Metrizoic acid

Metrizoic acid

Skeletal formula of metrizoic acid
Space-filling model of the metrizoic acid molecule
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 checkY
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
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 (imaging of blood vessels and heart chambers) and urography (imaging of the urinary tract), but it has been discontinued, at least in the US.

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.

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).

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.