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

• ChemBase编号: 1024
• 分子式: C20H15Cl3N2OS
• 平均质量: 437.7699
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
• IUPAC传统名: sertaconazole
• 商标名: Ertaczo
• 别名: Sertaconazol [Spanish]; Sertaconazolum [Latin]; Sertaconazole

登记号

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

理论计算性质

JChem

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 5.6981435
• LogD (pH = 7.4): 6.1626396
• Log P: 6.2283483
• 摩尔折射率: 111.6029 cm^3
• 极化性: 44.26195 Å^3
• 极化表面积: 27.05 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 5.74
• LOG S: -4.84
• 溶解度: 6.37e-03 g/l

分子性质

理化性质

• 溶解度: Practically insoluble
• 疏水性(logP): 6.2

详细说明

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