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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H16N2O5
Molecular Weight 256.2551
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TALAGLUMETAD

SMILES

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

InChI

InChIKey=UPSXYNJDCKOCFD-QIMCWZKGSA-N
InChI=1S/C11H16N2O5/c1-4(12)8(14)13-11(10(17)18)3-2-5-6(7(5)11)9(15)16/h4-7H,2-3,12H2,1H3,(H,13,14)(H,15,16)(H,17,18)/t4-,5-,6-,7-,11-/m0/s1

HIDE SMILES / InChI
Molecular Formula C11H16N2O5
Molecular Weight 256.2551
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
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
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
 99.0 nM [Ki]
Agonist
2752
 94.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
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
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
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/16192835
Disc. AE: allergic reaction, Dizziness...
AEs leading to
discontinuation/dose reduction:
allergic reaction (2 patients)
Dizziness (1 pt)
headache (1 pt)
Nausea (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
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
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/16192835
Nausea 1 pt
Disc. AE
200 mg 1 times / day multiple, oral
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
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/16192835
headache 1 pt
Disc. AE
200 mg 1 times / day multiple, oral
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
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/16192835
allergic reaction 2 patients
Disc. AE
200 mg 1 times / day multiple, oral
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
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/16192835
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
2052
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
2052
 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
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
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
mcule
MCULE-4405877923
https://mcule.com/MCULE-4405877923/
MedChem Express
HY-18941
https://www.medchemexpress.com/search.html?q=HY-18941&ft=&fa=&fp=
Molnova
M12658
https://www.molnova.com/en/serch-list.html?keywords=M12658
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
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
PubMed

PubMed

TitleDatePubMed
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).
2009-01
Efficacy and tolerability of an mGlu2/3 agonist in the treatment of generalized anxiety disorder.
2008-06
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).
2007-04
5-Hydroxytryptamine2A (5-HT2A) receptor regulation in rat prefrontal cortex: interaction of a phenethylamine hallucinogen and the metabotropic glutamate2/3 receptor agonist LY354740.
2006-08-07
The mGlu2/3 receptor agonist LY354740 suppresses immobilization stress-induced increase in rat prefrontal cortical BDNF mRNA expression.
2006-05-08
Gateways to clinical trials.
2005-06
LY-354740 (Eli Lilly).
2003-01
Modulation of DOI-induced increases in cortical BDNF expression by group II mGlu receptors.
2002-09
The role of striatal metabotropic glutamate receptors in Parkinson's disease.
2002
The antianxiety-like effects of antagonists of group I and agonists of group II and III metabotropic glutamate receptors after intrahippocampal administration.
2001-10
Characterization of [(3)H]-LY354740 binding to rat mGlu2 and mGlu3 receptors expressed in CHO cells using semliki forest virus vectors.
2000-07-24
The role of metabotropic glutamate receptor (mGluR) ligands in parkinsonian muscle rigidity.
2000
Potential anti-anxiety, anti-addictive effects of LY 354740, a selective group II glutamate metabotropic receptors agonist in animal models.
1999-12
[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.
1999-10
Cloning and functional expression of alternative spliced variants of the human metabotropic glutamate receptor 8.
1999-04-20
Synthesis, pharmacological characterization, and molecular modeling of heterobicyclic amino acids related to (+)-2-aminobicyclo[3.1.0] hexane-2,6-dicarboxylic acid (LY354740): identification of two new potent, selective, and systemically active agonists for group II metabotropic glutamate receptors.
1999-03-25
LY354740, a group II metabotropic glutamate receptor agonist with potential antiparkinsonian properties in rats.
1998-10
Characterization of [3H]-(2S,2'R,3'R)-2-(2',3'-dicarboxy-cyclopropyl)glycine ([3H]-DCG IV) binding to metabotropic mGlu2 receptor-transfected cell membranes.
1998-02
A novel orally active group 2 metabotropic glutamate receptor agonist: LY354740.
1997-04-14
LY354740 is a potent and highly selective group II metabotropic glutamate receptor agonist in cells expressing human glutamate receptors.
1997-01
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 Mon Mar 31 18:21:13 GMT 2025
Edited
by admin
on Mon Mar 31 18:21:13 GMT 2025
Record UNII
2OXQ1Z504M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TALAGLUMETAD
INN  
INN  
Official Name English
LY-544344
Preferred Name English
(1S,2S,5R,6S)-2-(L-ALANYLAMINO)BICYCLO(3.1.0)HEXANE-2,6-DICARBOXYLIC ACID
Systematic Name English
talaglumetad [INN]
Common Name English
BICYCLO(3.1.0)HEXANE-2,6-DICARBOXYLIC ACID, 2-(((2S)-2-AMINO-1-OXOPROPYL)AMINO)-, (1S,2S,5R,6S)-
Common Name English
LY544344
Code English
Classification Tree Code System Code
NCI_THESAURUS C28197
Created by admin on Mon Mar 31 18:21:13 GMT 2025 , Edited by admin on Mon Mar 31 18:21:13 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID801351482
Created by admin on Mon Mar 31 18:21:13 GMT 2025 , Edited by admin on Mon Mar 31 18:21:13 GMT 2025
PRIMARY
PUBCHEM
9857256
Created by admin on Mon Mar 31 18:21:13 GMT 2025 , Edited by admin on Mon Mar 31 18:21:13 GMT 2025
PRIMARY
ChEMBL
CHEMBL1189257
Created by admin on Mon Mar 31 18:21:13 GMT 2025 , Edited by admin on Mon Mar 31 18:21:13 GMT 2025
PRIMARY
NCI_THESAURUS
C81616
Created by admin on Mon Mar 31 18:21:13 GMT 2025 , Edited by admin on Mon Mar 31 18:21:13 GMT 2025
PRIMARY
SMS_ID
300000034381
Created by admin on Mon Mar 31 18:21:13 GMT 2025 , Edited by admin on Mon Mar 31 18:21:13 GMT 2025
PRIMARY
INN
8539
Created by admin on Mon Mar 31 18:21:13 GMT 2025 , Edited by admin on Mon Mar 31 18:21:13 GMT 2025
PRIMARY
FDA UNII
2OXQ1Z504M
Created by admin on Mon Mar 31 18:21:13 GMT 2025 , Edited by admin on Mon Mar 31 18:21:13 GMT 2025
PRIMARY
CAS
441765-98-6
Created by admin on Mon Mar 31 18:21:13 GMT 2025 , Edited by admin on Mon Mar 31 18:21:13 GMT 2025
PRIMARY
Related Record Type Details
Structure of TALAGLUMETAD HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of EGLUMETAD
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
Structure of EGLUMETAD
ACTIVE MOIETY
NIH
NCATS
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