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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

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C11H9I3N2O4
Molecular Weight 613.9136
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
An approach to the performance of contrast studies in contrast material-reactive persons.
1975 Aug
Thrombogenic potential of contrast media in an experimental model of laser-induced thrombosis.
2000 Nov 1
The role of early radiological studies after gastric bariatric surgery.
2001 Aug
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
Evaluation of suspected appendicitis in children using limited helical CT and colonic contrast material.
2001 Jan
Glucose alters the susceptibility of mesangial cells to contrast media.
2001 Jul
[Jejunum interposition as replacement of the pars descendens duodeni in extensive tubulovillous adenoma].
2001 Jul
Mixed-type hiatal hernia mimicking pulmonary cystic lesion diagnosed by oral urografin in ED.
2001 Jul
Effects in vivo of iohexol and diatrizoate on human plasma acetyl- and butyryl-cholinesterase activity.
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
Excretory urography by intraosseous injection of contrast media in a rabbit model.
2001 May-Jun
[Opportunities of delayed densitometry of "late (fixed) contrast" as a test for tumors in residual mediastinal lesion in primary mediastinal lymphosarcoma after polychemotherapy].
2002
Short-term moderate sodium restriction induces relative hyperfiltration in normotensive normoalbuminuric Type I diabetes mellitus.
2002 Apr
Aneurysmal bone cysts: treatment with direct percutaneous Ethibloc injection: long-term results.
2002 Jul-Aug
Type IV diaphragmatic hiatal hernia.
2002 Jun-Jul
Gastrocolocutaneous Fistula as a complication of peg tube placement.
2002 Mar
Iothalamate measured by capillary electrophoresis is a suitable alternative to radiolabeled inulin in renal micropuncture.
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
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:22:28 GMT 2025
Edited
by admin
on Mon Mar 31 19:22:28 GMT 2025
Record UNII
408463F217
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACIDUM AMIDOTRIZOICUM, DEHYDRATE [WHO-IP LATIN]
Preferred Name English
DIATRIZOIC ACID DIHYDRATE
Common Name English
AMIDOTRIZOIC ACID DIHYDRATE
Common Name English
AMIDOTRIZOIC ACID, DEHYDRATE [WHO-IP]
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 Mon Mar 31 19:22:28 GMT 2025 , Edited by admin on Mon Mar 31 19:22:28 GMT 2025
PRIMARY
EPA CompTox
DTXSID1048960
Created by admin on Mon Mar 31 19:22:28 GMT 2025 , Edited by admin on Mon Mar 31 19:22:28 GMT 2025
PRIMARY
CAS
50978-11-5
Created by admin on Mon Mar 31 19:22:28 GMT 2025 , Edited by admin on Mon Mar 31 19:22:28 GMT 2025
PRIMARY
EVMPD
SUB11703MIG
Created by admin on Mon Mar 31 19:22:28 GMT 2025 , Edited by admin on Mon Mar 31 19:22:28 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DIATRIZOIC ACID DIHYDRATE
Created by admin on Mon Mar 31 19:22:28 GMT 2025 , Edited by admin on Mon Mar 31 19:22:28 GMT 2025
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 Mon Mar 31 19:22:28 GMT 2025 , Edited by admin on Mon Mar 31 19:22:28 GMT 2025
PRIMARY
FDA UNII
408463F217
Created by admin on Mon Mar 31 19:22:28 GMT 2025 , Edited by admin on Mon Mar 31 19:22:28 GMT 2025
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP