brivaracetam   

GtoPdb Ligand ID: 9041

Synonyms: 2-(2-oxo-4-propylpyrrolidin-1-yl)butanamide | Briviact® | compound 83α [1] | UCB 34714 [3] | UCB-34714 | UCB34714
brivaracetam is an approved drug (EMA & FDA (2016))
Compound class: Synthetic organic
Comment: Brivaracetam is a 4-n-propyl analogue of levetiracetam with anticonvulsant properties [3]. Like levetiracetam this drug inhibits synaptic vesicle protein 2A (SV2A), but with 10X higher binding affinity. Brivaracetam is brain penetrant and has a fast onset of action [2]. It can also inhibit sodium channels.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 63.4
Molecular weight 212.15
XLogP 0.8
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCCC1CN(C(=O)C1)C(C(=O)N)CC
Isomeric SMILES CCC[C@H]1CN(C(=O)C1)[C@H](C(=O)N)CC
InChI InChI=1S/C11H20N2O2/c1-3-5-8-6-10(14)13(7-8)9(4-2)11(12)15/h8-9H,3-7H2,1-2H3,(H2,12,15)/t8-,9+/m1/s1
InChI Key MSYKRHVOOPPJKU-BDAKNGLRSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (EMA & FDA (2016))
IUPAC Name
(2S)-2-[(4R)-2-oxo-4-propylpyrrolidin-1-yl]butanamide
International Nonproprietary Names
INN number INN
8642 brivaracetam
Synonyms
2-(2-oxo-4-propylpyrrolidin-1-yl)butanamide | Briviact® | compound 83α [1] | UCB 34714 [3] | UCB-34714 | UCB34714
Database Links
BindingDB Ligand 50422531
CAS Registry No. 357336-20-0 (source: WHO INN record)
ChEMBL Ligand CHEMBL607400
DrugCentral Ligand 5068
GtoPdb PubChem SID 315661126
PubChem CID 9837243
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Wikipedia Brivaracetam