Metrizoic acid

Chemical compound From Wikipedia, the free encyclopedia

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]

ATC code
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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 Edit this at Wikidata
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
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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

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