Brivaracetam

Brivaracetam

Names
IUPAC name (2S)-2-[(4R)-2-oxo- 4-propylpyrrolidin-1-yl] butanamide
Identifiers
CAS Number	357336-20-0
ChEMBL	ChEMBL607400
ChemSpider	8012964
Jmol 3D model	Interactive image
PubChem	9837243
UNII	U863JGG2IA
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 InChI=1/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-BDAKNGLRBT
SMILES O=C(N)[C@@H](N1C(=O)C[C@@H](CCC)C1)CC
Properties
Chemical formula	C11H20N2O2
Molar mass	212.15 g/mol
Pharmacology
ATC code	N03AX23 (WHO)
Legal status	Investigational
Routes of administration	Oral
Pharmacokinetics:
Bioavailability	Nearly 100%
Protein binding	<20%
Metabolism	Hydrolysis, CYP2C8-mediated hydroxylation
Biological half-life	8 hrs
Excretion	>75% renal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Brivaracetam, the 4-n-propyl analog of levetiracetam, is a racetam derivative with anticonvulsant properties.^[1][2] Brivaracetam is believed to act by binding to the ubiquitous synaptic vesicle glycoprotein 2A (SV2A).^[3] Phase II clinical trials in adult patients with refractory partial seizures were promising. Positive preliminary results from stage III trials have been recorded,^[4][5] along with evidence that it is around 10 times more potent^[6] for the prevention of certain types of seizure in mouse models than levetiracetam, of which it is an analogue.

On 14 January 2016, the European Commission,^[7] and on 18 February 2016, the Food and Drug Administration^[8] approved brivaracetam under the trade name Briviact (by UCB). The product is currently being considered for scheduling by the Drug Enforcement Agency and will be made available for sale in the U.S. shortly. Currently, brivaracetam is still not approved in other countries like Australia, Canada and Switzerland.

References

1. von Rosenstiel P (Jan 2007). "Brivaracetam (UCB 34714)". Neurotherapeutics 4 (1): 84–7. doi:10.1016/j.nurt.2006.11.004. PMID 17199019.
2. Malawska B, Kulig K (Jul 2005). "Brivaracetam UCB". Current Opinion in Investigational Drugs 6 (7): 740–746. PMID 16044671.
3. Rogawski MA, Bazil CW (Jul 2008). "New molecular targets for antiepileptic drugs: alpha(2)delta, SV2A, and K(v)7/KCNQ/M potassium channels". Current Neurology and Neuroscience Reports 8 (4): 345–352. doi:10.1007/s11910-008-0053-7. PMC: 2587091. PMID 18590620.
4. Clinical trial number NCT00464269 for "Double-blind, Randomized Study Evaluating the Efficacy and Safety of Brivaracetam in Adults With Partial Onset Seizures" at ClinicalTrials.gov
5. Rogawski MA (Aug 2008). "Brivaracetam: a rational drug discovery success story". British Journal of Pharmacology 154 (8): 1555–7. doi:10.1038/bjp.2008.221. PMC: 2518467. PMID 18552880.
6. Matagne A, Margineanu DG, Kenda B, Michel P, Klitgaard H (Aug 2008). "Anti-convulsive and anti-epileptic properties of brivaracetam (ucb 34714), a high-affinity ligand for the synaptic vesicle protein, SV2A". British Journal of Pharmacology 154 (8): 1662. doi:10.1038/bjp.2008.198. PMID 18500360.
7. http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/medicines/003898/human_med_001945.jsp&mid=WC0b01ac058001d124
8. http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm486827.htm