GRN-529

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H15F2N3O2
Molecular Weight	391.3702
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC(F)OC1=CC=C(C=C1C#CC2=NC=CC=C2)C(=O)N3CC4=C(C3)N=CC=C4

InChI

InChIKey=JITMSIRHBAVREW-UHFFFAOYSA-N

InChI=1S/C22H15F2N3O2/c23-22(24)29-20-9-7-16(12-15(20)6-8-18-5-1-2-10-25-18)21(28)27-13-17-4-3-11-26-19(17)14-27/h1-5,7,9-12,22H,13-14H2

HIDE SMILES / InChI

Molecular Formula	C22H15F2N3O2
Molecular Weight	391.3702
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/22539775 | https://www.ncbi.nlm.nih.gov/pubmed/22551786

GRN-529 is a negative allosteric modulator of mGluR5. In a mouse model of autism, GRN-529 (named as PF-05212391 by Pfizer) decreased self-grooming and stereotyped jumping and increased social functioning compared with no treatment. In a mouse model of depression, GRN-529 had dose-dependent efficacy across a therapeutically relevant battery of animal models, comprising depression and 2 of the co-morbid symptoms overrepresented in treatment resistant depression, namely anxiety and pain

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Metabotropic glutamate receptor 5 40 Target ID: P41594 Gene ID: 2915.0 Gene Symbol: GRM5 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22539775	Negative Allosteric Modulator 43		0.001 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Autism 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22539775	Primary		Preclinical	Unknown Approved Use Unknown
Treatment-resistant depression 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22551786	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Neurophysiological signals as potential translatable biomarkers for modulation of metabotropic glutamate 5 receptors.	2013-12	23831682
Negative allosteric modulation of metabotropic glutamate receptor 5 results in broad spectrum activity relevant to treatment resistant depression.	2013-03	22551786
Negative allosteric modulation of the mGluR5 receptor reduces repetitive behaviors and rescues social deficits in mouse models of autism.	2012-04-25	22539775

Patents

Sample Use Guides

In Vivo Use Guide

Mice were given GRN-529 at doses of 0.3, 1.0, or 3.0 mg/kg intraperitoneally or orally (preclinical model).

Route of Administration: Other

In Vitro Use Guide

HEK293 expressing either human or mouse mGluR5 were treated with different concentrations of GRN-059 (10(-10)-10(-5) M) to test its effect on the receptor.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:19:53 GMT 2025` Edited by `admin` on `Wed Apr 02 09:19:53 GMT 2025`
Record UNII	D77QDV7E9J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GRN-529

Code

English

(4-(DIFLUOROMETHOXY)-3-(2-(2-PYRIDINYL)ETHYNYL)PHENYL)(5,7-DIHYDRO-6H-PYRROLO(3,4-B)PYRIDIN-6-YL)METHANONE

Preferred Name

English

(4-(DIFLUOROMETHOXY)-3-(2-PYRIDIN-2-YLETHYNYL)PHENYL)-(5,7-DIHYDROPYRROLO(3,4-B)PYRIDIN-6-YL)METHANONE

Systematic Name

English

METHANONE, (4-(DIFLUOROMETHOXY)-3-(2-(2-PYRIDINYL)ETHYNYL)PHENYL)(5,7-DIHYDRO-6H-PYRROLO(3,4-B)PYRIDIN-6-YL)-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID501030348