Iopanoic acid

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.

Iopanoic acid
Clinical data
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ATC code
Identifiers
  • (RS)-2-[(3-Amino-2,4,6-triiodophenyl)methyl]butanoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.002.310
Chemical and physical data
FormulaC11H12I3NO2
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)
  • Key:OIRFJRBSRORBCM-UHFFFAOYSA-N

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]

References
  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.
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