Eprotirome
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MedKoo CAT#: 319870

CAS#: 355129-15-6

Description: Eprotirome, also known as KB-2115, is a liver-selective thyroid hormone receptor agonist that has been shown to lower plasma LDL cholesterol concentrations in previous phase 1 and 2 studies of patients with dyslipidaemia. KB2115 lowers plasma LDL cholesterol and stimulates bile acid synthesis without cardiac effects in humans.


Price and Availability

Size Price Shipping out time Quantity
50mg USD 250 2 weeks
100mg USD 450 2 weeks
200mg USD 850 2 weeks
500mg USD 1850 2 weeks
1g USD 2950 2 weeks
2g USD 4850 2 weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-22. Prices are subject to change without notice.

Eprotirome, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 319870
Name: Eprotirome
CAS#: 355129-15-6
Chemical Formula: C18H17Br2NO5
Exact Mass: 484.9473
Molecular Weight: 487.144
Elemental Analysis: C, 44.38; H, 3.52; Br, 32.81; N, 2.88; O, 16.42


Synonym: KB-2115; KB 2115; KB2115; Eprotirome.

IUPAC/Chemical Name: 3-((3,5-Dibromo-4-(4-hydroxy-3-(1-methylethyl)phenoxy)phenyl)amino)-3-oxopropanoic acid

InChi Key: VPCSYAVXDAUHLT-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H17Br2NO5/c1-9(2)12-7-11(3-4-15(12)22)26-18-13(19)5-10(6-14(18)20)21-16(23)8-17(24)25/h3-7,9,22H,8H2,1-2H3,(H,21,23)(H,24,25)

SMILES Code: O=C(O)CC(NC1=CC(Br)=C(OC2=CC=C(O)C(C(C)C)=C2)C(Br)=C1)=O


Technical Data

Appearance:
Solid powder

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, not in water

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


Additional Information

Eprotirome can lower LDL cholesterol concentrations in patients with familial hypercholesterolaemia when added to conventional statin treatment with or without ezetimibe, but that it has the potential to induce liver injury. These findings, along with findings of cartilage damage in dogs, raise serious doubts about selective thyroid hormone mimetics as a therapeutic approach to lower LDL cholesterol concentrations.


References

1: Lammel Lindemann J, Webb P. Sobetirome: the past, present and questions about the future. Expert Opin Ther Targets. 2015 Feb;20(2):145-9. doi: 10.1517/14728222.2016.1090429. Epub 2015 Nov 13. PubMed PMID: 26565124.

2: Bonde Y, Breuer O, Lütjohann D, Sjöberg S, Angelin B, Rudling M. Thyroid hormone reduces PCSK9 and stimulates bile acid synthesis in humans. J Lipid Res. 2014 Nov;55(11):2408-15. doi: 10.1194/jlr.M051664. Epub 2014 Aug 29. PubMed PMID: 25172631; PubMed Central PMCID: PMC4617142.

3: Angelin B, Kristensen JD, Eriksson M, Carlsson B, Klein I, Olsson AG, Chester Ridgway E, Ladenson PW. Reductions in serum levels of LDL cholesterol, apolipoprotein B, triglycerides and lipoprotein(a) in hypercholesterolaemic patients treated with the liver-selective thyroid hormone receptor agonist eprotirome. J Intern Med. 2015 Mar;277(3):331-42. doi: 10.1111/joim.12261. Epub 2014 May 16. PubMed PMID: 24754313.

4: Rana R, Hegele RA. Inducing thyrotoxicosis in the liver to treat raised cholesterol. Lancet Diabetes Endocrinol. 2014 Jun;2(6):438-9. doi: 10.1016/S2213-8587(14)70026-9. Epub 2014 Feb 18. PubMed PMID: 24731675.

5: Sjouke B, Langslet G, Ceska R, Nicholls SJ, Nissen SE, Öhlander M, Ladenson PW, Olsson AG, Hovingh GK, Kastelein JJ. Eprotirome in patients with familial hypercholesterolaemia (the AKKA trial): a randomised, double-blind, placebo-controlled phase 3 study. Lancet Diabetes Endocrinol. 2014 Jun;2(6):455-63. doi: 10.1016/S2213-8587(14)70006-3. Epub 2014 Feb 18. PubMed PMID: 24731671.

6: Sharma P, Levesque T, Boilard E, Park EA. Thyroid hormone status regulates the expression of secretory phospholipases. Biochem Biophys Res Commun. 2014 Jan 31;444(1):56-62. doi: 10.1016/j.bbrc.2014.01.003. Epub 2014 Jan 16. PubMed PMID: 24440706; PubMed Central PMCID: PMC4687730.

