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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H9I3N2O4.C6H14N2O2
Molecular Weight 760.1011
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LYSINE AMIDOTRIZOATE

SMILES

NCCCC[C@H](N)C(O)=O.CC(=O)NC1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I

InChI

InChIKey=PGWLUYCTYOGUBP-ZSCHJXSPSA-N
InChI=1S/C11H9I3N2O4.C6H14N2O2/c1-3(17)15-9-6(12)5(11(19)20)7(13)10(8(9)14)16-4(2)18;7-4-2-1-3-5(8)6(9)10/h1-2H3,(H,15,17)(H,16,18)(H,19,20);5H,1-4,7-8H2,(H,9,10)/t;5-/m.0/s1

HIDE SMILES / InChI

Molecular Formula C6H14N2O2
Molecular Weight 146.1876
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Nephrotoxicity of high- and low-osmolar contrast media. The protective role of amlodipine in a rat model.
2000 Sep
The accordion sign at CT: report of a case of Crohn's disease with diffuse colonic involvement.
2001
Dose reduction in evacuation proctography.
2001
Spontaneous pneumomediastinum.
2001 Apr
Temporary pancreatic duct occlusion by ethibloc: cause of microcirculatory shutdown, acute inflammation, and pancreas necrosis.
2001 Apr
Laparoscopic inflatable band with Roux-en-Y gastric bypass.
2001 Aug
The role of early radiological studies after gastric bariatric surgery.
2001 Aug
An analysis of mechanisms underlying the antifibrinolytic properties of radiographic contrast agents.
2001 Dec
Preoperative bowel preparation with meglumine and sodium diatrizoate (Gastrografin): a prospective randomised comparison.
2001 Dec
Results after colectomy for colonic inertia: a sixteen-year experience.
2001 Dec
Flow-directed microcatheters for cerebral embolizations using Ethibloc--an in vitro study.
2001 Dec
Radiographic contrast media induced nephropathy: experimental observations and the protective effect of calcium channel blockers.
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
[Nephrotoxicity of X-ray contrast media].
2001 Jan-Feb
[Jejunum interposition as replacement of the pars descendens duodeni in extensive tubulovillous adenoma].
2001 Jul
Add-on angiotensin receptor blockade with maximized ACE inhibition.
2001 Jun
CT colonography without cathartic preparation: feasibility study.
2001 Jun
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
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
Videourodynamic and sphincter motor unit potential analyses in Parkinson's disease and multiple system atrophy.
2001 Nov
[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
Effect of iomeprol on rat hippocampal slice synaptic transmission: comparison with other X-ray contrast agents.
2002 Apr
Radiocontrast-induced renal tubular cell apoptosis: hypertonic versus oxidative stress.
2002 Aug
Emergency colonoscopy for distal intestinal obstruction syndrome in cystic fibrosis patients.
2002 Aug
Primary anastomosis and diverting colostomy in diffuse diverticular peritonitis.
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
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
Role of NO in endothelin-regulated drug transport in the renal proximal tubule.
2002 Mar
Do clinically relevant circulating concentrations of radiographic contrast agents inhibit platelet-dependent arterial thrombosis?
2002 Mar 1
A case of gastric duplication evaluated by gastric emptying scintigraphy.
2002 May
New strategies in nonoperative management of meconium ileus.
2002 May
Jejunum free flap in hypopharynx reconstruction: case series.
2002 May 10
Pressure-assisted micturating cystourethrography: reduction in duration of procedure and fluoroscopy time.
2002 Nov
Venous port salvage utilizing low dose tPA.
2002 Nov-Dec
Chronic renal dysfunction late after liver transplantation.
2002 Oct
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
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:29:47 GMT 2025
Edited
by admin
on Mon Mar 31 21:29:47 GMT 2025
Record UNII
O08Q0N9P6D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LYSINE AMIDOTRIZOATE
WHO-DD  
Common Name English
L-LYSINE, 3,5-BIS(ACETYLAMINO)-2,4,6-TRIIODOBENZOATE (1:1)
Preferred Name English
PERITRAST 400 COMPONENT
Common Name English
Lysine amidotrizoate [WHO-DD]
Common Name English
Code System Code Type Description
EVMPD
SUB14396MIG
Created by admin on Mon Mar 31 21:29:47 GMT 2025 , Edited by admin on Mon Mar 31 21:29:47 GMT 2025
PRIMARY
PUBCHEM
156987
Created by admin on Mon Mar 31 21:29:47 GMT 2025 , Edited by admin on Mon Mar 31 21:29:47 GMT 2025
PRIMARY
FDA UNII
O08Q0N9P6D
Created by admin on Mon Mar 31 21:29:47 GMT 2025 , Edited by admin on Mon Mar 31 21:29:47 GMT 2025
PRIMARY
SMS_ID
100000076790
Created by admin on Mon Mar 31 21:29:47 GMT 2025 , Edited by admin on Mon Mar 31 21:29:47 GMT 2025
PRIMARY
CAS
77035-55-3
Created by admin on Mon Mar 31 21:29:47 GMT 2025 , Edited by admin on Mon Mar 31 21:29:47 GMT 2025
PRIMARY
EPA CompTox
DTXSID10227842
Created by admin on Mon Mar 31 21:29:47 GMT 2025 , Edited by admin on Mon Mar 31 21:29:47 GMT 2025
PRIMARY
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