S-17092

S-17092
Legal status
Legal status	US: Investigational New Drug;
Identifiers
	IUPAC name [(2S,3aS,7aS)-1([(R,R)-2-phenylcyclopropyl]- carbonyl)-2-([thiazolidin-3-yl]carbonyl)octahydro-1H-indole;
CAS Number	176797-26-5 [UNII];
PubChem CID	9977327;
ChemSpider	8152919 ;
UNII	8W5MLJ83KU;
CompTox Dashboard (EPA)	DTXSID901028793 ;
Chemical and physical data
Formula	C23H29FN2O2
Molar mass	384.495 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N1CCCC1)[C@H]4N(C(=O)[C@H]3[C@H](c2ccc(F)cc2)C3)[C@H]5CCCC[C@H]5C4;
	InChI InChI=1S/C23H29FN2O2/c24-17-9-7-15(8-10-17)18-14-19(18)22(27)26-20-6-2-1-5-16(20)13-21(26)23(28)25-11-3-4-12-25/h7-10,16,18-21H,1-6,11-14H2/t16-,18-,19+,20-,21-/m0/s1 ; Key:JNUXCIMICQKTPX-RQUKQETFSA-N ;
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S-17092 is a drug which acts as a selective inhibitor of the enzyme prolyl endopeptidase.^[1] This enzyme is involved in the metabolic breakdown of a number of neuropeptide neurotransmitters in the brain,^[2]^[3] and so inhibiting the action of the enzyme increases the activity of these neuropeptides. This produces nootropic effects which make S-17092 a promising and novel treatment for neurodegenerative conditions such as Alzheimer's disease and Parkinson's disease.^[4]^[5]

References

^ Barelli H, Petit A, Hirsch E, Wilk S, De Nanteuil G, Morain P, Checler F (April 1999). "S 17092-1, a highly potent, specific and cell permeant inhibitor of human proline endopeptidase". Biochemical and Biophysical Research Communications. 257 (3): 657–61. doi:10.1006/bbrc.1999.0366. PMID 10208839.
^ Bellemère G, Morain P, Vaudry H, Jégou S (March 2003). "Effect of S 17092, a novel prolyl endopeptidase inhibitor, on substance P and alpha-melanocyte-stimulating hormone breakdown in the rat brain". Journal of Neurochemistry. 84 (5): 919–29. doi:10.1046/j.1471-4159.2003.01536.x. PMID 12603817. S2CID 24773419.
^ Bellemère G, Vaudry H, Morain P, Jégou S (May 2005). "Effect of prolyl endopeptidase inhibition on arginine-vasopressin and thyrotrophin-releasing hormone catabolism in the rat brain". Journal of Neuroendocrinology. 17 (5): 306–13. doi:10.1111/j.1365-2826.2005.01308.x. PMID 15869566. S2CID 9129184.
^ Morain P, Lestage P, De Nanteuil G, Jochemsen R, Robin JL, Guez D, Boyer PA (2002). "S 17092: a prolyl endopeptidase inhibitor as a potential therapeutic drug for memory impairment. Preclinical and clinical studies". CNS Drug Reviews. 8 (1): 31–52. doi:10.1111/j.1527-3458.2002.tb00214.x. PMC 6741683. PMID 12070525.
^ Morain P, Boeijinga PH, Demazières A, De Nanteuil G, Luthringer R (2007). "Psychotropic profile of S 17092, a prolyl endopeptidase inhibitor, using quantitative EEG in young healthy volunteers". Neuropsychobiology. 55 (3–4): 176–83. doi:10.1159/000107070. PMID 17700042. S2CID 27856130.

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[1] Barelli H, Petit A, Hirsch E, Wilk S, De Nanteuil G, Morain P, Checler F (April 1999). "S 17092-1, a highly potent, specific and cell permeant inhibitor of human proline endopeptidase". Biochemical and Biophysical Research Communications. 257 (3): 657–61. doi:10.1006/bbrc.1999.0366. PMID 10208839.

[2] Bellemère G, Morain P, Vaudry H, Jégou S (March 2003). "Effect of S 17092, a novel prolyl endopeptidase inhibitor, on substance P and alpha-melanocyte-stimulating hormone breakdown in the rat brain". Journal of Neurochemistry. 84 (5): 919–29. doi:10.1046/j.1471-4159.2003.01536.x. PMID 12603817. S2CID 24773419.

[3] Bellemère G, Vaudry H, Morain P, Jégou S (May 2005). "Effect of prolyl endopeptidase inhibition on arginine-vasopressin and thyrotrophin-releasing hormone catabolism in the rat brain". Journal of Neuroendocrinology. 17 (5): 306–13. doi:10.1111/j.1365-2826.2005.01308.x. PMID 15869566. S2CID 9129184.

[4] Morain P, Lestage P, De Nanteuil G, Jochemsen R, Robin JL, Guez D, Boyer PA (2002). "S 17092: a prolyl endopeptidase inhibitor as a potential therapeutic drug for memory impairment. Preclinical and clinical studies". CNS Drug Reviews. 8 (1): 31–52. doi:10.1111/j.1527-3458.2002.tb00214.x. PMC 6741683. PMID 12070525.

[5] Morain P, Boeijinga PH, Demazières A, De Nanteuil G, Luthringer R (2007). "Psychotropic profile of S 17092, a prolyl endopeptidase inhibitor, using quantitative EEG in young healthy volunteers". Neuropsychobiology. 55 (3–4): 176–83. doi:10.1159/000107070. PMID 17700042. S2CID 27856130.

[1]

[2]

[3]

[4]

[5]

Legal status

Legal status	US: Investigational New Drug
Identifiers
IUPAC name [(2S,3aS,7aS)-1([(R,R)-2-phenylcyclopropyl]- carbonyl)-2-([thiazolidin-3-yl]carbonyl)octahydro-1H-indole
CAS Number	176797-26-5^N[UNII]
PubChem CID	9977327
ChemSpider	8152919^N
UNII	8W5MLJ83KU
CompTox Dashboard (EPA)	DTXSID901028793
Chemical and physical data
Formula	C₂₃H₂₉FN₂O₂
Molar mass	384.495 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(N1CCCC1)[C@H]4N(C(=O)[C@H]3[C@H](c2ccc(F)cc2)C3)[C@H]5CCCC[C@H]5C4
InChI InChI=1S/C23H29FN2O2/c24-17-9-7-15(8-10-17)18-14-19(18)22(27)26-20-6-2-1-5-16(20)13-21(26)23(28)25-11-3-4-12-25/h7-10,16,18-21H,1-6,11-14H2/t16-,18-,19+,20-,21-/m0/s1^N Key:JNUXCIMICQKTPX-RQUKQETFSA-N^N
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S-17092

See also

References