Iopanoic acid

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Iopanoic acid
Iopanoic acid.png
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
ATC code
  • (RS)-2-[(3-Amino-2,4,6-triiodophenyl)methyl]butanoic acid
CAS Number
PubChem CID
CompTox Dashboard (EPA)
ECHA InfoCard100.002.310 Edit this at Wikidata
Chemical and physical data
Molar mass570.935 g·mol−1
3D model (JSmol)
Melting point162–163 °C (324–325 °F)
  • CCC(CC1=C(C(=C(C=C1I)I)N)I)C(=O)O
  • InChI=1S/C11H12I3NO2/c1-2-5(11(16)17)3-6-7(12)4-8(13)10(15)9(6)14/h4-5H,2-3,15H2,1H3,(H,16,17)

Iopanoic acid is an iodine-containing radiocontrast medium used in cholecystography. Both iopanoic acid and ipodate sodium are potent inhibitors of thyroid hormone release from thyroid gland, as well as of peripheral conversion of thyroxine (T4) to triiodothyronine (T3). These compounds inhibit 5'deiodinase (5'DID-1 and 5'DID-2) enzymes, which catalyse T4-T3 conversion in the thyroid cell, liver, kidney, skeletal muscle, heart, brain, pituitary. This accounts for the dramatic improvement in both subjective and objective symptoms of hyperthyroidism, particularly when they are used as an adjunctive therapy with thioamides (propylthiouracil, carbimazole). They can be used in the treatment of patients with severe thyrotoxicosis (thyroid storm) and significant morbidity (e.g., myocardial infarction, or stroke) for rapid control of elevated plasma triiodothyronine concentrations. The use of iopanoic acid for treatment of thyrotoxicosis has been discontinued in the United States.

In addition to inhibiting deiodinase enzymes, iopanoic acid is also a substrate of type 1 deiodinase. Iopanoic acid underwent monodeiodination in the presence of type 1 deiodinase in a microsomal mouse liver preparation.[1]


  1. ^ Renko K, Hoefig CS, Hiller F, Schomburg L, Köhrle J (May 2012). "Identification of iopanoic acid as substrate of type 1 deiodinase by a novel nonradioactive iodide-release assay". Endocrinology. 153 (5): 2506–13. doi:10.1210/en.2011-1863. PMID 22434082.