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Details

Stereochemistry ACHIRAL
Molecular Formula C13H13I3N2O4
Molecular Weight 641.9667
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIATRIZOATE ETHYL

SMILES

CCOC(=O)C1=C(I)C(NC(C)=O)=C(I)C(NC(C)=O)=C1I

InChI

InChIKey=OBISGMNJKBVZBT-UHFFFAOYSA-N
InChI=1S/C13H13I3N2O4/c1-4-22-13(21)7-8(14)11(17-5(2)19)10(16)12(9(7)15)18-6(3)20/h4H2,1-3H3,(H,17,19)(H,18,20)

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
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
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
[Nephrotoxicity of X-ray contrast media].
2001 Jan-Feb
[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
[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
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
[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
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
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
Systemic platelet effects of contrast media: implications for cardiologic research and clinical practice.
2002 Jan
Effects of intrathecal injection of diatrizoate on dopamine receptors.
2002 Jul
Local tissue toxicity in response to extravascular extravasation of magnetic resonance contrast media.
2002 Jul
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
[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
New strategies in nonoperative management of meconium ileus.
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
Chronic renal dysfunction late after liver transplantation.
2002 Oct
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 ETHYL
Common Name English
ETHYL DIATRIZOATE
Common Name English
ETHYL 3,5-BIS(ACETYLAMINO)-2,4,6-TRIIODOBENZOATE
Systematic Name English
WIN-8883
Code English
DIATRIZOIC ACID, ETHYL ESTER
Common Name English
3,5-DIACETAMIDO-2,4,6-TRIIODO-BENZOIC ACID ETHYL ESTER
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID70176069
Created by admin on Fri Dec 15 15:34:45 GMT 2023 , Edited by admin on Fri Dec 15 15:34:45 GMT 2023
PRIMARY
PUBCHEM
16567
Created by admin on Fri Dec 15 15:34:45 GMT 2023 , Edited by admin on Fri Dec 15 15:34:45 GMT 2023
PRIMARY
CAS
2168-75-4
Created by admin on Fri Dec 15 15:34:45 GMT 2023 , Edited by admin on Fri Dec 15 15:34:45 GMT 2023
PRIMARY
FDA UNII
85KD8I5N2U
Created by admin on Fri Dec 15 15:34:45 GMT 2023 , Edited by admin on Fri Dec 15 15:34:45 GMT 2023
PRIMARY