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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H19N3O3
Molecular Weight 337.3725
Optical Activity ( - )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TALAMPANEL

SMILES

C[C@@H]1CC2=CC3=C(OCO3)C=C2C(=NN1C(C)=O)C4=CC=C(N)C=C4

InChI

InChIKey=JACAAXNEHGBPOQ-LLVKDONJSA-N
InChI=1S/C19H19N3O3/c1-11-7-14-8-17-18(25-10-24-17)9-16(14)19(21-22(11)12(2)23)13-3-5-15(20)6-4-13/h3-6,8-9,11H,7,10,20H2,1-2H3/t11-/m1/s1

HIDE SMILES / InChI
Molecular Formula C19H19N3O3
Molecular Weight 337.3725
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: http://adisinsight.springer.com/drugs/800009634 http://www.drugbank.ca/drugs/DB04982 https://www.ncbi.nlm.nih.gov/pubmed/12581229

Talampanel (TLP) was developed as a noncompetitive (allosteric) antagonist of the AMPA receptor. Talampanel does not act directly on the AMPA receptor, but at an allosteric site referred to as the GYKI receptor. Talampanel is being studied in the treatment of brain tumors and other brain disorders, such as epilepsy, Parkinson disease, amyotrophic lateral sclerosis, dyskinesias, glioblastoma, multiple sclerosis. It is a type of AMPA receptor antagonist. Dizziness has been the most commonly reported adverse event, with some sedation and ataxia, drowsiness and headaches reported at higher doses.

CNS Activity

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 3.1 µM [IC50]
Antagonist
2849
 28.1 µM [IC50]
Antagonist
2849
 23.9 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
95.5 μg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12581229
35 mg single, oral
dose: 35 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TALAMPANEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
489 μg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12581229
35 mg single, oral
dose: 35 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TALAMPANEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.3 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12581229
35 mg single, oral
dose: 35 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TALAMPANEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P007FHJ
https://www.1pchem.com/search?query=1P007FHJ
AstaTech
C14993
http://astatechinc.com/CPSResult.php?CRNO=C14993
BOC Sciences
143691-37-6
http://www.bocsci.com/description.asp?cas=143691-37-6
BOC Sciences
161832-65-1
http://www.bocsci.com/description.asp?cas=161832-65-1
Chem Scene
CS-5225
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-5225
ChemShuttle
157193
https://www.chemshuttle.com/catalogsearch/result/?q=157193
eMolecules
109810805
https://orderbb.emolecules.com/search/#?query=109810805
eMolecules
261682282
https://orderbb.emolecules.com/search/#?query=261682282
eMolecules
301171711
https://orderbb.emolecules.com/search/#?query=301171711
eMolecules
50423840
https://orderbb.emolecules.com/search/#?query=50423840
eNovation Chemicals
D621771
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D621771&searchbtn.x=0&searchbtn.y=0
Lab Network
LN01346087
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01346087
mcule
MCULE-7505509249
https://mcule.com/MCULE-7505509249/
mcule
MCULE-8674722309
https://mcule.com/MCULE-8674722309/
MedChem Express
HY-15079
https://www.medchemexpress.com/search.html?q=HY-15079&ft=&fa=&fp=
MolPort
MolPort-006-170-041
https://www.molport.com/shop/molecule-link/MolPort-006-170-041
MuseChem
I002075
https://www.musechem.com/product/I002075.html
MuseChem
I007178
https://www.musechem.com/product/I007178.html
MuseChem
M097518
https://www.musechem.com/product/M097518.html
ShangHai Biochempartner
BCP07340
http://www.biochempartner.com/search_BCP07340
Tocris
5032
https://www.tocris.com/search.php?Type=QuickSearch&Value=5032
PubMed

PubMed

TitleDatePubMed
Mechanism of inhibition of the GluA2 AMPA receptor channel opening by talampanel and its enantiomer: the stereochemistry of the 4-methyl group on the diazepine ring of 2,3-benzodiazepine derivatives.
2013-04-17
Talampanel suppresses the acute and chronic effects of seizures in a rodent neonatal seizure model.
2009-04
Talampanel improves the functional deficit after transient focal cerebral ischemia in rats. A 30-day follow up study.
2006-01-15
Unified pharmacogenetics-based parent-metabolite pharmacokinetic model incorporating acetylation polymorphism for talampanel in humans.
2005-08
Influence of LY 300164, an AMPA/kainate receptor antagonist upon the anticonvulsant action of antiepileptic drugs against aminophylline-induced seizures in mice.
2003-07-15
Talampanel, a new antiepileptic drug: single- and multiple-dose pharmacokinetics and initial 1-week experience in patients with chronic intractable epilepsy.
2003-01
Talampanel, a novel noncompetitive AMPA antagonist, is neuroprotective after traumatic brain injury in rats.
2001-10
AMPA receptor blockade improves levodopa-induced dyskinesia in MPTP monkeys.
2000-04-25
Influence of LY 300164, an antagonist of AMPA/kainate receptors, on the anticonvulsant activity of clonazepam.
1999-09-10
Patents

