Brivaracetam

ligand for SV2A, selective and high-affinity CAS# 357336-20-0

Brivaracetam

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Chemical structure

Brivaracetam

3D structure

Chemical Properties of Brivaracetam

Cas No. 357336-20-0 SDF Download SDF
PubChem ID 9837243 Appearance Powder
Formula C11H20N2O2 M.Wt 212.29
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in DMSO
Chemical Name (2S)-2-[(4R)-2-oxo-4-propylpyrrolidin-1-yl]butanamide
SMILES CCCC1CC(=O)N(C1)C(CC)C(=O)N
Standard InChIKey MSYKRHVOOPPJKU-BDAKNGLRSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Brivaracetam Dilution Calculator

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Brivaracetam Molarity Calculator

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Preparing Stock Solutions of Brivaracetam

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.7105 mL 23.5527 mL 47.1054 mL 94.2107 mL 117.7634 mL
5 mM 0.9421 mL 4.7105 mL 9.4211 mL 18.8421 mL 23.5527 mL
10 mM 0.4711 mL 2.3553 mL 4.7105 mL 9.4211 mL 11.7763 mL
50 mM 0.0942 mL 0.4711 mL 0.9421 mL 1.8842 mL 2.3553 mL
100 mM 0.0471 mL 0.2355 mL 0.4711 mL 0.9421 mL 1.1776 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Brivaracetam

Brivaracetam is a selective and high-affinity ligand for SV2A with pKi value of 7.1 [1].

Synaptic vesicle protein 2A (SV2A) is a ubiquitous synaptic vesicle protein that involved in synaptic vesicle exocytosis and neurotransmitter release.

Brivaracetam is a selective and high-affinity SV2A ligand and also inhibits Na+ channels. In rat hippocampal slices, brivaracetam (3.2 µM) significantly inhibited evoked epileptiform responses [1]. In rat neuronal somas, brivaracetam inhibited voltage-dependent Na+ currents with IC50 values of 41 µM and 6.5 µM at the holding potential of −100 mV and −60 mV, respectively. These results suggested that brivaracetam regulated the voltage-activated Na+ currents, which might contribute to its antiepileptic activity [3].

In corneally kindled mice with partial epilepsy, brivaracetam protected mice from secondarily generalized motor seizures with ED50 value of 1.2 mg/kg [1]. In hippocampal-kindled rats, brivaracetam exhibited anti-kindling properties. In amygdala-kindled rats, brivaracetam significantly inhibited motor-seizure severity and reduced the after-discharge. In genetic absence epilepsy rats, brivaracetam completely inhibited spontaneous spike-and-wave discharges [2].

References:
[1].  von Rosenstiel P. Brivaracetam (UCB 34714). Neurotherapeutics, 2007, 4(1): 84-87.
[2].  Matagne A, Margineanu DG, Kenda B, et al. Anti-convulsive and anti-epileptic properties of brivaracetam (ucb 34714), a high-affinity ligand for the synaptic vesicle protein, SV2A. Br J Pharmacol, 2008, 154(8): 1662-1671.
[3].  Zona C, Pieri M, Carunchio I, et al. Brivaracetam (ucb 34714) inhibits Na(+) current in rat cortical neurons in culture. Epilepsy Res, 2010, 88(1): 46-54.

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References on Brivaracetam

Schedules of Controlled Substances: Placement of Brivaracetam Into Schedule V. Final rule.[Pubmed:28355045]

Fed Regist. 2017 Mar 9;82(45):13067-9.

This final rule adopts without change an interim final rule with request for comments published in the Federal Register on May 12, 2016. The Drug Enforcement Administration is placing the substance Brivaracetam ((2S)-2-[(4R)-2-oxo-4-propylpyrrolidin-1-yl] butanamide) (also referred to as BRV; UCB-34714; Briviact) (including its salts) into schedule V of the Controlled Substances Act. This scheduling action is pursuant to the Controlled Substances Act, as revised by the Improving Regulatory Transparency for New Medical Therapies Act which was signed into law on November 25, 2015.

