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MedKoo Cat#: 319870 | Name: Eprotirome
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Eprotirome
Eprotirome
CAS#355129-15-6

Theoretical Analysis

MedKoo Cat#: 319870

Name: Eprotirome

CAS#: 355129-15-6

Chemical Formula: C18H17Br2NO5

Exact Mass: 484.9473

Molecular Weight: 487.14

Elemental Analysis: C, 44.38; H, 3.52; Br, 32.81; N, 2.88; O, 16.42

Price and Availability

Size Price Availability Quantity
50mg USD 250.00 2 Weeks
100mg USD 450.00 2 Weeks
200mg USD 850.00 2 Weeks
500mg USD 1,850.00 2 Weeks
1g USD 2,950.00 2 Weeks
2g USD 4,850.00 2 Weeks
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Related CAS #
No Data
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
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
More Info
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.
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Eprotirome (KB2115) is a liver-selective thyroid hormone receptor (TR) agonist.
In vitro activity:
Quantitative hair cycle histomorphometry showed that KB2115 treatment significantly increased the percentage of anagen HFs compared with vehicle controls (Figure 1a). Reference: J Invest Dermatol. 2016 Aug;136(8):1711-1714. https://pubmed.ncbi.nlm.nih.gov/27066887/
In vivo activity:
As shown in Figure 1F, 1-week treatment with IP injections of KB2115 (25 and 12.5 μg/100 g b.w.) induced a strong rat hepatocyte proliferation, as assessed by BrdU incorporation. Indeed, LI displayed a five- to sixfold increase compared to controls. Notably, the extent of hepatocyte proliferation elicited by KB2115 was similar to that observed by repeated injections of T3. Reference: Gene Expr. 2017; 17(3): 207–218. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5896737/
Solvent mg/mL mM
Solubility
DMSO 84.0 172.43
DMF 30.0 61.58
Ethanol 63.5 130.35
Ethanol:PBS (pH 7.2) (1:1) 0.5 1.03
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 487.14 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.

Recalculate based on batch purity %
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. Oláh A, Gherardini J, Bertolini M, Chéret J, Ponce L, Kloepper J, Bíró T, Soeberdt M, Abels C, Paus R. The Thyroid Hormone Analogue KB2115 (Eprotirome) Prolongs Human Hair Growth (Anagen) Ex Vivo. J Invest Dermatol. 2016 Aug;136(8):1711-1714. doi: 10.1016/j.jid.2016.03.033. Epub 2016 Apr 8. PMID: 27066887. 2. Szydlowska M, Pibiri M, Perra A, Puliga E, Mattu S, Ledda-Columbano GM, Columbano A, Leoni VP. The Thyromimetic KB2115 (Eprotirome) Induces Rat Hepatocyte Proliferation. Gene Expr. 2017 Jul 7;17(3):207-218. doi: 10.3727/105221617X695438. Epub 2017 Apr 13. PMID: 28409553; PMCID: PMC5896737.
In vitro protocol:
1. Oláh A, Gherardini J, Bertolini M, Chéret J, Ponce L, Kloepper J, Bíró T, Soeberdt M, Abels C, Paus R. The Thyroid Hormone Analogue KB2115 (Eprotirome) Prolongs Human Hair Growth (Anagen) Ex Vivo. J Invest Dermatol. 2016 Aug;136(8):1711-1714. doi: 10.1016/j.jid.2016.03.033. Epub 2016 Apr 8. PMID: 27066887.
In vivo protocol:
1. Szydlowska M, Pibiri M, Perra A, Puliga E, Mattu S, Ledda-Columbano GM, Columbano A, Leoni VP. The Thyromimetic KB2115 (Eprotirome) Induces Rat Hepatocyte Proliferation. Gene Expr. 2017 Jul 7;17(3):207-218. doi: 10.3727/105221617X695438. Epub 2017 Apr 13. PMID: 28409553; PMCID: PMC5896737.
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.

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