U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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=CC=CC=C2C#N)C3=CC=CC=N3)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 No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including http://www.eisai.com/news/news201551.html; http://www.deadiversion.usdoj.gov/fed_regs/rules/2013/fr1022_8.htm; http://www.ncbi.nlm.nih.gov/pubmed/?term=24421482;

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

Curator's Comment: Cross the blood-brain barrier in in vitro ischemia model in murine brain endothelial cells.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FYCOMPA

Approved Use

Indicated as adjunctive therapy for the treatment of Partial-Onset Seizures with or without secondarily generalized seizures in patients with epilepsy 12 years of age and older; Primary Generalized Tonic-Clonic Seizures in patients with epilepsy 12 years of age and older

Launch Date

2012
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
371.9 μg/L
4 mg 1 times / day multiple, oral
dose: 4 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PERAMPANEL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
123.3 μg/L
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PERAMPANEL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
7352 μg × h/L
4 mg 1 times / day multiple, oral
dose: 4 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PERAMPANEL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
8.092 μg × h/L
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PERAMPANEL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
98.1 h
4 mg 1 times / day multiple, oral
dose: 4 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PERAMPANEL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
117.4 h
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PERAMPANEL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
4.5%
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PERAMPANEL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
10 mg single, oral
Overdose
Dose: 10 mg
Route: oral
Route: single
Dose: 10 mg
Sources:
healthy, 2 years
n = 1
Health Status: healthy
Age Group: 2 years
Sex: F
Population Size: 1
Sources:
Other AEs: Drowsiness, Ataxia...
Other AEs:
Drowsiness (1 patient)
Ataxia (1 patient)
Sources:
2 mg single, oral
Overdose
Dose: 2 mg
Route: oral
Route: single
Dose: 2 mg
Sources:
healthy, 2 years
n = 1
Health Status: healthy
Age Group: 2 years
Sex: M
Population Size: 1
Sources:
Other AEs: Coordination and balance disturbances...
Other AEs:
Coordination and balance disturbances (1 patient)
Sources:
12 mg 1 times / day steady, oral
Recommended
Dose: 12 mg, 1 times / day
Route: oral
Route: steady
Dose: 12 mg, 1 times / day
Sources:
unhealthy, 35 years
n = 255
Health Status: unhealthy
Condition: epilepsy
Age Group: 35 years
Sex: M+F
Population Size: 255
Sources:
Disc. AE: Dizziness, Somnolence...
AEs leading to
discontinuation/dose reduction:
Dizziness
Somnolence
Vertigo
Ataxia
Blurred vision
Dysarthria
Sources:
300 mg single, oral
Overdose
Dose: 300 mg
Route: oral
Route: single
Dose: 300 mg
Sources:
unhealthy, 54 years
n = 1
Health Status: unhealthy
Condition: refractory seizures
Age Group: 54 years
Sex: M
Population Size: 1
Sources:
Other AEs: Somnolence, Bradycardia...
Other AEs:
Somnolence (1 patient)
Bradycardia (1 patient)
Hyponatremia (1 patient)
Sources:
264 mg single, oral
Overdose
Dose: 264 mg
Route: oral
Route: single
Dose: 264 mg
Sources:
unknown
n = 1
Health Status: unknown
Population Size: 1
Sources:
Other AEs: Agitation, Aggressive behavior...
Other AEs:
Agitation (1 patient)
Aggressive behavior (1 patient)
Sources:
12 mg 1 times / day steady, oral
Recommended
Dose: 12 mg, 1 times / day
Route: oral
Route: steady
Dose: 12 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: epilepsy
Sources:
Disc. AE: Hostility, Aggression...
AEs leading to
discontinuation/dose reduction:
Hostility (20%)
Aggression (20%)
Irritability
Anger
Anxiety
Sources:
AEs

