You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameDiatrizoate
Accession NumberDB00271  (APRD00913)
TypeSmall Molecule
GroupsApproved
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
Synonyms
SynonymLanguageCode
2,4,6-Triiodo-3,5-diacetamidobenzoic acidNot AvailableNot Available
3,5-Bis(acetylamino)-2,4,6-triiodobenzoic acidNot AvailableNot Available
3,5-diacetamido-2,4,6-triiodobenzoic acidNot AvailableNot Available
Acide amidotrizoiqueNot AvailableNot Available
Acidum amidotrizoicumNot AvailableNot Available
Acidum diacetylaminotrijodbenzoicumNot AvailableNot Available
AmidotrizoateNot AvailableNot Available
Amidotrizoic AcidNot AvailableNot Available
Amidotrizoic acid (anhydrous)Not AvailableNot Available
DiatrizoateNot AvailableNot Available
DiatrizoesaureNot AvailableNot Available
Diatrizoic acidNot AvailableNot Available
Diatrizoic acid (anhydrous)Not AvailableNot Available
Methalamic acidNot AvailableNot Available
TriombrinNot AvailableNot Available
Urografin acidNot AvailableNot Available
Urogranoic acidNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Gastrografinliquid660; 100 mg/mL; mg/mLoral; rectalBRACCO DIAGNOSTICS INC1958-02-26Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Md-gastroviewsolution600; 100 mg/mL; mg/mLoral; rectalMallinckrodt Inc.2009-08-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
CardiografinNot Available
HypaqueAmersham
OdistonNot Available
UrovisonZydus
UrovistBayer
Brand mixtures
Brand NameIngredients
SinografinDiatrizoate Meglumine + Meglumine Iodipamide
Salts
Name/CASStructureProperties
Diatrizoate meglumine
Thumb
  • InChI Key: MIKKOBKEXMRYFQ-WZTVWXICSA-N
  • Monoisotopic Mass: 808.880309705
  • Average Mass: 809.1272
DBSALT000844
Diatrizoate sodium
737-31-5
Thumb
  • InChI Key: ZEYOIOAKZLALAP-UHFFFAOYSA-M
  • Monoisotopic Mass: 635.751581689
  • Average Mass: 635.8954
DBSALT000267
Categories
CAS number117-96-4
WeightAverage: 613.9136
Monoisotopic: 613.769637046
Chemical FormulaC11H9I3N2O4
InChI KeyYVPYQUNUQOZFHG-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)
IUPAC Name
3,5-diacetamido-2,4,6-triiodobenzoic acid
SMILES
CC(=O)NC1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzoic acids
Alternative Parents
Substituents
  • N-arylamide
  • Halobenzoic acid
  • 4-halobenzoic acid
  • 2-halobenzoic acid
  • Halobenzoic acid or derivatives
  • 4-halobenzoic acid or derivatives
  • 2-halobenzoic acid or derivatives
  • Acetanilide
  • Aminobenzoic acid
  • Benzoic acid
  • Benzoyl
  • Iodobenzene
  • Halobenzene
  • Aryl iodide
  • Aryl halide
  • Acetamide
  • Vinylogous halide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organoiodide
  • Organohalogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationUsed, 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.
PharmacodynamicsDiatrizoate 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 actionDiatrizoate 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationHowever, 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 lifeNot Available
ClearanceNot Available
ToxicityHigh 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8406
Blood Brain Barrier+0.9152
Caco-2 permeable+0.5151
P-glycoprotein substrateNon-substrate0.7998
P-glycoprotein inhibitor INon-inhibitor0.9476
P-glycoprotein inhibitor IINon-inhibitor0.9752
Renal organic cation transporterNon-inhibitor0.9705
CYP450 2C9 substrateNon-substrate0.7632
CYP450 2D6 substrateNon-substrate0.8853
CYP450 3A4 substrateNon-substrate0.6258
CYP450 1A2 substrateNon-inhibitor0.73
CYP450 2C9 substrateNon-inhibitor0.8696
CYP450 2D6 substrateNon-inhibitor0.94
CYP450 2C19 substrateNon-inhibitor0.9271
CYP450 3A4 substrateNon-inhibitor0.9376
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9268
Ames testAMES toxic0.508
CarcinogenicityNon-carcinogens0.6241
BiodegradationNot ready biodegradable0.9832
Rat acute toxicity1.9136 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9975
hERG inhibition (predictor II)Non-inhibitor0.9623
Pharmacoeconomics
Manufacturers
  • Bayer healthcare pharmaceuticals inc
  • Bracco diagnostics inc
  • Ge healthcare
  • Mallinckrodt inc
  • Mallinckrodt medical inc
  • Isotex diagnostics
Packagers
Dosage forms
FormRouteStrength
Liquidoral; rectal660; 100 mg/mL; mg/mL
Solutionoral; rectal600; 100 mg/mL; mg/mL
Prices
Unit descriptionCostUnit
Gastrografin 66-10 solution0.92USD ml
Hypaque sodium oral powder0.68USD g
Conray 60% vial0.36USD ml
Cystografin 30% infus. btl0.22USD ml
Conray-43 vial0.2USD ml
Conray-30 infusion bottle0.16USD ml
Hypaque 41.66% liquid0.16USD ml
Cystografin-dilute 18% btl0.13USD ml
Cysto-conray 17.2% vial0.11USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point>250Larsen, A.A.; US. Patent 3,076,024; January 29, 1963; assigned to Sterling Drug,Inc.
logP3.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.107 mg/mLALOGPS
logP2.27ALOGPS
logP2.89ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)2.17ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.5 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity103.13 m3·mol-1ChemAxon
Polarizability38.43 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Larsen, A.A.; US. Patent 3,076,024; January 29, 1963; assigned to Sterling Drug,Inc.

General ReferenceNot Available
External Links
ATC CodesV08AA01
AHFS Codes
  • 36:68.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.2 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on April 11, 2014 10:53