SR9011

SR9011
Identifiers
	IUPAC name 3-(((4-chlorobenzyl)((5-nitrothiophen-2-yl)methyl)amino)methyl)-N-pentylpyrrolidine-1-carboxamide;
CAS Number	1379686-29-9;
PubChem CID	57394021;
ChemSpider	28487552;
UNII	VYI79FLZ6W;
ChEMBL	ChEMBL1961797;
Chemical and physical data
Formula	C23H31ClN4O3S
Molar mass	479.04 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCNC(=O)N1CCC(CN(Cc2ccc(Cl)cc2)Cc3ccc(s3)[N+](=O)[O-])C1;
	InChI InChI=1S/C23H31ClN4O3S/c1-2-3-4-12-25-23(29)27-13-11-19(16-27)15-26(14-18-5-7-20(24)8-6-18)17-21-9-10-22(32-21)28(30)31/h5-10,19H,2-4,11-17H2,1H3,(H,25,29); Key:PPUYOYQTTWJTIU-UHFFFAOYSA-N;

SR9011 is a research drug that was developed by Professor Thomas Burris of Scripps as an agonist of Rev-ErbAα with a half-maximum inhibitory concentration (IC₅₀) = 790 nM for Rev-Erbα and IC₅₀ = 560 nM for Rev-ErbAβ.[1] It has been used in the study of the regulation of the circadian rhythm and its links to immune system function, inflammation and cancer.[2][3][4][5][6][7]

References

Solt LA, Wang Y, Banerjee S, Hughes T, Kojetin DJ, Lundasen T, et al. (March 2012). "Regulation of circadian behaviour and metabolism by synthetic REV-ERB agonists". Nature. 485 (7396): 62–8. Bibcode:2012Natur.485...62S. doi:10.1038/nature11030. PMC 3343186. PMID 22460951. Lay summary – Nature Magazine.
Banerjee S, Wang Y, Solt LA, Griffett K, Kazantzis M, Amador A, et al. (December 2014). "Pharmacological targeting of the mammalian clock regulates sleep architecture and emotional behaviour". Nature Communications. 5: 5759. doi:10.1038/ncomms6759. PMID 25536025.
Ercolani L, Ferrari A, De Mei C, Parodi C, Wade M, Grimaldi B (October 2015). "Circadian clock: Time for novel anticancer strategies?". Pharmacological Research. 100: 288–95. doi:10.1016/j.phrs.2015.08.008. PMID 26319800.
Thevis M, Schänzer W (March 2016). "Emerging drugs affecting skeletal muscle function and mitochondrial biogenesis - Potential implications for sports drug testing programs". Rapid Communications in Mass Spectrometry. 30 (5): 635–51. doi:10.1002/rcm.7470. PMID 26842585.
Sulli G, Rommel A, Wang X, Kolar MJ, Puca F, Saghatelian A, et al. (January 2018). "Pharmacological activation of REV-ERBs is lethal in cancer and oncogene-induced senescence". Nature. 553 (7688): 351–355. doi:10.1038/nature25170. PMC 5924733. PMID 29320480.
Amador A, Kamenecka TM, Solt LA, Burris TP (April 2018). "REV-ERBβ is required to maintain normal wakefulness and the wake-inducing effect of dual REV-ERB agonist SR9009". Biochemical Pharmacology. 150: 1–8. doi:10.1016/j.bcp.2018.01.009. PMID 29355503.
Wolff SE, Wang XL, Jiao H, Sun J, Kalsbeek A, Yi CX, Gao Y. "The Effect of Rev-erbα Agonist SR9011 on the Immune Response and Cell Metabolism of Microglia". Frontiers in Immunology. 11: 550145. doi:10.3389/fimmu.2020.550145. PMID 33101272.

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[pmid22460951-1] Solt LA, Wang Y, Banerjee S, Hughes T, Kojetin DJ, Lundasen T, et al. (March 2012). "Regulation of circadian behaviour and metabolism by synthetic REV-ERB agonists". Nature. 485 (7396): 62–8. Bibcode:2012Natur.485...62S. doi:10.1038/nature11030. PMC 3343186. PMID 22460951. Lay summary – Nature Magazine.

[2] Banerjee S, Wang Y, Solt LA, Griffett K, Kazantzis M, Amador A, et al. (December 2014). "Pharmacological targeting of the mammalian clock regulates sleep architecture and emotional behaviour". Nature Communications. 5: 5759. doi:10.1038/ncomms6759. PMID 25536025.

[3] Ercolani L, Ferrari A, De Mei C, Parodi C, Wade M, Grimaldi B (October 2015). "Circadian clock: Time for novel anticancer strategies?". Pharmacological Research. 100: 288–95. doi:10.1016/j.phrs.2015.08.008. PMID 26319800.

[4] Thevis M, Schänzer W (March 2016). "Emerging drugs affecting skeletal muscle function and mitochondrial biogenesis - Potential implications for sports drug testing programs". Rapid Communications in Mass Spectrometry. 30 (5): 635–51. doi:10.1002/rcm.7470. PMID 26842585.

[5] Sulli G, Rommel A, Wang X, Kolar MJ, Puca F, Saghatelian A, et al. (January 2018). "Pharmacological activation of REV-ERBs is lethal in cancer and oncogene-induced senescence". Nature. 553 (7688): 351–355. doi:10.1038/nature25170. PMC 5924733. PMID 29320480.

[6] Amador A, Kamenecka TM, Solt LA, Burris TP (April 2018). "REV-ERBβ is required to maintain normal wakefulness and the wake-inducing effect of dual REV-ERB agonist SR9009". Biochemical Pharmacology. 150: 1–8. doi:10.1016/j.bcp.2018.01.009. PMID 29355503.

[7] Wolff SE, Wang XL, Jiao H, Sun J, Kalsbeek A, Yi CX, Gao Y. "The Effect of Rev-erbα Agonist SR9011 on the Immune Response and Cell Metabolism of Microglia". Frontiers in Immunology. 11: 550145. doi:10.3389/fimmu.2020.550145. PMID 33101272.

SR9011

See also

References