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Metrizoic acid

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.016.147Edit 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

Metrizoic acid is apharmaceutical drug that was used as aniodinated contrast medium forX-ray imaging. Its uses includedangiography[1] (imaging of blood vessels andheart chambers) andurography[2] (imaging of theurinary tract), but it has been discontinued, at least in the US.[3]

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

Chemistry

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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

[edit]

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

[edit]
  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. Retrieved3 March 2017.
  4. ^"Metrizoic acid - C12H11I3N2O4".PubChem. U.S. National Library of Medicine. Retrieved3 March 2017.
  5. ^Patel R."Applications in contrast imaging: contrast media basics - important considerations for the pharmacist"(PDF). Braco Diagnostics, Inc. Archived fromthe original(PDF) on 15 December 2022. Retrieved15 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.
X-ray and CT
Iodinated,
Water soluble
Nephrotropic,
high osmolar
Nephrotropic,
low osmolar
Hepatotropic
Iodinated,
Water insoluble
Non-iodinated
MRI
Paramagnetic
Superparamagnetic
Other
Ultrasound
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