Metrizoic acid

Metrizoic acid
Clinical data
ATC code	V08AA02 (WHO) ;
Identifiers
	IUPAC name 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 ;
CompTox Dashboard (EPA)	DTXSID6023311 ;
ECHA InfoCard	100.016.147
Chemical and physical data
Formula	C12H11I3N2O4
Molar mass	627.943 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)NC1=C(C(=C(C(=C1I)C(=O)O)I)N(C)C(=O)C)I;
	InChI 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 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]

References[]

^ 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.
^ 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.

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[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.

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Clinical data


ATC code	V08AA02 (WHO)
Identifiers
IUPAC name 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 InfoCard	100.016.147
Chemical and physical data
Formula	C₁₂H₁₁I₃N₂O₄
Molar mass	627.943 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(=O)NC1=C(C(=C(C(=C1I)C(=O)O)I)N(C)C(=O)C)I
InChI 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