The optical resolution of 2,3-diaminopropionic acid.
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Biomedical subjects
Publications and source records attributed to E Felder.
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A series of 5-hydroxyacylamino-2,4,6-triiodo-N,N'-hydroxy-alkyl-isophtalamides was prepared in order to study the structural requirements for high water solubility and low toxicity. Among the amides substituted by 2-hydroxyethyl; 2,3-dihydroxypropyl; 1,3-dihydroxypropyl-; and 1,1-dihydroxy-methyl-2-oxyethyl- groups, the highest water solubility was obtained with the 1,3-dihydroxypropyl- group. Neither optical resolution of the 2,3-dihydroxypropyl moiety nor amide formation with two different amines improved the water solubility. The optimal solubility was obtained with S-5-alpha-hydroxypropionylamino-2,4,6-triiodoisophtalic acid di-(1,3-dihydroxy-2-propylamide), iopamidol. Iopamidol forms anhydrous and monohydrate crystals, characterized by differential thermal analyses, x-ray diffraction patterns, and solubility patterns. A method for enzymatic assay of the optical purity of iopamidol with lactodehydrogenase is described as well as partition coefficient, ionization constant of the oxyacylamido-group, critical micelle formation, surface tension, and osmolarity.
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Iopamidol was rapidly eliminated from the central nervous system of dogs (greater than 90% in 24 hours). In rabbits, renal excretion involved tubular mechanisms at low blood levels, and predominant glomerular filtration at higher levels. Injection of iopamidol into the right atriums of rabbits produced hemodynamic effects similar to those of other contrast media, but less severe. The effect of iopamidol on peripheral vascular resistance was significantly lower than that of metrizamide. Iopamidol was found useful in clinical neuroradiology and angiography.