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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
3,5-diacetamido-2,4,6-triiodobenzoic acidNot AvailableNot Available
AmidotrizoateNot AvailableNot Available
Amidotrizoic AcidNot AvailableNot Available
Diatrizoic acidNot AvailableNot Available
Salts
Name/CAS Structure Properties
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
Brand names
NameCompany
CardiografinNot Available
GastrografinBayer
HypaqueAmersham
MD-GASTROVIEWNot Available
OdistonNot Available
UrovisonZydus
UrovistBayer
Brand mixtures
Brand NameIngredients
SinografinDiatrizoate Meglumine + Meglumine Iodipamide
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassBenzoic Acid and Derivatives
Direct parentAminobenzoic Acid Derivatives
Alternative parentsAnilides; Benzoic Acids; Benzoyl Derivatives; Iodobenzenes; Aryl Iodides; Secondary Carboxylic Acid Amides; Carboxylic Acids; Polyamines; Enolates; Organoiodides
Substituentsbenzoyl; iodobenzene; aryl iodide; aryl halide; secondary carboxylic acid amide; carboxamide group; carboxylic acid derivative; polyamine; enolate; carboxylic acid; organoiodide; organohalogen; amine; organonitrogen compound
Classification descriptionThis compound belongs to the aminobenzoic acid derivatives. These are benzoic acids (or derivative thereof) containing an amine group attached to the benzene moiety.
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
Property Value Probability
Human Intestinal Absorption - 0.8406
Blood Brain Barrier + 0.9152
Caco-2 permeable + 0.5151
P-glycoprotein substrate Non-substrate 0.7998
P-glycoprotein inhibitor I Non-inhibitor 0.9476
P-glycoprotein inhibitor II Non-inhibitor 0.9752
Renal organic cation transporter Non-inhibitor 0.9705
CYP450 2C9 substrate Non-substrate 0.7632
CYP450 2D6 substrate Non-substrate 0.8853
CYP450 3A4 substrate Non-substrate 0.6258
CYP450 1A2 substrate Non-inhibitor 0.73
CYP450 2C9 substrate Non-inhibitor 0.8696
CYP450 2D6 substrate Non-inhibitor 0.94
CYP450 2C19 substrate Non-inhibitor 0.9271
CYP450 3A4 substrate Non-inhibitor 0.9376
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9268
Ames test AMES toxic 0.508
Carcinogenicity Non-carcinogens 0.6241
Biodegradation Not ready biodegradable 0.9832
Rat acute toxicity 1.9136 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9975
hERG inhibition (predictor II) Non-inhibitor 0.9623
Pharmacoeconomics
Manufacturers
  • Bayer healthcare pharmaceuticals inc
  • Bracco diagnostics inc
  • Ge healthcare
  • Mallinckrodt inc
  • Mallinckrodt medical inc
  • Isotex diagnostics
Packagers
Dosage forms
FormRouteStrength
LiquidIntravenous
PowderOral
SolutionIntravenous
SolutionUrethral
Prices
Unit descriptionCostUnit
Gastrografin 66-10 solution0.92USDml
Hypaque sodium oral powder0.68USDg
Conray 60% vial0.36USDml
Cystografin 30% infus. btl0.22USDml
Conray-43 vial0.2USDml
Conray-30 infusion bottle0.16USDml
Hypaque 41.66% liquid0.16USDml
Cystografin-dilute 18% btl0.13USDml
Cysto-conray 17.2% vial0.11USDml
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 solubility1.07e-01 g/lALOGPS
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 area95.5ChemAxon
rotatable bond count3ChemAxon
refractivity103.13ChemAxon
polarizability38.43ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
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
ResourceLink
KEGG DrugD01013
PubChem Compound2140
PubChem Substance46504704
ChemSpider2055
PharmGKBPA449281
Drug Product Database2237155
WikipediaDiatrizoate
ATC CodesV08AA01V08AA04
AHFS Codes
  • 36:68.00
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(73.2 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on June 13, 2005 07:24 / Updated on April 11, 2014 10:53