LGD-2226

LGD-2226
Legal status
Legal status
Identifiers
IUPAC name
  • 6-(bis-(2,2,2-trifluoroethyl)amino)-4-trifluoromethyl-1H-quinolin-2-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.230.470
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Chemical and physical data
FormulaC14H9F9N2O
Molar mass392.225 g·mol−1
3D model (JSmol)
SMILES
  • FC(F)(F)c(c2)c1cc(N(CC(F)(F)F)CC(F)(F)F)ccc1[nH]c2=O
InChI
  • InChI=1S/C14H9F9N2O/c15-12(16,17)5-25(6-13(18,19)20)7-1-2-10-8(3-7)9(14(21,22)23)4-11(26)24-10/h1-4H,5-6H2,(H,24,26)
  • Key:ULBPQWIGZUGPHU-UHFFFAOYSA-N
  (verify)

LGD-2226 is an investigational selective androgen receptor modulator (SARM),[1] which is being developed for treatment of muscle wasting and osteoporosis.[2]

LGD-2226 is an orally active, potent and selective agonist for androgen receptors which was shown to have anabolic effects in both muscle and bone tissue, but with considerably less effects on prostate weight and lutenizing hormone levels than testosterone.[3][4]

Selective androgen receptor modulators may also be used by athletes to assist in training and increase physical stamina and fitness, potentially producing effects similar to anabolic steroids but with significantly less side effects. For this reason, SARMs have already been banned by the World Anti-Doping Agency since January 2008 despite no drugs from this class yet being in clinical use, and blood tests for all known SARMs are currently being developed,[5][6] including LGD-2226.[7]

References

  1. ↑ van Oeveren A, Motamedi M, Mani NS, Marschke KB, López FJ, Schrader WT, et al. (October 2006). "Discovery of 6-N,N-bis(2,2,2-trifluoroethyl)amino- 4-trifluoromethylquinolin-2(1H)-one as a novel selective androgen receptor modulator". Journal of Medicinal Chemistry. 49 (21): 6143–6. doi:10.1021/jm060792t. PMID 17034117.
  2. ↑ Gao W, Dalton JT (March 2007). "Expanding the therapeutic use of androgens via selective androgen receptor modulators (SARMs)". Drug Discovery Today. 12 (5–6): 241–8. doi:10.1016/j.drudis.2007.01.003. PMC 2072879. PMID 17331889.
  3. ↑ Miner JN, Chang W, Chapman MS, Finn PD, Hong MH, López FJ, et al. (January 2007). "An orally active selective androgen receptor modulator is efficacious on bone, muscle, and sex function with reduced impact on prostate". Endocrinology. 148 (1): 363–73. doi:10.1210/en.2006-0793. PMID 17023534.
  4. ↑ Hong MH, Sun H, Jin CH, Chapman M, Hu J, Chang W, et al. (March 2008). "Cell-specific activation of the human skeletal alpha-actin by androgens". Endocrinology. 149 (3): 1103–12. doi:10.1210/en.2007-0530. PMID 18063690.
  5. ↑ Thevis M, Kohler M, Schlörer N, Kamber M, Kühn A, Linscheid MW, Schänzer W (May 2008). "Mass spectrometry of hydantoin-derived selective androgen receptor modulators". Journal of Mass Spectrometry. 43 (5): 639–50. Bibcode:2008JMSp...43..639T. doi:10.1002/jms.1364. PMID 18095383.
  6. ↑ Thevis M, Kohler M, Thomas A, Maurer J, Schlörer N, Kamber M, Schänzer W (May 2008). "Determination of benzimidazole- and bicyclic hydantoin-derived selective androgen receptor antagonists and agonists in human urine using LC-MS/MS". Analytical and Bioanalytical Chemistry. 391 (1): 251–61. doi:10.1007/s00216-008-1882-6. PMID 18270691. S2CID 206899531.
  7. ↑ Thevis M, Kohler M, Maurer J, Schlörer N, Kamber M, Schänzer W (2007). "Screening for 2-quinolinone-derived selective androgen receptor agonists in doping control analysis". Rapid Communications in Mass Spectrometry. 21 (21): 3477–86. Bibcode:2007RCMS...21.3477T. doi:10.1002/rcm.3247. PMID 17985352.
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