Brivaracetam

Brivaracetam
Clinical data
Pronunciation	/ˌbrɪvəˈræsətəm/ BRIV-ə-RASS-ə-təm
Trade names	Briviact, Nubriveo, Brivajoy
AHFS/Drugs.com	Monograph
MedlinePlus	a616027
License data	US DailyMed: Brivaracetam;
Pregnancy; category	AU: B3; ;
Routes of; administration	By mouth, intravenous
ATC code	N03AX23 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); CA: ℞-only; US: Schedule V; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Nearly 100%
Protein binding	≤20%
Metabolism	Hydrolysis by amidase, CYP2C19-mediated hydroxylation
Metabolites	3 inactive metabolites
Elimination half-life	≈9 hours
Excretion	Kidneys (>95%)
Identifiers
	IUPAC name (2S)-2-[(4R)-2-oxo-4-propylpyrrolidin-1-yl] butanamide;
CAS Number	357336-20-0 [chemspider];
PubChem CID	9837243;
DrugBank	DB05541;
ChemSpider	8012964 ;
UNII	U863JGG2IA;
KEGG	D08879;
ChEBI	CHEBI:133013 ;
ChEMBL	ChEMBL607400 ;
CompTox Dashboard (EPA)	DTXSID00905081 ;
ECHA InfoCard	100.118.642
Chemical and physical data
Formula	C11H20N2O2
Molar mass	212.293 g·mol−1
3D model (JSmol)	Interactive image;
Specific rotation	[α]D −60°
Melting point	72 to 77 °C (162 to 171 °F)
	SMILES O=C(N)[C@@H](N1C(=O)C[C@@H](CCC)C1)CC;
	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 ; Key:MSYKRHVOOPPJKU-BDAKNGLRSA-N ;

Brivaracetam, sold under the brand name Briviact among others, is a chemical analog of levetiracetam, a racetam derivative with anticonvulsant (antiepileptic) properties.^[5]^[6] It has been approved since 2016. It is marketed by the pharmaceutical company UCB.^[7]^[8] It is used to treat partial-onset seizures with or without secondary generalisation, in combination with other antiepileptic drugs.

^ "Prescription medicines: registration of new chemical entities in Australia, 2016". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 10 April 2023. Retrieved 10 April 2023.
^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
^ "Health Canada New Drug Authorizations: 2016 Highlights". Health Canada. 14 March 2017. Retrieved 7 April 2024.
^ ^a ^b Cite error: The named reference Briviact FDA label was invoked but never defined (see the help page).
^ von Rosenstiel P (January 2007). "Brivaracetam (UCB 34714)". Neurotherapeutics. 4 (1): 84–87. doi:10.1016/j.nurt.2006.11.004. PMC 7479692. PMID 17199019.
^ Malawska B, Kulig K (July 2005). "Brivaracetam UCB". Current Opinion in Investigational Drugs. 6 (7): 740–746. PMID 16044671.
^ "Briviact Product Page". UCB. Archived from the original on 19 September 2020. Retrieved 1 January 2020.
^ "Brivaracetam". DrugBank. Archived from the original on 10 January 2020. Retrieved 1 January 2020.

[1] "Prescription medicines: registration of new chemical entities in Australia, 2016". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 10 April 2023. Retrieved 10 April 2023.

[2] Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.

[3] "Health Canada New Drug Authorizations: 2016 Highlights". Health Canada. 14 March 2017. Retrieved 7 April 2024.

[Briviact_FDA_label-4] Cite error: The named reference Briviact FDA label was invoked but never defined (see the help page).

[5] von Rosenstiel P (January 2007). "Brivaracetam (UCB 34714)". Neurotherapeutics. 4 (1): 84–87. doi:10.1016/j.nurt.2006.11.004. PMC 7479692. PMID 17199019.

[6] Malawska B, Kulig K (July 2005). "Brivaracetam UCB". Current Opinion in Investigational Drugs. 6 (7): 740–746. PMID 16044671.

[ucb-7] "Briviact Product Page". UCB. Archived from the original on 19 September 2020. Retrieved 1 January 2020.

[8] "Brivaracetam". DrugBank. Archived from the original on 10 January 2020. Retrieved 1 January 2020.

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Clinical data

Pronunciation	/ˌbrɪvəˈræsətəm/ BRIV-ə-RASS-ə-təm
Trade names	Briviact, Nubriveo, Brivajoy
AHFS/Drugs.com	Monograph
MedlinePlus	a616027
License data	US DailyMed: Brivaracetam
Pregnancy category	AU: B3
Routes of administration	By mouth, intravenous
ATC code	N03AX23 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)^[1] BR: Class C1 (Other controlled substances)^[2] CA: ℞-only^[3] US: Schedule V^[4] EU: Rx-only In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Nearly 100%
Protein binding	≤20%
Metabolism	Hydrolysis by amidase, CYP2C19-mediated hydroxylation
Metabolites	3 inactive metabolites
Elimination half-life	≈9 hours
Excretion	Kidneys (>95%)^[4]
Identifiers
IUPAC name (2S)-2-[(4R)-2-oxo-4-propylpyrrolidin-1-yl] butanamide
CAS Number	357336-20-0^{Y[chemspider]}
PubChem CID	9837243
DrugBank	DB05541
ChemSpider	8012964^Y
UNII	U863JGG2IA
KEGG	D08879
ChEBI	CHEBI:133013^Y
ChEMBL	ChEMBL607400^Y
CompTox Dashboard (EPA)	DTXSID00905081
ECHA InfoCard	100.118.642
Chemical and physical data
Formula	C₁₁H₂₀N₂O₂
Molar mass	212.293 g·mol⁻¹
3D model (JSmol)	Interactive image
Specific rotation	[α]_D −60°
Melting point	72 to 77 °C (162 to 171 °F)
SMILES O=C(N)[C@@H](N1C(=O)C[C@@H](CCC)C1)CC
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^Y Key:MSYKRHVOOPPJKU-BDAKNGLRSA-N^Y