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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

[H][C@@]12CC[C@@](NC(=O)[C@H](C)N)(C(O)=O)[C@]1([H])[C@H]2C(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 4 / 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.

Approval Year

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:
unhealthy
n = 18
Health Status: unhealthy
Condition: panic disorder
Sex: M+F
Food Status: UNKNOWN
Population Size: 18
Sources:
Disc. AE: headache, Nausea...
AEs leading to
discontinuation/dose reduction:
headache (1 pt)
Nausea (1 pt)
allergic reaction (2 patients)
Dizziness (1 pt)
Sources:
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:
unhealthy
n = 18
Health Status: unhealthy
Condition: panic disorder
Sex: M+F
Food Status: UNKNOWN
Population Size: 18
Sources:
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:
unhealthy
n = 18
Health Status: unhealthy
Condition: panic disorder
Sex: M+F
Food Status: UNKNOWN
Population Size: 18
Sources:
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:
unhealthy
n = 18
Health Status: unhealthy
Condition: panic disorder
Sex: M+F
Food Status: UNKNOWN
Population Size: 18
Sources:
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:
unhealthy
n = 18
Health Status: unhealthy
Condition: panic disorder
Sex: M+F
Food Status: UNKNOWN
Population Size: 18
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
LY354740 is a potent and highly selective group II metabotropic glutamate receptor agonist in cells expressing human glutamate receptors.
1997 Jan
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 Feb
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 Mar 25
[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
The antianxiety-like effects of antagonists of group I and agonists of group II and III metabotropic glutamate receptors after intrahippocampal administration.
2001 Oct
Modulation of DOI-induced increases in cortical BDNF expression by group II mGlu receptors.
2002 Sep
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
Patents

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
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 Fri Dec 15 16:11:18 GMT 2023
Edited
by admin
on Fri Dec 15 16:11:18 GMT 2023
Record UNII
2OXQ1Z504M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TALAGLUMETAD
INN  
INN  
Official 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
LY-544344
Code English
LY544344
Code English
Classification Tree Code System Code
NCI_THESAURUS C28197
Created by admin on Fri Dec 15 16:11:18 GMT 2023 , Edited by admin on Fri Dec 15 16:11:18 GMT 2023
Code System Code Type Description
PUBCHEM
9857256
Created by admin on Fri Dec 15 16:11:18 GMT 2023 , Edited by admin on Fri Dec 15 16:11:18 GMT 2023
PRIMARY
ChEMBL
CHEMBL1189257
Created by admin on Fri Dec 15 16:11:18 GMT 2023 , Edited by admin on Fri Dec 15 16:11:18 GMT 2023
PRIMARY
NCI_THESAURUS
C81616
Created by admin on Fri Dec 15 16:11:18 GMT 2023 , Edited by admin on Fri Dec 15 16:11:18 GMT 2023
PRIMARY
SMS_ID
300000034381
Created by admin on Fri Dec 15 16:11:18 GMT 2023 , Edited by admin on Fri Dec 15 16:11:18 GMT 2023
PRIMARY
INN
8539
Created by admin on Fri Dec 15 16:11:18 GMT 2023 , Edited by admin on Fri Dec 15 16:11:18 GMT 2023
PRIMARY
FDA UNII
2OXQ1Z504M
Created by admin on Fri Dec 15 16:11:18 GMT 2023 , Edited by admin on Fri Dec 15 16:11:18 GMT 2023
PRIMARY
CAS
441765-98-6
Created by admin on Fri Dec 15 16:11:18 GMT 2023 , Edited by admin on Fri Dec 15 16:11:18 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
ACTIVE MOIETY