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

• ChemBase ID: 4263
• Molecular Formular: C20H14I6N2O6
• Molecular Mass: 1139.76178
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{5-[(3-carboxy-2,4,6-triiodophenyl)carbamoyl]pentanamido}-2,4,6-triiodobenzoic acid
• IUPAC Traditional name: iodipamide
• Brand Name: Transbilix; Cholospect; Cholografin; Biligrafin; Bilignostum; Bilignost
• Synonyms: 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; 3,3′-(己二酰二亚氨基)双(2,4,6-三碘苯甲酸); 胆影酸

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.0255375
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 2.217679
• LogD (pH = 7.4): 1.2136091
• Log P: 8.248091
• Molar Refractivity: 183.981 cm^3
• Polarizability: 70.95157 Å^3
• Polar Surface Area: 132.8 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.42
• LOG S: -5.57
• Solubility (Water): 3.06e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.46 mg/mL at 20 oC [BEILSTEIN]; Acetone; Ethanol; Methanol
• Apperance: Crystalline Solid
• Melting Point: 306-308°C (dec.)

Safety Information

• RTECS: DG0949500
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Grade: analytical standard, for drug analysis

DETAILS

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).

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
• 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)