AEs

AESignificanceDosePopulation
Ataxia 1 patient
10 mg single, oral
Overdose
Dose: 10 mg
Route: oral
Route: single
Dose: 10 mg
Sources:
healthy, 2 years
n = 1
Health Status: healthy
Age Group: 2 years
Sex: F
Population Size: 1
Sources:
Drowsiness 1 patient
10 mg single, oral
Overdose
Dose: 10 mg
Route: oral
Route: single
Dose: 10 mg
Sources:
healthy, 2 years
n = 1
Health Status: healthy
Age Group: 2 years
Sex: F
Population Size: 1
Sources:
Coordination and balance disturbances 1 patient
2 mg single, oral
Overdose
Dose: 2 mg
Route: oral
Route: single
Dose: 2 mg
Sources:
healthy, 2 years
n = 1
Health Status: healthy
Age Group: 2 years
Sex: M
Population Size: 1
Sources:
Ataxia Disc. AE
12 mg 1 times / day steady, oral
Recommended
Dose: 12 mg, 1 times / day
Route: oral
Route: steady
Dose: 12 mg, 1 times / day
Sources:
unhealthy, 35 years
n = 255
Health Status: unhealthy
Condition: epilepsy
Age Group: 35 years
Sex: M+F
Population Size: 255
Sources:
Blurred vision Disc. AE
12 mg 1 times / day steady, oral
Recommended
Dose: 12 mg, 1 times / day
Route: oral
Route: steady
Dose: 12 mg, 1 times / day
Sources:
unhealthy, 35 years
n = 255
Health Status: unhealthy
Condition: epilepsy
Age Group: 35 years
Sex: M+F
Population Size: 255
Sources:
Dizziness Disc. AE
12 mg 1 times / day steady, oral
Recommended
Dose: 12 mg, 1 times / day
Route: oral
Route: steady
Dose: 12 mg, 1 times / day
Sources:
unhealthy, 35 years
n = 255
Health Status: unhealthy
Condition: epilepsy
Age Group: 35 years
Sex: M+F
Population Size: 255
Sources:
Dysarthria Disc. AE
12 mg 1 times / day steady, oral
Recommended
Dose: 12 mg, 1 times / day
Route: oral
Route: steady
Dose: 12 mg, 1 times / day
Sources:
unhealthy, 35 years
n = 255
Health Status: unhealthy
Condition: epilepsy
Age Group: 35 years
Sex: M+F
Population Size: 255
Sources:
Somnolence Disc. AE
12 mg 1 times / day steady, oral
Recommended
Dose: 12 mg, 1 times / day
Route: oral
Route: steady
Dose: 12 mg, 1 times / day
Sources:
unhealthy, 35 years
n = 255
Health Status: unhealthy
Condition: epilepsy
Age Group: 35 years
Sex: M+F
Population Size: 255
Sources:
Vertigo Disc. AE
12 mg 1 times / day steady, oral
Recommended
Dose: 12 mg, 1 times / day
Route: oral
Route: steady
Dose: 12 mg, 1 times / day
Sources:
unhealthy, 35 years
n = 255
Health Status: unhealthy
Condition: epilepsy
Age Group: 35 years
Sex: M+F
Population Size: 255
Sources:
Bradycardia 1 patient
300 mg single, oral
Overdose
Dose: 300 mg
Route: oral
Route: single
Dose: 300 mg
Sources:
unhealthy, 54 years
n = 1
Health Status: unhealthy
Condition: refractory seizures
Age Group: 54 years
Sex: M
Population Size: 1
Sources:
Hyponatremia 1 patient
300 mg single, oral
Overdose
Dose: 300 mg
Route: oral
Route: single
Dose: 300 mg
Sources:
unhealthy, 54 years
n = 1
Health Status: unhealthy
Condition: refractory seizures
Age Group: 54 years
Sex: M
Population Size: 1
Sources:
Somnolence 1 patient
300 mg single, oral
Overdose
Dose: 300 mg
Route: oral
Route: single
Dose: 300 mg
Sources:
unhealthy, 54 years
n = 1
Health Status: unhealthy
Condition: refractory seizures
Age Group: 54 years
Sex: M
Population Size: 1
Sources:
Aggressive behavior 1 patient
264 mg single, oral
Overdose
Dose: 264 mg
Route: oral
Route: single
Dose: 264 mg
Sources:
unknown
n = 1
Health Status: unknown
Population Size: 1
Sources:
Agitation 1 patient
264 mg single, oral
Overdose
Dose: 264 mg
Route: oral
Route: single
Dose: 264 mg
Sources:
unknown
n = 1
Health Status: unknown
Population Size: 1
Sources:
Aggression 20%
Disc. AE
12 mg 1 times / day steady, oral
Recommended
Dose: 12 mg, 1 times / day
Route: oral
Route: steady
Dose: 12 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: epilepsy
Sources:
Hostility 20%
Disc. AE
12 mg 1 times / day steady, oral
Recommended
Dose: 12 mg, 1 times / day
Route: oral
Route: steady
Dose: 12 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: epilepsy
Sources:
Anger Disc. AE
12 mg 1 times / day steady, oral
Recommended
Dose: 12 mg, 1 times / day
Route: oral
Route: steady
Dose: 12 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: epilepsy
Sources:
Anxiety Disc. AE
12 mg 1 times / day steady, oral
Recommended
Dose: 12 mg, 1 times / day
Route: oral
Route: steady
Dose: 12 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: epilepsy
Sources:
Irritability Disc. AE
12 mg 1 times / day steady, oral
Recommended
Dose: 12 mg, 1 times / day
Route: oral
Route: steady
Dose: 12 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: epilepsy
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
likely
no
no
no
no
no
no
no
no
no
no
weak [IC50 >30 uM]
weak [Inhibition 30 uM]
weak [Inhibition 30 uM]
weak
weak
weak
weak
weak
weak
weak
weak
yes [Ki 40.6 uM]
weak (co-administration study)
Comment: time-dependent inhibition;decreased AUC0-inf and Cmax of midazolam (a CYP3A4 substrate) by 13% and 15%, respectively
Page: 164;193
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
likely
likely
likely
likely
likely
no
no
no
no
no
no
no
no
no
no
no
yes
weak (co-administration study)
Comment: Co-administration with ketoconazole (a strong inhibitor of CYP3A4) increased perampanel AUC by 20%;
Page: 164;192
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Safety and efficacy of perampanel in advanced Parkinson's disease: a randomized, placebo-controlled study.
2010 May 15
Patents

