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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H20N2O2
Molecular Weight 212.2887
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Brivaracetam

SMILES

CCC[C@H]1CN([C@@H](CC)C(N)=O)C(=O)C1

InChI

InChIKey=MSYKRHVOOPPJKU-BDAKNGLRSA-N
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

HIDE SMILES / InChI

Molecular Formula C11H20N2O2
Molecular Weight 212.2887
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Brivaracetam (UCB 34714, trade name Briviact), the 4-n-propyl analog of levetiracetam, is a racetam derivative with anticonvulsant properties. Briviact is indicated as adjunctive therapy in the treatment of partial-onset seizures in patients 16 years of age and older with epilepsy. Brivaracetam is believed to act by binding to the ubiquitous synaptic vesicle glycoprotein 2A (SV2A), like levetiracetam, but with 20-fold greater affinity. There is some evidence that racetams including levetiracetam and brivaracetam access the luminal side of recycling synaptic vesicles during vesicular endocytosis. They may reduce excitatory neurotransmitter release and enhance synaptic depression during trains of high-frequency activity, such as is believed to occur during epileptic activity.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BRIVIACT

Cmax

ValueDoseCo-administeredAnalytePopulation
2.2 μg/mL
200 mg single, oral
BRIVARACETAM plasma
Homo sapiens
4.7 μg/mL
400 mg single, oral
BRIVARACETAM plasma
Homo sapiens
9 μg/mL
800 mg single, oral
BRIVARACETAM plasma
Homo sapiens
3.5 μg/mL
200 mg 1 times / day multiple, oral
BRIVARACETAM plasma
Homo sapiens
7.7 μg/mL
400 mg 1 times / day multiple, oral
BRIVARACETAM plasma
Homo sapiens
13.3 μg/mL
800 mg 1 times / day multiple, oral
BRIVARACETAM plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
27.5 μg × h/mL
200 mg single, oral
BRIVARACETAM plasma
Homo sapiens
56 μg × h/mL
400 mg single, oral
BRIVARACETAM plasma
Homo sapiens
104.1 μg × h/mL
800 mg single, oral
BRIVARACETAM plasma
Homo sapiens
28 μg × h/mL
200 mg 1 times / day multiple, oral
BRIVARACETAM plasma
Homo sapiens
55.4 μg × h/mL
400 mg 1 times / day multiple, oral
BRIVARACETAM plasma
Homo sapiens
90.8 μg × h/mL
800 mg 1 times / day multiple, oral
BRIVARACETAM plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7.7 h
200 mg single, oral
BRIVARACETAM plasma
Homo sapiens
7.3 h
400 mg single, oral
BRIVARACETAM plasma
Homo sapiens
7.8 h
800 mg single, oral
BRIVARACETAM plasma
Homo sapiens
7.3 h
200 mg 1 times / day multiple, oral
BRIVARACETAM plasma
Homo sapiens
6.8 h
400 mg 1 times / day multiple, oral
BRIVARACETAM plasma
Homo sapiens
6.3 h
800 mg 1 times / day multiple, oral
BRIVARACETAM plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
80%
unknown, unknown
BRIVARACETAM plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
The recommended starting dosage is 50 mg twice daily (100 mg per day). Based on individual patient tolerability and therapeutic response, the dosage may be adjusted down to 25 mg twice daily (50 mg per day) or up to 100 mg twice daily (200 mg per day). BRIVIACT (brivaracetam) injection may be used when oral administration is temporarily not feasible. BRIVIACT injection should be administered at the same dosage and same frequency as BRIVIACT tablets and oral solution.
Route of Administration: Other
In Vitro Use Guide
Brivaracetam (BRV) is able to modulate the voltage-activated Na(+) inflow in cortical neurons. Voltage-activated Na(+) currents were recorded by whole-cell patch-clamp on neuronal somas of rat neocortical neurons, grown in dissociated cell culture for up to 12 days. BRV, dissolved at the desired final concentration (between 0.2 microM and 1 mM) was applied by a multi-barrel pipette system near the soma of the recorded neuron. BRV produced a concentration-dependent inhibition of voltage-dependent Na(+) currents with IC(50) values of 41 microM at the holding potential of -100 mV, and of 6.5 microM at the holding potential of -60 mV. The voltage-dependence of activation and the kinetics of fast inactivation were not modified in the presence of BRV (30 microM).
Substance Class Chemical
Record UNII
U863JGG2IA
Record Status Validated (UNII)
Record Version