Eprotirome | CAS#355129-15-6 | thyroid hormone receptor agonist

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

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.

Chemical Structure

Eprotirome

CAS# 355129-15-6

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319870
Name: Eprotirome
CAS#: 355129-15-6
Chemical Formula: C18H17Br2NO5
Exact Mass: 484.95
Molecular Weight: 487.144
Elemental Analysis: C, 44.38; H, 3.52; Br, 32.81; N, 2.88; O, 16.42

Price and Availability

Size	Price	Availability
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
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. 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

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.

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.

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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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