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Identification
Name Diatrizoate
Accession Number DB00271 (APRD00913)
Type small molecule
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]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Amidotrizoate
  • Amidotrizoic Acid
  • Diatriazoate
  • Diatrizoate sodium
  • Diatrizoate sodium salt
  • Diatrizoic acid
  • Diatrizoic acid sodium salt
  • Meglumine diatrizoate
  • Methalamic acid
  • Sodium amidotrizoate
  • Sodium diatrizoate
  • Urografin acid
  • Urogranoic acid
Brand names
  • 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
Brand name mixtures
  • Gastrografin Liq (Diatrizoate Meglumine + Diatrizoate Sodium)
  • Hypaque-M 76% (Diatrizoate Meglumine + Diatrizoate Sodium)
  • Hypaque-M Liq 76% Usp (Diatrizoate Meglumine + Diatrizoate Sodium)
  • Md-60 (Diatrizoate Meglumine + Diatrizoate Sodium)
  • Md-76 (Diatrizoate Meglumine + Diatrizoate Sodium)
  • Renocal-76 (Diatrizoate Meglumine + Diatrizoate Sodium)
  • Renografin-60 - Liq Iv (Diatrizoate Meglumine + Diatrizoate Sodium)
  • Renografin-60 Liq (Diatrizoate Meglumine + Diatrizoate Sodium)
  • Renografin-76 - Liq Iv (Diatrizoate Meglumine + Diatrizoate Sodium)
  • Renografin-76 Liq (Diatrizoate Meglumine + Diatrizoate Sodium)
  • Sinografin (Diatrizoate Meglumine + Meglumine Iodipamide)
Categories
  • Contrast Media
CAS number 117-96-4
Weight Average: 613.9136
Monoisotopic: 613.769637046
Chemical Formula C11H9I3N2O4
InChI Key InChIKey=YVPYQUNUQOZFHG-UHFFFAOYSA-N
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)
Plain Text
IUPAC Name
3,5-diacetamido-2,4,6-triiodobenzoic acid
SMILES
CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Aminobenzoates
  • Acetanilides
Substructures
  • Aminobenzoates
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Acetates
  • Benzoates
  • Amino Ketones
  • Benzene and Derivatives
  • Acetanilides
  • Carboxylic Acids and Derivatives
  • Aryl Halides
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Halobenzenes
  • Benzoyl Derivatives
  • Anilines
Pharmacology
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.
Pharmacodynamics 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.
Mechanism of action Diatrizoate is an iodine-containing X-ray contrast agent. Iodated contrast agents were among the first contrast agents developed. Iodine is known to be particular electron-dense and to effectively scatter or stop X-rays. A good contrast agent requires a high density of electron-dense atoms. Therefore, the more iodine, the more "dense" the x-ray effect. Iodine based contrast media are water soluble and harmless to the body. These contrast agents are sold as clear colorless water solutions, the concentration is usually expressed as mg I/ml. Modern iodinated contrast agents can be used almost anywhere in the body. Most often they are used intravenously, but for various purposes they can also be used intraarterially, intrathecally (the spine) and intraabdominally - just about any body cavity or potential space.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of 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.
Half life Not Available
Clearance Not Available
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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Bayer healthcare pharmaceuticals inc
  • Bracco diagnostics inc
  • Ge healthcare
  • Mallinckrodt inc
  • Mallinckrodt medical inc
  • Isotex diagnostics
Packagers
Dosage forms
Form Route Strength
Liquid Intravenous
Powder Oral
Solution Intravenous
Solution Urethral
Prices
Unit description Cost Unit
Gastrografin 66-10 solution 0.92 USD ml
Hypaque sodium oral powder 0.68 USD g
Conray 60% vial 0.36 USD ml
Cystografin 30% infus. btl 0.22 USD ml
Conray-43 vial 0.2 USD ml
Conray-30 infusion bottle 0.16 USD ml
Hypaque 41.66% liquid 0.16 USD ml
Cystografin-dilute 18% btl 0.13 USD ml
Cysto-conray 17.2% vial 0.11 USD ml
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP 3.3 PhysProp
Predicted Properties
Property Value Source
water solubility 1.07e-01 g/l ALOGPS
logP 2.27 ALOGPS
logP 0.29 ChemAxon Molconvert
logS -3.76 ALOGPS
pKa 11.84 ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 3 ChemAxon Molconvert
polar surface area 95.50 ChemAxon Molconvert
rotatable bond count 3 ChemAxon Molconvert
refractivity 103.13 ChemAxon Molconvert
polarizability 38.45 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D01013 Link_out
PubChem Compound 2140 Link_out
PubChem Substance 46504704 Link_out
ChemSpider 2055 Link_out
Drug Product Database 2237155 Link_out
Wikipedia http://en.wikipedia.org/wiki/Diatrizoate Link_out
ATC Codes
  • V08AA01
  • V08AA04
AHFS Codes
  • 36:68.00
PDB Entries Not Available
FDA label Not Available
MSDS show (73.2 KB)
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Comments
Drug created on June 13, 2005 07:24 / Updated on January 31, 2011 12:46

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