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	437.94026 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]

Activation of Rev-ErbA-α by SR9009 in mice increases exercise capacity by increasing mitochondria counts in skeletal muscle.^[3]

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".^[4]^[5]

References

^ Dodson B (2013-08-20). "New drug mimics the beneficial effects of exercise". Health and Wellbeing. Gizmag. Retrieved 2013-08-21.
^ Solt LA; Wang Y; Banerjee S; Hughes T; Kojetin DJ; Lundasen T; Shin Y; Liu J; Cameron MD; Noel R; Yoo SH; Takahashi JS; Butler AA; Kamenecka TM; Burris TP (May 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. {{cite journal}}: Unknown parameter |lay-url= ignored (help); Unknown parameter |laysource= ignored (help)
^ Woldt E; Sebti Y; Solt LA; Duhem C; Lancel S; Eeckhoute J; Hesselink MK; Paquet C; Delhaye S; Shin Y; Kamenecka TM; Schaart G; Lefebvre P; Nevière R; Burris TP; Schrauwen P; Staels B; Duez H (August 2013). "Rev-erb-α modulates skeletal muscle oxidative capacity by regulating mitochondrial biogenesis and autophagy". Nat. Med. 19 (8): 1039–46. doi:10.1038/nm.3213. PMC 3737409. PMID 23852339. {{cite journal}}: Unknown parameter |lay-url= ignored (help); Unknown parameter |laydate= ignored (help); Unknown parameter |laysource= ignored (help)
^ "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 Test Anal. 10 (11–12): 1670–1681. doi:10.1002/dta.2538. hdl:11573/1291262. PMID 30395700.

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

[pmid22460951-2] Solt LA; Wang Y; Banerjee S; Hughes T; Kojetin DJ; Lundasen T; Shin Y; Liu J; Cameron MD; Noel R; Yoo SH; Takahashi JS; Butler AA; Kamenecka TM; Burris TP (May 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. {{cite journal}}: Unknown parameter |lay-url= ignored (help); Unknown parameter |laysource= ignored (help)

[pmid23852339-3] Woldt E; Sebti Y; Solt LA; Duhem C; Lancel S; Eeckhoute J; Hesselink MK; Paquet C; Delhaye S; Shin Y; Kamenecka TM; Schaart G; Lefebvre P; Nevière R; Burris TP; Schrauwen P; Staels B; Duez H (August 2013). "Rev-erb-α modulates skeletal muscle oxidative capacity by regulating mitochondrial biogenesis and autophagy". Nat. Med. 19 (8): 1039–46. doi:10.1038/nm.3213. PMC 3737409. PMID 23852339. {{cite journal}}: Unknown parameter |lay-url= ignored (help); Unknown parameter |laydate= ignored (help); Unknown parameter |laysource= ignored (help)

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

[5] 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 Test Anal. 10 (11–12): 1670–1681. doi:10.1002/dta.2538. hdl:11573/1291262. PMID 30395700.

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See also

References