Patents

EP 492485
1
JP2008513466A
22
US 5536832
1

Sample Use Guides

In Vivo Use Guide
25 or 50mg Talampanel 3 times per day (during 52 weeks).
Route of Administration: Oral
In Vitro Use Guide
[3H]GYKI 53405 binds specifically to Xenopus brain membranes with KD and Bmax values of 4.5 microM and 35 pmol mg-1 protein respectively. Binding is increased in the presence of Mg2+ and is unaffected by AMPA or kainate.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:27:27 GMT 2025
Edited
by admin
on Mon Mar 31 19:27:27 GMT 2025
Record UNII
CVS43XG1L5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TALAMPANEL
INN   MI  
USAN   INN  
Official Name English
LY300164
Preferred Name English
1-[(8R)-5-(4-Aminophenyl)-8-methyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-7-yl]ethanone
Systematic Name English
GYKI-53773
Code English
TALAMPANEL [USAN]
Common Name English
TALAMPANEL [MI]
Common Name English
LY-300164
Code English
(-)-Talampanel
Common Name English
talampanel [INN]
Common Name English
7H-1,3-Dioxolo[4,5-h][2,3]benzodiazepine, 7-acetyl-5-(4-aminophenyl)-8,9-dihydro-8-methyl-, (8R)-
Systematic Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/09/631
Created by admin on Mon Mar 31 19:27:27 GMT 2025 , Edited by admin on Mon Mar 31 19:27:27 GMT 2025
NCI_THESAURUS C47795
Created by admin on Mon Mar 31 19:27:27 GMT 2025 , Edited by admin on Mon Mar 31 19:27:27 GMT 2025
FDA ORPHAN DRUG 274408
Created by admin on Mon Mar 31 19:27:27 GMT 2025 , Edited by admin on Mon Mar 31 19:27:27 GMT 2025
FDA ORPHAN DRUG 256007
Created by admin on Mon Mar 31 19:27:27 GMT 2025 , Edited by admin on Mon Mar 31 19:27:27 GMT 2025
Code System Code Type Description
INN
7820
Created by admin on Mon Mar 31 19:27:27 GMT 2025 , Edited by admin on Mon Mar 31 19:27:27 GMT 2025
PRIMARY
ChEMBL
CHEMBL61872
Created by admin on Mon Mar 31 19:27:27 GMT 2025 , Edited by admin on Mon Mar 31 19:27:27 GMT 2025
PRIMARY
CAS
161832-65-1
Created by admin on Mon Mar 31 19:27:27 GMT 2025 , Edited by admin on Mon Mar 31 19:27:27 GMT 2025
PRIMARY
DRUG BANK
DB04982
Created by admin on Mon Mar 31 19:27:27 GMT 2025 , Edited by admin on Mon Mar 31 19:27:27 GMT 2025
PRIMARY
SMS_ID
100000175298
Created by admin on Mon Mar 31 19:27:27 GMT 2025 , Edited by admin on Mon Mar 31 19:27:27 GMT 2025
PRIMARY
FDA UNII
CVS43XG1L5
Created by admin on Mon Mar 31 19:27:27 GMT 2025 , Edited by admin on Mon Mar 31 19:27:27 GMT 2025
PRIMARY
MERCK INDEX
m10434
Created by admin on Mon Mar 31 19:27:27 GMT 2025 , Edited by admin on Mon Mar 31 19:27:27 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
TALAMPANEL
Created by admin on Mon Mar 31 19:27:27 GMT 2025 , Edited by admin on Mon Mar 31 19:27:27 GMT 2025
PRIMARY
USAN
JJ-33
Created by admin on Mon Mar 31 19:27:27 GMT 2025 , Edited by admin on Mon Mar 31 19:27:27 GMT 2025
PRIMARY
EPA CompTox
DTXSID10167259
Created by admin on Mon Mar 31 19:27:27 GMT 2025 , Edited by admin on Mon Mar 31 19:27:27 GMT 2025
PRIMARY
NCI_THESAURUS
C38139
Created by admin on Mon Mar 31 19:27:27 GMT 2025 , Edited by admin on Mon Mar 31 19:27:27 GMT 2025
PRIMARY
PUBCHEM
164509
Created by admin on Mon Mar 31 19:27:27 GMT 2025 , Edited by admin on Mon Mar 31 19:27:27 GMT 2025
PRIMARY
Related Record Type Details
AMPA-SELECTIVE GLUTAMATE RECEPTOR 2
TARGET->NEGATIVE ALLOSTERIC MODULATOR (NAM)
Structure of TALAMPANEL, (S)-
ENANTIOMER -> ENANTIOMER
Related Record Type Details
Structure of TALAMPANEL
ACTIVE MOIETY
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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