SM-130686

SM-130686 is a small-molecule drug which acts as a potent, orally-active agonist of the ghrelin/growth hormone secretagogue receptor (GHSR) and growth hormone secretagogue,[1] with around half the potency of the endogenous agonist ghrelin as a stimulator of growth hormone release.[2][3] It produces dose-dependent increases in muscle mass and decrease in body fat, and is under investigation for the treatment of growth hormone deficiency and other medical conditions.[4] Concerns about its potential use as a performance-enhancing drug for athletes have led to the development of urine tests for SM-130686 and other GHSR agonists, even though no drugs from this class have yet progressed to clinical use.[5]

SM-130686
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • (+)-(3S)-3-(2-chlorophenyl)-1-[2-(diethylamino)ethyl]-3-hydroxo-2-oxo-4-(trifluoromethyl)indoline-6-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC22H23ClF3N3O3
Molar mass469.89 g·mol−1
3D model (JSmol)
SMILES
  • FC(F)(F)c3c1c(cc(c3)C(N)=O)N(CCN(CC)CC)C(=O)C1(O)c2ccccc2Cl
InChI
  • InChI=1S/C22H23ClF3N3O3/c1-3-28(4-2)9-10-29-17-12-13(19(27)30)11-15(22(24,25)26)18(17)21(32,20(29)31)14-7-5-6-8-16(14)23/h5-8,11-12,32H,3-4,9-10H2,1-2H3,(H2,27,30)/t21-/m1/s1
  • Key:YSSPGXCFFITNCE-OAQYLSRUSA-N
  (verify)

See also

References
  1. Tokunaga T, Hume WE, Nagamine J, Kawamura T, Taiji M, Nagata R (April 2005). "Structure-activity relationships of the oxindole growth hormone secretagogues". Bioorganic & Medicinal Chemistry Letters. 15 (7): 1789–92. doi:10.1016/j.bmcl.2005.02.042. PMID 15780607.
  2. Nagamine J, Nagata R, Seki H, Nomura-Akimaru N, Ueki Y, Kumagai K, et al. (December 2001). "Pharmacological profile of a new orally active growth hormone secretagogue, SM-130686". The Journal of Endocrinology. 171 (3): 481–9. doi:10.1677/joe.0.1710481. PMID 11739014.
  3. Tokunaga T, Hume WE, Umezome T, Okazaki K, Ueki Y, Kumagai K, et al. (December 2001). "Oxindole derivatives as orally active potent growth hormone secretagogues". Journal of Medicinal Chemistry. 44 (26): 4641–9. doi:10.1021/jm0103763. PMID 11741481.
  4. Nagamine J, Kawamura T, Tokunaga T, Hume WE, Nagata R, Nakagawa T, Taiji M (March 2006). "Synthesis and pharmacological profile of an orally-active growth hormone secretagogue, SM-130686". Combinatorial Chemistry & High Throughput Screening. 9 (3): 187–96. doi:10.2174/138620706776055548. PMID 16533152.
  5. Thevis M, Wilkens F, Geyer H, Schänzer W (2006). "Determination of therapeutics with growth-hormone secretagogue activity in human urine for doping control purposes". Rapid Communications in Mass Spectrometry. 20 (22): 3393–402. Bibcode:2006RCMS...20.3393T. doi:10.1002/rcm.2758. PMID 17051614.
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