S-17092

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 522520

CAS#: 176797-26-5

Description: S-17092 is a drug which acts as a selective inhibitor of the enzyme prolyl endopeptidase. This enzyme is involved in the metabolic breakdown of a number of neuropeptide neurotransmitters in the brain, nd 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.


Chemical Structure

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S-17092
CAS# 176797-26-5

Theoretical Analysis

MedKoo Cat#: 522520
Name: S-17092
CAS#: 176797-26-5
Chemical Formula: C22H28N2O2S
Exact Mass: 384.1871
Molecular Weight: 384.54
Elemental Analysis: C, 68.72; H, 7.34; N, 7.29; O, 8.32; S, 8.34

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Synonym: S-17092; S 17092; S17092.

IUPAC/Chemical Name: [(2S,3aS,7aS)-Octahydro-1-[[(1R,2R)-2-phenylcyclopropyl]carbonyl]-1H-indol-2-yl]-3-thiazolidinyl--methanone

InChi Key: NXSXRIHXEQSYEZ-KNJMJIDISA-N

InChi Code: InChI=1S/C22H28N2O2S/c25-21(18-13-17(18)15-6-2-1-3-7-15)24-19-9-5-4-8-16(19)12-20(24)22(26)23-10-11-27-14-23/h1-3,6-7,16-20H,4-5,8-14H2/t16-,17-,18+,19-,20-/m0/s1

SMILES Code: O=C([C@H]1N(C([C@H]2[C@H](C3=CC=CC=C3)C2)=O)[C@@]4([H])CCCC[C@@]4([H])C1)N5CSCC5

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 384.54 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Kim JD, Toda C, D'Agostino G, Zeiss CJ, DiLeone RJ, Elsworth JD, Kibbey RG, Chan O, Harvey BK, Richie CT, Savolainen M, Myöhänen T, Jeong JK, Diano S. Hypothalamic prolyl endopeptidase (PREP) regulates pancreatic insulin and glucagon secretion in mice. Proc Natl Acad Sci U S A. 2014 Aug 12;111(32):11876-81. doi: 10.1073/pnas.1406000111. Epub 2014 Jul 28. Erratum in: Proc Natl Acad Sci U S A. 2014 Sep 23;111(38):14003. PubMed PMID: 25071172; PubMed Central PMCID: PMC4136568.

2: Li P, Xiao HD, Xu J, Ong FS, Kwon M, Roman J, Gal A, Bernstein KE, Fuchs S. Angiotensin-converting enzyme N-terminal inactivation alleviates bleomycin-induced lung injury. Am J Pathol. 2010 Sep;177(3):1113-21. doi: 10.2353/ajpath.2010.081127. Epub 2010 Jul 22. PubMed PMID: 20651228; PubMed Central PMCID: PMC2928946.

3: Di Daniel E, Glover CP, Grot E, Chan MK, Sanderson TH, White JH, Ellis CL, Gallagher KT, Uney J, Thomas J, Maycox PR, Mudge AW. Prolyl oligopeptidase binds to GAP-43 and functions without its peptidase activity. Mol Cell Neurosci. 2009 Jul;41(3):373-82. doi: 10.1016/j.mcn.2009.03.003. Epub 2009 Mar 28. PubMed PMID: 19332125.

4: Morain P, Boeijinga PH, Demazières A, De Nanteuil G, Luthringer R. Psychotropic profile of S 17092, a prolyl endopeptidase inhibitor, using quantitative EEG in young healthy volunteers. Neuropsychobiology. 2007;55(3-4):176-83. Epub 2007 Aug 14. PubMed PMID: 17700042.

5: Leprince J, Cosquer D, Bellemère G, Chatenet D, Tollemer H, Jégou S, Tonon MC, Vaudry H. Catabolism of the octadecaneuropeptide ODN by prolyl endopeptidase: identification of an unusual cleavage site. Peptides. 2006 Jun;27(6):1561-9. Epub 2006 Jan 6. PubMed PMID: 16406204.

6: Bellemère G, Vaudry H, Morain P, Jégou S. Effect of prolyl endopeptidase inhibition on arginine-vasopressin and thyrotrophin-releasing hormone catabolism in the rat brain. J Neuroendocrinol. 2005 May;17(5):306-13. PubMed PMID: 15869566.

7: Cavasin MA, Rhaleb NE, Yang XP, Carretero OA. Prolyl oligopeptidase is involved in release of the antifibrotic peptide Ac-SDKP. Hypertension. 2004 May;43(5):1140-5. Epub 2004 Mar 22. PubMed PMID: 15037553.

8: Bellemère G, Morain P, Vaudry H, Jégou S. Effect of S 17092, a novel prolyl endopeptidase inhibitor, on substance P and alpha-melanocyte-stimulating hormone breakdown in the rat brain. J Neurochem. 2003 Mar;84(5):919-29. PubMed PMID: 12603817.

9: Morain P, Lestage P, De Nanteuil G, Jochemsen R, Robin JL, Guez D, Boyer PA. S 17092: a prolyl endopeptidase inhibitor as a potential therapeutic drug for memory impairment. Preclinical and clinical studies. CNS Drug Rev. 2002 Spring;8(1):31-52. Review. PubMed PMID: 12070525.

10: Schneider JS, Giardiniere M, Morain P. Effects of the prolyl endopeptidase inhibitor S 17092 on cognitive deficits in chronic low dose MPTP-treated monkeys. Neuropsychopharmacology. 2002 Feb;26(2):176-82. PubMed PMID: 11790513.

11: Morain P, Robin JL, De Nanteuil G, Jochemsen R, Heidet V, Guez D. Pharmacodynamic and pharmacokinetic profile of S 17092, a new orally active prolyl endopeptidase inhibitor, in elderly healthy volunteers. A phase I study. Br J Clin Pharmacol. 2000 Oct;50(4):350-9. PubMed PMID: 11012558; PubMed Central PMCID: PMC2014995.

12: Petit A, Barelli H, Morain P, Checler F. Novel proline endopeptidase inhibitors do not modify Abeta40/42 formation and degradation by human cells expressing wild-type and swedish mutated beta-amyloid precursor protein. Br J Pharmacol. 2000 Aug;130(7):1613-7. PubMed PMID: 10928965; PubMed Central PMCID: PMC1572208.

13: Marighetto A, Touzani K, Etchamendy N, Torrea CC, De Nanteuil G, Guez D, Jaffard R, Morain P. Further evidence for a dissociation between different forms of mnemonic expressions in a mouse model of age-related cognitive decline: effects of tacrine and S 17092, a novel prolyl endopeptidase inhibitor. Learn Mem. 2000 May-Jun;7(3):159-69. PubMed PMID: 10837505; PubMed Central PMCID: PMC311328.

14: Barelli H, Petit A, Hirsch E, Wilk S, De Nanteuil G, Morain P, Checler F. S 17092-1, a highly potent, specific and cell permeant inhibitor of human proline endopeptidase. Biochem Biophys Res Commun. 1999 Apr 21;257(3):657-61. PubMed PMID: 10208839.