GSK5182
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MedKoo CAT#: 531877

CAS#: 877387-37-6 (free base)

Description: GSK5182 is a specific inverse agonist for estrogen-related receptor γ.


Chemical Structure

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GSK5182
CAS# 877387-37-6 (free base)

Theoretical Analysis

MedKoo Cat#: 531877
Name: GSK5182
CAS#: 877387-37-6 (free base)
Chemical Formula: C27H31NO3
Exact Mass: 417.2304
Molecular Weight: 417.55
Elemental Analysis: C, 77.67; H, 7.48; N, 3.35; O, 11.49

Price and Availability

Size Price Availability Quantity
5.0mg USD 150.0 Ready to ship
10.0mg USD 250.0 Ready to ship
25.0mg USD 550.0 Ready to ship
50.0mg USD 950.0 Ready to ship
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Related CAS #: 877387-37-6 (free base)   1936468-29-9 (HCl)    

Synonym: GSK5182; GSK 5182; GSK-5182.

IUPAC/Chemical Name: 4-[(Z)-1-[4-(2-dimethylaminoethoxy)phenyl]-5-hydroxy-2-phenylpent-1-enyl]phenol

InChi Key: ZVSFNBNLNLXEFQ-RQZHXJHFSA-N

InChi Code: InChI=1S/C27H31NO3/c1-28(2)18-20-31-25-16-12-23(13-17-25)27(22-10-14-24(30)15-11-22)26(9-6-19-29)21-7-4-3-5-8-21/h3-5,7-8,10-17,29-30H,6,9,18-20H2,1-2H3/b27-26-

SMILES Code: OC1=CC=C(/C(C2=CC=C(OCCN(C)C)C=C2)=C(C3=CC=CC=C3)\CCCO)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

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: GSK5182 is a highly selective and orally active inverse agonist of estrogen-related receptor γ (ERRγ) with an IC50 of 79 nM.
In vitro activity: Consistent with the results from experiments involving endogenous knockdown of ERRγ, this study found that treatment with GSK5182 led to a significant and dose-dependent reduction in the number of proliferating PLC/PRF/5 cells (Figure 4b). GSK5182 also caused a dose-dependent increase in the expression of p21 and p27 while at the same time reducing the level of p-pRb (Figure 4c). The results obtained from flow cytometry revealed that GSK5182 induced cell cycle arrest at G1 phase, which in turn induced a corresponding dose-dependent reduction in the percentage of cells in S phase (Figure 4d). Taken together, these data indicate that the antitumor effect of GSK5182 in HCC cells is mediated by the induction of cell cycle arrest at the G1/S checkpoint. Reference: Exp Mol Med. 2016 Mar 4;48(3):e213. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4892874/
In vivo activity: Interestingly, GSK5182 treatment improved the liver toxicity caused by diabetes progression in db/db mice, and there were no signs of kidney, muscle, or heart toxicity (Table 2 for BUN, CRE, and CK levels). Furthermore, GSK5182 treatment significantly decreased food intake and body weight and reduced hepatic fat accumulation as well as gonadal and inguinal fat mass (Fig. 5C–F). Reference: Diabetes. 2013 Sep;62(9):3093-102. https://pubmed.ncbi.nlm.nih.gov/23775767/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 54.5 130.52
Ethanol 84.0 201.17

