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    Chemistry

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    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
    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

    Perampanel

    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.

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    23-Mar-2021
    16-Oct-2024
    KGS
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