SM-130686

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	259666-71-2 ;
PubChem CID	9890863;
ChemSpider	7980503 ;
UNII	1GH34I6261;
Chemical and physical data
Formula	C22H23ClF3N3O3
Molar mass	469.89 g·mol−1
3D model (JSmol)	Interactive image;
	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)

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]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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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[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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v t e GH/IGF-1 axis signaling modulators
GH (somatotropin)	Agonists: Albusomatropin Bovine somatotropin Efpegsomatropin Eftansomatropin alfa Growth hormone Human placental lactogen Lonapegsomatropin Placental growth hormone (growth hormone variant) Somagrebove Somapacitan Somatosalm Somatotropin Somatropin pegol Somatrem Sometribove Somatrogon (MOD-4023; hGH-CTP) Somavaratan Somavubove Somidobove Antagonists: G120K-hGH Pegvisomant Antisense oligonucleotides: Atesidorsen Binding proteins: GHBPTooltip Growth hormone-binding protein
GHIH (somatostatin)	Agonists: BIM-23052 CH-275 Cortistatin-14 Depreotide Edotreotide Ilatreotide L-803,087 L-817,818 Lanreotide NNC 26-9100 Octreotate Octreotide Pasireotide Pentetreotide RC-160 Seglitide Somatostatin (GHIH) Somatostatin (1-28) SRIF-14 SRIF-28 TT-232 Vapreotide Veldoreotide Antagonists: BIM-23056 Cyclosomatostatin CYN-154806 Satoreotide
GHRH (somatocrinin)	Agonists: Peptide: ALRN-5281 CJC-1295 Dumorelin GHRH Modified GRF (1-29) Rismorelin Sermorelin Somatorelin Tesamorelin Antagonists: MZ-5-156
GHS (ghrelin)	Agonists: Peptide: Alexamorelin Cortistatin-14 EP-51216 Examorelin (hexarelin) Ghrelin GHRP-1 GHRP-3 GHRP-4 GHRP-5 GHRP-6 Ipamorelin Lenomorelin Livoletide LY-444711 Pralmorelin (GHRP-2) Relamorelin Tabimorelin Ulimorelin; Non-peptide: Adenosine Anamorelin Capromorelin CP-464709 Ibutamoren (MK-677) L-692,585 Macimorelin SM-130686; Unsorted: LY-426410 LY-444711 Antagonists: A-778193 Cortistatin-8 (D-Lys³)-GHRP-6 JMV2959 YIL-781
IGF-1 (somatomedin)	See here instead.

See also

References