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;
CompTox Dashboard (EPA)	DTXSID601045516 ;
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.
^ 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. Bibcode:2014NatCo...5.5759B. doi:10.1038/ncomms6759. PMC 4495958. 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. Bibcode:2016RCMS...30..635T. doi:10.1002/rcm.7470. PMID 26842585. S2CID 206444739.
^ 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. Bibcode:2018Natur.553..351S. 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. S2CID 205971979.
^ Wolff SE, Wang XL, Jiao H, Sun J, Kalsbeek A, Yi CX, Gao Y (2020). "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. PMC 7546349. 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.

[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. Bibcode:2014NatCo...5.5759B. doi:10.1038/ncomms6759. PMC 4495958. 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. Bibcode:2016RCMS...30..635T. doi:10.1002/rcm.7470. PMID 26842585. S2CID 206444739.

[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. Bibcode:2018Natur.553..351S. 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. S2CID 205971979.

[7] Wolff SE, Wang XL, Jiao H, Sun J, Kalsbeek A, Yi CX, Gao Y (2020). "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. PMC 7546349. PMID 33101272.

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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
CompTox Dashboard (EPA)	DTXSID601045516
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

See also

References