7: Raparti G, Jain S, Ramteke K, Murthy M, Ghanghas R, Ramanand S, Ramanand J. Selective thyroid hormone receptor modulators. Indian J Endocrinol Metab. 2013 Mar;17(2):211-8. doi: 10.4103/2230-8210.109663. PubMed PMID: 23776891; PubMed Central PMCID: PMC3683193.

8: Vatner DF, Weismann D, Beddow SA, Kumashiro N, Erion DM, Liao XH, Grover GJ, Webb P, Phillips KJ, Weiss RE, Bogan JS, Baxter J, Shulman GI, Samuel VT. Thyroid hormone receptor-β agonists prevent hepatic steatosis in fat-fed rats but impair insulin sensitivity via discrete pathways. Am J Physiol Endocrinol Metab. 2013 Jul 1;305(1):E89-100. doi: 10.1152/ajpendo.00573.2012. Epub 2013 May 7. PubMed PMID: 23651850; PubMed Central PMCID: PMC3725564.

9: Unnikrishnan AG, Baruah M, Kalra S. Thyromimetics: What does the future hold? Indian J Endocrinol Metab. 2012 Dec;16(Suppl 2):S159-61. doi: 10.4103/2230-8210.104029. PubMed PMID: 23565368; PubMed Central PMCID: PMC3603016.

10: Lin JZ, Martagón AJ, Hsueh WA, Baxter JD, Gustafsson JÅ, Webb P, Phillips KJ. Thyroid hormone receptor agonists reduce serum cholesterol independent of the LDL receptor. Endocrinology. 2012 Dec;153(12):6136-44. doi: 10.1210/en.2011-2081. Epub 2012 Oct 19. PubMed PMID: 23087171; PubMed Central PMCID: PMC3512058.

11: Shoemaker TJ, Kono T, Mariash CN, Evans-Molina C. Thyroid hormone analogues for the treatment of metabolic disorders: new potential for unmet clinical needs? Endocr Pract. 2012 Nov-Dec;18(6):954-64. doi: 10.4158/EP12086.RA. Review. PubMed PMID: 22784847; PubMed Central PMCID: PMC3745011.

12: Shiohara H, Nakamura T, Kikuchi N, Ozawa T, Nagano R, Matsuzawa A, Ohnota H, Miyamoto T, Ichikawa K, Hashizume K. Discovery of novel indane derivatives as liver-selective thyroid hormone receptor β (TRβ) agonists for the treatment of dyslipidemia. Bioorg Med Chem. 2012 Jun 1;20(11):3622-34. doi: 10.1016/j.bmc.2012.03.056. Epub 2012 Apr 11. PubMed PMID: 22542282.

13: Parhofer KG. Lipoprotein(a): medical treatment options for an elusive molecule. Curr Pharm Des. 2011;17(9):871-6. Review. PubMed PMID: 21476974.

14: Olsson AG. Recent advances in preventing cardiovascular disorders by managing lipid levels. F1000 Med Rep. 2010 Sep 8;2:66. doi: 10.3410/M2-66. PubMed PMID: 21173859; PubMed Central PMCID: PMC2990461.

15: Angelin B, Rudling M. Lipid lowering with thyroid hormone and thyromimetics. Curr Opin Lipidol. 2010 Dec;21(6):499-506. doi: 10.1097/MOL.0b013e3283402e9c. Review. PubMed PMID: 20935564.

16: Webb P. Thyroid hormone receptor and lipid regulation. Curr Opin Investig Drugs. 2010 Oct;11(10):1135-42. Review. PubMed PMID: 20872316.

17: Cioffi F, Lanni A, Goglia F. Thyroid hormones, mitochondrial bioenergetics and lipid handling. Curr Opin Endocrinol Diabetes Obes. 2010 Oct;17(5):402-7. doi: 10.1097/MED.0b013e32833cf354. Review. PubMed PMID: 20625286.

18: Koch L. Lipids: Eprotirome shows promise as a novel way to target dyslipidemia. Nat Rev Endocrinol. 2010 Jul;6(7):354. doi: 10.1038/nrendo.2010.74. PubMed PMID: 20583340.

19: Ladenson PW, Kristensen JD, Ridgway EC, Olsson AG, Carlsson B, Klein I, Baxter JD, Angelin B. Use of the thyroid hormone analogue eprotirome in statin-treated dyslipidemia. N Engl J Med. 2010 Mar 11;362(10):906-16. doi: 10.1056/NEJMoa0905633. PubMed PMID: 20220185.

20: Tancevski I, Eller P, Patsch JR, Ritsch A. The resurgence of thyromimetics as lipid-modifying agents. Curr Opin Investig Drugs. 2009 Sep;10(9):912-8. Review. PubMed PMID: 19705333; PubMed Central PMCID: PMC2993058.