SR9009

SR9009
Identifiers
	IUPAC name ethyl-3-(((4-chlorobenzyl)((5-nitrothiophen-2-yl)methyl)amino)methyl)pyrrolidine-1-carboxylate;
CAS Number	1379686-30-2;
PubChem CID	57394020;
ChemSpider	28487410;
UNII	X5DCA09N30;
ChEMBL	ChEMBL1961796;
CompTox Dashboard (EPA)	DTXSID901045515 ;
Chemical and physical data
Formula	C20H24ClN3O4S
Molar mass	437.94 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCOC(=O)N1CCC(C1)CN(CC2=CC=C(C=C2)Cl)CC3=CC=C(S3)[N+](=O)[O-];
	InChI InChI=1S/C20H24ClN3O4S/c1-2-28-20(25)23-10-9-16(13-23)12-22(11-15-3-5-17 (21)6-4-15)14-18-7-8-19(29-18)24(26)27/h3-8,16H,2,9-14H2,1H3; Key:MMJJNHOIVCGAAP-UHFFFAOYSA-N;

SR9009, also known as Stenabolic, is a research drug that was developed by professor Thomas Burris of the Scripps Research Institute as an agonist of Rev-ErbA (i.e., increases the constitutive repression of genes regulated by Rev-ErbA)^[1] with a half-maximum inhibitory concentration (IC₅₀) = 670 nM for Rev-ErbAα and IC₅₀ = 800 nM for Rev-ErbAβ.^[2] In an animal study, some of its effects were found to be independent of REV-ERB with an unknown mechanism of action.^[3]

Activation of Rev-ErbA-α by SR9009 in mice increases exercise capacity by increasing mitochondria counts in skeletal muscle.^[4]

Abuse of SR9009 has been reported within the bodybuilding community, resulting in SR9009 being placed on the World Anti-Doping Agency list of prohibited drugs. SR9009 and the related SR9011 drug are described as "Hormone and Metabolic Modulators".^[5]^[6]

References

^ Dodson B (2013-08-20). "New drug mimics the beneficial effects of exercise". Gizmag. Retrieved 2013-08-21.
^ 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): 62–68. Bibcode:2012Natur.485...62S. doi:10.1038/nature11030. PMC 3343186. PMID 22460951.
^ Dierickx P, Emmett MJ, Jiang C, Uehara K, Liu M, Adlanmerini M, Lazar MA (June 2019). "SR9009 has REV-ERB-independent effects on cell proliferation and metabolism". Proceedings of the National Academy of Sciences of the United States of America. 116 (25): 12147–12152. Bibcode:2019PNAS..11612147D. doi:10.1073/pnas.1904226116. PMC 6589768. PMID 31127047.
^ Woldt E, Sebti Y, Solt LA, Duhem C, Lancel S, Eeckhoute J, et al. (August 2013). "Rev-erb-α modulates skeletal muscle oxidative capacity by regulating mitochondrial biogenesis and autophagy". Nature Medicine. 19 (8): 1039–1046. doi:10.1038/nm.3213. PMC 3737409. PMID 23852339.
^ "Prohibited List". 2014-07-22.
^ Mazzarino M, Rizzato N, Stacchini C, de la Torre X, Botrè F (November 2018). "A further insight into the metabolic profile of the nuclear receptor Rev-erb agonist, SR9009". Drug Testing and Analysis. 10 (11–12): 1670–1681. doi:10.1002/dta.2538. hdl:11573/1291262. PMID 30395700. S2CID 53223664.

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[url_Gizmag-1] Dodson B (2013-08-20). "New drug mimics the beneficial effects of exercise". Gizmag. Retrieved 2013-08-21.

[pmid22460951-2] 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): 62–68. Bibcode:2012Natur.485...62S. doi:10.1038/nature11030. PMC 3343186. PMID 22460951.

[3] Dierickx P, Emmett MJ, Jiang C, Uehara K, Liu M, Adlanmerini M, Lazar MA (June 2019). "SR9009 has REV-ERB-independent effects on cell proliferation and metabolism". Proceedings of the National Academy of Sciences of the United States of America. 116 (25): 12147–12152. Bibcode:2019PNAS..11612147D. doi:10.1073/pnas.1904226116. PMC 6589768. PMID 31127047.

[pmid23852339-4] Woldt E, Sebti Y, Solt LA, Duhem C, Lancel S, Eeckhoute J, et al. (August 2013). "Rev-erb-α modulates skeletal muscle oxidative capacity by regulating mitochondrial biogenesis and autophagy". Nature Medicine. 19 (8): 1039–1046. doi:10.1038/nm.3213. PMC 3737409. PMID 23852339.

[5] "Prohibited List". 2014-07-22.

[6] Mazzarino M, Rizzato N, Stacchini C, de la Torre X, Botrè F (November 2018). "A further insight into the metabolic profile of the nuclear receptor Rev-erb agonist, SR9009". Drug Testing and Analysis. 10 (11–12): 1670–1681. doi:10.1002/dta.2538. hdl:11573/1291262. PMID 30395700. S2CID 53223664.

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See also

References