Iopanoic acid

• CAT Number: R017289
• CAS Number: 96-83-3
• Molecular Formula: C11H12I3NO2
• Molecular Weight: 570.93
• Purity: ≥95%
• Synonyms: 2-[(3-amino-2,4,6-triiodophenyl)methyl]butanoic acid
• 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)
• InChIKey: OIRFJRBSRORBCM-UHFFFAOYSA-N
• SMILES: CCC(CC1=C(C(=C(C=C1I)I)N)I)C(=O)O

Iopanoic acid is an inhibitor of 5′-Deiodinase and also an iodinated contrast medium.
The thyrotropin-releasing-hormone (TRH)-induced thyrotropin (TSH) release from the pituitary fragments is inhibited by 3,5,3′-triiodothyronin (T3) (10-7 M), by triiodothyroacetic acid (10-7 to 10-7 M), and by high concentrations of iodide (10-4 or 10-5 M). Iopanoic acid has no significant effect at the concentrations tested[2].
Iopanoic acid (IOP) administration to pregnant rats during days 18 and 19 postconception does not modify litter size (controls: 11.8±0.5 fetusesldam, Iopanoic acid-treated: 11.6±0.6 fetusesldam) or body weight at day 20 (controls: 3.27±0.12 g, Iopanoic acid-treated: 3.42±0.20 g). Iopanoic acid treatment produces a significant blockage of 5′-Deiodinase (5’D) activity in interscapular brown adipose tissue (IBAT) and brain; in contrast, liver 5’D is not modified. 3,5,3′-triiodothyronin (T3) content is similar in IBAT and slightly increased in brain and liver nuclei of Iopanoic acid-treated fetuses when compare with control fetuses at day 20 (p<0.05). However, when administered to adult rats, Iopanoic acid produces a significant reduction in IBAT nuclear T3 content and plasma T3 concentration. Iopanoic acid inhibition of IBAT 5'D activity in fetuses at term is as effective as at day 20[1].

Reference

[1]. Tuca A, et al. Inhibition of iodothyronine 5′-deiodinase by iopanoic acid does not block nuclear T3 accumulation during rat fetal development. Pediatr Res. 1994 Jan;35(1):91-5.
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[2]. Szabolcs I, et al. Effects of triiodothyronine, triiodothyroacetic acid, iopanoic acid and iodide on the thyrotropin-releasing hormone-induced thyrotropin release from superfused rat pituitary fragments. Acta Endocrinol (Copenh). 1991 Oct;125(4):427-34.
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