Tyropanoic acid

Tyropanoic acid and its salt sodium tyropanoate are radiocontrast agents used in cholecystography (X-ray diagnosis of gallstones). Trade names include Bilopaque, Lumopaque, Tyropaque, and Bilopac.[1] This molecule contains three heavy iodine atoms which obstruct X-rays in the same way as the calcium in bones to produce a visible image. After injection it is rapidly excreted into the bile.[2]

Tyropanoic acid
Ball-and-stick model of the tyropanoic acid molecule
Names
Preferred IUPAC name
2-[(3-Butanamido-2,4,6-triiodophenyl)methyl]butanoic acid
Other names
2-(3-Butyramido-2,4,6-triiodobenzyl)butanoic acid
2-[[2,4,6-Triiodo-3-(1-oxobutylamino)phenyl]methyl]butanoic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.043.976
EC Number
  • 248-389-8
KEGG
MeSH D014441
UNII
  • InChI=1S/C15H18I3NO3/c1-3-5-12(20)19-14-11(17)7-10(16)9(13(14)18)6-8(4-2)15(21)22/h7-8H,3-6H2,1-2H3,(H,19,20)(H,21,22) ☒N
    Key: YMOXVLQZFAUUKI-UHFFFAOYSA-N ☒N
  • CCCC(=O)NC1=C(C=C(C(=C1I)CC(CC)C(=O)O)I)I
Properties
C15H18I3NO3
Molar mass 641.02 g/mol
Pharmacology
V08AC09 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. "PubChem CID 5611".
  2. Felicetta, James V.; Green, William L.; Nelp, Wil B. (May 1980). "Inhibition of hepatic binding of thyroxine by cholecystographic agents". J. Clin. Invest. 65 (5): 1032–40. doi:10.1172/JCI109755. PMC 371433. PMID 7364937.


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