Chemical Properties
Diatrizoate 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%.
Originator
Hypaque Sodium,Winthrop,US,1955
Uses
Diatrizoate Sodium(737-31-5) 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.
Definition
ChEBI: 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,
ngiography, and urography.
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)
Mode of action
The 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.
