brivaracetam   Click here for help

GtoPdb Ligand ID: 9041

Synonyms: 2-(2-oxo-4-propylpyrrolidin-1-yl)butanamide | Briviact® | compound 83α [1] | UCB 34714 [3] | UCB-34714 | UCB34714
Approved drug
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.
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2D Structure
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Physico-chemical Properties
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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
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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
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
synaptic vesicle glycoprotein 2A Primary target of this compound Rn Inhibitor Inhibition 7.0 pIC50 - 1
pIC50 7.0 (IC50 1x10-7 M) [1]
Description: In vitro inhibitory activity against [3H](2S)-2-[4-(3-azidophenyl)-2-oxopyrrolidin-1-yl]butanamide binding to levetiracetam binding site, in rat brain homogenate.