Perampanel
Identification
- Summary
Perampanel is a non-competitive AMPA glutamate receptor antagonist used to treat partial-onset seizures with or without secondarily generalized seizures, and as adjunctive treatment of primary generalized tonic-clonic seizures in patients with epilepsy.
- Brand Names
- Fycompa
- Generic Name
- Perampanel
- DrugBank Accession Number
- DB08883
- Background
Perampanel is a noncompetitive AMPA glutamate receptor antagonist. It is marketed under the name Fycompa™ and is indicated as an adjunct in patients over 12 years old for the treatment of partial-onset seizures that may or may not occur with generalized seizures. The FDA label includes an important black-boxed warning of serious or life-threatening behavioral and psychiatric reactions in patients taking Fycompa™.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Perampanel (DB08883)
- Weight
- Average: 349.393
Monoisotopic: 349.121512115 - Chemical Formula
- C23H15N3O
- Synonyms
- 3-(2-Cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one
- Perampanel
- Pérampanel
- Perampanelum
- External IDs
- E-2007
- E2007
- ER-155055-90
Pharmacology
- Indication
Used in patients over 12 years old for the treatment of partial-onset seizures that may or may not occur with generalized seizures.
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- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
Perampanel is involved in inhibiting neuronal excitation in the central nervous system leading to such effects as decreased pyschomotor performance.
- Mechanism of action
The exact mechanism of action of perampanel in seizures is not yet determined, but it is known that perampanel decreases neuronal excitation by non-competitive ihibition of the AMPA receptor.
Target Actions Organism AGlutamate receptor 1 antagonistHumans - Absorption
After oral adminitration, perampanel is absorbed rapidly and completely.
- Volume of distribution
The volume of distribution of perampanel was not quantified.
- Protein binding
Perampanel is 95-96% plasma protein bound with most binding to the plasma proteins α1-acid glycoprotein and albumin.
- Metabolism
Perampanel is highly metabolized by CYP3A4 and/or CYP3A5 primary oxidation and by sequential glucuronidation.
- Route of elimination
Perampanel is eliminated mostely in the feces (48%) and to a lesser exten in the urine (22%).
- Half-life
Perampanel has a long elmination half-life of about 105 hours.
- Clearance
In healthy patients, perampanel has a clearance of about 12 mL/min.
- Adverse Effects
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The FDA label includes an important warning of serious or life-threatening behavioral and psychiatric adverse reactions including aggression, hostility, irritability, anger, and homicidal thoughts in patients taking perampanel.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine Perampanel may increase the central nervous system depressant (CNS depressant) activities of 1,2-Benzodiazepine. Abametapir The serum concentration of Perampanel can be increased when it is combined with Abametapir. Abatacept The metabolism of Perampanel can be increased when combined with Abatacept. Abemaciclib The metabolism of Abemaciclib can be increased when combined with Perampanel. Abiraterone The serum concentration of Perampanel can be increased when it is combined with Abiraterone. Acalabrutinib The metabolism of Perampanel can be increased when combined with Acalabrutinib. Acenocoumarol The metabolism of Acenocoumarol can be increased when combined with Perampanel. Acetaminophen The metabolism of Perampanel can be increased when combined with Acetaminophen. Acetazolamide Perampanel may increase the central nervous system depressant (CNS depressant) activities of Acetazolamide. Acetophenazine Perampanel may increase the central nervous system depressant (CNS depressant) activities of Acetophenazine. 
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- Take with or without food. Food slows the rate of absorption but not the extent.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Product Ingredients
Ingredient UNII CAS InChI Key Perampanel hydrate 8LIX22217M 1571982-04-1 PDWMJDKMSASBNE-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Fycompa Tablet, film coated 8 mg Oral Eisai Limited 2016-09-07 Not applicable EU 
Fycompa Tablet, film coated 6 mg Oral Eisai Limited 2016-09-07 Not applicable EU Fycompa Tablet, film coated 2 mg Oral Eisai Limited 2016-09-07 Not applicable EU Fycompa Tablet, film coated 4 mg Oral Eisai Limited 2016-09-07 Not applicable EU Fycompa Suspension 0.5 mg/1mL Oral Delpharm Huningue 2016-04-30 Not applicable US 
Fycompa Tablet 8.0 mg Oral Eisai Limited 2013-06-19 Not applicable Canada 
Fycompa Tablet, film coated 12 mg Oral Eisai Limited 2016-09-07 Not applicable EU Fycompa Tablet 12.0 mg Oral Eisai Limited 2013-05-17 Not applicable Canada Fycompa Tablet, film coated 10 mg Oral Eisai Limited 2016-09-07 Not applicable EU Fycompa Tablet, film coated 2 mg Oral Eisai Limited 2016-09-07 Not applicable EU - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Fycompa Perampanel (2 mg/1) + Perampanel (4 mg/1) Kit Oral Eisai Inc. 2012-10-22 2012-10-15 US Fycompa Perampanel (2 mg/1) + Perampanel (4 mg/1) Kit Oral Eisai Inc. 2012-10-22 2012-10-15 US
Categories
- ATC Codes
- N03AX22 — Perampanel
- Drug Categories
- AMPA Receptor Antagonists
- Anticonvulsants
- Central Nervous System Depressants
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2B6 Inducers
- Cytochrome P-450 CYP2B6 Inducers (weak)
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Substrates
- Miscellaneous Anticonvulsants
- Nervous System
- Noncompetitive AMPA Glutamate Receptor Antagonist
- Pyridines
- Receptors, AMPA, antagonists & inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyridines and derivatives
- Sub Class
- Bipyridines and oligopyridines
- Direct Parent
- Bipyridines and oligopyridines
- Alternative Parents
- Phenylpyridines / Benzonitriles / Pyridinones / Dihydropyridines / Heteroaromatic compounds / Lactams / Nitriles / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds show 2 more
- Substituents
- 3-phenylpyridine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Benzonitrile / Bipyridine / Carbonitrile / Dihydropyridine / Heteroaromatic compound / Hydrocarbon derivative show 11 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- nitrile, pyridone, bipyridines (CHEBI:71013)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- H821664NPK
- CAS number
- 380917-97-5
- InChI Key
- PRMWGUBFXWROHD-UHFFFAOYSA-N
- 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
- IUPAC Name
- 2-{6'-oxo-1'-phenyl-1',6'-dihydro-[2,3'-bipyridine]-5'-yl}benzonitrile
- SMILES
- O=C1N(C=C(C=C1C1=CC=CC=C1C#N)C1=NC=CC=C1)C1=CC=CC=C1
References
- Synthesis Reference
Francesco Fontana, "METHODS FOR PREPARING INTERMEDIATES OF PERAMPANEL." U.S. Patent US20130109862, issued May 02, 2013.
