Jump to content
Wikipedia The Free Encyclopedia

Iopanoic acid

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Iopanoic acid
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
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 InfoCard 100.002.310 Edit this at Wikidata
Chemical and physical data
Formula C11H12I3NO2
Molar mass 570.935 g·mol−1
3D model (JSmol)
Melting point 162–163 °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

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

[edit ]
  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.
X-ray and CT
Iodinated,
Water soluble
Nephrotropic,
high osmolar
Nephrotropic,
low osmolar
Hepatotropic
Iodinated,
Water insoluble
Non-iodinated
MRI
Paramagnetic
Superparamagnetic
Other
Ultrasound
Receptor
(ligands)
THR Tooltip Thyroid hormone receptor
Agonists
Thyromimetics
(selective agonists)
Antagonists
Transporter
(blockers)
NIS Tooltip Sodium-iodide symporter
 
Enzyme
(inhibitors)
TPO Tooltip Thyroid peroxidase
DIO Tooltip Iodothyronine deiodinase
Others
Stub icon

This pharmacology-related article is a stub. You can help Wikipedia by expanding it.

AltStyle によって変換されたページ (->オリジナル) /