Metrizoic acid

Metrizoic acid
Skeletal formula of metrizoic acid
Space-filling model of the metrizoic acid molecule
Clinical data
ATC code
Identifiers
IUPAC name
  • 3-(acetylamino)-5-[acetyl(methyl)amino]-2,4,6-triiodobenzoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.016.147
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Chemical and physical data
FormulaC12H11I3N2O4
Molar mass627.943 g·mol−1
3D model (JSmol)
SMILES
  • CC(=O)NC1=C(C(=C(C(=C1I)C(=O)O)I)N(C)C(=O)C)I
InChI
  • InChI=1S/C12H11I3N2O4/c1-4(18)16-10-7(13)6(12(20)21)8(14)11(9(10)15)17(3)5(2)19/h1-3H3,(H,16,18)(H,20,21)
  • Key:GGGDNPWHMNJRFN-UHFFFAOYSA-N

Metrizoic acid is a pharmaceutical drug that was used as an iodinated contrast medium for X-ray imaging. Its uses included angiography[1] (imaging of blood vessels and heart chambers) and urography[2] (imaging of the urinary tract), but it has been discontinued, at least in the US.[3]

It was used in form of its salts, metrizoates. Due to its high osmolality, metrizoic acid had a risk of inducing allergic reactions higher than that of lower osmolar contrast media.[4]

References

  1. ↑ Vik-Mo H, Danielsen R, Skinningsrud K, Haider T, Bjørkhaug A (1997). "Cardiovascular and electrocardiographic effects of iopentol in left ventricular angiography. Comparison of the low-osmolar, non-ionic iopentol (Imagopaque 350) and the hyper-osmolar, ionic metrizoate meglumine-Na-Ca (Isopaque Coronar 370) in patients with coronary heart disease". European Radiology. 7 Suppl 4: S156-61. doi:10.1007/pl00006885. PMID 9204361. S2CID 27742637.
  2. ↑ Zachrisson BE, Jagenburg R (1983). "Comparison of iohexol with metrizoate in urography. A single blind parallel investigation". Acta Radiologica. Supplementum. 366: 30–7. PMID 6147958.
  3. ↑ "Metrizoic acid - DrugBank". Retrieved 3 March 2017.
  4. ↑ "Metrizoic acid - C12H11I3N2O4 - PubChem". Retrieved 3 March 2017.
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