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Details

Stereochemistry ACHIRAL
Molecular Formula C11H9I3N2O4
Molecular Weight 613.9136
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIATRIZOIC ACID

SMILES

CC(=O)NC1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I

InChI

InChIKey=YVPYQUNUQOZFHG-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/010040s171lbl.pdf

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. A commonly used x-ray contrast medium. 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. 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.

Originator

Curator's Comment: Diatrizoic acid was discovered in 1953 simultaneously and independently by Schering AG in Berlin and by Sterling-Winthrop in the USA.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Cystografin

Approved Use

Retrograde cystourethrography

Launch Date

1955
Diagnostic
Gastrografin

Approved Use

Gastrografin (DIATRIZOIC ACID) is indicated for radiographic examination of segments of the gastrointestinal tract (esophagus, stomach, proximal small intestine, and colon).

Launch Date

1958
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.6 mg/mL
3.36 mg/kg single, intravenous
dose: 3.36 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
HYDROGEN IODIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
7 mg/mL
7.2 mg/kg single, intravenous
dose: 7.2 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
HYDROGEN IODIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
110 min
3.36 mg/kg single, intravenous
dose: 3.36 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
HYDROGEN IODIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
102 min
7.2 mg/kg single, intravenous
dose: 7.2 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
HYDROGEN IODIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
An approach to the performance of contrast studies in contrast material-reactive persons.
1975 Aug
Reversibility of experimental acute renal failure in rats: assessment with USPIO-enhanced MR imaging.
2000 Aug
Nephrotoxicity of high- and low-osmolar contrast media. The protective role of amlodipine in a rat model.
2000 Sep
Dose reduction in evacuation proctography.
2001
Spontaneous pneumomediastinum.
2001 Apr
Temporary pancreatic duct occlusion by ethibloc: cause of microcirculatory shutdown, acute inflammation, and pancreas necrosis.
2001 Apr
Shielding effects of metallic encapsulations and radiographic contrast agents for catheter-based intravascular brachytherapy.
2001 Apr-Jun
The use of dilute Calogen as a fat density oral contrast medium in upper abdominal computed tomography, compared with the use of water and positive oral contrast media.
2001 Aug
Flow-directed microcatheters for cerebral embolizations using Ethibloc--an in vitro study.
2001 Dec
The selective adenosine A1 receptor antagonist KW-3902 prevents radiocontrast media-induced nephropathy in rats with chronic nitric oxide deficiency.
2001 Feb 23
Review of studies establishing the aging male spontaneously hypertensive rat as a detector and quantifier of the kidney toxicity of radiocontrast media and other chemicals.
2001 Jan
[Evaluation of aqueous compartments of the body by integral bioimpedance spectrometry in x-ray surgical interventions in children].
2001 Jan-Feb
Mixed-type hiatal hernia mimicking pulmonary cystic lesion diagnosed by oral urografin in ED.
2001 Jul
CT colonography without cathartic preparation: feasibility study.
2001 Jun
Harmonic scalpel in laparoscopic colorectal surgery.
2001 Mar
Contrast medium precipitation in the stomach between contiguous plain and contrast CT scans.
2001 May-Jun
Retrospective study on the effects of lipiodolization before a potentially curative hepatectomy for colorectal liver metastases: long-term results of a pilot study.
2001 May-Jun
Rapid diagnosis of sigmoid volvulus with water soluble urografin in emergency service.
2001 Nov
Appendiceal disease in women with endometriosis and right lower quadrant pain.
2001 Nov
Videourodynamic and sphincter motor unit potential analyses in Parkinson's disease and multiple system atrophy.
2001 Nov
Pseudomembranous colitis without diarrhea presenting clinically as acute intestinal pseudo-obstruction.
2001 Sep
Ionic radiocontrast media disrupt intercellular contacts via an extracellular calcium-independent mechanism.
2002
Short-term moderate sodium restriction induces relative hyperfiltration in normotensive normoalbuminuric Type I diabetes mellitus.
2002 Apr
Diagnosis and management of enterovesical fistulas in patients with Crohn's disease.
2002 Aug
Electrocardiographic effects of diagnostic imaging agents.
2002 Aug
Thumbprinting due to ischemic colitis in a patient on oral anticoagulation.
2002 Aug-Sep
Use of near-infrared reflection spectroscopy to study the effects of X-ray contrast media on renal tolerance in rats: effects of a prostacyclin analogue and of phosphodiesterase inhibitors.
2002 Dec
Rectal washout with cytotoxic solution can be extended to the whole colon.
2002 Dec
Evidence for involvement of mast cell degranulation and subsequent stimulation of histamine H1 and H2 receptors in radiographic contrast media-increased vascular permeability in rats.
2002 Dec
The utility of contrast studies and drains in the management of patients after Roux-en-Y gastric bypass.
2002 Feb
Effects of intrathecal injection of diatrizoate on dopamine receptors.
2002 Jul
Contrast radiography and intestinal obstruction.
2002 Jul
Therapeutic value of gastrografin in adhesive small bowel obstruction after unsuccessful conservative treatment: a prospective randomized trial.
2002 Jul
Laparoscopic repair for perforated peptic ulcer: a randomized controlled trial.
2002 Mar
Do clinically relevant circulating concentrations of radiographic contrast agents inhibit platelet-dependent arterial thrombosis?
