Identification
- Summary
Diatrizoate is an injected contrast agent used in radiology.
- Brand Names
- Cystografin, Cystografin Dilute, Gastrografin, Hypaque, Md-Gastroview
- Generic Name
- Diatrizoate
- DrugBank Accession Number
- DB00271
- Background
A commonly used x-ray contrast medium. As diatrizoate meglumine and as Diatrizoate sodium, it is used for gastrointestinal studies, angiography, and urography.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Diatrizoate (DB00271)
- Weight
- Average: 613.9136
Monoisotopic: 613.769637046 - Chemical Formula
- C11H9I3N2O4
- 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)
- Diatrizoesaure
- Diatrizoic acid
- Diatrizoic acid (anhydrous)
- Methalamic acid
- Triombrin
- Urografin acid
- Urogranoic acid
- External IDs
- NSC-262168
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.
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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
- Not Available
- 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
- Adverse Effects
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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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Diatrizoate may decrease the excretion rate of Abacavir which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Diatrizoate which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Diatrizoate which could result in a higher serum level. Acetaminophen Diatrizoate may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Diatrizoate which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Diatrizoate meglumine 3X9MR4N98U 131-49-7 MIKKOBKEXMRYFQ-WZTVWXICSA-N Diatrizoate sodium V5403H8VG7 737-31-5 ZEYOIOAKZLALAP-UHFFFAOYSA-M Diatrizoic acid dihydrate 408463F217 50978-11-5 JHQKUXXJPHSPOL-UHFFFAOYSA-N - Active Moieties
Name Kind UNII CAS InChI Key Iodine unknown 9679TC07X4 7553-56-2 PNDPGZBMCMUPRI-UHFFFAOYSA-N - International/Other Brands
- Cardiografin / Odiston / Urovison (Zydus) / Urovist (Bayer)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cystografin Injection, solution 300 mg/1mL Intravenous Bracco Diagnostics Inc 1970-11-03 Not applicable US 
Cystografin Dilute Injection, solution 180 mg/1mL Intravesical Bracco Diagnostics Inc 1982-11-09 Not applicable US Hypaque - Cysto Injection, solution 30 g/100mL Intravenous Amersham Health Inc. 2007-08-03 Not applicable US Hypaque Oral Liquid - 50g/120ml Liquid 50 g / 120 mL Oral; Rectal Nycomed Imaging A.S. 1997-03-17 1998-04-21 Canada 
Hypaque Oral Powder Powder 997.4 mg / g Oral; Rectal Ge Healthcare 1998-02-19 2011-07-27 Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Hypaque Oral Liquid 50gm/120ml Liquid 50 g / 120 mL Oral; Rectal Sanofi 1958-12-31 1997-07-30 Canada Hypaque Sodium Liq 50% Liquid 50 % Intravenous Sanofi 1954-12-31 1997-07-30 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Diatrizoate Meglumine and Diatrizoate Sodium Diatrizoate meglumine (660 mg/1mL) + Diatrizoate sodium (100 mg/1mL) Solution Oral; Rectal Camber Pharmaceuticals, Inc. 2023-11-17 Not applicable US Diatrizoate Meglumine and Diatrizoate Sodium Diatrizoate meglumine (660 mg/1mL) + Diatrizoate sodium (100 mg/1mL) Solution Oral; Rectal Guardian Drug Company 2019-12-18 Not applicable US Diatrizoate Meglumine and Diatrizoate Sodium Diatrizoate meglumine (660 mg/1mL) + Diatrizoate sodium (100 mg/1mL) Solution Oral; Rectal Guardian Drug Company 2019-12-18 Not applicable US Diatrizoate Meglumine and Diatrizoate Sodium Diatrizoate meglumine (660 mg/1mL) + Diatrizoate sodium (100 mg/1mL) Solution Oral; Rectal Guardian Drug Company 2019-12-18 Not applicable US Diatrizoate Meglumine and Diatrizoate Sodium Diatrizoate meglumine (660 mg/1mL) + Diatrizoate sodium (100 mg/1mL) Solution Oral; Rectal Camber Pharmaceuticals, Inc. 2023-11-17 Not applicable US
Categories
- ATC Codes
- V08AA01 — Diatrizoic acid
- Drug Categories
- Acids, Carbocyclic
- Alcohols
- Amino Sugars
- Benzene Derivatives
- Benzoates
- Carbohydrates
- Compounds used in a research, industrial, or household setting
- Contrast Media
- Diagnostic Uses of Chemicals
- Drugs that are Mainly Renally Excreted
- Hexosamines
- Iodinated Contrast Agents
- Iodobenzoates
- Radiographic Contrast Agent
- Roentgenography
- Sugar Alcohols
- Triiodobenzoic Acids
- Watersoluble, Nephrotropic, High Osmolar X-Ray Contrast Media
- X-Ray Contrast Activity
- X-Ray Contrast Media, Iodinated
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as halobenzoic acids. These are benzoic acids carrying a halogen atom on the benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzoic acids and derivatives
- Direct Parent
- Halobenzoic acids