Preparing Stock Solutions

The following data is based on the product molecular weight 417.55 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. Kim HJ, Yoon HJ, Lee DK, Jin X, Che X, Choi JY. The estrogen-related receptor γ modulator, GSK5182, inhibits osteoclast differentiation and accelerates osteoclast apoptosis. BMB Rep. 2021 May;54(5):266-271. doi: 10.5483/BMBRep.2021.54.5.243. PMID: 33612148; PMCID: PMC8167243. 2. Kim JH, Choi YK, Byun JK, Kim MK, Kang YN, Kim SH, Lee S, Jang BK, Park KG. Estrogen-related receptor γ is upregulated in liver cancer and its inhibition suppresses liver cancer cell proliferation via induction of p21 and p27. Exp Mol Med. 2016 Mar 4;48(3):e213. doi: 10.1038/emm.2015.115. PMID: 26940882; PMCID: PMC4892874. 3. Min Y, Kim D, Suminda GGD, Zhao X, Kim M, Zhao Y, Son YO. GSK5182, 4-Hydroxytamoxifen Analog, a New Potential Therapeutic Drug for Osteoarthritis. Pharmaceuticals (Basel). 2020 Nov 27;13(12):429. doi: 10.3390/ph13120429. PMID: 33261216; PMCID: PMC7761342. 4. Kim DK, Gang GT, Ryu D, Koh M, Kim YN, Kim SS, Park J, Kim YH, Sim T, Lee IK, Choi CS, Park SB, Lee CH, Koo SH, Choi HS. Inverse agonist of nuclear receptor ERRγ mediates antidiabetic effect through inhibition of hepatic gluconeogenesis. Diabetes. 2013 Sep;62(9):3093-102. doi: 10.2337/db12-0946. Epub 2013 Jun 17. PMID: 23775767; PMCID: PMC3749343.
In vitro protocol: 1. Kim HJ, Yoon HJ, Lee DK, Jin X, Che X, Choi JY. The estrogen-related receptor γ modulator, GSK5182, inhibits osteoclast differentiation and accelerates osteoclast apoptosis. BMB Rep. 2021 May;54(5):266-271. doi: 10.5483/BMBRep.2021.54.5.243. PMID: 33612148; PMCID: PMC8167243. 2. Kim JH, Choi YK, Byun JK, Kim MK, Kang YN, Kim SH, Lee S, Jang BK, Park KG. Estrogen-related receptor γ is upregulated in liver cancer and its inhibition suppresses liver cancer cell proliferation via induction of p21 and p27. Exp Mol Med. 2016 Mar 4;48(3):e213. doi: 10.1038/emm.2015.115. PMID: 26940882; PMCID: PMC4892874.
In vivo protocol: 1. Min Y, Kim D, Suminda GGD, Zhao X, Kim M, Zhao Y, Son YO. GSK5182, 4-Hydroxytamoxifen Analog, a New Potential Therapeutic Drug for Osteoarthritis. Pharmaceuticals (Basel). 2020 Nov 27;13(12):429. doi: 10.3390/ph13120429. PMID: 33261216; PMCID: PMC7761342. 2. Kim DK, Gang GT, Ryu D, Koh M, Kim YN, Kim SS, Park J, Kim YH, Sim T, Lee IK, Choi CS, Park SB, Lee CH, Koo SH, Choi HS. Inverse agonist of nuclear receptor ERRγ mediates antidiabetic effect through inhibition of hepatic gluconeogenesis. Diabetes. 2013 Sep;62(9):3093-102. doi: 10.2337/db12-0946. Epub 2013 Jun 17. PMID: 23775767; PMCID: PMC3749343.

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1: Kim HJ, Yoon HJ, Lee DK, Jin X, Che X, Choi JY. The estrogen-related receptor
γ modulator, GSK5182, inhibits osteoclast differentiation and accelerates
osteoclast apoptosis. BMB Rep. 2021 May;54(5):266-271. doi:
10.5483/BMBRep.2021.54.5.243. PMID: 33612148; PMCID: PMC8167243.

2: Min Y, Kim D, Suminda GGD, Zhao X, Kim M, Zhao Y, Son YO. GSK5182,
4-Hydroxytamoxifen Analog, a New Potential Therapeutic Drug for Osteoarthritis.
Pharmaceuticals (Basel). 2020 Nov 27;13(12):429. doi: 10.3390/ph13120429. PMID:
33261216; PMCID: PMC7761342.

3: Radhakrishnan K, Kim YH, Jung YS, Kim J, Kim DK, Cho SJ, Lee IK, Dooley S,
Lee CH, Choi HS. Orphan Nuclear Receptor ERRγ Is a Novel Transcriptional
Regulator of IL-6 Mediated Hepatic BMP6 Gene Expression in Mice. Int J Mol Sci.
2020 Sep 28;21(19):7148. doi: 10.3390/ijms21197148. PMID: 32998264; PMCID:
PMC7582774.