2002 Mar 1
A case of gastric duplication evaluated by gastric emptying scintigraphy.
2002 May
Long-term survival of patients with stage IV hypopharyngeal cancer: impact of fundus rotation gastroplasty.
2002 May
New strategies in nonoperative management of meconium ileus.
2002 May
Jejunum free flap in hypopharynx reconstruction: case series.
2002 May 10
The role of theophylline in contrast-induced nephropathy: a case-control study.
2002 Nov
The value of contrast radiology for postoperative adhesive small bowel obstruction.
2002 Nov-Dec
Venous port salvage utilizing low dose tPA.
2002 Nov-Dec
Renal chemoembolization with mitomycin c/Ethibloc: pharmacokinetics and efficacy in an animal model.
2002 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: For radiographic examination of segments of the gastrointestinal tract (Gastrografin) oral administration: adult oral dosage may range from 30 to 90 mL (11 to 33 g iodine), depending on the nature of the examination and the size of the patient. For Enemas or Enterostomy Instillations: should be diluted when it is used for enemas and enterostomy instillations. When used as an enema, the suggested dilution for adults is 240 mL (88 g iodine) in 1,000 mL of tap water. http://www.drugs.com/pro/gastrografin.html ;
The dose for retrograde use in cystography and voiding cystourethrography ranges from 25 to 300 mL depending on the age of the patient and the degree of bladder irritability
Route of Administration: Other
In Vitro Use Guide
Unknown
Name Type Language
DIATRIZOIC ACID
HSDB   II   MI   USAN   USP  
USAN  
Official Name English
UROGRANOIC ACID
Common Name English
DIATRIZOIC ACID [USAN]
Common Name English
AMIDOTRIZOIC ACID
MART.   WHO-DD   WHO-IP  
Common Name English
UROGRAFIN ACID
Common Name English
NSC-262168
Code English
ODISTON
Brand Name English
AMIDOTRIZOIC ACID, ANHYDROUS [WHO-IP]
Common Name English
ACIDUM AMIDOTRIZOICUM, ANHYDROUS [WHO-IP LATIN]
Common Name English
3,5-BIS-ACETAMIDO-2,4,6-TRIIODOBENZOIC ACID
Systematic Name English
DIATRIZOIC ACID [USP MONOGRAPH]
Common Name English
AMIDOTRIZOIC ACID [MART.]
Common Name English
AMIDOTRIZOIC ACID [JAN]
Common Name English
DIATRIZOIC ACID [HSDB]
Common Name English
DIATRIZOATE [VANDF]
Common Name English
UROTRAST
Brand Name English
Amidotrizoic acid [WHO-DD]
Common Name English
DIATRIZOIC ACID [USP-RS]
Common Name English
AMIDOTRIZOIC ACID [WHO-IP]
Common Name English
DIATRIZOATE
VANDF  
Common Name English
DIATRIZOIC ACID [II]
Common Name English
DIATRIZOIC ACID [MI]
Common Name English
ACIDUM AMIDOTRIZOICUM [WHO-IP LATIN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C390
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NDF-RT N0000180185
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WHO-VATC QV08AA01
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WHO-ATC V08AA01
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NDF-RT N0000010258
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Code System Code Type Description
DRUG BANK
DB00271
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PRIMARY
MERCK INDEX
m4263
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PRIMARY Merck Index
SMS_ID
100000091574
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PRIMARY
CHEBI
59733
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PRIMARY
MESH
C016826
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PRIMARY
NCI_THESAURUS
C47483
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PRIMARY
EPA CompTox
DTXSID0044521
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PRIMARY
LACTMED
Diatrizoate
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PRIMARY
HSDB
4042
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PRIMARY
RS_ITEM_NUM
1184005
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PRIMARY
DAILYMED
5UVC90J1LK
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DIATRIZOIC ACID
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PRIMARY Description: A white or almost white, crystalline powder; odourless. Solubility: Very slightly soluble in water and ethanol (~750 g/l) TS; soluble in dimethylformamide R; sparingly soluble in methanol R; practically insoluble in ether R; dissolves in solutions of alkali hydroxides. Category: Used in the preparation of meglumine amidotrizoate as a radiocontrast medium. Storage: Amidotrizoic acid should be kept in a well-closed container, protected from light. Labelling: The designation on the container of amidotrizoic acid should state whether the substance is the dihydrate or the anhydrous form. Requirement: Amidotrizoic acid contains not less than 98.0% and not more than the equivalent of 102.0% of C11H9I3N2O4, calculated with reference to the dried substance.
EVMPD
SUB00443MIG
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PRIMARY
FDA UNII
5UVC90J1LK
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PRIMARY
CAS
117-96-4
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PRIMARY
NSC
262168
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PRIMARY
DRUG CENTRAL
851
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PRIMARY
RXCUI
1546223
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PRIMARY
MESH
D003973
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PRIMARY
WIKIPEDIA
DIATRIZOIC ACID
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PRIMARY
PUBCHEM
2140
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PRIMARY
ChEMBL
CHEMBL1201220
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PRIMARY
ECHA (EC/EINECS)
204-223-6
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PRIMARY
RXCUI
3319
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ALTERNATIVE
CHEBI
53691
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PRIMARY