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SR9009

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Chemica compound, Agonist of Rev-ErbA Pharmaceutical compound
SR9009
Identifiers
IUPAC name
  • ethyl-3-(((4-chlorobenzyl)((5-nitrothiophen-2-yl)methyl)amino)methyl)pyrrolidine-1-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H24ClN3O4S
Molar mass437.94 g·mol
3D model (JSmol)
SMILES
  • CCOC(=O)N1CCC(C1)CN(CC2=CC=C(C=C2)Cl)CC3=CC=C(S3)(=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) with a half-maximum inhibitory concentration (IC50) = 670 nM for Rev-ErbAα and IC50 = 800 nM for Rev-ErbAβ. In an animal study, some of its effects were found to be independent of REV-ERB with an unknown mechanism of action.

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

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".

See also

References

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