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    Brivaracetam

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    2D Structure
    Also known as: 357336-20-0, Briviact, Ucb-34714, Ucb 34714, Ucb34714, 2-(2-oxo-4-propylpyrrolidin-1-yl)butanamide
    Molecular Formula
    C11H20N2O2
    Molecular Weight
    212.29  g/mol
    InChI Key
    MSYKRHVOOPPJKU-BDAKNGLRSA-N
    FDA UNII
    U863JGG2IA
    Brivaracetam is an orally bioavailable levetiracetam derivative, with anticonvulsant activity. Although the exact mechanism through which brivaracetam exerts its effects is not fully known, this agent targets and binds to synaptic vesicle protein 2A (SV2A) in the brain. This prevents synaptic vesicle exocytosis and the synaptic release of certain, as of yet not fully known, excitatory neurotransmitters. This may inhibit impulse conduction across synapses, decrease neuronal (hyper-)excitability, and may modulate epileptogenesis. SV2A, a membrane glycoprotein present in neuronal synaptic vesicles, plays a key role in action potential-induced neurotransmitter release in the brain.
    The mechanism of action of brivaracetam is as an Epoxide Hydrolase Inhibitor.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-2-[(4R)-2-oxo-4-propylpyrrolidin-1-yl]butanamide
    2.1.2 InChI
    InChI=1S/C11H20N2O2/c1-3-5-8-6-10(14)13(7-8)9(4-2)11(12)15/h8-9H,3-7H2,1-2H3,(H2,12,15)/t8-,9+/m1/s1
    2.1.3 InChI Key
    MSYKRHVOOPPJKU-BDAKNGLRSA-N
    2.1.4 Canonical SMILES
    CCCC1CC(=O)N(C1)C(CC)C(=O)N
    2.1.5 Isomeric SMILES
    CCC[C@@H]1CC(=O)N(C1)[C@@H](CC)C(=O)N
    2.2 Other Identifiers
    2.2.1 UNII
    U863JGG2IA
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (2s)-2-((4r)-2-oxo-4-propylpyrrolidin-1-yl)butanamide

    2. 1-pyrrolidineacetamide, Alpha-ethyl-2-oxo-4-propyl-, (alphas,4r)-

    3. 2-(2-oxo-4-propylpyrrolidin-1-yl)butanamide

    4. Briviact

    5. Ucb 34714

    6. Ucb-34714

    7. Ucb34714

    2.3.2 Depositor-Supplied Synonyms

    1. 357336-20-0

    2. Briviact

    3. Ucb-34714

    4. Ucb 34714

    5. Ucb34714

    6. 2-(2-oxo-4-propylpyrrolidin-1-yl)butanamide

    7. (2s)-2-[(4r)-2-oxo-4-propylpyrrolidin-1-yl]butanamide

    8. (2s)-2-((4r)-2-oxo-4-propylpyrrolidin-1-yl)butanamide

    9. U863jgg2ia

    10. Rikelta

    11. Brivaracetam [usan:inn]

    12. Unii-u863jgg2ia

    13. Compound 83alpha

    14. 1-pyrrolidineacetamide, Alpha-ethyl-2-oxo-4-propyl-, (alphas,4r)-

    15. Brivaracetam 97%

    16. Briviact (tn)

    17. Brivaracetam [mi]

    18. Brivaracetam [inn]

    19. Brivaracetam [jan]

    20. Brivaracetam [usan]

    21. Brivaracetam [mart.]

    22. Brivaracetam [who-dd]

    23. Schembl122081

    24. Brivaracetam (jan/usan/inn)

    25. Chembl607400

    26. Gtpl9041

    27. Dtxsid00905081

    28. Chebi:133013

    29. Brivaracetam [orange Book]

    30. Ex-a2748

    31. Zinc3979899

    32. Bdbm50422531

    33. Mfcd25976668

    34. Akos027324306

    35. Ccg-266666

    36. Cs-3418

    37. Db05541

    38. Ncgc00390779-02

    39. Ac-29289

    40. As-35277

    41. Bb161996

    42. Hy-14449

    43. D08879

    44. Q408099

    45. (s)-2-((r)-2-oxo-4-propylpyrrolidin-1-yl)butanamide

    46. (2s)-2-((4r)-2-oxo-4-n-propyl-1-pyrrolidinyl)butanamide

    47. (2s)-2-((4r)-2-oxo-4-propyltetrahydro-1h-pyrrol-1-yl) Butanamide

    48. 1-pyrrolidineacetamide, .alpha.-ethyl-2-oxo-4-propyl (.alpha.s,4r)-

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 212.29 g/mol
    Molecular Formula C11H20N2O2
    XLogP31
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count5
    Exact Mass212.152477885 g/mol
    Monoisotopic Mass212.152477885 g/mol
    Topological Polar Surface Area63.4 Ų
    Heavy Atom Count15
    Formal Charge0
    Complexity253
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Used as adjunctive therapy for partial-onset seizures in patients 16 years of age or older.

    FDA Label

    Briviact is indicated as adjunctive therapy in the treatment of partial-onset seizures with or without secondary generalisation in adult and adolescent patients from 16 years of age with epilepsy.

    Treatment of epilepsy with partial-onset seizures, Treatment of neonatal seizures

    Treatment of neonatal seizures, Treatment of paediatric epilepsy syndromes

    Treatment of epilepsy with partial-onset seizures

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Brivaracetam binds SV2A with high affinity. SV2A is known to play a role in epileptogenesis through modulation of synaptic GABA release. It is thought that brivaracetam exerts its anti-epileptogenic effects through its binding to SV2A. Brivaracetam is also known to inhibit Na+ channels which may also contribute to its anti-epileptogenic action.

    5.2 MeSH Pharmacological Classification

    Anticonvulsants

    Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    BRIVARACETAM
    5.3.2 FDA UNII
    U863JGG2IA
    5.3.3 Pharmacological Classes
    Epoxide Hydrolase Inhibitors [MoA]
    5.4 ATC Code

    N03AX23

    N03AX23

    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

    N03AX23 - Brivaracetam

    5.5 Absorption, Distribution and Excretion

    Absorption

    Nearly 100% oral bioavailability.

    Route of Elimination

    \>95% excreted in urine with <10% of the parent compound unchanged. <1% excreted in feces.

    Volume of Distribution

    0.5L/kg.

    Clearance

    CL/F of 0.7-1.07 mL/min kg. Clearance is primarily metabolic with less than 10% of the parent drug excreted unchanged.

    5.6 Metabolism/Metabolites

    Primarily metabolized by hydrolysis of the acetamide moeity to form a carboxylic acid metabolite. Another metabolite is created via oxidation of the propyl side chain by CYP2C8 as well as CYP3A4, CYP2C19, and CYP2B6. Some conjugation with glucuronic acid and taurine account for a small amount of metabolism.

    5.7 Biological Half-Life

    7-8h.

    5.8 Mechanism of Action

    The precise mechanism of brivaracetam's anti-epileptogenic activity is unknown.