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Details

Stereochemistry ACHIRAL
Molecular Formula 4C23H15N3O.3H2O
Molecular Weight 1451.5846
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PERAMPANEL HYDRATE (4:3)

SMILES

O.O.O.O=C1N(C=C(C=C1C2=CC=CC=C2C#N)C3=CC=CC=N3)C4=CC=CC=C4.O=C5N(C=C(C=C5C6=CC=CC=C6C#N)C7=CC=CC=N7)C8=CC=CC=C8.O=C9N(C=C(C=C9C%10=CC=CC=C%10C#N)C%11=CC=CC=N%11)C%12=CC=CC=C%12.O=C%13N(C=C(C=C%13C%14=CC=CC=C%14C#N)C%15=CC=CC=N%15)C%16=CC=CC=C%16

InChI

InChIKey=PDWMJDKMSASBNE-UHFFFAOYSA-N
InChI=1S/4C23H15N3O.3H2O/c4*24-15-17-8-4-5-11-20(17)21-14-18(22-12-6-7-13-25-22)16-26(23(21)27)19-9-2-1-3-10-19;;;/h4*1-14,16H;3*1H2

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
MOL RATIO 3 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C23H15N3O
Molecular Weight 349.3847
Charge 0
Count
MOL RATIO 4 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
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

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FYCOMPA

Cmax

ValueDoseCo-administeredAnalytePopulation
123.3 μg/L
4 mg single, oral
PERAMPANEL plasma
Homo sapiens
371.9 μg/L
4 mg 1 times / day multiple, oral
PERAMPANEL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
8.092 μg × h/L
4 mg single, oral
PERAMPANEL plasma
Homo sapiens
7352 μg × h/L
4 mg 1 times / day multiple, oral
PERAMPANEL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
117.4 h
4 mg single, oral
PERAMPANEL plasma
Homo sapiens
98.1 h
4 mg 1 times / day multiple, oral
PERAMPANEL plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
4.5%
4 mg single, oral
PERAMPANEL plasma
Homo sapiens

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

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
Record UNII
8LIX22217M
Record Status Validated (UNII)
Record Version