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Details

Stereochemistry ACHIRAL
Molecular Formula C11H9I3N2O4.2H2O
Molecular Weight 649.9441
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIATRIZOIC ACID DIHYDRATE

SMILES

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

InChI

InChIKey=JHQKUXXJPHSPOL-UHFFFAOYSA-N
InChI=1S/C11H9I3N2O4.2H2O/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);2*1H2

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
Transcervical catheterization and cervical patency during the oestrous cycle in domestic cats.
2001
The accordion sign at CT: report of a case of Crohn's disease with diffuse colonic involvement.
2001
Spontaneous pneumomediastinum.
2001 Apr
An analysis of mechanisms underlying the antifibrinolytic properties of radiographic contrast agents.
2001 Dec
Effects of radiographic contrast media on pulmonary vascular resistance of normoxic and chronically hypoxic pulmonary hypertensive rats.
2001 Dec
Radiographic contrast media induced nephropathy: experimental observations and the protective effect of calcium channel blockers.
2001 Dec
Re: Renal artery embolization with diluted hot contrast medium: an experimental study.
2001 Dec
A simple method for the identification and assay of iopamidol and iothalamate meglumine in pharmaceutical samples based on proton nuclear magnetic resonance spectroscopy.
2001 Feb
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
Mixed-type hiatal hernia mimicking pulmonary cystic lesion diagnosed by oral urografin in ED.
2001 Jul
Nephrotoxicants induce endothelin release and signaling in renal proximal tubules: effect on drug efflux.
2001 Jun
Harmonic scalpel in laparoscopic colorectal surgery.
2001 Mar
BaSO4-loaded agarose: a construction material for multimodality imaging phantoms.
2001 May
Changes in intrarenal oxygenation as evaluated by BOLD MRI in a rat kidney model for radiocontrast nephropathy.
2001 May
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
Excretory urography by intraosseous injection of contrast media in a rabbit model.
2001 May-Jun
Oesophageal rupture resulting from airbag deployment during a motor vehicle accident.
2001 Sep
[Opportunities of delayed densitometry of "late (fixed) contrast" as a test for tumors in residual mediastinal lesion in primary mediastinal lymphosarcoma after polychemotherapy].
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
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
The utility of contrast studies and drains in the management of patients after Roux-en-Y gastric bypass.
2002 Feb
Plasma exogenous creatinine clearance test in dogs: comparison with other methods and proposed limited sampling strategy.
2002 Jan-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
Early esophageal transit study after laparoscopic fundoplication: how useful is it?
2002 Mar
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
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
Renal chemoembolization with mitomycin c/Ethibloc: pharmacokinetics and efficacy in an animal model.
2002 Sep
Ex vivo expansion of megakaryocyte progenitors from cryopreserved umbilical cord blood. A potential source of megakaryocytes for transplantation.
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 DIHYDRATE
Common Name English
AMIDOTRIZOIC ACID DIHYDRATE
Common Name English
AMIDOTRIZOIC ACID, DEHYDRATE [WHO-IP]
Common Name English
ACIDUM AMIDOTRIZOICUM, DEHYDRATE [WHO-IP LATIN]
Common Name English
AMIDOTRIZOIC ACID DIHYDRATE [EP MONOGRAPH]
Common Name English
BENZOIC ACID, 3,5-BIS(ACETYLAMINO)-2,4,6-TRIIODO-, HYDRATE (1:2)
Common Name English
Code System Code Type Description
SMS_ID
100000076674
Created by admin on Fri Dec 15 18:50:55 GMT 2023 , Edited by admin on Fri Dec 15 18:50:55 GMT 2023
PRIMARY
EPA CompTox
DTXSID1048960
Created by admin on Fri Dec 15 18:50:55 GMT 2023 , Edited by admin on Fri Dec 15 18:50:55 GMT 2023
PRIMARY
CAS
50978-11-5
Created by admin on Fri Dec 15 18:50:55 GMT 2023 , Edited by admin on Fri Dec 15 18:50:55 GMT 2023
PRIMARY
EVMPD
SUB11703MIG
Created by admin on Fri Dec 15 18:50:55 GMT 2023 , Edited by admin on Fri Dec 15 18:50:55 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DIATRIZOIC ACID DIHYDRATE
Created by admin on Fri Dec 15 18:50:55 GMT 2023 , Edited by admin on Fri Dec 15 18:50:55 GMT 2023
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.
PUBCHEM
12598086
Created by admin on Fri Dec 15 18:50:55 GMT 2023 , Edited by admin on Fri Dec 15 18:50:55 GMT 2023
PRIMARY
FDA UNII
408463F217
Created by admin on Fri Dec 15 18:50:55 GMT 2023 , Edited by admin on Fri Dec 15 18:50:55 GMT 2023
PRIMARY