Synonym
Iopanoic Acid; Telepaque; BRN 2220381; BRN-2220381; BRN2220381
IUPAC/Chemical Name
2-(3-amino-2,4,6-triiodobenzyl)butanoic acid
InChi Key
OIRFJRBSRORBCM-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=C(O)C(CC)CC1=C(I)C=C(I)C(N)=C1I
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Iopanoic acid is an inhibitor of 5'-Deiodinase and also an iodinated contrast medium.
In vitro activity:
IOP (iopanoic acid) blocked Akt phosphorylation, Rac activation, and cell migration induced by T4, but not by T3 or S1P (Figure 3, A–C, and Figure 4A). S1P stimulated phosphorylation of Akt, Erk, and Src with or without IOP (Figure 3A), indicating the viability of HUVECs after treatment with IOP. These results suggest that deiodination of T4 is a key step in T4-induced Akt phosphorylation, Rac activation, and cell migration of HUVECs.
Reference: Endocrinology. 2015 Nov;156(11):4312-24. https://pubmed.ncbi.nlm.nih.gov/26284425/
In vivo activity:
IOP (iopanoic acid) treatment reduced the amount of NG2 stain in 3 dpf larvae, as compared to controls, while 7 dpf controls and IOP-treated larvae were no longer significantly different. To further analyze a possible myelination delay in vivo, myelin fluorescent signal was followed in living larvae at the onset of myelination (2.5 dpf) and once myelin formation is ongoing (3 dpf) using mbp:egfp transgenic larvae with or without IOP treatment.
Reference: PLoS One. 2021 Aug 17;16(8):e0256207. https://pubmed.ncbi.nlm.nih.gov/34403440/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
100.0 |
175.15 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
570.94
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Aoki T, Tsunekawa K, Araki O, Ogiwara T, Nara M, Sumino H, Kimura T, Murakami M. Type 2 Iodothyronine Deiodinase Activity Is Required for Rapid Stimulation of PI3K by Thyroxine in Human Umbilical Vein Endothelial Cells. Endocrinology. 2015 Nov;156(11):4312-24. doi: 10.1210/en.2014-1988. Epub 2015 Aug 18. PMID: 26284425; PMCID: PMC4606755.
2. Farías-Serratos BM, Lazcano I, Villalobos P, Darras VM, Orozco A. Thyroid hormone deficiency during zebrafish development impairs central nervous system myelination. PLoS One. 2021 Aug 17;16(8):e0256207. doi: 10.1371/journal.pone.0256207. PMID: 34403440; PMCID: PMC8370640.
3. Kojima Y, Kondo Y, Fujishita T, Mishiro-Sato E, Kajino-Sakamoto R, Taketo MM, Aoki M. Stromal iodothyronine deiodinase 2 (DIO2) promotes the growth of intestinal tumors in ApcΔ716 mutant mice. Cancer Sci. 2019 Aug;110(8):2520-2528. doi: 10.1111/cas.14100. Epub 2019 Jul 7. PMID: 31215118; PMCID: PMC6676103.
In vitro protocol:
1. Aoki T, Tsunekawa K, Araki O, Ogiwara T, Nara M, Sumino H, Kimura T, Murakami M. Type 2 Iodothyronine Deiodinase Activity Is Required for Rapid Stimulation of PI3K by Thyroxine in Human Umbilical Vein Endothelial Cells. Endocrinology. 2015 Nov;156(11):4312-24. doi: 10.1210/en.2014-1988. Epub 2015 Aug 18. PMID: 26284425; PMCID: PMC4606755.
In vivo protocol:
1. Farías-Serratos BM, Lazcano I, Villalobos P, Darras VM, Orozco A. Thyroid hormone deficiency during zebrafish development impairs central nervous system myelination. PLoS One. 2021 Aug 17;16(8):e0256207. doi: 10.1371/journal.pone.0256207. PMID: 34403440; PMCID: PMC8370640.
