1-(butan-2-yl)-4-{4-[4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one

• ChemBase编号: 106199
• 分子式: C35H38Cl2N8O4
• 平均质量: 705.63342
• 单一同位素质量: 704.2393071
• SMILES: CCC(C)n1ncn(c1=O)c1ccc(cc1)N1CCN(CC1)c1ccc(OCC2COC(Cn3cncn3)(O2)c2ccc(Cl)cc2Cl)cc1
• Canonical SMILES: CCC(n1ncn(c1=O)c1ccc(cc1)N1CCN(CC1)c1ccc(cc1)OCC1COC(O1)(Cn1cncn1)c1ccc(cc1Cl)Cl)C
• InChI: InChI=1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3
• InChIKey: VHVPQPYKVGDNFY-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-(butan-2-yl)-4-{4-[4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one
• IUPAC传统名: @itraconazole; itraconazole
• 别名: Oriconazole, R51211, Sporanox; ITRACONAZOLE; Oriconazole; R51211; Sporanox; Itraconazole

登记号

• CAS号: 84625-61-6
• MDL号: MFCD00870168
• PubChem SID: 162087202
• PubChem CID: 3793

理论计算性质

• 质子受体: 9
• 质子供体: 0
• LogD (pH = 5.5): 7.3001556
• LogD (pH = 7.4): 7.3112283
• Log P: 7.3113713
• 摩尔折射率: 200.4 cm^3
• 极化性: 71.596016 Å^3
• 极化表面积: 100.79 Å^2
• 可自由旋转的化学键: 11
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: chloroform: soluble50 mg/mL, clear, colorless
• 熔点: 166.0-168.0°C

安全信息

• 保存条件: 2-8°C
• RTECS编号: XZ5481000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38; R:36/37/38
• 安全公开号: 22-26-36; S:22-26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (TLC); 95+%
• Empirical Formula (Hill Notation): C35H38Cl2N8O4

详细说明

Sigma Aldrich - I6657

Application
Itraconazole is a triazole antifungal agent. It is used to inhibit cytochrome P-450-dependent enzymes and ergosterol synthesis. It has been used against histoplasmosis, blastomycosis, cryptococcal meningitis, and aspergillosis. It′s different formulations are used to study Candida strains in murine invasive infections1. It has been used to study proliferative changes of the forestomach mucosa in alloxan-induced diabetic rats2.
Biochem/physiol Actions
Itraconazole inhibits cytochrome P-450-dependent enzymes which results in the inhibition of ergosterol synthesis. It does so by interacting with 14-α demethylase, which is a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. Ergosterol is a crucial compenent of fungal cell membranes. Therefore, it′s inhibition results in increased cellular permeability causing leakage of cellular contents. Itraconazole 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.

参考文献

• Chau, A.S., "Molecular basis for enhanced activity of posaconazole against Absidia corymbifera and Rhizopus oryzae." Antimicrob. Agents Chemother. 50, 3917-3919, (2006)
• Xiong, Q., et al., "Cholesterol import by Aspergillus fumigatus and its influence on antifungal potency of sterol biosynthesis inhibitors." Antimicrob. Agents Chemother. 49, 518-524, (2005)
• Sabatelli, F., et al., "In vitro activities of posaconazole, fluconazole, itraconazole, voriconazole, and amphotericin B against a large collection of clinically important molds and yeasts." Antimicrob. Agents Chemother. 50, 2009-2015, (2006)
• Vanden Bossche, H., et al., "Effects of itraconazole on cytochrome P-450-dependent sterol 14α-demethylation and reduction of 3-ketosteroids in Cryptococcus neoformans." Antimicrob. Agents Chemother. 37, 2101-2105, (1993)