S-17092

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H28N2O2S
Molecular Weight	384.535
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12C[C@H](N(C(=O)[C@@H]3C[C@H]3C4=CC=CC=C4)[C@@]1([H])CCCC2)C(=O)N5CCSC5

InChI

InChIKey=NXSXRIHXEQSYEZ-KNJMJIDISA-N

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

HIDE SMILES / InChI

Molecular Formula	C22H28N2O2S
Molecular Weight	384.535
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11012558 | https://www.ncbi.nlm.nih.gov/pubmed/10208839
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12603817 | https://www.ncbi.nlm.nih.gov/pubmed/12070525

S-17092, a prolyl endopeptidase inhibitor, is in phase I investigations with Servier in France for its potential in cognition disorders. Prolyl endopeptidase is involved in the metabolic breakdown of a number of neuropeptide neurotransmitters in the brain, 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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prolyl endopeptidase 9 Target ID: CHEMBL3202 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12603817 \| https://www.ncbi.nlm.nih.gov/pubmed/20058865	Inhibitor 8297		1.5 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cognitive disorders 8 Sources: http://adisinsight.springer.com/drugs/800011104 https://www.ncbi.nlm.nih.gov/pubmed/17700042 https://www.ncbi.nlm.nih.gov/pubmed/11012558	Primary		Phase I 428	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10208839 http://adisinsight.springer.com/drugs/800011104	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Pharmacodynamic and pharmacokinetic profile of S 17092, a new orally active prolyl endopeptidase inhibitor, in elderly healthy volunteers. A phase I study.	2000 Oct	11012558
S 17092: a prolyl endopeptidase inhibitor as a potential therapeutic drug for memory impairment. Preclinical and clinical studies.	2002 Spring	12070525
Effect of S 17092, a novel prolyl endopeptidase inhibitor, on substance P and alpha-melanocyte-stimulating hormone breakdown in the rat brain.	2003 Mar	12603817

Patents

Sample Use Guides

In Vivo Use Guide

S-17092 (100, 200, 400 or 600 mg) were administered once daily for 10 days in a rising multiple-dose scheme.

Route of Administration: Oral

In Vitro Use Guide

In vitro experiments revealed that S-17092 inhibits in a dose-dependent manner PEP activity in rat cortical extracts (IC50 = 8.3 nm).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 18:59:13 GMT 2023` Edited by `admin` on `Sat Dec 16 18:59:13 GMT 2023`
Record UNII	8W5MLJ83KU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

S-17092

Code

English

((2R,3AR,7AS)-2-(1,3-THIAZOLIDIN-3-YLCARBONYL)-2,3,3A,4,5,6,7,7A-OCTAHYDROINDOL-1-YL)-((1S,2S)-2-PHENYLCYCLOPROPYL)METHANONE

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID70433003