Sample Use Guides

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 Fri Dec 15 15:56:39 GMT 2023
Edited
by admin
on Fri Dec 15 15:56:39 GMT 2023
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 Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
WHO-ATC N03AX22
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
WHO-VATC QN03AX22
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
DEA NO. 2261
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
NCI_THESAURUS C47795
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
FDA ORPHAN DRUG 380912
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
LIVERTOX NBK548508
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
NDF-RT N0000186106
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
Code System Code Type Description
FDA UNII
H821664NPK
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
PRIMARY
DAILYMED
H821664NPK
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
PRIMARY
INN
8834
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PRIMARY
CAS
380917-97-5
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PRIMARY
DRUG BANK
DB08883
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
PRIMARY
CHEBI
71015
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
PRIMARY
SMS_ID
100000124527
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PRIMARY
EPA CompTox
DTXSID80191501
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PRIMARY
ChEMBL
CHEMBL1214124
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PRIMARY
PUBCHEM
9924495
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
PRIMARY
NCI_THESAURUS
C75029
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PRIMARY
EVMPD
SUB32160
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
PRIMARY
DRUG CENTRAL
4684
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
PRIMARY
IUPHAR
7050
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
PRIMARY
RXCUI
1356552
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
PRIMARY RxNorm
CHEBI
71013
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PRIMARY
LACTMED
Perampanel
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
PRIMARY
MERCK INDEX
m11706
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
PRIMARY
WIKIPEDIA
PERAMPANEL
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
PRIMARY
NDF-RT
N0000020016
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
PRIMARY AMPA Receptor Antagonists [MoA]
MESH
C551441
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PRIMARY
USAN
SS-46
Created by admin on Fri Dec 15 15:56:39 GMT 2023 , Edited by admin on Fri Dec 15 15:56:39 GMT 2023
PRIMARY
Related Record Type Details
TARGET->NEGATIVE ALLOSTERIC MODULATOR (NAM)
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
TRANSPORTER -> INHIBITOR
Thus, the unbound Cmax is about 0.09 μM, much lower than 8.5 μM. Therefore, E2007 is unlikely to inhibit OAT1, OAT3, OCT1 and OCT3 in vivo.
Ki
TRANSPORTER -> INHIBITOR
Thus, the unbound Cmax is about 0.09 μM, much lower than 8.5 μM. Therefore, E2007 is unlikely to inhibit OAT1, OAT3, OCT1 and OCT3 in vivo.
TRANSPORTER -> INHIBITOR
Thus, the unbound Cmax is about 0.09 μM, much lower than 8.5 μM. Therefore, E2007 is unlikely to inhibit OAT1, OAT3, OCT1 and OCT3 in vivo.
Ki
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
SOLVATE->ANHYDROUS
TRANSPORTER -> INHIBITOR
Thus, the unbound Cmax is about 0.09 μM, much lower than 8.5 μM. Therefore, E2007 is unlikely to inhibit OAT1, OAT3, OCT1 and OCT3 in vivo.
Ki
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 -> PARENT
METABOLITE INACTIVE -> PARENT
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 -> PARENT
METABOLITE INACTIVE -> PARENT
FECAL; URINE
METABOLITE -> PARENT
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