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Brivaracetam

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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

Brivaracetam

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 Formula	C₁₁H₂₀N₂O₂
Molecular Weight	212.29 g/mol
XLogP3	1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	5
Exact Mass	212.152477885 g/mol
Monoisotopic Mass	212.152477885 g/mol
Topological Polar Surface Area	63.4 Å²
Heavy Atom Count	15
Formal Charge	0
Complexity	253
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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

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.