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Identification
NameDiatrizoate
Accession NumberDB00271  (APRD00913)
TypeSmall Molecule
GroupsApproved, Vet 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
Synonyms
2,4,6-Triiodo-3,5-diacetamidobenzoic acid
3,5-Bis(acetylamino)-2,4,6-triiodobenzoic acid
3,5-diacetamido-2,4,6-triiodobenzoic acid
Acide amidotrizoique
Acidum amidotrizoicum
Acidum diacetylaminotrijodbenzoicum
Amidotrizoate
Amidotrizoic Acid
Amidotrizoic acid (anhydrous)
Diatrizoate
Diatrizoesaure
Diatrizoic acid
Diatrizoic acid (anhydrous)
Methalamic acid
Triombrin
Urografin acid
Urogranoic acid
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cystografininjection, solution300 mg/mLintravenousBRACCO DIAGNOSTICS INC1970-11-032016-04-23Us
Cystografin Diluteinjection, solution180 mg/mLintravesicalBRACCO DIAGNOSTICS INC1982-11-092016-04-23Us
Hypaque Oral Liquid - 50g/120mlliquid50 goral; rectalNycomed Imaging A.S.1997-03-171998-04-21Canada
Hypaque Oral Powderpowder997.4 mgoral; rectalGe Healthcare Canada Inc1998-02-192011-07-27Canada
Hypaque Oral Powder 0.9974g/gpowder997.4 mgoral; rectalSanofi Canada, Inc.1960-12-311997-07-30Canada
Hypaque Pwr 100%powder100 %oralSterling Winthrop Inc.1992-12-311996-09-10Canada
Hypaque Sodium 50% - Liq IVliquid50 %intravenousNycomed Imaging A.S.1998-04-222000-04-03Canada
Hypaque Sodium 50% Liqliquid50 %intravenousSterling Winthrop Inc.1991-12-311996-09-10Canada
Hypaque-M 18%solution18 %intravenous; cystographyAmersham Health Inc1997-08-272006-07-26Canada
Hypaque-M 18% Liqliquid18 %intravenous; cystographySanofi Canada, Inc.1979-12-311997-07-30Canada
Hypaque-M 30%solution30 %intravenous; cystographyAmersham Health Inc1998-01-162007-01-11Canada
Hypaque-M 30% Liqliquid30 %intravenous; cystographySanofi Canada, Inc.1969-12-311997-07-30Canada
Hypaque-M 60%solution60 %intravenous; cystography; arthographyAmersham Health Inc1997-04-162006-12-22Canada
Hypaque-M 60% Liqliquid60 %intravenous; cystography; arthographySanofi Canada, Inc.1968-12-311997-07-30Canada
Reno-60liquid600 mgintravenousBracco Imaging Canada1999-07-012010-01-05Canada
Reno-dipliquid30 %intravenousBracco Imaging Canada1998-07-202010-01-05Canada
Reno-M-60liquid600 mgintramuscular; intravenousSquibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.1976-12-311997-08-14Canada
Reno-M-dip Liq 30%liquid30 %intravenousSquibb Diagnostics, Division Of Bristol Myers Squibb Canada Inc.1981-12-311998-07-30Canada
Generic Prescription ProductsNot Available
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Hypaque Oral Liquid 50gm/120mlliquid50 goral; rectalSanofi Canada, Inc.1958-12-311997-07-30Canada
Hypaque Sodium Liq 50%liquid50 %intravenousSanofi Canada, Inc.1954-12-311997-07-30Canada
International Brands
NameCompany
CardiografinNot Available
HypaqueAmersham
OdistonNot Available
UrovisonZydus
UrovistBayer
Brand mixtures
NameLabellerIngredients
GastrografinBRACCO DIAGNOSTICS INC
Gastrografin - Liq OrlBracco Imaging Canada
Gastrografin LiqSquibb Diagnostics, Division Of Bristol Myers Squibb Canada Inc.
Hypaque-M 76%Amersham Health Inc
Hypaque-M 76% LiqSanofi Canada, Inc.
Hypaque-M Liq 76% USPSterling Winthrop Inc.
Md-60Tyco Healthcare
Md-76Tyco Healthcare
Md-76rMallinckrodt Inc.
Md-gastroviewMallinckrodt Inc.
Renocal-76Bracco Imaging Canada
Renografin-60 - Liq IVBracco Imaging Canada
Renografin-60 LiqSquibb Diagnostics, Division Of Bristol Myers Squibb Canada Inc.
Renografin-76 - Liq IVBracco Imaging Canada
Renografin-76 LiqSquibb Diagnostics, Division Of Bristol Myers Squibb Canada Inc.
SinografinBRACCO DIAGNOSTICS INC
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
UNII5UVC90J1LK
CAS number117-96-4
WeightAverage: 613.9136
Monoisotopic: 613.769637046
Chemical FormulaC11H9I3N2O4
InChI KeyInChIKey=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)
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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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 inhibitorNon-inhibitor0.8696
CYP450 2D6 inhibitorNon-inhibitor0.94
CYP450 2C19 inhibitorNon-inhibitor0.9271
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Bayer healthcare pharmaceuticals inc
  • Bracco diagnostics inc
  • Ge healthcare
  • Mallinckrodt inc
  • Mallinckrodt medical inc
  • Isotex diagnostics
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintravenous300 mg/mL
Injection, solutionintravesical180 mg/mL
Liquidoral; rectal
Solutionoral
Liquidoral; refer (see dosage form)
Liquidoral; rectal50 g
Powderoral; rectal997.4 mg
Powderoral100 %
Liquidintravenous50 %
Solutionintravenous; cystography18 %
Liquidintravenous; cystography18 %
Solutionintravenous; cystography30 %
Liquidintravenous; cystography30 %
Solutionintravenous; cystography; arthography60 %
Liquidintravenous; cystography; arthography60 %
Solutionintra-arterial; intravenous
Liquidintra-arterial; intravenous
Liquidintravenous
Solutionintravenous
Solutionoral; rectal
Liquidintravenous600 mg
Liquidintramuscular; intravenous600 mg
Liquidintravenous30 %
Injection, solutionintrauterine
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 ReferencesNot Available
External Links
ATC CodesV08AA01
AHFS Codes
  • 36:68.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.2 KB)
Interactions
Drug Interactions
Drug
AldesleukinThe risk of a hypersensitivity reaction to Diatrizoate is increased when it is combined with Aldesleukin.
Food InteractionsNot Available
Comments
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Drug created on June 13, 2005 07:24 / Updated on April 11, 2014 10:53