4: Catucci G, Gilardi G, Sadeghi SJ. Production of drug metabolites by human
FMO3 in Escherichia coli. Microb Cell Fact. 2020 Mar 20;19(1):74. doi:
10.1186/s12934-020-01332-1. PMID: 32197603; PMCID: PMC7085137.

5: Vernier M, Dufour CR, McGuirk S, Scholtes C, Li X, Bourmeau G, Kuasne H, Park
M, St-Pierre J, Audet-Walsh E, Giguère V. Estrogen-related receptors are
targetable ROS sensors. Genes Dev. 2020 Apr 1;34(7-8):544-559. doi:
10.1101/gad.330746.119. Epub 2020 Feb 20. PMID: 32079653; PMCID: PMC7111261.

6: Zhao H, Liu S, Ma C, Ma S, Chen G, Yuan L, Chen L, Zhao H. Estrogen-Related
Receptor γ Induces Angiogenesis and Extracellular Matrix Degradation of
Temporomandibular Joint Osteoarthritis in Rats. Front Pharmacol. 2019 Nov
6;10:1290. doi: 10.3389/fphar.2019.01290. PMID: 31780931; PMCID: PMC6851845.

7: Catucci G, Bortolussi S, Rampolla G, Cusumano D, Gilardi G, Sadeghi SJ.
Flavin-Containing Monooxygenase 3 Polymorphic Variants Significantly Affect
Clearance of Tamoxifen and Clomiphene. Basic Clin Pharmacol Toxicol. 2018
Dec;123(6):687-691. doi: 10.1111/bcpt.13089. Epub 2018 Aug 2. PMID: 29959872.

8: Lim D, Kim KS, Jeong JH, Marques O, Kim HJ, Song M, Lee TH, Kim JI, Choi HS,
Min JJ, Bumann D, Muckenthaler MU, Choy HE. The hepcidin-ferroportin axis
controls the iron content of Salmonella-containing vacuoles in macrophages. Nat
Commun. 2018 May 29;9(1):2091. doi: 10.1038/s41467-018-04446-8. PMID: 29844422;
PMCID: PMC5974375.

9: Zhang Y, Kim DK, Lu Y, Jung YS, Lee JM, Kim YH, Lee YS, Kim J, Dewidar B,
Jeong WI, Lee IK, Cho SJ, Dooley S, Lee CH, Li X, Choi HS. Orphan nuclear
receptor ERRγ is a key regulator of human fibrinogen gene expression. PLoS One.
2017 Jul 27;12(7):e0182141. doi: 10.1371/journal.pone.0182141. PMID: 28750085;
PMCID: PMC5531639.

10: Lee SB, Lee HW, Singh TD, Li Y, Kim SK, Cho SJ, Lee SW, Jeong SY, Ahn BC,
Choi S, Lee IK, Lim DK, Lee J, Jeon YH. Visualization of Macrophage Recruitment
to Inflammation Lesions using Highly Sensitive and Stable Radionuclide-Embedded
Gold Nanoparticles as a Nuclear Bio-Imaging Platform. Theranostics. 2017 Feb
12;7(4):926-934. doi: 10.7150/thno.17131. PMID: 28382164; PMCID: PMC5381254.

11: Jung YS, Lee JM, Kim DK, Lee YS, Kim KS, Kim YH, Kim J, Lee MS, Lee IK, Kim
SH, Cho SJ, Jeong WI, Lee CH, Harris RA, Choi HS. The Orphan Nuclear Receptor
ERRγ Regulates Hepatic CB1 Receptor-Mediated Fibroblast Growth Factor 21 Gene
Expression. PLoS One. 2016 Jul 25;11(7):e0159425. doi:
10.1371/journal.pone.0159425. PMID: 27455076; PMCID: PMC4959684.

12: Kim JH, Choi YK, Byun JK, Kim MK, Kang YN, Kim SH, Lee S, Jang BK, Park KG.
Estrogen-related receptor γ is upregulated in liver cancer and its inhibition
suppresses liver cancer cell proliferation via induction of p21 and p27. Exp Mol
Med. 2016 Mar 4;48(3):e213. doi: 10.1038/emm.2015.115. PMID: 26940882; PMCID:
PMC4892874.

