U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H11NO4
Molecular Weight 185.1772
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EGLUMETAD

SMILES

[H][C@@]12CC[C@@](N)(C(O)=O)[C@]1([H])[C@H]2C(O)=O

InChI

InChIKey=VTAARTQTOOYTES-RGDLXGNYSA-N
InChI=1S/C8H11NO4/c9-8(7(12)13)2-1-3-4(5(3)8)6(10)11/h3-5H,1-2,9H2,(H,10,11)(H,12,13)/t3-,4-,5-,8-/m0/s1

HIDE SMILES / InChI
Molecular Formula C8H11NO4
Molecular Weight 185.1772
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: http://adisinsight.springer.com/drugs/800008428 https://en.wikipedia.org/wiki/Eglumegad https://www.ncbi.nlm.nih.gov/pubmed/17712352 https://www.ncbi.nlm.nih.gov/pubmed/17204749

Talaglumetad (also known as LY-544344) is a bicyclohexane derivative patented by Eli Lilly and Company as modulators of metabotropic glutamate receptor. Talaglumetad acts as a prodrug of Eglumegad, a selective agonist of metabotropic glutamate receptors (mGluR2/3) and metabolized to release active compound by both human jejunal homogenates and rat liver homogenates. In experiments on mice, Talaglumetad was found to be as effective as diazepam for treating anxiety symptoms in several standard tests, but without producing any of the negative side effects of diazepam such as sedation and memory impairment.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 99.0 nM [Ki]
Agonist
2678
 94.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
200 mg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/16192835
unhealthy
n = 18
Health Status: unhealthy
Condition: panic disorder
Sex: M+F
Food Status: UNKNOWN
Population Size: 18
Sources:
https://pubmed.ncbi.nlm.nih.gov/16192835
Disc. AE: headache, Nausea...
AEs leading to
discontinuation/dose reduction:
headache (1 pt)
Nausea (1 pt)
allergic reaction (2 patients)
Dizziness (1 pt)
Sources:
https://pubmed.ncbi.nlm.nih.gov/16192835
AEs

AEs

AESignificanceDosePopulation
Dizziness 1 pt
Disc. AE
200 mg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/16192835
unhealthy
n = 18
Health Status: unhealthy
Condition: panic disorder
Sex: M+F
Food Status: UNKNOWN
Population Size: 18
Sources:
https://pubmed.ncbi.nlm.nih.gov/16192835
Nausea 1 pt
Disc. AE
200 mg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/16192835
unhealthy
n = 18
Health Status: unhealthy
Condition: panic disorder
Sex: M+F
Food Status: UNKNOWN
Population Size: 18
Sources:
https://pubmed.ncbi.nlm.nih.gov/16192835
headache 1 pt
Disc. AE
200 mg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/16192835
unhealthy
n = 18
Health Status: unhealthy
Condition: panic disorder
Sex: M+F
Food Status: UNKNOWN
Population Size: 18
Sources:
https://pubmed.ncbi.nlm.nih.gov/16192835
allergic reaction 2 patients
Disc. AE
200 mg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/16192835
unhealthy
n = 18
Health Status: unhealthy
Condition: panic disorder
Sex: M+F
Food Status: UNKNOWN
Population Size: 18
Sources:
https://pubmed.ncbi.nlm.nih.gov/16192835
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1537
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
1537
 no
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P0024X8
https://www.1pchem.com/search?query=1P0024X8
ApexBio Technology
B7328
https://www.apexbt.com/catalogsearch/result/?q=B7328
BLD Pharm
BD630456
http://www.bldpharm.com/search/Search.html?keyword=BD630456
BOC Sciences
118457-14-0
http://www.bocsci.com/description.asp?cas=118457-14-0
BOC Sciences
176199-48-7
http://www.bocsci.com/description.asp?cas=176199-48-7
Capot Chemical
18158
https://www.capotchem.com/search.do?q=18158
Chem Scene
CS-5052
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-5052
Chemspace
CSC015520788
https://chem-space.com/CSC015520788
Chemspace
CSC015596037
https://chem-space.com/CSC015596037
Chemspace
CSC015819205
https://chem-space.com/CSC015819205
Chemspace
CSC037827371
https://chem-space.com/CSC037827371
Chemspace
CSC055343638
https://chem-space.com/CSC055343638
Debye Scientific
DB-028800
https://www.debyesci.com/index.php?id=product&ext[cno]=DB-028800
Enamine
BBV-107321178
http://www.enaminestore.com/catalog/BBV-107321178
Enamine
BBV-77536105
http://www.enaminestore.com/catalog/BBV-77536105
Enamine
BBV-77594264
http://www.enaminestore.com/catalog/BBV-77594264
Enamine
BBV-77710497
http://www.enaminestore.com/catalog/BBV-77710497
Enamine
BBV-93151106
http://www.enaminestore.com/catalog/BBV-93151106
MedChem Express
HY-18941
https://www.medchemexpress.com/search.html?q=HY-18941&ft=&fa=&fp=
MolPort
MolPort-004-797-150
https://www.molport.com/shop/molecule-link/MolPort-004-797-150
MolPort
MolPort-023-276-716
https://www.molport.com/shop/molecule-link/MolPort-023-276-716
Molnova
M12658
https://www.molnova.com/en/serch-list.html?keywords=M12658
Tocris
3246
https://www.tocris.com/search.php?Type=QuickSearch&Value=3246
Toronto Research Chemicals
L503128
https://www.trc-canada.com/product-detail/?CatNum=L503128
Wonderchem
WD05L2P
http://www.wonder-chem.com/search.html?text=WD05L2P
eMolecules
31420520
https://orderbb.emolecules.com/search/#?query=31420520
eMolecules
36500492
https://orderbb.emolecules.com/search/#?query=36500492
eMolecules
48882962
https://orderbb.emolecules.com/search/#?query=48882962
mcule
MCULE-4405877923
https://mcule.com/MCULE-4405877923/
PubMed

