Sobetirome
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MedKoo CAT#: 319857

CAS#: 211110-63-3

Description: Sobetirome, also known as GC-1 and QRX-431, is a thyroid hormone receptor β (TRβ) agonist. Sobetirome inhibits proliferation but induces differentiation and TRβ mRNA expression in mouse and rat osteoblast-like cells. Sobetirome selectively binds to and activates TRβ over TRα and this receptor selectivity led to the hypothesis that sobetirome would lower cholesterol through activation of liver TRβ without stimulating cardiac function through TRα activation in the heart. The tissue selective thyromimetic properties of sobetirome have been demonstrated in numerous animal models, which led to its clinical development as a novel cholesterol-lowering agent.

Chemical Structure

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Sobetirome
CAS# 211110-63-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319857
Name: Sobetirome
CAS#: 211110-63-3
Chemical Formula: C20H24O4
Exact Mass: 328.17
Molecular Weight: 328.410
Elemental Analysis: C, 73.15; H, 7.37; O, 19.49

Price and Availability

Size Price Availability Quantity
5mg USD 315 2 weeks
25mg USD 800 2 weeks
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Synonym: GC-1; GC1; GC 1; QRX-431; QRX 431; QRX431; Sobetirome

IUPAC/Chemical Name: 2-(4-(4-hydroxy-3-isopropylbenzyl)-3,5-dimethylphenoxy)acetic acid

InChi Key: QNAZTOHXCZPOSA-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H24O4/c1-12(2)17-9-15(5-6-19(17)21)10-18-13(3)7-16(8-14(18)4)24-11-20(22)23/h5-9,12,21H,10-11H2,1-4H3,(H,22,23)

SMILES Code: O=C(O)COC1=CC(C)=C(CC2=CC=C(O)C(C(C)C)=C2)C(C)=C1

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:

Product Data:
Product Data
Instruction:
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Biological target: Sobetirome is a thyroid hormone receptor β (TRβ)-specific agonist which bind selectively to TRβ-1 with an EC50 of 0.16 μM.
In vitro activity: Sobetirome may be a promising thyromimetic compound targeting an important neuropathological hallmark of multiple system atrophy (MSA), a rare and rapidly progressive atypical Parkinsonian disorder. Sobetirome enhanced the production of myelin-related proteins in both normal and MSA-related cells. It also increased myelin length and quantity in oligodendrocytes. Reference: Eur J Neurosci. 2024 Jan;59(2):308-315. https://pubmed.ncbi.nlm.nih.gov/38086536/
In vivo activity: Specific activation of TRβ by sobetirome impeded tumor growth and restored gene expression in colorectal cancer (CRC) tumors in mice. Tumor growth analysis showed that sobetirome profoundly inhibited tumor growth and 18FDG uptake. TRβ expression was decreased in CRC tumors; however, it was upregulated by sobetirome administration. Reference: J Recept Signal Transduct Res. 2022 Oct;42(5):495-502. https://pubmed.ncbi.nlm.nih.gov/35473566/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 100.0 304.51

