Chemical Properties
White Solid
Uses
Density gradient reagent for blood cell seperation. Diagnostic aid (radiopaque medium)
Definition
ChEBI: A member of the class of benzoic acids that is benzoic acid having iodo substituents at the 2-, 4- and 6-positions and acetamido substituents at the 3- and 5-positions. It is used, mainly as its N-methylglucamine and sodium salts, as an
-ray contrast medium in gastrointestinal studies, angiography, and urography.
Originator
Hypaque Sodium,Winthrop,US,1955
Manufacturing Process
3,5-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 name
Md (Mallinckrodt); Urovist Sodium (Berlex).
Therapeutic Function
Diagnostic aid (radiopaque medium)
General Description
Diatrizoate is a water-soluble, ionicmonomer. It is commercially available as the megluminesalt, sodium salt, or as fixed combinations of the two saltforms. These triiodobenzoic acid salts contain 47% organicallybound iodine.
Numerous products with various concentrations of one ortwo of the salt forms are available for various imaging procedures.Indicated uses include angiography, venography,excretory urography, retrograde cystourethrography, retrogradeor ascending pyelography, operative, T-tube, or percutaneoustranshepatic cholangiography, splenoportography,arthrography; discography, radiographic examinationof the GI tract when barium sulfate is contraindicated (i.e.,suspected perforation of the GI tract), adjunct contrast enhancementin CT of the torso (dual contrast study), and hysterosalpingography.
