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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H9I3N2O4.C7H17NO5
Molecular Weight 809.1272
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIATRIZOATE MEGLUMINE

SMILES

CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CC(=O)NC1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I

InChI

InChIKey=MIKKOBKEXMRYFQ-WZTVWXICSA-N
InChI=1S/C11H9I3N2O4.C7H17NO5/c1-3(17)15-9-6(12)5(11(19)20)7(13)10(8(9)14)16-4(2)18;1-8-2-4(10)6(12)7(13)5(11)3-9/h1-2H3,(H,15,17)(H,16,18)(H,19,20);4-13H,2-3H2,1H3/t;4-,5+,6+,7+/m.0/s1

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
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
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
An analysis of mechanisms underlying the antifibrinolytic properties of radiographic contrast agents.
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
[Evaluation of aqueous compartments of the body by integral bioimpedance spectrometry in x-ray surgical interventions in children].
2001 Jan-Feb
Glucose alters the susceptibility of mesangial cells to contrast media.
2001 Jul
Nephrotoxicants induce endothelin release and signaling in renal proximal tubules: effect on drug efflux.
2001 Jun
Effects in vivo of iohexol and diatrizoate on human plasma acetyl- and butyryl-cholinesterase activity.
2001 Mar
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
Videourodynamic and sphincter motor unit potential analyses in Parkinson's disease and multiple system atrophy.
2001 Nov
Effect of ionic and nonionic contrast media on fibrinolysis in patients undergoing angiocardiography.
2001 Oct
[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
Effect of iomeprol on rat hippocampal slice synaptic transmission: comparison with other X-ray contrast agents.
2002 Apr
Electrocardiographic effects of diagnostic imaging agents.
2002 Aug
Radiocontrast-induced renal tubular cell apoptosis: hypertonic versus oxidative stress.
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
Primary anastomosis and diverting colostomy in diffuse diverticular peritonitis.
2002 Feb
Systemic platelet effects of contrast media: implications for cardiologic research and clinical practice.
2002 Jan
Plasma exogenous creatinine clearance test in dogs: comparison with other methods and proposed limited sampling strategy.
2002 Jan-Feb
Assessment of hypothalamic-pituitary-adrenal axis function after corticosteroid therapy in inflammatory bowel disease.
2002 Jul
Local tissue toxicity in response to extravascular extravasation of magnetic resonance contrast media.
2002 Jul
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
Long-term survival of patients with stage IV hypopharyngeal cancer: impact of fundus rotation gastroplasty.
2002 May
Renal excretion of ingested gastrografin: clinical relevance in early postoperative treatment of patients who have undergone gastric surgery.
2002 May
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
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
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
DIATRIZOATE MEGLUMINE
GREEN BOOK   ORANGE BOOK   USP   VANDF  
Common Name English
MEGLUMINE AMIDOTRIZOATE
MART.   WHO-DD  
Preferred Name English
CARDIOGRAFIN
Brand Name English
DIATRIZOATE MEGLUMINE [GREEN BOOK]
Common Name English
ANGIOVIST 282
Brand Name English
DIATRIZOIC ACID MEGLUMINE SALT
MI  
Common Name English
MEGLUMINE AMIDOTRIZOATE INJECTION [JAN]
Common Name English
RENOVIST COMPONENT DIATRIZOATE MEGLUMINE
Common Name English
1-DEOXY-1-(METHYLAMINO)-D-GLUCITOL 3,5-DIACETAMIDO-2,4,6-TRIIODOBENZOATE (SALT)
Common Name English
DIATRIZOATE MEGLUMINE [VANDF]
Common Name English
GASTROVIST COMPONENT DIATRIZOATE MEGLUMINE
Common Name English
Meglumine amidotrizoate [WHO-DD]
Common Name English
GASTROGRAFIN COMPONENT DIATRIZOATE MEGLUMINE
Common Name English
MEGLUMINE AMIDOTRIZOATE INJECTION
Common Name English
SINOGRAFIN COMPONENT DIATRIZOATE MEGLUMINE
Common Name English
MEGLUMINE DIATRIZOATE
Common Name English
RENO
Brand Name English
DIATRIZOATE MEGLUMINE [ORANGE BOOK]
Common Name English
DIATRIZOATE MEGLUMINE [USP MONOGRAPH]
Common Name English
RENOGRAFIN COMPONENT DIATRIZOATE MEGLUMINE
Common Name English
DIATRIZOIC ACID MEGLUMINE SALT [MI]
Common Name English
MEGLUMINE AMIDOTRIZOATE [MART.]
Common Name English
ANGIOVIST COMPONENT DIATRIZOATE MEGLUMINE
Common Name English
RENOCAL COMPONENT DIATRIZOATE MEGLUMINE
Common Name English
UROVIST MEGLUMINE DIU/CT
Brand Name English
BENZOIC ACID, 3,5-BIS(ACETYLAMINO)-2,4,6-TRIIODO-, COMPD. WITH 1-DEOXY-1-(METHYLAMINO)-D-GLUCITOL (1:1)
Common Name English
UROVIST CYSTO PEDIATRIC
Brand Name English
MD-GASTROVIEW COMPONENT DIATRIZOATE MEGLUMINE
Common Name English
CYSTOGRAFIN
Brand Name English
HYPAQUE
Brand Name English
UROVIST CYSTO
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C28500
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
CFR 21 CFR 522.563
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
Code System Code Type Description
SMS_ID
100000091437
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
PRIMARY
CAS
131-49-7
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
PRIMARY
CHEBI
31812
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
PRIMARY
ChEMBL
CHEMBL1201220
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID20897171
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
PRIMARY
MERCK INDEX
m4263
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
205-024-7
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
PRIMARY
CHEBI
53692
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
PRIMARY
DRUG CENTRAL
4208
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
PRIMARY
FDA UNII
3X9MR4N98U
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
PRIMARY
EVMPD
SUB03119MIG
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
PRIMARY
DAILYMED
3X9MR4N98U
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
PRIMARY
DRUG BANK
DBSALT000844
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
PRIMARY
PUBCHEM
8566
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
PRIMARY
NCI_THESAURUS
C29247
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
PRIMARY
MESH
D003974
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
PRIMARY
RXCUI
3320
Created by admin on Mon Mar 31 17:52:17 GMT 2025 , Edited by admin on Mon Mar 31 17:52:17 GMT 2025
PRIMARY RxNorm