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Details

Stereochemistry ACHIRAL
Molecular Formula C23H15N3O
Molecular Weight 349.3847
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PERAMPANEL

SMILES

O=C1N(C=C(C=C1C2=C(C=CC=C2)C#N)C3=NC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=PRMWGUBFXWROHD-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C23H15N3O
Molecular Weight 349.3847
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Perampanel (trade name Fycompa) is an antiepileptic drug developed by Eisai Co. that acts as a selective non-competitive antagonist of AMPA receptors, the major subtype of ionotropic glutamate receptors. Although the mechanism of action through which perampanel exerts its antiepileptic effect has not been fully elucidated, this agent antagonizes the AMPA subtype of the excitatory glutamate receptor found on postsynaptic neurons in the central nervous system (CNS). This antagonistic action prevents AMPA receptor activation by glutamate and results in the inhibition of neuronal excitation, repetitive neuronal firing, and the stabilization of hyper-excited neural membranes. Glutamate, the primary excitatory neurotransmitter in the CNS, plays an important role in various neurological disorders caused by neuronal hyperexcitation. The drug is currently approved, for the control of partial-onset seizures, in those of both sexes who suffer from epilepsy and who are 12 years of age and older, by the Food and Drug Administration. Perampanel is also approved for the treatment of primary generalized tonic-clonic seizures in patients with epilepsy aged 12 years and older. It is designated as a Schedule III controlled substance by the Drug Enforcement Administration. Perampanel has been studied in other clinical indications including Parkinson's disease.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
New frontiers in the pharmacological management of Parkinson's disease.
2008 Jul
Gateways to clinical trials.
2009 Mar
Progress report on new antiepileptic drugs: a summary of the Tenth Eilat Conference (EILAT X).
2010 Dec
Gateways to clinical trials.
2010 Mar
Safety and efficacy of perampanel in advanced Parkinson's disease: a randomized, placebo-controlled study.
2010 May 15
Patents

Sample Use Guides

In Vivo Use Guide
Starting dose is 2 mg once daily at bedtime. May increase dose based on clinical response and tolerability by increments of 2 mg once daily no more frequently than at weekly intervals. Recommended maintenance dose is for Partial-Onset Seizures – 8 to 12 mg once daily at bedtime; for Primary Generalized Tonic-Clonic Seizures – 8 mg once daily at bedtime. Individual dosing should be adjusted based on clinical response and tolerability.
Route of Administration: Oral
In Vitro Use Guide
in vitro ischemia model in murine brain endothelial cells
Substance Class Chemical
Created
by admin
on Mon Oct 21 22:15:13 UTC 2019
Edited
by admin
on Mon Oct 21 22:15:13 UTC 2019
Record UNII
H821664NPK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PERAMPANEL
DASH   INN   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
FYCOMPA
Brand Name English
PERAMPANEL [VANDF]
Common Name English
E-2007
Code English
PERAMPANEL [INN]
Common Name English
ER-155055-90
Code English
PERAMPANEL [ORANGE BOOK]
Common Name English
PERAMPANEL [MI]
Common Name English
BENZONITRILE, 2-(1',6'-DIHYDRO-6'-OXO-1'-PHENYL(2,3'-BIPYRIDIN)-5'-YL)-
Systematic Name English
5'-(2-CYANOPHENYL)-1'-PHENYL-2,3'-BIPYRIDINYL-6'(1'H)-ONE
Systematic Name English
PERAMPANEL [WHO-DD]
Common Name English
PERAMPANEL [USAN]
Common Name English
E2007
Code English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS FYCOMPA (AUTHORIZED: EPILEPSIES, PARTIAL)
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
WHO-ATC N03AX22
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
WHO-VATC QN03AX22
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
DEA NO. 2261
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
NCI_THESAURUS C47795
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
FDA ORPHAN DRUG 380912
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
LIVERTOX 761
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
NDF-RT N0000186106
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
Code System Code Type Description
INN
8834
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
PRIMARY
CAS
380917-97-5
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
PRIMARY
DRUG BANK
DB08883
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
PRIMARY
EPA CompTox
380917-97-5
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
PRIMARY
ChEMBL
CHEMBL1214124
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
PRIMARY
PUBCHEM
9924495
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
PRIMARY
NCI_THESAURUS
C75029
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
PRIMARY
EVMPD
SUB32160
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
PRIMARY
IUPHAR
7050
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
PRIMARY
RXCUI
1356552
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
PRIMARY RxNorm
MERCK INDEX
M11706
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
PRIMARY
LactMed
380917-97-5
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
PRIMARY
WIKIPEDIA
PERAMPANEL
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
PRIMARY
NDF-RT
N0000020016
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
PRIMARY AMPA Receptor Antagonists [MoA]
MESH
C551441
Created by admin on Mon Oct 21 22:15:13 UTC 2019 , Edited by admin on Mon Oct 21 22:15:13 UTC 2019
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
EXCRETED UNCHANGED
URINE
Related Record Type Details
METABOLITE INACTIVE -> PARENT
In vitro studies show that the primary oxidative metabolic route of perampanel is via cytochrome P450 (CYP)3A4 and/or CYP3A5, based on the results of metabolism by recombinant human CYPs, and inhibition studies using anti-CYP3A4 and ketoconazole in human liver microsomes.
FECAL; URINE
METABOLITE INACTIVE -> PARENT
URINE
METABOLITE INACTIVE -> PARENT
In vitro studies show that the primary oxidative metabolic route of perampanel is via cytochrome P450 (CYP)3A4 and/or CYP3A5, based on the results of metabolism by recombinant human CYPs, and inhibition studies using anti-CYP3A4 and ketoconazole in human liver microsomes.
FECAL; URINE
METABOLITE INACTIVE -> PARENT
FECAL; URINE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

Tmax PHARMACOKINETIC HIGH-FAT MEAL

FED CONDITION