Diatrizoate

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

Status : approved

Category

Contrast Media

Therapeutic Classification

X-RAY CONTRAST MEDIA, IODINATED

VARIOUS
CONTRAST MEDIA
X-RAY CONTRAST MEDIA, IODINATED

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]

Used

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.

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.

Dosage

Form Route Strength
Injection, solution intravenous 300 mg/mL
Injection, solution intravesical 180 mg/mL
Liquid oral; rectal 660; 100 mg/mL; mg/mL
Solution oral 66 %
Liquid oral; refer (see dosage form) 66 %
Liquid oral; rectal 50 g
Powder oral; rectal 997.4 mg
Powder oral 100 %
Liquid intravenous 50 %
Solution intravenous; cystography 18 %
Liquid intravenous; cystography 18 %
Solution intravenous; cystography 30 %
Liquid intravenous; cystography 30 %
Solution intravenous; cystography; arthography 60 %
Liquid intravenous; cystography; arthography 60 %
Solution intra-arterial; intravenous 66 %
Liquid intra-arterial; intravenous 66 %
Liquid intravenous 66 %
Solution intra-arterial; intravenous 520 mg
Solution intra-arterial; intravenous 660 mg
Solution intravenous 660; 100 mg/mL; mg/mL
Solution oral; rectal 600; 100 mg/mL; mg/mL
Liquid intravenous 600 mg
Liquid intramuscular; intravenous 600 mg
Liquid intravenous 30 %
Liquid intravenous 52 %

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.

Toxic Effect

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.

Elimination Route

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.

Chemical Classification

This 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.

Aminobenzoic acids

Organic compounds

Benzenoids

Benzene and substituted derivatives

Benzoic acids and derivatives

Salt : Diatrizoate meglumine

Chemical Name

2,4,6-Triiodo-3,5-diacetamidobenzoic acid

Brands

name Dosage form Country
Cystografin injection, solution US
Cystografin Dilute injection, solution US
Gastrografin liquid US
Gastrografin liquid US
Gastrografin – Liq Orl solution Canada
Gastrografin – Liq Orl solution Canada
Gastrografin Liq liquid Canada
Gastrografin Liq liquid Canada
Hypaque Oral Liquid – 50g/120ml liquid Canada
Hypaque Oral Liquid 50gm/120ml liquid Canada
Hypaque Oral Powder powder Canada
Hypaque Oral Powder 0.9974g/g powder Canada
Hypaque Pwr 100% powder Canada
Hypaque Sodium 50% – Liq IV liquid Canada
Hypaque Sodium 50% Liq liquid Canada
Hypaque Sodium Liq 50% liquid Canada
Hypaque-m 18% solution Canada
Hypaque-m 18% Liq liquid Canada
Hypaque-m 30% solution Canada
Hypaque-m 30% Liq liquid Canada
Hypaque-m 60% solution Canada
Hypaque-m 60% Liq liquid Canada
Hypaque-m 76% solution Canada
Hypaque-m 76% solution Canada
Hypaque-m 76% Liq liquid Canada
Hypaque-m 76% Liq liquid Canada
Hypaque-m Liq 76% USP liquid Canada
Hypaque-m Liq 76% USP liquid Canada
Md-60 solution Canada
Md-60 solution Canada
Md-76 solution Canada
Md-76 solution Canada
Md-76r solution US
Md-76r solution US
Md-gastroview solution US
Md-gastroview solution US
Reno-60 liquid Canada
Reno-dip liquid Canada
Reno-m-60 liquid Canada
Reno-m-dip Liq 30% liquid Canada
Renocal-76 liquid Canada
Renocal-76 liquid Canada
Renografin-60 – Liq IV liquid Canada
Renografin-60 – Liq IV liquid Canada
Renografin-60 Liq liquid Canada
Renografin-60 Liq liquid Canada
Renografin-76 – Liq IV liquid Canada
Renografin-76 – Liq IV liquid Canada
Renografin-76 Liq liquid Canada
Renografin-76 Liq liquid Canada

Drug Drug Interactions

  •  Aldesleukin  : May enhance the potential for allergic or hypersensitivity reactions to Iodinated Contrast Agents.

Calculated Property

kind Value Source
logP 2.27 ALOGPS
logS -3.8 ALOGPS
Water Solubility 1.07e-01 g/l ALOGPS
logP 2.89 ChemAxon
IUPAC Name 3,5-diacetamido-2,4,6-triiodobenzoic acid ChemAxon
Traditional IUPAC Name diatrizoate ChemAxon
Molecular Weight 613.9136 ChemAxon
Monoisotopic Weight 613.769637046 ChemAxon
SMILES CC(=O)NC1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I ChemAxon
Molecular Formula C11H9I3N2O4 ChemAxon
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) ChemAxon
InChIKey InChIKey=YVPYQUNUQOZFHG-UHFFFAOYSA-N ChemAxon
Polar Surface Area (PSA) 95.5 ChemAxon
Refractivity 103.13 ChemAxon
Polarizability 38.43 ChemAxon
Rotatable Bond Count 3 ChemAxon
H Bond Acceptor Count 4 ChemAxon
H Bond Donor Count 3 ChemAxon
pKa (strongest acidic) 2.17 ChemAxon
pKa (strongest basic) -4.2 ChemAxon
Physiological Charge -1 ChemAxon
Number of Rings 1 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 0 ChemAxon
Ghose Filter 0 ChemAxon
MDDR-Like Rule 0 ChemAxon

Affected organism

Humans and other mammals