perampanel   Click here for help

GtoPdb Ligand ID: 7050

Synonyms: E2007 | ER-155055-90 | Fycompa®
Approved drug PDB Ligand
perampanel is an approved drug (FDA and EMA (2012))
Compound class: Synthetic organic
Comment: Perampanel is an anticonvulsant. The drug is administered as perampanel hydrate.
It is first and only FDA-approved non-competitive AMPA (alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid) receptor antagonist.
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View more information in the IUPHAR Pharmacology Education Project: perampanel

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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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 3
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 58.16
Molecular weight 349.12
XLogP 5.29
No. Lipinski's rules broken 1

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 N#Cc1ccccc1c1cc(cn(c1=O)c1ccccc1)c1ccccn1
Isomeric SMILES N#Cc1ccccc1c1cc(cn(c1=O)c1ccccc1)c1ccccn1
InChI InChI=1S/C23H15N3O/c24-15-17-8-4-5-11-20(17)21-14-18(22-12-6-7-13-25-22)16-26(23(21)27)19-9-2-1-3-10-19/h1-14,16H
InChI Key PRMWGUBFXWROHD-UHFFFAOYSA-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/)
No information available.
Summary of Clinical Use Click here for help
Perampanel is used to treat seizures in adults and children (>12 yrs). In June 2015, the US FDA expanded approval to include the treatment of patients (≥12 years old) suffering from primary generalized tonic-clonic (PGTC) seizures.
Fycompa® is available in tablet form and as a bioequivalent oral suspension (Fycompa® CIII Oral Suspension, FDA approved in May 2016).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Perampanel appears to decrease neuronal excitation by ihibiting the ionic glutamate (AMPA) receptors (GRIA1-4), although downstream mechanisms causing its anti-seizure action remain undetermined.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)