Preparing Stock Solutions

The following data is based on the product molecular weight 328.41 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. Mészáros L, Himmler M, Schneider Y, Arnold P, Dörje F, Schubert DW, Winkler J. Sobetirome rescues α-synuclein-mediated demyelination in an in vitro model of multiple system atrophy. Eur J Neurosci. 2024 Jan;59(2):308-315. doi: 10.1111/ejn.16215. Epub 2023 Dec 12. PMID: 38086536. 2. Gu HJ, Ahn JS, Ahn GJ, Shin SH, Ryu BY. Restoration of PM2.5-induced spermatogonia GC-1 cellular damage by parthenolide via suppression of autophagy and inflammation: An in vitro study. Toxicology. 2023 Nov;499:153651. doi: 10.1016/j.tox.2023.153651. Epub 2023 Oct 17. PMID: 37858773. 3. Bohlen JF, Cleary CM, Das D, Sripathy SR, Sadowski N, Shim G, Kenney RF, Buchler IP, Banerji T, Scanlan TS, Mulkey DK, Maher BJ. Promyelinating drugs promote functional recovery in an autism spectrum disorder mouse model of Pitt-Hopkins syndrome. Brain. 2023 Aug 1;146(8):3331-3346. doi: 10.1093/brain/awad057. PMID: 37068912; PMCID: PMC10393406. 4. Pourvali K, Shimi G, Ghorbani A, Shakery A, Shirazi FH, Zand H. Selective thyroid hormone receptor beta agonist, GC-1, is capable to reduce growth of colorectal tumor in syngeneic mouse models. J Recept Signal Transduct Res. 2022 Oct;42(5):495-502. doi: 10.1080/10799893.2022.2032748. Epub 2022 Apr 27. PMID: 35473566.
In vitro protocol: 1. Mészáros L, Himmler M, Schneider Y, Arnold P, Dörje F, Schubert DW, Winkler J. Sobetirome rescues α-synuclein-mediated demyelination in an in vitro model of multiple system atrophy. Eur J Neurosci. 2024 Jan;59(2):308-315. doi: 10.1111/ejn.16215. Epub 2023 Dec 12. PMID: 38086536. 2. Gu HJ, Ahn JS, Ahn GJ, Shin SH, Ryu BY. Restoration of PM2.5-induced spermatogonia GC-1 cellular damage by parthenolide via suppression of autophagy and inflammation: An in vitro study. Toxicology. 2023 Nov;499:153651. doi: 10.1016/j.tox.2023.153651. Epub 2023 Oct 17. PMID: 37858773.
In vivo protocol: 1. Bohlen JF, Cleary CM, Das D, Sripathy SR, Sadowski N, Shim G, Kenney RF, Buchler IP, Banerji T, Scanlan TS, Mulkey DK, Maher BJ. Promyelinating drugs promote functional recovery in an autism spectrum disorder mouse model of Pitt-Hopkins syndrome. Brain. 2023 Aug 1;146(8):3331-3346. doi: 10.1093/brain/awad057. PMID: 37068912; PMCID: PMC10393406. 2. Pourvali K, Shimi G, Ghorbani A, Shakery A, Shirazi FH, Zand H. Selective thyroid hormone receptor beta agonist, GC-1, is capable to reduce growth of colorectal tumor in syngeneic mouse models. J Recept Signal Transduct Res. 2022 Oct;42(5):495-502. doi: 10.1080/10799893.2022.2032748. Epub 2022 Apr 27. PMID: 35473566.

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21: Beber EH, Capelo LP, Fonseca TL, Costa CC, Lotfi CF, Scanlan TS, Gouveia CH. The thyroid hormone receptor (TR) beta-selective agonist GC-1 inhibits proliferation but induces differentiation and TR beta mRNA expression in mouse and rat osteoblast-like cells. Calcif Tissue Int. 2009 Apr;84(4):324-33. doi: 10.1007/s00223-009-9230-1. Epub 2009 Mar 11. PubMed PMID: 19280098.

22: Cable EE, Finn PD, Stebbins JW, Hou J, Ito BR, van Poelje PD, Linemeyer DL, Erion MD. Reduction of hepatic steatosis in rats and mice after treatment with a liver-targeted thyroid hormone receptor agonist. Hepatology. 2009 Feb;49(2):407-17. doi: 10.1002/hep.22572. PubMed PMID: 19072834.

23: Denver RJ, Hu F, Scanlan TS, Furlow JD. Thyroid hormone receptor subtype specificity for hormone-dependent neurogenesis in Xenopus laevis. Dev Biol. 2009 Feb 1;326(1):155-68. doi: 10.1016/j.ydbio.2008.11.005. Epub 2008 Nov 20. PubMed PMID: 19056375.

24: Scanlan TS. Sobetirome: a case history of bench-to-clinic drug discovery and development. Heart Fail Rev. 2010 Mar;15(2):177-82. doi: 10.1007/s10741-008-9122-x. Epub 2008 Nov 11. Review. PubMed PMID: 19002578.

25: Josseaume C, Lorcy Y. [Thyroid hormone analogs: an important biological supply and new therapeutic possibilities]. Ann Endocrinol (Paris). 2008 Sep;69 Suppl 1:S33-6. doi: 10.1016/S0003-4266(08)73966-0. French. PubMed PMID: 18954857.

26: Perra A, Simbula G, Simbula M, Pibiri M, Kowalik MA, Sulas P, Cocco MT, Ledda-Columbano GM, Columbano A. Thyroid hormone (T3) and TRbeta agonist GC-1 inhibit/reverse nonalcoholic fatty liver in rats. FASEB J. 2008 Aug;22(8):2981-9. doi: 10.1096/fj.08-108464. Epub 2008 Apr 23. PubMed PMID: 18434432.

27: Scanlan TS. Thyroid hormone analogues: useful biological probes and potential therapeutic agents. Ann Endocrinol (Paris). 2008 Apr;69(2):157-9. doi: 10.1016/j.ando.2008.02.017. Epub 2008 Apr 21. Review. PubMed PMID: 18430408.

28: Bleicher L, Aparicio R, Nunes FM, Martinez L, Gomes Dias SM, Figueira AC, Santos MA, Venturelli WH, da Silva R, Donate PM, Neves FA, Simeoni LA, Baxter JD, Webb P, Skaf MS, Polikarpov I. Structural basis of GC-1 selectivity for thyroid hormone receptor isoforms. BMC Struct Biol. 2008 Jan 31;8:8. doi: 10.1186/1472-6807-8-8. PubMed PMID: 18237438; PubMed Central PMCID: PMC2275733.

