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Details

Stereochemistry ACHIRAL
Molecular Formula C21H19F3N2O4S.ClH
Molecular Weight 488.908
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LY-487379 HYDROCHLORIDE

SMILES

Cl.COC1=CC=CC=C1OC2=CC=C(C=C2)N(CC3=CC=CN=C3)S(=O)(=O)CC(F)(F)F

InChI

InChIKey=LPWFRDWTOKLHJC-UHFFFAOYSA-N
InChI=1S/C21H19F3N2O4S.ClH/c1-29-19-6-2-3-7-20(19)30-18-10-8-17(9-11-18)26(14-16-5-4-12-25-13-16)31(27,28)15-21(22,23)24;/h2-13H,14-15H2,1H3;1H

HIDE SMILES / InChI
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
Molecular Formula C21H19F3N2O4S
Molecular Weight 452.447
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/14500736 | https://www.ncbi.nlm.nih.gov/pubmed/16123306

N-(4-(2-Methoxyphenoxy)-phenyl-N-(2,2,2-trifluoroethylsulfonyl)-pyrid-3-ylmethylamine (LY487379) is a selective positive allosteric modulator at metabotropic glutamate subtype 2 receptors (mGluR2). The compound exerts antipsychotic and anxiolytic actions.

CNS Activity

Originator

Eli Lilly
237
Curator's Comment: # Eli Lilly

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Positive Allosteric Modulator
179
 1.7 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Discovery of allosteric potentiators for the metabotropic glutamate 2 receptor: synthesis and subtype selectivity of N-(4-(2-methoxyphenoxy)phenyl)-N-(2,2,2- trifluoroethylsulfonyl)pyrid-3-ylmethylamine.
2003 Jul 17
Pharmacological characterization and identification of amino acids involved in the positive modulation of metabotropic glutamate receptor subtype 2.
2003 Oct
Metabotropic glutamate receptor 2 modulates excitatory synaptic transmission in the rat globus pallidus.
2005
A selective allosteric potentiator of metabotropic glutamate (mGlu) 2 receptors has effects similar to an orthosteric mGlu2/3 receptor agonist in mouse models predictive of antipsychotic activity.
2005 Dec
Stimulation of the metabotropic glutamate 2/3 receptor attenuates social novelty discrimination deficits induced by neonatal phencyclidine treatment.
2007 Jul
A novel family of potent negative allosteric modulators of group II metabotropic glutamate receptors.
2007 Jul
The difference in effect of mGlu2/3 and mGlu5 receptor agonists on cognitive impairment induced by MK-801.
2010 Aug 10
Effects of a positive allosteric modulator of group II metabotropic glutamate receptors, LY487379, on cognitive flexibility and impulsive-like responding in rats.
2010 Dec
On the mechanism of anti-hyperthermic effects of LY379268 and LY487379, group II mGlu receptors activators, in the stress-induced hyperthermia in singly housed mice.
2012 Jan
Patents

Patents

WO2004106932A1
2
WO2011122701A1
2

Sample Use Guides

In Vivo Use Guide
rats: 30 mg/kg
Route of Administration: Intraperitoneal
In Vitro Use Guide
3-30 uM LY487379 potentiates the effect of DCG-IV on medial perforant path-dentate gyrus synapses in rat hippocampal slices.
Substance Class Chemical
Created
by admin
on Sat Dec 16 18:11:27 GMT 2023
Edited
by admin
on Sat Dec 16 18:11:27 GMT 2023
Record UNII
UQP3N7RUC3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LY-487379 HYDROCHLORIDE
Code English
2,2,2-TRIFLUORO-N-(4-(2-METHOXYPHENOXY)PHENYL)-N-(PYRIDIN-3-YLMETHYL)ETHANESULFONAMIDE HYDROCHLORIDE
Systematic Name English
ETHANESULFONAMIDE, 2,2,2-TRIFLUORO-N-(4-(2-METHOXYPHENOXY)PHENYL)-N-(3-PYRIDINYLMETHYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
ETHANESULFONAMIDE, 2,2,2-TRIFLUORO-N-(4-(2-METHOXYPHENOXY)PHENYL)-N-(3-PYRIDINYLMETHYL)-, MONOHYDROCHLORIDE
Systematic Name English
Code System Code Type Description
FDA UNII
UQP3N7RUC3
Created by admin on Sat Dec 16 18:11:27 GMT 2023 , Edited by admin on Sat Dec 16 18:11:27 GMT 2023
PRIMARY
CAS
353229-59-1
Created by admin on Sat Dec 16 18:11:27 GMT 2023 , Edited by admin on Sat Dec 16 18:11:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID50719337
Created by admin on Sat Dec 16 18:11:27 GMT 2023 , Edited by admin on Sat Dec 16 18:11:27 GMT 2023
PRIMARY
PUBCHEM
56972206
Created by admin on Sat Dec 16 18:11:27 GMT 2023 , Edited by admin on Sat Dec 16 18:11:27 GMT 2023
PRIMARY
Related Record Type Details
Structure of LY-487379
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of LY-487379
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