SID: 160964487; 46507290
• PubChem CID: 65863

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.6981435
• LogD (pH = 7.4): 6.1626396
• Log P: 6.2283483
• Molar Refractivity: 111.6029 cm^3
• Polarizability: 44.26195 Å^3
• Polar Surface Area: 27.05 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.74
• LOG S: -4.84
• Solubility (Water): 6.37e-03 g/l

PROPERTIES

Physical Property

• Solubility: Practically insoluble
• Hydrophobicity(logP): 6.2

DETAILS

DrugBank - DB01153

• Drug Groups: approved
• Description: Sertaconazole nitrate is an antifungal medication of the imidazole class. It is available as a cream to treat skin infections such as athlete's foot. [Wikipedia]
• Indication: For the topical treatment of interdigital tinea pedis in immunocompetent patients 12 years of age and older, caused by Trichophyton rubrum, Trichophyton mentagrophytes, and Epidermophyton floccosum.
• Pharmacology: Sertaconazole is an imidazole/triazole type antifungal agent. Sertaconazole is a highly selective inhibitor of fungal cytochrome P-450 sterol C-14 α-demethylation via the inhibition of the enzyme cytochrome P450 14α-demethylase. This enzyme converts lanosterol to ergosterol, and is required in fungal cell wall synthesis. The subsequent loss of normal sterols correlates with the accumulation of 14 α-methyl sterols in fungi and may be partly responsible for the fungistatic activity of fluconazole. Mammalian cell demethylation is much less sensitive to fluconazole inhibition. Sertaconazole exhibits in vitro activity against Cryptococcus neoformans and Candida spp. Fungistatic activity has also been demonstrated in normal and immunocompromised animal models for systemic and intracranial fungal infections due to Cryptococcus neoformans and for systemic infections due to Candida albicans.
• Affected Organisms: Yeast and other fungi
• Absorption: Bioavailability is negligible.
• Protein Binding: >99% to plasma
• External Links: Wikipedia; RxList; Drugs.com