Metrizoic acid

Last updated
Metrizoic acid
Metrizoic acid.png
Metrizoic-acid-3D-spacefill.png
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 InfoCard 100.016.147 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C12H11I3N2O4
Molar mass 627.943 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

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 its approval for use has been discontinued in the United States by the FDA. [3]

Contents

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 - C12H11I3N2O4". PubChem. U.S. National Library of Medicine. Retrieved 20 December 2024.
  4. ↑ "Metrizoic acid - C12H11I3N2O4". PubChem. U.S. National Library of Medicine. Retrieved 20 December 2024.
  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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