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2D Structure
Also known as: 380917-97-5, Fycompa, E2007, Er-155055-90, E-2007, 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one
Molecular Formula
C23H15N3O
Molecular Weight
349.4  g/mol
InChI Key
PRMWGUBFXWROHD-UHFFFAOYSA-N
FDA UNII
H821664NPK

Perampanel is an orally active, non-competitive, and selective alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) glutamate receptor antagonist, with anti-epileptic activity. 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.
Perampanel is a Noncompetitive AMPA Glutamate Receptor Antagonist. The mechanism of action of perampanel is as an AMPA Receptor Antagonist, and UGT2B7 Inhibitor, and UGT1A9 Inhibitor, and Cytochrome P450 3A4 Inhibitor, and Cytochrome P450 2C8 Inhibitor.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)benzonitrile
2.1.2 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
2.1.3 InChI Key
PRMWGUBFXWROHD-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)N2C=C(C=C(C2=O)C3=CC=CC=C3C#N)C4=CC=CC=N4
2.2 Other Identifiers
2.2.1 UNII
H821664NPK
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one

2. E-2007

3. E2007

4. Er-155055-90

5. Fycompa

6. Perampanel Hydrate

7. Perampanel Hydrate (4:3)

2.3.2 Depositor-Supplied Synonyms

1. 380917-97-5

2. Fycompa

3. E2007

4. Er-155055-90

5. E-2007

6. 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one

7. E 2007

8. Perampanel (usan)

9. Chebi:71013

10. Benzonitrile, 2-(1',6'-dihydro-6'-oxo-1'-phenyl[2,3'-bipyridin]-5'-yl)-

11. 2-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)benzonitrile

12. H821664npk

13. Perampanel [usan]

14. Fycompa (tn)

15. 5'-(2-cyanophenyl)-1'-phenyl-2,3'-bipyridinyl-6'(1'h)-one

16. 2-(6'-oxo-1'-phenyl-1',6'-dihydro-2,3'-bipyridin-5'-yl)benzonitrile

17. 2-(6'-oxo-1'-phenyl[1',6'-dihydro[2,3'-bipyridine]]-5'-yl)benzonitrile

18. Benzonitrile, 2-(1',6'-dihydro-6'-oxo-1'-phenyl(2,3'-bipyridin)-5'-yl)-

19. Perampanel [usan:inn]

20. Perampanelum

21. Unii-h821664npk

22. Perampanel(e2007

23. Perampanel [mi]

24. Perampanel [inn]

25. Perampanel [vandf]

26. Perampanel [who-dd]

27. Schembl194370

28. Gtpl7050

29. Chembl1214124

30. Perampanel [orange Book]

31. Dtxsid80191501

32. Bcp06505

33. Ex-a2128

34. Bdbm50184410

35. Zinc30691797

36. Akos016340421

37. Ch-0056

38. Cs-1160

39. Db08883

40. Sb16816

41. Ncgc00378863-02

42. Ac-27375

43. Am806751

44. Hy-14745

45. D08964

46. Q868658

47. 2-(6-oxo-1-phenyl-1,6-dihydro-[2,3-bipyridin]-5-yl)benzonitrile

48. 3-(2-cyanophenyl)-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one

49. 1174302-51-2

50. 6zp

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 349.4 g/mol
Molecular Formula C23H15N3O
XLogP33.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass349.121512110 g/mol
Monoisotopic Mass349.121512110 g/mol
Topological Polar Surface Area57 Ų
Heavy Atom Count27
Formal Charge0
Complexity664
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameFycompa
PubMed HealthPerampanel (By mouth)
Drug ClassesAnticonvulsant, Central Nervous System Agent
Drug LabelFYCOMPA tablets contain perampanel, a non-competitive AMPA receptor antagonist. Perampanel is described chemically as 2-(2-oxo-1-phenyl-5-pyridin-2-yl-1,2-dihydropyridin-3-yl) benzonitrile hydrate (4:3).The molecular formula is C23H15N3O 3/4H2O,...
Active IngredientPerampanel
Dosage FormTablet
RouteOral
Strength8mg; 4mg; 12mg; 6mg; 2mg; 10mg
Market StatusPrescription
CompanyEisai

2 of 2  
Drug NameFycompa
PubMed HealthPerampanel (By mouth)
Drug ClassesAnticonvulsant, Central Nervous System Agent
Drug LabelFYCOMPA tablets contain perampanel, a non-competitive AMPA receptor antagonist. Perampanel is described chemically as 2-(2-oxo-1-phenyl-5-pyridin-2-yl-1,2-dihydropyridin-3-yl) benzonitrile hydrate (4:3).The molecular formula is C23H15N3O 3/4H2O,...
Active IngredientPerampanel
Dosage FormTablet
RouteOral
Strength8mg; 4mg; 12mg; 6mg; 2mg; 10mg
Market StatusPrescription
CompanyEisai

4.2 Drug Indication

Used in patients over 12 years old for the treatment of partial-onset seizures that may or may not occur with generalized seizures.


FDA Label


Fycompa is indicated for the adjunctive treatment of partial-onset seizures with or without secondarily generalised seizures in adult and adolescent patients from 12 years of age with epilepsy.

Fycompa is indicated for the adjunctive treatment of primary generalised tonic-clonic seizures in adult and adolescent patients from 12 years of age with idiopathic generalised epilepsy.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Perampanel is involved in inhibiting neuronal excitation in the central nervous system leading to such effects as decreased pyschomotor performance.


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
PERAMPANEL
5.2.2 FDA UNII
H821664NPK
5.2.3 Pharmacological Classes
Cytochrome P450 2C8 Inhibitors [MoA]; Cytochrome P450 3A4 Inhibitors [MoA]; Noncompetitive AMPA Glutamate Receptor Antagonist [EPC]; UGT1A9 Inhibitors [MoA]; UGT2B7 Inhibitors [MoA]; AMPA Receptor Antagonists [MoA]
5.3 ATC Code

N03AX22


N03AX22

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


N - Nervous system

N03 - Antiepileptics

N03A - Antiepileptics

N03AX - Other antiepileptics

N03AX22 - Perampanel


5.4 Absorption, Distribution and Excretion

Absorption

After oral adminitration, perampanel is absorbed rapidly and completely.


Route of Elimination

Perampanel is eliminated mostely in the feces (48%) and to a lesser exten in the urine (22%).


Volume of Distribution

The volume of distribution of perampanel was not quantified.


Clearance

In healthy patients, perampanel has a clearance of about 12 mL/min.


5.5 Metabolism/Metabolites

Perampanel is highly metabolized by CYP3A4 and/or CYP3A5 primary oxidation and by sequential glucuronidation.


5.6 Biological Half-Life

Perampanel has a long elmination half-life of about 105 hours.


5.7 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.