WAY-213613

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H13BrF2N2O4
Molecular Weight	415.186
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@@H](CC(=O)NC1=CC=C(OC2=CC(F)=C(F)C=C2Br)C=C1)C(O)=O

InChI

InChIKey=BNYDDAAZMBUFRG-ZDUSSCGKSA-N

InChI=1S/C16H13BrF2N2O4/c17-10-5-11(18)12(19)6-14(10)25-9-3-1-8(2-4-9)21-15(22)7-13(20)16(23)24/h1-6,13H,7,20H2,(H,21,22)(H,23,24)/t13-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C16H13BrF2N2O4
Molecular Weight	415.186
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16014807
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/19364521 | https://www.ncbi.nlm.nih.gov/pubmed/17088867

WAY-213613 to be a potent, EAAT2-preferring, competitive nonsubstrate inhibitor of EAAT2. WAY-213613 was devoid of either agonist or antagonist activity at the ionotropic NMDA and AMPA receptors expressed natively in cultured hippocampal neurons, or at the human mGlu receptors 1, 2, and 4 heterologously expressed in stable cell lines. It is used in scientific research into the function of the glutamate transporters.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Excitatory amino acid transporter 2 2 Target ID: CHEMBL4973 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16014807	Inhibitor 8297	85.0 nM [IC50]
Excitatory amino acid transporter 1 1 Target ID: CHEMBL3085 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16014807	Inhibitor 8297	5.0 µM [IC50]
Excitatory amino acid transporter 3 1 Target ID: CHEMBL2721 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16014807	Inhibitor 8297	3.8 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Characterization of novel aryl-ether, biaryl, and fluorene aspartic acid and diaminopropionic acid analogs as potent inhibitors of the high-affinity glutamate transporter EAAT2.	2005 Oct	16014807
Transporters for L-glutamate: an update on their molecular pharmacology and pathological involvement.	2007 Jan	17088867
Protein kinase C-dependent trafficking of glutamate transporters excitatory amino acid carrier 1 and glutamate transporter 1b in cultured cerebellar granule cells.	2009 Jul 7	19364521
Differential regulation of glutamate transporter subtypes by pro-inflammatory cytokine TNF-α in cortical astrocytes from a rat model of amyotrophic lateral sclerosis.	2014	24836816

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Еhe effect of WAY-213613 on glutamateinduced currents in oocytes was examined. Application of 30 uM WAY-213613 (or indeed the other three compounds described in this study) to EAAT2 injected oocytes failed to induce a transporter-like current, indicating the compound to be a nonsubstrate.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 19:04:52 GMT 2023` Edited by `admin` on `Sat Dec 16 19:04:52 GMT 2023`
Record UNII	8QTE6AZR4F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

WAY-213613

Code

English

L-ASPARAGINE, N-(4-(2-BROMO-4,5-DIFLUOROPHENOXY)PHENYL)-

Systematic Name

English

WAY-213,613

Code

English

N-(4-(2-BROMO-4,5-DIFLUOROPHENOXY)PHENYL)-L-ASPARAGINE

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

WAY-213,613