PubMed

TitleDatePubMed
LY354740, a group II metabotropic glutamate receptor agonist with potential antiparkinsonian properties in rats.
1998 Oct
Cloning and functional expression of alternative spliced variants of the human metabotropic glutamate receptor 8.
1999 Apr 20
Potential anti-anxiety, anti-addictive effects of LY 354740, a selective group II glutamate metabotropic receptors agonist in animal models.
1999 Dec
[3H]-LY341495 as a novel antagonist radioligand for group II metabotropic glutamate (mGlu) receptors: characterization of binding to membranes of mGlu receptor subtype expressing cells.
1999 Oct
The role of metabotropic glutamate receptor (mGluR) ligands in parkinsonian muscle rigidity.
2000
Characterization of [(3)H]-LY354740 binding to rat mGlu2 and mGlu3 receptors expressed in CHO cells using semliki forest virus vectors.
2000 Jul 24
The antianxiety-like effects of antagonists of group I and agonists of group II and III metabotropic glutamate receptors after intrahippocampal administration.
2001 Oct
The role of striatal metabotropic glutamate receptors in Parkinson's disease.
2002
Modulation of DOI-induced increases in cortical BDNF expression by group II mGlu receptors.
2002 Sep
LY-354740 (Eli Lilly).
2003 Jan
Gateways to clinical trials.
2005 Jun
5-Hydroxytryptamine2A (5-HT2A) receptor regulation in rat prefrontal cortex: interaction of a phenethylamine hallucinogen and the metabotropic glutamate2/3 receptor agonist LY354740.
2006 Aug 7
The mGlu2/3 receptor agonist LY354740 suppresses immobilization stress-induced increase in rat prefrontal cortical BDNF mRNA expression.
2006 May 8
Pharmacological and pharmacokinetic properties of a structurally novel, potent, and selective metabotropic glutamate 2/3 receptor agonist: in vitro characterization of agonist (-)-(1R,4S,5S,6S)-4-amino-2-sulfonylbicyclo[3.1.0]-hexane-4,6-dicarboxylic acid (LY404039).
2007 Apr
Efficacy and tolerability of an mGlu2/3 agonist in the treatment of generalized anxiety disorder.
2008 Jun
Transepithelial transport of the group II metabotropic glutamate 2/3 receptor agonist (1S,2S,5R,6S)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylate (LY354740) and its prodrug (1S,2S,5R,6S)-2-[(2'S)-(2'-amino)propionyl]aminobicyclo[3.1.0]hexane-2,6-dicarboxylate (LY544344).
2009 Jan
Patents