US20130109862- General References
- Hanada T, Hashizume Y, Tokuhara N, Takenaka O, Kohmura N, Ogasawara A, Hatakeyama S, Ohgoh M, Ueno M, Nishizawa Y: Perampanel: a novel, orally active, noncompetitive AMPA-receptor antagonist that reduces seizure activity in rodent models of epilepsy. Epilepsia. 2011 Jul;52(7):1331-40. doi: 10.1111/j.1528-1167.2011.03109.x. Epub 2011 Jun 2. [Article]
- External Links
- KEGG Drug
- D08964
- PubChem Compound
- 9924495
- PubChem Substance
- 347827808
- ChemSpider
- 8100130
- BindingDB
- 50184410
- 1356552
- ChEBI
- 71013
- ChEMBL
- CHEMBL1214124
- ZINC
- ZINC000030691797
- PDBe Ligand
- 6ZP
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Perampanel
- AHFS Codes
- 28:12.92 — Miscellaneous Anticonvulsants
- PDB Entries
- 5l1f
- FDA label
- Download (611 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Epilepsies 1 4 Completed Treatment Grand mal Generalized tonic-clonic seizure / Partial-Onset Seizures / Secondarily Generalized Seizures 1 4 Completed Treatment Primary Brain Tumors 1 4 Not Yet Recruiting Treatment Epilepsies 1 4 Recruiting Prevention Epilepsy, Intractable / Gliomas, Malignant / Seizures Disorders 1 4 Recruiting Treatment Epilepsies 1 4 Suspended Treatment Healthy Volunteers 1 4 Terminated Treatment Epilepsies 1 4 Unknown Status Not Available Electroencephalography 1 4 Withdrawn Treatment Epilepsy, Localization Related 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Kit Oral Suspension Oral Suspension Oral 0.5 mg/ml Suspension Oral 0.5 mg / mL Suspension Oral 0.5 mg/1mL Tablet Oral 10 mg/1 Tablet Oral 10.0 mg Tablet Oral 12 mg/1 Tablet Oral 12.0 mg Tablet Oral 2 mg/1 Tablet Oral 2.0 mg Tablet Oral 4 mg/1 Tablet Oral 4.0 mg Tablet Oral 6 mg/1 Tablet Oral 6.0 mg Tablet Oral 8 mg/1 Tablet Oral 8.0 mg Tablet, film coated Oral Tablet, film coated Oral 10 mg Tablet, film coated Oral 12 mg Tablet, film coated Oral 2 mg Tablet, film coated Oral 4 mg Tablet, film coated Oral 6 mg Tablet, film coated Oral 8 mg Tablet, coated Oral 2 mg Tablet, coated Oral 4 mg Tablet, coated Oral 8 mg Tablet, coated Oral 12 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6949571 No 2005-09-27 2021-06-08 US US8772497 No 2014-07-08 2026-05-16 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Practically insoluble in water. From FDA label. - Predicted Properties
Property Value Source Water Solubility 0.0056 mg/mL ALOGPS logP 3.54 ALOGPS logP 4.11 ChemAxon logS -4.8 ALOGPS pKa (Strongest Basic) 4.01 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 56.99 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 104.74 m3·mol-1 ChemAxon Polarizability 38.03 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Pdz domain binding
- Specific Function
- Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a co...
- Gene Name
- GRIA1
- Uniprot ID
- P42261
- Uniprot Name
- Glutamate receptor 1
- Molecular Weight
- 101505.245 Da
References
- Hanada T, Hashizume Y, Tokuhara N, Takenaka O, Kohmura N, Ogasawara A, Hatakeyama S, Ohgoh M, Ueno M, Nishizawa Y: Perampanel: a novel, orally active, noncompetitive AMPA-receptor antagonist that reduces seizure activity in rodent models of epilepsy. Epilepsia. 2011 Jul;52(7):1331-40. doi: 10.1111/j.1528-1167.2011.03109.x. Epub 2011 Jun 2. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInducer
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Fycompa (Perampanel) FDA Label [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Fycompa (Perampanel) FDA Label [Link]
Drug created on May 22, 2013 01:44 / Updated on June 18, 2021 14:15