- Alternative Parents
- 2-halobenzoic acids / 4-halobenzoic acids / Benzoic acids / 1-carboxy-2-haloaromatic compounds / Benzoyl derivatives / Iodobenzenes / Aryl iodides / Vinylogous halides / Monocarboxylic acids and derivatives / Carboximidic acids show 7 more
- Substituents
- 1-carboxy-2-haloaromatic compound / 2-halobenzoic acid / 2-halobenzoic acid or derivatives / 4-halobenzoic acid / 4-halobenzoic acid or derivatives / Aromatic homomonocyclic compound / Aryl halide / Aryl iodide / Benzoic acid / Benzoyl show 20 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- organoiodine compound, acetamides, benzoic acids (CHEBI:53691)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 5UVC90J1LK
- CAS number
- 117-96-4
- InChI Key
- 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
References
- Synthesis Reference
Larsen, A.A.; US. Patent 3,076,024; January 29, 1963; assigned to Sterling Drug,Inc.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014416
- KEGG Drug
- D01013
- PubChem Compound
- 2140
- PubChem Substance
- 46504704
- ChemSpider
- 2055
- BindingDB
- 62875
- 1546223
- ChEBI
- 53691
- ChEMBL
- CHEMBL1201220
- ZINC
- ZINC000004097476
- PharmGKB
- PA449281
- Wikipedia
- Diatrizoate
- MSDS
- Download (73.2 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Diagnostic Healthy Volunteers (HV) 1 4 Completed Treatment Adhesive Small Intestine Obstruction 1 4 Completed Treatment Meconium Ileus / Very Low Birthweight Infants 1 4 Completed Treatment Postoperative paralytic ileus 1 4 Withdrawn Treatment Fetal Malformation / Gastroschisis / Intestinal Obstruction 1
Pharmacoeconomics
- Manufacturers
- Bayer healthcare pharmaceuticals inc
- Bracco diagnostics inc
- Ge healthcare
- Mallinckrodt inc
- Mallinckrodt medical inc
- Isotex diagnostics
- Packagers
- Bayer Healthcare
- Bracco Diagnostics Inc.
- Bristol-Myers Squibb Co.
- EZ-EM Inc.
- GE Healthcare Inc.
- Kaiser Foundation Hospital
- KBAS Party Ltd.
- Mallinckrodt Inc.
- Nycomed Inc.
- Patheon Inc.
- Dosage Forms
Form Route Strength Injection, solution Intravesical 180 mg/1mL Liquid Oral; Rectal Liquid Oral Solution Oral; Rectal 66 g/100ml Solution Oral; Rectal 0.66 g/ml Injection, solution Intravenous Injection, solution Intravenous 30 g/100mL Liquid Oral; Rectal 50 g / 120 mL Powder Oral; Rectal 997.4 mg / g Powder Oral 100 % Injection, solution Intravenous 500 mg/1mL Injection, solution Intravenous 60 g/100mL Powder, for solution Oral 600 mg/1g Liquid Intravenous 50 % Solution Intravenous 18 % Liquid Intravenous 18 % Solution Intravenous 30 % Solution Intravenous 60 % Liquid Intravenous 60 % Solution Intra-arterial; Intravenous Liquid Intra-arterial; Intravenous Liquid Intravenous Solution Oral; Rectal Solution Intravenous Solution Parenteral Solution Rectal 36 % Injection Intravenous 60 g Injection, solution Intravenous 600 mg/1mL Liquid Intravenous 600 mg / mL Injection, solution Intravenous 300 mg/1mL Liquid Intramuscular; Intravenous 600 mg / mL Liquid Intravenous 30 % Injection, solution Intravascular Injection, solution Intrauterine Liquid Intrauterine Solution Intravascular - Prices
Unit description Cost Unit Gastrografin 66-10 solution 0.92USD ml Hypaque sodium oral powder 0.68USD g Conray 60% vial 0.36USD ml Cystografin 30% infus. btl 0.22USD ml Conray-43 vial 0.2USD ml Conray-30 infusion bottle 0.16USD ml Hypaque 41.66% liquid 0.16USD ml Cystografin-dilute 18% btl 0.13USD ml Cysto-conray 17.2% vial 0.11USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) >250 Larsen, A.A.; US. Patent 3,076,024; January 29, 1963; assigned to Sterling Drug,Inc. logP 3.3 Not Available - Predicted Properties
Property Value Source Water Solubility 0.107 mg/mL ALOGPS logP 2.27 ALOGPS logP 2.89 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 2.17 Chemaxon pKa (Strongest Basic) -4.2 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 95.5 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 103.13 m3·mol-1 Chemaxon Polarizability 38.43 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.8696 CYP450 2D6 inhibitor Non-inhibitor 0.94 CYP450 2C19 inhibitor Non-inhibitor 0.9271 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 175.8341793 predictedDarkChem Lite v0.1.0 [M-H]- 174.9752793 predictedDarkChem Lite v0.1.0 [M-H]- 189.12387 predictedDeepCCS 1.0 (2019) [M+H]+ 177.8341793 predictedDarkChem Lite v0.1.0 [M+H]+ 177.5199793 predictedDarkChem Lite v0.1.0 [M+H]+ 191.82835 predictedDeepCCS 1.0 (2019) [M+Na]+ 177.4553793 predictedDarkChem Lite v0.1.0 [M+Na]+ 176.9835793 predictedDarkChem Lite v0.1.0 [M+Na]+ 199.62701 predictedDeepCCS 1.0 (2019)
Drug created at June 13, 2005 13:24 / Updated at April 16, 2024 12:20