5071. Ipodate

Nomenclature

CAS number: 5587-89-3
3-[[(Dimethylamino)methylene]amino]-2,4,6-triiodobenzenepropanoic acid; 3-[(dimethylaminomethylene)amino]-2,4,6-triiodohydrocinnamic acid; 2,4,6-triiodo-3-[(dimethylaminomethylene)amino]hydrocinnamic acid; β-(3-dimethylaminomethyleneamino-2,4,6-triiodophenyl)propionic acid.
C12H13I3N2O2; mol wt 597.96.
C 24.10%, H 2.19%, I 63.67%, N 4.68%, O 5.35%.

Description and references

Prepn: Priewe, Poljak, Ber. 93, 2347 (1960). Toxicity data: J. O. Hoppe et al., J. Med. Chem. 13, 997 (1970).

Chemical structure

Properties

Crystals, mp 168-169° (dec 225°). Practically insol in water. Very sol in methanol, ethanol, chloroform, acetone, dil sulfuric acid. Estimated pK 5-5.5.

Derivative

Sodium salt.

Nomenclature

CAS number: 1221-56-3
Sodium ipodate; Biloptin (Schering AG); Oragrafin Sodium (BMS).
C12H12I3N2NaO2; mol wt 619.94.
C 23.25%, H 1.95%, I 61.41%, N 4.52%, Na 3.71%, O 5.16%.

Properties

Bitter leaflets from water + acetone, mp 303-304° (decompn with evolution of iodine). Very freely sol in water; freely sol in methanol, ethanol. Practically insol in acetone, ether. Soly in DMF and DMSO about 33 g/100 ml; in dimethylacetamide about 66 g/100 ml. LD50 in mice (mg/kg): 290 i.v.; 2570 orally (Hoppe).

Derivative

Calcium salt.

Nomenclature

CAS number: 1151-11-7
Calcium ipodate; Solu-Biloptin (Schering AG); Oragrafin Calcium (BMS).
C24H24CaI6N4O4; mol wt 1233.98.
C 23.36%, H 1.96%, Ca 3.25%, I 61.70%, N 4.54%, O 5.19%.

Properties

Crystals, mp 298-302°. Soly in water at 20°: 0.1%. Sol in chloroform, dimethylformamide, hot propylene glycol.

Derivative

Ethyl ester.

Nomenclature

SH-617L.
C14H17I3N2O2; mol wt 626.01.
C 26.86%, H 2.74%, I 60.82%, N 4.47%, O 5.11%.

Therapeutic Category

Diagnostic aid (radiopaque medium—cholecystographic).

Keywords

Diagnostic Aid (Radiopaque Medium)