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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
Clinical data
ATC code
Identifiers
  • 3-(acetylamino)-5-[acetyl(methyl)amino]-2,4,6-triiodobenzoic acid
CAS Number
  • 1949-45-7
PubChem CID
  • 2528
DrugBank
  • DB09346
ChemSpider
  • 2433
UNII
  • CM1N99QR1M
KEGG
  • C14165
ChEBI
  • CHEBI:34847
ChEMBL
  • ChEMBL1736 Y
CompTox Dashboard (EPA)
  • DTXSID6023311
ECHA InfoCard100.016.147
Chemical and physical data
FormulaC12H11I3N2O4
Molar mass627.943 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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 Edit

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: S156-61. 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: 30–7. PMID 6147958.
  3. ^ "Metrizoic acid - DrugBank". Retrieved 3 March 2017.
  4. ^ "Metrizoic acid - C12H11I3N2O4 - PubChem". Retrieved 3 March 2017.
  5. ^ (PDF). Braco Diagnostics Inc. Archived from the original (PDF) on 15 December 2022. Retrieved 15 December 2022.
  6. ^ Steinberg, Israel; Evans, John A. (September 1967). "ISOPAQUE 440 (METRIZOATE); A NEW CARDIO-VASCULAR CONTRAST MEDIUM: EXPERIENCE WITH 100 CONSECUTIVE CASES". American Journal of Roentgenology. 101 (1): 229–233. doi:10.2214/ajr.101.1.229. ISSN 0361-803X.


metrizoic, acid, pharmaceutical, drug, that, used, iodinated, contrast, medium, imaging, uses, included, angiography, imaging, blood, vessels, heart, chambers, urography, imaging, urinary, tract, been, discontinued, least, clinical, dataatc, codev08aa02, ident. 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 acidClinical dataATC codeV08AA02 WHO IdentifiersIUPAC name 3 acetylamino 5 acetyl methyl amino 2 4 6 triiodobenzoic acidCAS Number1949 45 7PubChem CID2528DrugBankDB09346ChemSpider2433UNIICM1N99QR1MKEGGC14165ChEBICHEBI 34847ChEMBLChEMBL1736 YCompTox Dashboard EPA DTXSID6023311ECHA InfoCard100 016 147Chemical and physical dataFormulaC 12H 11I 3N 2O 4Molar mass627 943 g mol 13D model JSmol Interactive imageSMILES CC O NC1 C C C C C1I C O O I N C C O C IInChI 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 NIt 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 EditThe 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 EditSide 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 Vik Mo H Danielsen R Skinningsrud K Haider T Bjorkhaug 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 61 doi 10 1007 pl00006885 PMID 9204361 S2CID 27742637 Zachrisson BE Jagenburg R 1983 Comparison of iohexol with metrizoate in urography A single blind parallel investigation Acta Radiologica Supplementum 366 30 7 PMID 6147958 Metrizoic acid DrugBank Retrieved 3 March 2017 Metrizoic acid C12H11I3N2O4 PubChem Retrieved 3 March 2017 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 Steinberg Israel Evans John A September 1967 ISOPAQUE 440 METRIZOATE A NEW CARDIO VASCULAR CONTRAST MEDIUM EXPERIENCE WITH 100 CONSECUTIVE CASES American Journal of Roentgenology 101 1 229 233 doi 10 2214 ajr 101 1 229 ISSN 0361 803X This pharmacology related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Metrizoic acid amp oldid 1133368636, wikipedia, wiki, book, books, library,

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