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Details

Stereochemistry ACHIRAL
Molecular Formula C11H9I3N2O4
Molecular Weight 613.914
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIATRIZOIC ACID

SMILES

CC(=Nc1c(c(c(c(c1I)N=C(C)O)I)C(=O)O)I)O

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

-4.70102409E11
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

-3.77308807E11
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 analysis of mechanisms underlying the antifibrinolytic properties of radiographic contrast agents.
2001 Dec
[Opportunities of delayed densitometry of "late (fixed) contrast" as a test for tumors in residual mediastinal lesion in primary mediastinal lymphosarcoma after polychemotherapy].
2002
Ionic radiocontrast media disrupt intercellular contacts via an extracellular calcium-independent mechanism.
2002
[Which imaging in case of sigmoid diverticulitis? The value of ultrasound (Conventional B-mode in combination with hydrocolonsonography and colour flow Doppler) in comparison to the well-established modalities like contrast enema and helical computertomography].
2002 Apr
Short-term moderate sodium restriction induces relative hyperfiltration in normotensive normoalbuminuric Type I diabetes mellitus.
2002 Apr
Gastrografin administration in the treatment of postoperative delayed gastric emptying.
2002 Apr
Effect of iomeprol on rat hippocampal slice synaptic transmission: comparison with other X-ray contrast agents.
2002 Apr
Diagnosis and management of enterovesical fistulas in patients with Crohn's disease.
2002 Aug
Electrocardiographic effects of diagnostic imaging agents.
2002 Aug
Radiocontrast-induced renal tubular cell apoptosis: hypertonic versus oxidative stress.
2002 Aug
Application of oral contrast media in coregistered positron emission tomography-CT.
2002 Aug
Emergency colonoscopy for distal intestinal obstruction syndrome in cystic fibrosis patients.
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
Primary anastomosis and diverting colostomy in diffuse diverticular peritonitis.
2002 Feb
Virtual gastroduodenoscopy: a new look at the bypassed stomach and duodenum after laparoscopic Roux-en-Y gastric bypass for morbid obesity.
2002 Feb
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
Assessment of hypothalamic-pituitary-adrenal axis function after corticosteroid therapy in inflammatory bowel disease.
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
Local tissue toxicity in response to extravascular extravasation of magnetic resonance contrast media.
2002 Jul
Iodinated contrast medium-induced potassium release: the effect of mixing ratios.
2002 Jul-Aug
Aneurysmal bone cysts: treatment with direct percutaneous Ethibloc injection: long-term results.
2002 Jul-Aug
Type IV diaphragmatic hiatal hernia.
2002 Jun-Jul
Early esophageal transit study after laparoscopic fundoplication: how useful is it?
2002 Mar
Gastrocolocutaneous Fistula as a complication of peg tube placement.
2002 Mar
Changes in the fibrinolytic system during angiography with ionic and with nonionic contrast media.
2002 Mar
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
[Ultrasound and X-ray urethrography and urethroscopy during endoscopic operations on the urethra].
2002 Mar-Apr
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
Renal excretion of ingested gastrografin: clinical relevance in early postoperative treatment of patients who have undergone gastric surgery.
2002 May
Jejunum free flap in hypopharynx reconstruction: case series.
2002 May 10
Safety and efficacy of postoperative continuous positive airway pressure to prevent pulmonary complications after Roux-en-Y gastric bypass.
2002 May-Jun
The role of theophylline in contrast-induced nephropathy: a case-control study.
2002 Nov
Pressure-assisted micturating cystourethrography: reduction in duration of procedure and fluoroscopy time.
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
Chronic renal dysfunction late after liver transplantation.
2002 Oct
Renal chemoembolization with mitomycin c/Ethibloc: pharmacokinetics and efficacy in an animal model.
2002 Sep
The diagnostic yield of colonoscopy and the therapeutic value of intraduodenal amidotrizoic acid injection in intestinal Diphyllobothrium latum infection: report of a case.
2002 Sep
Ex vivo expansion of megakaryocyte progenitors from cryopreserved umbilical cord blood. A potential source of megakaryocytes for transplantation.
2002 Sep
Is same-day sonography of the gallbladder feasible after intravenous urography or contrast-enhanced computed tomography?
2002 Sep
Iothalamate measured by capillary electrophoresis is a suitable alternative to radiolabeled inulin in renal micropuncture.
2002 Sep
[Fast method of labelling leukocytes with 99mTc HM PAO].
2002 Sep-Oct
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
AMIDOTRIZOIC ACID [WHO-DD]
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
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
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
NDF-RT N0000180185
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
WHO-VATC QV08AA01
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
WHO-ATC V08AA01
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
NDF-RT N0000010258
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
Code System Code Type Description
DRUG BANK
DB00271
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY
MERCK INDEX
M4263
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY Merck Index
MESH
C016826
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY
NCI_THESAURUS
C47483
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY
EPA CompTox
117-96-4
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY
LACTMED
Diatrizoate
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY
HSDB
4042
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DIATRIZOIC ACID
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
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
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY
USP_CATALOG
1184005
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY USP-RS
FDA UNII
5UVC90J1LK
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY
CAS
117-96-4
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY
DRUG CENTRAL
851
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY
RXCUI
1546223
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY
MESH
D003973
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY
WIKIPEDIA
DIATRIZOIC ACID
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY
PUBCHEM
2140
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201220
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-223-6
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
PRIMARY
RXCUI
3319
Created by admin on Fri Jun 25 20:59:50 UTC 2021 , Edited by admin on Fri Jun 25 20:59:50 UTC 2021
ALTERNATIVE