3-{5-[(3-carboxy-2,4,6-triiodophenyl)carbamoyl]pentanamido}-2,4,6-triiodobenzoic acid

• ChemBase编号: 4263
• 分子式: C20H14I6N2O6
• 平均质量: 1139.76178
• 单一同位素质量: 1139.51202418
• SMILES: Ic1c(NC(=O)CCCCC(=O)Nc2c(I)c(c(I)cc2I)C(=O)O)c(I)cc(I)c1C(=O)O
• Canonical SMILES: O=C(Nc1c(I)cc(c(c1I)C(=O)O)I)CCCCC(=O)Nc1c(I)cc(c(c1I)C(=O)O)I
• InChI: InChI=1S/C20H14I6N2O6/c21-7-5-9(23)17(15(25)13(7)19(31)32)27-11(29)3-1-2-4-12(30)28-18-10(24)6-8(22)14(16(18)26)20(33)34/h5-6H,1-4H2,(H,27,29)(H,28,30)(H,31,32)(H,33,34)
• InChIKey: FFINMCNLQNTKLU-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-{5-[(3-carboxy-2,4,6-triiodophenyl)carbamoyl]pentanamido}-2,4,6-triiodobenzoic acid
• IUPAC传统名: iodipamide
• 商标名: Transbilix; Cholospect; Cholografin; Biligrafin; Bilignostum; Bilignost
• 别名: 3,3′-(己二酰二亚氨基)双(2,4,6-三碘苯甲酸); 胆影酸; Iodipamide; 3,3'-[(1,6-dioxohexane-1,6-diyl)diimino]bis(2,4,6-triiodobenzoic acid); Iodipamic acid; Adipiodone; Adipiodonum [INN-Latin]; Adipiodona [INN-Spanish]; IDB; Iodipamide; 3,3'-[(1,6-Dioxo-1,6-hexanediyl)diimino]bis[2,4,6-triiodobenzoic Acid; 3,3'-(Adipoyldiimino)-bis(2,4,6-triiodobenzoic Acid); Adipic Acid Bis(3-carboxy-2,4,6-triiodoanilide); Cholografin; Cholospect

登记号

• CAS号: 606-17-7
• EC号: 210-105-5
• MDL号: MFCD00058983
• PubChem SID: 24895909; 160967695; 46507320
• PubChem CID: 3739

理论计算性质

JChem

• Acid pKa: 2.0255375
• 质子受体: 6
• 质子供体: 4
• LogD (pH = 5.5): 2.217679
• LogD (pH = 7.4): 1.2136091
• Log P: 8.248091
• 摩尔折射率: 183.981 cm^3
• 极化性: 70.95157 Å^3
• 极化表面积: 132.8 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 3.42
• LOG S: -5.57
• 溶解度: 3.06e-03 g/l

分子性质

理化性质

• 溶解度: 0.46 mg/mL at 20 oC [BEILSTEIN]; Acetone; Ethanol; Methanol
• 外观: Crystalline Solid
• 熔点: 306-308°C (dec.)

安全信息

• RTECS编号: DG0949500
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 级别: analytical standard, for drug analysis

详细说明

DrugBank - DB04711

• Drug Groups: approved
• Description: Iodipamide is a water-soluble radiographic contrast media for cholecystography and intravenous cholangiography. [PubChem]
• Indication: Iodipamide is used as a contrast agent for cholecystography and intravenous cholangiography.
• Toxicity: Ionic radiocontrast agents like iodipamide are cytotoxic to renal cells. The toxic effects include apoptosis, cellular energy failure, disruption of calcium homeostasis, and disturbance of tubular cell polarity, and are thought to be linked to oxidative stress. Acute IV LD50 is 5000 mg/kg in rat, 3195 mg/kg in mouse, and 1200 mg/kg in dog.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• References: Lin SK, Moss AA, Riegelman S: Iodipamide kinetics: capacity-limited biliary excretion with simultaneous pseudo-first-order renal excretion. J Pharm Sci. 1977 Dec;66(12):1670-4. [Pubmed]

Toronto Research Chemicals - I666800

Diagnostic aid (radiopaque medium-cholecystographic).

参考文献

• Lin SK, Moss AA, Riegelman S: Iodipamide kinetics: capacity-limited biliary excretion with simultaneous pseudo-first-order renal excretion. J Pharm Sci. 1977 Dec;66(12):1670-4. Pubmed
• Kiyano, et al.: Radioisotopes, 20, 78 (1971)
• Lerner, H.H., et al.: Anal. Profiles Drug Subs., 3, 333 (1971)
• Rosenberg, F.J., et al.: Invest. Radiol., 15, S142 (1971)