29: Manzano J, Cuadrado M, Morte B, Bernal J. Influence of thyroid hormone and thyroid hormone receptors in the generation of cerebellar gamma-aminobutyric acid-ergic interneurons from precursor cells. Endocrinology. 2007 Dec;148(12):5746-51. Epub 2007 Aug 30. PubMed PMID: 17761765.

30: Villicev CM, Freitas FR, Aoki MS, Taffarel C, Scanlan TS, Moriscot AS, Ribeiro MO, Bianco AC, Gouveia CH. Thyroid hormone receptor beta-specific agonist GC-1 increases energy expenditure and prevents fat-mass accumulation in rats. J Endocrinol. 2007 Apr;193(1):21-9. PubMed PMID: 17400799.

31: Chapo J, Peng Y, Pitts KR. A phosphorimager-based filter binding thyroid hormone receptor competition assay for chemical screening. J Pharmacol Toxicol Methods. 2007 Jul-Aug;56(1):28-33. Epub 2006 Dec 22. PubMed PMID: 17276701.

32: Columbano A, Pibiri M, Deidda M, Cossu C, Scanlan TS, Chiellini G, Muntoni S, Ledda-Columbano GM. The thyroid hormone receptor-beta agonist GC-1 induces cell proliferation in rat liver and pancreas. Endocrinology. 2006 Jul;147(7):3211-8. Epub 2006 Mar 30. PubMed PMID: 16574785.

33: Mousa SA, O'Connor LJ, Bergh JJ, Davis FB, Scanlan TS, Davis PJ. The proangiogenic action of thyroid hormone analogue GC-1 is initiated at an integrin. J Cardiovasc Pharmacol. 2005 Sep;46(3):356-60. PubMed PMID: 16116342.

34: Gloss B, Giannocco G, Swanson EA, Moriscot AS, Chiellini G, Scanlan T, Baxter JD, Dillmann WH. Different configurations of specific thyroid hormone response elements mediate opposite effects of thyroid hormone and GC-1 on gene expression. Endocrinology. 2005 Nov;146(11):4926-33. Epub 2005 Aug 4. PubMed PMID: 16081636.

35: Opitz R, Lutz I, Nguyen NH, Scanlan TS, Kloas W. Analysis of thyroid hormone receptor betaA mRNA expression in Xenopus laevis tadpoles as a means to detect agonism and antagonism of thyroid hormone action. Toxicol Appl Pharmacol. 2006 Apr 1;212(1):1-13. Epub 2005 Jul 22. PubMed PMID: 16040072.

36: Johansson L, Rudling M, Scanlan TS, Lundåsen T, Webb P, Baxter J, Angelin B, Parini P. Selective thyroid receptor modulation by GC-1 reduces serum lipids and stimulates steps of reverse cholesterol transport in euthyroid mice. Proc Natl Acad Sci U S A. 2005 Jul 19;102(29):10297-302. Epub 2005 Jul 8. PubMed PMID: 16006512; PubMed Central PMCID: PMC1177400.

37: Shi Y, Ye H, Link KH, Putnam MC, Hubner I, Dowdell S, Koh JT. Mutant-selective thyromimetics for the chemical rescue of thyroid hormone receptor mutants associated with resistance to thyroid hormone. Biochemistry. 2005 Mar 29;44(12):4612-26. PubMed PMID: 15779888.

38: Freitas FR, Capelo LP, O'Shea PJ, Jorgetti V, Moriscot AS, Scanlan TS, Williams GR, Zorn TM, Gouveia CH. The thyroid hormone receptor beta-specific agonist GC-1 selectively affects the bone development of hypothyroid rats. J Bone Miner Res. 2005 Feb;20(2):294-304. Epub 2004 Nov 22. PubMed PMID: 15647824.

39: Mishra MK, Wilson FE, Scanlan TS, Chiellini G. Thyroid hormone-dependent seasonality in American tree sparrows (Spizella arborea): effects of GC-1, a thyroid receptor beta-selective agonist, and of iopanoic acid, a deiodinase inhibitor. J Comp Physiol B. 2004 Aug;174(6):471-9. Epub 2004 Jul 2. PubMed PMID: 15235810.

40: Baxter JD, Webb P, Grover G, Scanlan TS. Selective activation of thyroid hormone signaling pathways by GC-1: a new approach to controlling cholesterol and body weight. Trends Endocrinol Metab. 2004 May-Jun;15(4):154-7. Review. PubMed PMID: 15109613.