sodium acetrizoate

Originator

Urokon Sodium ,Mallinckrodt Inc. ,US ,1950

Manufacturing Process

3-Amino-2,4,6-triiodobenzoic acid (51.5 g) was mixed with 125 ml of acetic anhydride containing 2 drops of concentrated sulfuric acid and refluxed for thirty minutes. The mixture was allowed to cool slightly, and then was poured into 600 ml of water at room temperature and stirred until crystallization was complete. The mixed anhydride of 3-acetylamino-2,4,6-triiodobenzoic acid with acetic acid thus prepared was then separated by filtration and washed with water. Without drying, the solid was suspended in 600 ml of water and hydrolyzed with a slight excess of ammonium hydroxide. It was necessary to warm the mixture slightly and stir it for about one-half hour in order to dissolve all the solid. The solution was then treated with activated carbon, filtered and precipitated with an excess of hydrochloric acid, filtered, washed and dried at 70°C. The yield was 51.5 g of 3-acetylamino-2,4,6-triiodobenzoic acid which melted at 276.6-278.2°C with decomposition when placed in the melting block at 260°C and heated at the rate of 3°C per minute. Due to decomposition, the melting point varied from about 269-280°C, depending upon the rate of heating and other conditions.
3-Acetylamino-2,4,6-triiodobenzoic acid (28 g) was dissolved in a little over 50 ml of 1 N sodium hydroxide in a round-bottom flask. The pH was adjusted to slightly over 7 and the solution was evaporated on a steam bath under reduced pressure. After the residue became solid, it was further dried overnight in a vacuum desiccator containing calcium chloride. The salt weighed 31.2 g, theory being 29.0 g, indicating that the product contains about 7% water of crystallization when dried under these conditions. The finished salt was scraped from the flask and ground.

brand name

Salpix (Ortho-McNeil).

Therapeutic Function

Diagnostic aid (radiopaque medium)

Safety Profile

Mildly toxic by intravenous route.When heated to decomposition it emits very toxic fumes ofNOx, Na2O, and HI.