ADX-47273

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H17F2N3O2
Molecular Weight	369.3647
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(CCCN(C1)C(=O)C2=CC=C(F)C=C2)C3=NC(=NO3)C4=CC=C(F)C=C4

InChI

InChIKey=VXQCCZHCFBHTTD-HNNXBMFYSA-N

InChI=1S/C20H17F2N3O2/c21-16-7-3-13(4-8-16)18-23-19(27-24-18)15-2-1-11-25(12-15)20(26)14-5-9-17(22)10-6-14/h3-10,15H,1-2,11-12H2/t15-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C20H17F2N3O2
Molecular Weight	369.3647
Charge	0
Count

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

Description
Sources: http://www.addextherapeutics.com/fileadmin/user_upload/Media_Exposure/Novel_approach_to_a_drug_discovery.pdf
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23869026

ADX-47273 is a research pharmaceutical developed by Addex Therapeutics. It is a novel positive allosteric modulator of the metabotropic glutamate receptor subtype 5 (mGluR5). ADX-47273 displays antipsychotic, neuromodulatory, and cognition enhancing activities. In vivo, ADX 47273 increases waking and decreases deep sleep behaviors; it also increases late phase long-term potentiation (LTP) and enhances adaptive learning. In other animal models, ADX-47273 decreases amphetamine- and phencyclidine-induced hyperlocomotion and accumbal dopamine levels.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Metabotropic glutamate receptor 5 39 Target ID: CHEMBL3227 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24050755	Positive Allosteric Modulator 179		157.0 nM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Alzheimer’s disease 272 Sources: http://adisinsight.springer.com/drugs/800024114	Primary	Preclinical	Unknown Approved Use Unknown
Cognition disorders 21 Sources: http://adisinsight.springer.com/drugs/800024114 http://www.addextherapeutics.com/fileadmin/user_upload/Media_Exposure/Novel_approach_to_a_drug_discovery.pdf	Primary	Preclinical	Unknown Approved Use Unknown
Schizophrenia 298 Sources: http://adisinsight.springer.com/drugs/800024114 http://www.addextherapeutics.com/fileadmin/user_upload/Media_Exposure/Novel_approach_to_a_drug_discovery.pdf	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Beyond the dopamine receptor: novel therapeutic targets for treating schizophrenia.	2010	20954431
Metabotropic glutamate receptors: potential drug targets for psychiatric disorders.	2010 May 27	21160908
In vitro characterisation of the novel positive allosteric modulators of the mGlu₅ receptor, LSN2463359 and LSN2814617, and their effects on sleep architecture and operant responding in the rat.	2013 Jan	22884720

Patents

Sample Use Guides

In Vivo Use Guide

Rats: ADX-47273 (1-100mg/kg) was evaluated in rat models used for detecting antipsychotic-like activity

Route of Administration: Intraperitoneal

In Vitro Use Guide

30uM ADX-47273 induces a concentration-dependent ∼13-fold shift to the left in the glutamate EC50.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:09:25 GMT 2023` Edited by `admin` on `Sat Dec 16 08:09:25 GMT 2023`
Record UNII	4C4P7L0W63
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ADX-47273

Common Name

English

METHANONE, (4-FLUOROPHENYL)((3S)-3-(3-(4-FLUOROPHENYL)-1,2,4-OXADIAZOL-5-YL)-1-PIPERIDINYL)-

Systematic Name

English

PIPERIDINE, 1-(4-FLUOROBENZOYL)-3-(3-(4-FLUOROPHENYL)-1,2,4-OXADIAZOL-5-YL)-, (3S)-

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

ADX-47273