PNU-282987 MONOHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H17ClN2O.ClH.H2O
Molecular Weight	319.227
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.Cl.ClC1=CC=C(C=C1)C(=O)N[C@H]2CN3CCC2CC3

InChI

InChIKey=OCWLMMBVXIESNP-GXKRWWSZSA-N

InChI=1S/C14H17ClN2O.ClH.H2O/c15-12-3-1-11(2-4-12)14(18)16-13-9-17-7-5-10(13)6-8-17;;/h1-4,10,13H,5-9H2,(H,16,18);1H;1H2/t13-;;/m0../s1

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C14H17ClN2O
Molecular Weight	264.751
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20630711 | https://www.ncbi.nlm.nih.gov/pubmed/15523001
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27729414

PNU-282987 is a potent and selective a7 nAChR agonist. This compound showed high affinity for the rat a7 nAChR (Ki = 26 nM) and activity at the a7–5-HT3 chimera (EC50 = 128 nM). In addition, PNU-282987 was found to be inactive at all tested monoamine, muscarine, glutamate, and GABA receptors at 1 uM concentration, except 5-HT3 receptors (Ki = 930 nM). The highly selective and potent a7 nAChR agonist PNU-282987 enhances GABAergic synaptic activity in the hippocampus in vitro, and reverses amphetamine induced auditory gating deficit in anesthetized rats. In addition, PNU-282987 improves the inherent gating deficit observed in a subset of rats and enhances amphetamine induced hippocampal activity. These results support the concept that a7 nAChR agonists represent a novel, potential pharmacotherapy in treatment of schizophrenia. It also has being shown that acute lung injury is reduced by PNU-282987 through changes in the macrophage profile.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Neuronal acetylcholine receptor protein alpha-7 subunit 77 Target ID: CHEMBL2492 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20828128 \| https://www.ncbi.nlm.nih.gov/pubmed/24901260	Agonist 2678		24.55 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Acute respiratory distress syndrome 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27729414	Primary	Preclinical	Unknown Approved Use Unknown
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23938346	Primary	Preclinical	Unknown Approved Use Unknown
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20630711 http://adisinsight.springer.com/drugs/800018656	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The selective alpha7 nicotinic acetylcholine receptor agonist PNU-282987 [N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-4-chlorobenzamide hydrochloride] enhances GABAergic synaptic activity in brain slices and restores auditory gating deficits in anesthetized rats.	2005 Mar	15523001
Alpha7 nicotinic acetylcholine receptor activation ameliorates scopolamine-induced behavioural changes in a modified continuous Y-maze task in mice.	2009 Jan 5	18848931

Patents

Sample Use Guides

In Vivo Use Guide

Rats: eye drops of PNU-282987 resulted in neuroprotection against etinal ganglion cells (RGCs) loss in a dose-dependent manner using concentrations between 100 uM and 2 mM PNU-282987

Route of Administration: Topical

In Vitro Use Guide

PNU-282987 (1, 3, and 10 uM) incubated for 16 h after the 8-h rot/oligo period in SH-SY5Y cells produced a concentration-dependent protective effect; the maximum protective effect was achieved with 10 uM PNU282987 (50% neuroprotection)

Substance Class	Chemical Created by `admin` on `Sat Dec 16 06:52:48 GMT 2023` Edited by `admin` on `Sat Dec 16 06:52:48 GMT 2023`
Record UNII	916D7SP4CX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PNU-282987 MONOHYDRATE

Common Name

English

BENZAMIDE, N-(3R)-1-AZABICYCLO(2.2.2)OCT-3-YL-4-CHLORO-, HYDROCHLORIDE, HYDRATE (1:1:1)

Systematic Name

English

PNU-282987 HYDRATE

Code

English

Code System Code Type Description

FDA UNII

916D7SP4CX

Created by admin on Sat Dec 16 06:52:48 GMT 2023 , Edited by admin on Sat Dec 16 06:52:48 GMT 2023

PRIMARY

PUBCHEM

16219883

Created by admin on Sat Dec 16 06:52:48 GMT 2023 , Edited by admin on Sat Dec 16 06:52:48 GMT 2023

PRIMARY

CAS

1049739-43-6

Created by admin on Sat Dec 16 06:52:48 GMT 2023 , Edited by admin on Sat Dec 16 06:52:48 GMT 2023

PRIMARY

Related Record Type Details


					810P1694K2

PNU-282987

ANHYDROUS->SOLVATE

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					27M563MU5U

PNU-282987 FREE BASE

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20630711 | https://www.ncbi.nlm.nih.gov/pubmed/15523001Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27729414

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20630711 | https://www.ncbi.nlm.nih.gov/pubmed/15523001
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27729414