3,5-diacetamido-2,4,6-triiodobenzoic acid

• ChemBase ID: 156
• Molecular Formular: C11H9I3N2O4
• Molecular Mass: 613.91357
• Monoisotopic Mass: 613.76965078
• SMILES: Ic1c(NC(=O)C)c(I)c(c(I)c1NC(=O)C)C(=O)O
• Canonical SMILES: CC(=O)Nc1c(I)c(NC(=O)C)c(c(c1I)C(=O)O)I
• InChI: InChI=1S/C11H9I3N2O4/c1-3(17)15-9-6(12)5(11(19)20)7(13)10(8(9)14)16-4(2)18/h1-2H3,(H,15,17)(H,16,18)(H,19,20)
• InChIKey: YVPYQUNUQOZFHG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-diacetamido-2,4,6-triiodobenzoic acid
• IUPAC Traditional name: diatrizoate
• Brand Name: Angiovist 282; Cardiografin; Conray 35; Diat; Gastrografin; Hypaque; Iothalamate; Odiston; Reno-dip; Renografin 76; Triombrin; Triombrine; Urotrast; Urovison; Urovist Cysto; Urovist Cysto Pediatric; Urovist Sodium 300; Vascoray
• Synonyms: Diatrizoic acid; 3,5-Bis(acetylamino)-2,4,6-triiodobenzoic Acid; 2,4,6-Triiodo-3,5-diacetamidobenzoic Acid; Diatrizoate; Odiston; Urotrast; Amidotrizoic Acid; 3,5-Diacetamido-2,4,6-triiodobenzoic acid; Amidotrizoic Acid; Amidotrizoate; Diatriazoate; Diatrizoate sodium; Diatrizoate sodium salt; Diatrizoic acid; Diatrizoic acid sodium salt; Meglumine diatrizoate; Methalamic acid; Sodium amidotrizoate; Sodium diatrizoate; Urografin acid; Urogranoic acid; Diatrizoate; NSC 262168; Diatrizoic acid; DIATRIZOIC ACID DIHYDRATE; 3,5-双(乙酰胺基)-2,4,6-三碘苯甲酸; 泛影酸

Database IDs

• CAS Number: 117-96-4; 737-31-5; 50978-11-5
• EC Number: 204-223-6
• MDL Number: MFCD00069960
• PubChem SID: 46504704; 24894277; 160963619
• PubChem CID: 2140
• CHEBI ID: 53691
• ATC CODE: V08AA01
• CHEMBL: 1201220
• Chemspider ID: 2055
• DrugBank ID: DB00271
• KEGG ID: D02240
• Wikipedia Title: Diatrizoic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.16767
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.22589728
• LogD (pH = 7.4): -0.627878
• Log P: 2.8930829
• Molar Refractivity: 103.1277 cm^3
• Polarizability: 38.97926 Å^3
• Polar Surface Area: 95.5 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 2.27
• LOG S: -3.76
• Solubility (Water): 1.07e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: >300°C
• Hydrophobicity(logP): 3.3

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer; Room Temperature (15-30°C), Protect from light
• RTECS: DG5950000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95+%
• Empirical Formula (Hill Notation): C11H9I3N2O4

DETAILS

MP Biomedicals - 02191501

(Amidotrizoic Acid)

DrugBank - DB00271

• Drug Groups: approved
• Description: A commonly used x-ray contrast medium. As diatrizoate meglumine and as Diatrizoate sodium, it is used for gastrointestinal studies, angiography, and urography. [PubChem]
• Indication: Used, alone or in combination, for a wide variety of diagnostic imaging methods, including angiography, urography, cholangiography, computed tomography, hysterosalpingography, and retrograde pyelography. It can be used for imaging the gastrointestinal tract in patients allergic to barium.
• Pharmacology: Diatrizoate is the most commonly used water-soluble, iodinated, radiopaque x-ray contrast medium. Radiopaque agents are drugs used to help diagnose certain medical problems. They contain iodine, which blocks x-rays. Depending on how the radiopaque agent is given, it localizes or builds up in certain areas of the body. The resulting high level of iodine allows the x-rays to make a "picture" of the area. The areas of the body in which the radiopaque agent localizes will appear white on the x-ray film. This creates the needed distinction, or contrast, between one organ and other tissues. The contrast will help the doctor see any special conditions that may exist in that organ or part of the body.
• Toxicity: High osmolal radiocontrast agents like diatrizoate 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.
• Affected Organisms: Humans and other mammals
• Elimination: However, it is not metabolized but excreted unchanged in the urine, each diatrizoate molecule remaining "obligated" to its sodium moiety. The liver and small intestine provide the major alternate route of excretion for diatrizoate. Injectable radiopaque diagnostic agents are excreted unchanged in human milk. Saliva is a minor secretory pathway for injectable radiopaque diagnostic agents.
• External Links: Wikipedia

Toronto Research Chemicals - A576800

Density gradient reagent for blood cell seperation. Diagnostic aid (radiopaque medium).

REFERENCES

• Kalmer, J.R., et al., J. Immunol. Methods, 110, 275 (1988)
• Wang, Y., et al.: Br. J. Radiol., 170, 1229 (1988)
• Wong, V., et al.: Eur. J. Pharmacol., 433, 135 (2001).