Diatrizoate sodium

Diatrizoate sodium Basic information
Description References
Product Name:Diatrizoate sodium
Synonyms:3,5-DIACETAMIDO-2,4,6-TRIIODOBENZOIC ACID SODIUM SALT;3,5-BIS[ACETYLAMINO]-2,4,6-TRIIODOBENZOIC ACID, SODIUM;DIATRIZOIC ACID SODIUM SALT;DIATRIZOATE SODIUM;HYPAQUE SODIUM;LABOTEST-BB LT00455174;SODIUM DIATRIZOATE;Sodium amidotrizoate
CAS:737-31-5
MF:C11H8I3N2NaO4
MW:635.9
EINECS:212-004-1
Product Categories:Organics;737-31-5
Mol File:737-31-5.mol
Diatrizoate sodium Structure
Diatrizoate sodium Chemical Properties
Melting point 261-262° (dec)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility H2O: 0.35 g/mL, slightly turbid, colorless
form White Powder
BRN 4082984
InChIInChI=1S/C11H9I3N2O4.Na/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);/q;+1/p-1
InChIKeyZEYOIOAKZLALAP-UHFFFAOYSA-M
SMILESC1(NC(=O)C)C(I)=C(C(I)=C(C([O-])=O)C=1I)NC(=O)C.[Na+]
CAS DataBase Reference737-31-5(CAS DataBase Reference)
EPA Substance Registry SystemBenzoic acid, 3,5-bis(acetylamino)-2,4,6-triiodo-, monosodium salt (737-31-5)
Safety Information
Hazard Codes Xn
Risk Statements 42/43
Safety Statements 36
WGK Germany 3
RTECS DG6125000
8-10
HS Code 29242100
Hazardous Substances Data737-31-5(Hazardous Substances Data)
ToxicityLD50 i.v. in rats: 14.7 g/kg (Langecker)
MSDS Information
ProviderLanguage
SigmaAldrich English
Diatrizoate sodium Usage And Synthesis
DescriptionDiatrizoate sodium is a contrast agent used during the X-rays test. It can be used as a diagnostic aid agent during angiography, urography and radiography. It can be applied during visualizing veins, the urinary system, gastrointestinal tract, spleen and joints as well as during the computer tomography (CT scan). It is used in cases where barium is not suitable for application such as patient being allergic to barium.
Referenceshttps://en.wikipedia.org/wiki/Diatrizoate
https://pubchem.ncbi.nlm.nih.gov/compound/Diatrizoate_sodium
Chemical PropertiesDiatrizoate sodium is a white or almost white powder that has no odor and a slightly salty taste. It dissolves easily in water but only slightly dissolves in ethanol, and it does not dissolve in ether. A 50% aqueous solution has a pH between 6.5 and 8.0. The substance has an iodine content of approximately 59.9%.
OriginatorHypaque Sodium,Winthrop,US,1955
UsesDiatrizoate Sodium is an iodinated radiopaque X-ray contrast medium used in radiology for diagnostic purposes. It is also used as a density gradient reagent to separate blood cells.
DefinitionChEBI: Sodium amidotrizoate is the sodium salt of a benzoic acid having iodo substituents at the 2-, 4- and 6-positions and acetamido substituents at the 3- and 5-positions. It is used, often as a mixture with the meglumine salt, as an X-ray contrast medium in gastrointestinal studies, angiography, and urography. It has a role as a radioopaque medium. It is an organoiodine compound and an organic sodium salt. It contains an amidotrizoic acid anion.
Manufacturing Process3,5-Dinitrobenzoic acid (15.9 g) was dissolved in an equivalent amount of sodium hydroxide solution, and the solution was diluted to 310 ml with water. The solution was refluxed with Raney nickel for fifteen minutes, filtered, and the filtrate was hydrogenated at elevated pressure using platinum oxide catalyst. After the amount of hydrogen calculated to reduce both nitro groups had been absorbed, the mixture was filtered, and the filtrate was acidified with an equal volume of concentrated hydrochloric acid. Iodine monochloride (17 ml) in 100 ml of 6N HCl was then added with stirring. The reaction mixture was allowed to stand for two and one-half hours at room temperature, then diluted with an equal amount of water with vigorous stirring, and the solid material was collected by filtration and recrystallized
from dilute methanol, giving 18.5 g of 3,5-diamino-2,4,6-triiodobenzoic acid, MP about 135°C with decomposition. The 18.5 g of 3,5-diamino-2,4,6- triiodobenzoic acid was suspended in 150 ml of acetic anhydride containing 5 drops of 70% perchloric acid, and the mixture was heated on a steam bath for three and one-half hours. The reaction mixture was poured into 300 ml of ice water, and then heated on a steam bath until crystallization took place. The solid material was collected by filtration, dissolvedin dilute sodium hydroxide solution, filtered, and hydrochloric acid was added to the filtrate to reprecipitate the acid product. The latter was again dissolved in sodium hydroxide and reprecipitated with acid, giving 9 g of 3,5-diacetamido-2,4,6- triiodobenzoic acid, MP above 250°C.
The acid may be used as the sodium salt or as the meglumate.

Brand nameMd (Mallinckrodt); Urovist Sodium (Berlex).
Therapeutic FunctionDiagnostic aid (radiopaque medium)
Mode of actionThe mechanism of action of Diatrizoate sodium is that it can block the X-rays so that the body structure containing iodine to be delineated in contrast to those structures that free of iodine, further allowing the visualization of those related areas.
Diatrizoate sodium Preparation Products And Raw materials
Raw materialsIodine monochloride-->Sodium hydroxide-->Hydrogen-->2-Chloro-3,5-dinitrobenzoic acid-->DIATRIZOIC ACID
Sodium benzoate Diatrizoic Acid Dihydrate Sodium acetate sodium Sodium chloride Sodium percarbonate Diatrizoate sodium Sodium D-pantothenate Sodium silicate Sodium formate Sodium citrate Sodium chlorate Sodium bicarbonate Sodium hydroxide Sodium chlorite Sodium gluconate Trisodium citrate dihydrate Sodium carbonate

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