levetiracetam   Click here for help

GtoPdb Ligand ID: 6826

Synonyms: Keppra® | Spritam® | UCB L059 | UCB-L 059
Approved drug PDB Ligand
levetiracetam is an approved drug (FDA (1999), EMA (2000))
Compound class: Synthetic organic
Comment: In addition to being assigned an INN in its own right, levetiracetam is the biologically active enantiomer of racemic formulation etiracetam, also assigned an INN.
Levetiracetam is the active compound in Spritam®, the first 3D printed pill to be approved by the US FDA (in August 2015).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: levetiracetam

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 63.4
Molecular weight 170.11
XLogP -0.63
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCC(N1CCCC1=O)C(=O)N
Isomeric SMILES CC[C@H](N1CCCC1=O)C(=O)N
InChI InChI=1S/C8H14N2O2/c1-2-6(8(9)12)10-5-3-4-7(10)11/h6H,2-5H2,1H3,(H2,9,12)/t6-/m0/s1
InChI Key HPHUVLMMVZITSG-LURJTMIESA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1999), EMA (2000))
IUPAC Name Click here for help
(2S)-2-(2-oxopyrrolidin-1-yl)butanamide
International Nonproprietary Names Click here for help
INN number INN
4516 etiracetam
6450 levetiracetam
Synonyms Click here for help
Keppra® | Spritam® | UCB L059 | UCB-L 059
Database Links Click here for help
CAS Registry No. 102767-28-2
ChEBI CHEBI:6437
ChEMBL Ligand CHEMBL1286
DrugCentral Ligand 1563
GtoPdb PubChem SID 178103432
PubChem CID 5284583
RCSB PDB Ligand UKX
Search Google for chemical match using the InChIKey HPHUVLMMVZITSG-LURJTMIESA-N
Search Google for chemicals with the same backbone HPHUVLMMVZITSG
Search PubMed clinical trials levetiracetam
Search PubMed titles levetiracetam
Search PubMed titles/abstracts levetiracetam
UniChem Compound Search for chemical match using the InChIKey HPHUVLMMVZITSG-LURJTMIESA-N
UniChem Connectivity Search for chemical match using the InChIKey HPHUVLMMVZITSG-LURJTMIESA-N
Wikipedia Levetiracetam