13: Kim J, Im CY, Yoo EK, Ma MJ, Kim SB, Hong E, Chin J, Hwang H, Lee S, Kim ND,
Jeon JH, Lee IK, Jeon YH, Choi HS, Kim SH, Cho SJ. Identification of Selective
ERRγ Inverse Agonists. Molecules. 2016 Jan 12;21(1):80. doi:
10.3390/molecules21010080. PMID: 26771593; PMCID: PMC6273807.

14: Zhang Y, Kim DK, Lee JM, Park SB, Jeong WI, Kim SH, Lee IK, Lee CH, Chiang
JY, Choi HS. Orphan nuclear receptor oestrogen-related receptor γ (ERRγ) plays a
key role in hepatic cannabinoid receptor type 1-mediated induction of CYP7A1
gene expression. Biochem J. 2015 Sep 1;470(2):181-93. doi: 10.1042/BJ20141494.
Epub 2015 Jun 29. PMID: 26348907; PMCID: PMC5333639.

15: Singh TD, Jeong SY, Lee SW, Ha JH, Lee IK, Kim SH, Kim J, Cho SJ, Ahn BC,
Lee J, Jeon YH. Inverse Agonist of Estrogen-Related Receptor γ Enhances Sodium
Iodide Symporter Function Through Mitogen-Activated Protein Kinase Signaling in
Anaplastic Thyroid Cancer Cells. J Nucl Med. 2015 Nov;56(11):1690-6. doi:
10.2967/jnumed.115.160366. Epub 2015 Sep 3. PMID: 26338896.

16: Misra J, Chanda D, Kim DK, Cho SR, Koo SH, Lee CH, Back SH, Choi HS. Orphan
nuclear receptor Errγ induces C-reactive protein gene expression through
induction of ER-bound Bzip transmembrane transcription factor CREBH. PLoS One.
2014 Jan 22;9(1):e86342. doi: 10.1371/journal.pone.0086342. Erratum in: PLoS
One. 2015;10(5):e0125536. PMID: 24466039; PMCID: PMC3899246.

17: Kim DK, Gang GT, Ryu D, Koh M, Kim YN, Kim SS, Park J, Kim YH, Sim T, Lee
IK, Choi CS, Park SB, Lee CH, Koo SH, Choi HS. Inverse agonist of nuclear
receptor ERRγ mediates antidiabetic effect through inhibition of hepatic
gluconeogenesis. Diabetes. 2013 Sep;62(9):3093-102. doi: 10.2337/db12-0946. Epub
2013 Jun 17. PMID: 23775767; PMCID: PMC3749343.

18: Lee JH, Kim EJ, Kim DK, Lee JM, Park SB, Lee IK, Harris RA, Lee MO, Choi HS.
Hypoxia induces PDK4 gene expression through induction of the orphan nuclear
receptor ERRγ. PLoS One. 2012;7(9):e46324. doi: 10.1371/journal.pone.0046324.
Epub 2012 Sep 25. PMID: 23050013; PMCID: PMC3457976.

19: Kim DK, Kim YH, Jang HH, Park J, Kim JR, Koh M, Jeong WI, Koo SH, Park TS,
Yun CH, Park SB, Chiang JYL, Lee CH, Choi HS. Estrogen-related receptor γ
controls hepatic CB1 receptor-mediated CYP2E1 expression and oxidative liver
injury by alcohol. Gut. 2013 Jul;62(7):1044-54. doi: 10.1136/gutjnl-2012-303347.
Epub 2012 Sep 29. PMID: 23023167; PMCID: PMC3812689.

20: Kim DK, Ryu D, Koh M, Lee MW, Lim D, Kim MJ, Kim YH, Cho WJ, Lee CH, Park
SB, Koo SH, Choi HS. Orphan nuclear receptor estrogen-related receptor γ (ERRγ)
is key regulator of hepatic gluconeogenesis. J Biol Chem. 2012 Jun
22;287(26):21628-39. doi: 10.1074/jbc.M111.315168. Epub 2012 May 1. PMID:
22549789; PMCID: PMC3381127.

GSK5182

5.0mg / USD 150.0