Iopanoic acid

Iopanoic acid
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
ATC code	V08AC06 (WHO) ;
Identifiers
	IUPAC name (RS)-2-[(3-Amino-2,4,6-triiodophenyl)methyl]butanoic acid;
CAS Number	96-83-3;
PubChem CID	3735;
DrugBank	DB08946 ;
ChemSpider	3604;
UNII	FE9794P71J;
KEGG	D01014;
ChEMBL	ChEMBL867 ;
CompTox Dashboard (EPA)	DTXSID6023159 ;
ECHA InfoCard	100.002.310
Chemical and physical data
Formula	C11H12I3NO2
Molar mass	570.935 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	162–163 °C (324–325 °F)
	SMILES CCC(CC1=C(C(=C(C=C1I)I)N)I)C(=O)O;
	InChI 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;

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]

References

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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[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.