Patents

20040077879
4
20040121962
4
20070265342
4
20080004321
4
WO2002055485
4

Sample Use Guides

In Vivo Use Guide
Curator's Comment: 8 or 16 mg twice per day (LY544344). LY544344 is a LY354740 prodrug that increases LY354740 bioavailability. https://www.ncbi.nlm.nih.gov/pubmed/17712352
100 or 200 mg (LY354740)
Route of Administration: Oral
In Vitro Use Guide
LY354740 failed to inhibit Dopamine D(2) receptor binding in both native striatal tissue homogenates and cloned receptors at concentrations up to 10 uM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:20:05 UTC 2023
Edited
by admin
on Sat Dec 16 16:20:05 UTC 2023
Record UNII
ONU5A67T2S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EGLUMETAD
INN   USAN  
USAN   INN  
Official Name English
EGLUMETAD [USAN]
Common Name English
EGLUMETAD ANHYDROUS
Common Name English
(+)-(1S,2S,5R,6S)-2-AMINOBICYCLO(3.1.0)HEXANE-2,6-DICARBOXYLIC ACID
Systematic Name English
EGLUMEGAD
Common Name English
eglumetad [INN]
Common Name English
BICYCLO(3.1.0)HEXANE-2,6-DICARBOXYLIC ACID, 2-AMINO-, (1S,2S,5R,6S)-
Common Name English
LY-354740
Code English
LY354740
Code English
Classification Tree Code System Code
NCI_THESAURUS C28197
Created by admin on Sat Dec 16 16:20:06 UTC 2023 , Edited by admin on Sat Dec 16 16:20:06 UTC 2023
Code System Code Type Description
MESH
C104753
Created by admin on Sat Dec 16 16:20:06 UTC 2023 , Edited by admin on Sat Dec 16 16:20:06 UTC 2023
PRIMARY
EPA CompTox
DTXSID40170094
Created by admin on Sat Dec 16 16:20:06 UTC 2023 , Edited by admin on Sat Dec 16 16:20:06 UTC 2023
PRIMARY
USAN
PP-77
Created by admin on Sat Dec 16 16:20:06 UTC 2023 , Edited by admin on Sat Dec 16 16:20:06 UTC 2023
PRIMARY
INN
8244
Created by admin on Sat Dec 16 16:20:06 UTC 2023 , Edited by admin on Sat Dec 16 16:20:06 UTC 2023
PRIMARY
NCI_THESAURUS
C76505
Created by admin on Sat Dec 16 16:20:06 UTC 2023 , Edited by admin on Sat Dec 16 16:20:06 UTC 2023
PRIMARY
ChEMBL
CHEMBL8759
Created by admin on Sat Dec 16 16:20:06 UTC 2023 , Edited by admin on Sat Dec 16 16:20:06 UTC 2023
PRIMARY
FDA UNII
ONU5A67T2S
Created by admin on Sat Dec 16 16:20:06 UTC 2023 , Edited by admin on Sat Dec 16 16:20:06 UTC 2023
PRIMARY
CAS
176199-48-7
Created by admin on Sat Dec 16 16:20:06 UTC 2023 , Edited by admin on Sat Dec 16 16:20:06 UTC 2023
PRIMARY
PUBCHEM
213056
Created by admin on Sat Dec 16 16:20:06 UTC 2023 , Edited by admin on Sat Dec 16 16:20:06 UTC 2023
PRIMARY
WIKIPEDIA
EGLUMEGAD
Created by admin on Sat Dec 16 16:20:06 UTC 2023 , Edited by admin on Sat Dec 16 16:20:06 UTC 2023
PRIMARY
SMS_ID
300000034213
Created by admin on Sat Dec 16 16:20:06 UTC 2023 , Edited by admin on Sat Dec 16 16:20:06 UTC 2023
PRIMARY
Related Record Type Details
METABOTROPIC GLUTAMATE RECEPTOR 3
TARGET -> AGONIST
METABOTROPIC GLUTAMATE RECEPTOR 2
TARGET -> AGONIST
Structure of EGLUMETAD MONOHYDRATE
SOLVATE->ANHYDROUS
Structure of EGLUMETAD MONOHYDRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of TALAGLUMETAD
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
Structure of EGLUMETAD
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966