Chemistry:Metrizoic acid

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Short description: Chemical compound
Metrizoic acid
Skeletal formula of metrizoic acid
Space-filling model of the metrizoic acid molecule
Clinical data
ATC code
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC12H11I3N2O4
Molar mass627.943 g·mol−1
3D model (JSmol)

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]

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. "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. 1997. doi:10.1007/pl00006885. PMID 9204361. 
  2. "Comparison of iohexol with metrizoate in urography. A single blind parallel investigation". Acta Radiologica. Supplementum 366: 30–37. 1983. PMID 6147958. 
  3. "Metrizoic acid". DrugBank. https://www.drugbank.ca/drugs/DB09346. 
  4. "Metrizoic acid - C12H11I3N2O4". PubChem. U.S. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/Metrizoic_acid#section=Top. 
  5. "Applications in contrast imaging: contrast media basics - important considerations for the pharmacist". Braco Diagnostics, Inc.. https://www.appliedradiology.org/courses/4559/Interactive/Pharma_Mono_vMDFDECE_rev.pdf. 
  6. "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. September 1967. doi:10.2214/ajr.101.1.229. PMID 4166780.