Ipodate
Title: Ipodate
CAS Registry Number: 5587-89-3
CAS Name: 3-[[(Dimethylamino)methylene]amino]-2,4,6-triiodobenzenepropanoic acid
Additional Names: 3-[(dimethylaminomethylene)amino]-2,4,6-triiodohydrocinnamic acid; 2,4,6-triiodo-3-[(dimethylaminomethylene)amino]hydrocinnamic acid; b-(3-dimethylaminomethyleneamino-2,4,6-triiodophenyl)propionic acid
Molecular Formula: C12H13I3N2O2
Molecular Weight: 597.96
Percent Composition: C 24.10%, H 2.19%, I 63.67%, N 4.68%, O 5.35%
Literature References: Prepn: Priewe, Poljak, Ber. 93, 2347 (1960). Toxicity data: J. O. Hoppe et al., J. Med. Chem. 13, 997 (1970).
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.
Melting point: mp 168-169° (dec 225°)
pKa: pK 5-5.5
 
Derivative Type: Sodium salt
CAS Registry Number: 1221-56-3
Additional Names: Sodium ipodate
Trademarks: Biloptin (Schering AG); Oragrafin Sodium (BMS)
Molecular Formula: C12H12I3N2NaO2
Molecular Weight: 619.94
Percent Composition: 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).
Melting point: mp 303-304° (decompn with evolution of iodine)
Toxicity data: LD50 in mice (mg/kg): 290 i.v.; 2570 orally (Hoppe)
 
Derivative Type: Calcium salt
CAS Registry Number: 1151-11-7
Additional Names: Calcium ipodate
Trademarks: Solu-Biloptin (Schering AG); Oragrafin Calcium (BMS)
Molecular Formula: C24H24CaI6N4O4
Molecular Weight: 1233.98
Percent Composition: 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.
Melting point: mp 298-302°
 
Derivative Type: Ethyl ester
Manufacturers' Codes: SH-617L
Molecular Formula: C14H17I3N2O2
Molecular Weight: 626.01
Percent Composition: C 26.86%, H 2.74%, I 60.82%, N 4.47%, O 5.11%
 
Therap-Cat: Diagnostic aid (radiopaque medium¾cholecystographic).
Keywords: Diagnostic Aid (Radiopaque Medium).

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