Real-life experience with brivaracetam in 101 patients with difficult-to-treat epilepsy-A monocenter survey.[Pubmed:28364655]

Seizure. 2017 May;48:11-14.

PURPOSE: To assess the efficiency of Brivaracetam under real-world conditions in a tertiary referral epilepsy center. METHODS: We consecutively collected patients treated at our center with Brivaracetam (BRV). After a minimum observation period of six months we retrospectively analyzed the efficiency of BRV. RESULTS: Data of 101 patients (mean age 42 years, range 18-81 years, 54 females,) were analyzed. The median number of antiepileptic drugs (AEDs) used prior to BRV was 10 (range 2-18). The initial dose of BRV was at least 50mg per day, the mean maintenance dose at cut-off was 168.6mg (median 200mg, range 50-400mg). Efficacy data were assessed for the last three months or at the time of the last observation carried forward if BRV had been discontinued prematurely. Responder rate was 27.8% (n=28) with 7% seizure-free patients. Adverse events (AEs) occurred in 37 patients (37%). Most frequent AEs were dizziness (16%) and somnolence (11%). Psychiatric adverse events comprised irritability, aggression, depression and psychosis in single cases. Retention rate after six months was 51.5%. Main reason for discontinuation was a lack of efficacy. In 43 cases LEV and BRV were switched. The switch was performed abruptly without complications. In 26 cases (60%) BRV was discontinued and re-switched to LEV within weeks, mainly due to a lack of better efficacy. After the switch from LEV to BRV we even saw an aggravation both of seizure frequency and severity in 5 cases. Retention rate in patients who had not been on LEV was 57%. CONCLUSION: In our hands BRV appeared to be well tolerated and easy to handle. The retention rate was influenced by patients who were switched from LEV and re-switched because BRV was not more efficient. Switching from and re-switching to LEV was easy.

New developments in the management of partial-onset epilepsy: role of brivaracetam.[Pubmed:28293101]

Drug Des Devel Ther. 2017 Mar 6;11:643-657.

Currently, a number of novel anticonvulsant drugs, the so-called third generation, are in various stages of development. Several of them are already available or in ongoing clinical trials. These new compounds should take advantage of new insights into the basic pathophysiology of epileptogenesis, drug metabolism and drug interactions. Many of them still need to be further evaluated mainly in real-world observational trials and registries. Among newer anticonvulsant drugs for partial-onset seizures (POSs), rufinamide, lacosamide, eslicarbazepine and perampanel are those new treatment options for which more substantial clinical evidence is currently available, both in adults and, to some extent, in children. Among the newest anticonvulsant drugs, Brivaracetam, a high-affinity synaptic vesicle protein 2A ligand, reported to be 10- to 30-fold more potent than levetiracetam, is highly effective in a broad range of experimental models of focal and generalized seizures. Unlike levetiracetam, Brivaracetam does not inhibit high-voltage Ca(2+) channels and AMPA receptors and appears to inhibit neuronal voltage-gated sodium channels playing a role as a partial antagonist. Brivaracetam has a linear pharmacokinetic profile, is extensively metabolized and is excreted by urine (only 8%-11% unchanged). It does not seem to influence the pharmacokinetics of other antiepileptic drugs. It was approved in the European Union in January 2016 and in the US in February 2016 as an adjunctive therapy for the treatment of POS in patients older than 16 years of age. To date, its clinical efficacy as adjunctive antiepileptic treatment in adults with refractory POS at doses between 50 and 200 mg daily has been extensively assessed in two Phase IIb and four Phase III randomized controlled studies. Long-term extension studies show sustained efficacy of Brivaracetam. Overall, the drug is generally well tolerated with only mild-to-moderate side effects. This is true also by intravenous route. Brivaracetam has not yet been evaluated as monotherapy or in comparison with other new anticonvulsant drugs.

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