2. Kojima Y, Kondo Y, Fujishita T, Mishiro-Sato E, Kajino-Sakamoto R, Taketo MM, Aoki M. Stromal iodothyronine deiodinase 2 (DIO2) promotes the growth of intestinal tumors in ApcΔ716 mutant mice. Cancer Sci. 2019 Aug;110(8):2520-2528. doi: 10.1111/cas.14100. Epub 2019 Jul 7. PMID: 31215118; PMCID: PMC6676103.
1: Way JS, Shen Y, Martinez DS. Iopanoic Acid to Treat Acute Psychiatric Crisis Associated With Thyrotoxicosis: Three Case Reports and Review of the Literature. J Clin Psychopharmacol. 2015 Dec;35(6):743-5. doi: 10.1097/JCP.0000000000000418. Review. PubMed PMID: 26474011.
2: Renko K, Hoefig CS, Hiller F, Schomburg L, Köhrle J. Identification of iopanoic acid as substrate of type 1 deiodinase by a novel nonradioactive iodide-release assay. Endocrinology. 2012 May;153(5):2506-13. doi: 10.1210/en.2011-1863. Epub 2012 Mar 20. PubMed PMID: 22434082.
3: Gallagher AE, Panciera DL. Efficacy of iopanoic acid for treatment of spontaneous hyperthyroidism in cats. J Feline Med Surg. 2011 Jun;13(6):441-7. doi: 10.1016/j.jfms.2011.02.003. Epub 2011 Apr 22. PubMed PMID: 21515081.
4: Renko K, Schäche S, Hoefig CS, Welsink T, Schwiebert C, Braun D, Becker NP, Köhrle J, Schomburg L. An Improved Nonradioactive Screening Method Identifies Genistein and Xanthohumol as Potent Inhibitors of Iodothyronine Deiodinases. Thyroid. 2015 Aug;25(8):962-8. doi: 10.1089/thy.2015.0058. Epub 2015 Jun 25. PubMed PMID: 25962824.
5: Bhumika S, Lemmens K, Vancamp P, Moons L, Darras VM. Decreased thyroid hormone signaling accelerates the reinnervation of the optic tectum following optic nerve crush in adult zebrafish. Mol Cell Neurosci. 2015 Sep;68:92-102. doi: 10.1016/j.mcn.2015.04.002. Epub 2015 Apr 22. PubMed PMID: 25913150.
6: Dersch JM, Nguyen TT, Østergaard J, Stürup S, Gammelgaard B. Selective analysis of human serum albumin based on SEC-ICP-MS after labelling with iophenoxic acid. Anal Bioanal Chem. 2015 Apr;407(10):2829-36. doi: 10.1007/s00216-015-8507-7. Epub 2015 Feb 4. PubMed PMID: 25650002.
7: Earles SM, Gerrits PM, Transue DJ. Iopanoic acid in the management of neonatal Graves' disease. J Perinatol. 2004 Feb;24(2):105-8. PubMed PMID: 14762455.
8: Ramos-Dias JC, Lengyel AM. Iopanoic acid-induced decrease of circulating T3 causes a significant increase in GH responsiveness to GH releasing hormone in thyrotoxic patients. Clin Endocrinol (Oxf). 1999 Oct;51(4):461-7. PubMed PMID: 10583313.
9: Gupta SK, Mithal A, Godbole MM. Iopanoic acid as an adjunct to carbimazole in the management of hyperthyroidism. Natl Med J India. 1992 May-Jun;5(3):108-11. Erratum in: Natl Med J India 1992 Jul-Aug;5(4):172. PubMed PMID: 1304283.
10: Tajima K, Mashita K, Shimizu M, Tarui S. Inhibitory effect of iopanoic acid on the thyrotropin-stimulated release of cyclic adenosine 3',5'-monophosphate and of 3,5,3'-triiodothyronine from perifused rat thyroids. Endocrinology. 1985 Nov;117(5):1813-7. PubMed PMID: 2412801.
