Metrizoic acid

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]

Metrizoic acid
Skeletal formula of metrizoic acid
Space-filling model of the metrizoic acid molecule
Clinical data
ATC code
Identifiers
  • 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
Chemical and physical data
FormulaC12H11I3N2O4
Molar mass627.943 g·mol−1
3D model (JSmol)
  • CC(=O)NC1=C(C(=C(C(=C1I)C(=O)O)I)N(C)C(=O)C)I
  • 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

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]

Chemistry

The iodine content of metrizoate ranged from 370 mg/ml to 440 mg/ml, with osmolarity has high as 2100 mOsm/kg. The viscosity is 3.4 cP at 37 degree Celsius (human body temperature).[5]

Adverse effects

Side effects of metrizoate are: urticaria, headache, nausea, vomiting, dizziness, and hypotension. Other side effects include minor electrocardiographic changes such as tachycardia, bradycardia, and inversion of T waves.[6]

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–S161. 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: 30–37. PMID 6147958.
  3. "Metrizoic acid". DrugBank. Retrieved 3 March 2017.
  4. "Metrizoic acid - C12H11I3N2O4". PubChem. U.S. National Library of Medicine. Retrieved 3 March 2017.
  5. Patel R. "Applications in contrast imaging: contrast media basics - important considerations for the pharmacist" (PDF). Braco Diagnostics, Inc. Archived from the original (PDF) on 15 December 2022. Retrieved 15 December 2022.
  6. Steinberg I, Evans JA (September 1967). "Isopaque 440 (metrizoate); a new cardiovascular contrast medium. Experience with 100 consecutive cases". The American Journal of Roentgenology, Radium Therapy, and Nuclear Medicine. 101 (1): 229–233. doi:10.2214/ajr.101.1.229. PMID 4166780.
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