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
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
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 Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1998 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19914041 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | BRIVIACT Approved UseBRIVIACT is indicated as adjunctive therapy in the treatment of partial-onset seizures in patients 16 years of age and older with epilepsy Launch Date2016 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
7.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
13.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
800 mg 1 times / day multiple, oral dose: 800 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
27.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
56 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
104.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
28 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
55.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
90.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
800 mg 1 times / day multiple, oral dose: 800 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
7.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
7.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
7.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
6.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
6.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341673 |
800 mg 1 times / day multiple, oral dose: 800 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
BRIVARACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
80% |
unknown, unknown |
BRIVARACETAM plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1400 mg single, oral Highest studied dose|MID |
healthy, 18-55 years |
Other AEs: Somnolence, Blurred vision... Other AEs: Somnolence (severe, 2 patients) Sources: Blurred vision (1 patient) Dizziness (2 patients) Agitation (1 patient) Bradyphrenia (1 patient) Disorientation (1 patient) Euphoric mood (1 patient) |
1000 mg single, oral MTD |
healthy, 18-55 years |
Other AEs: Somnolence, Blurred vision... Other AEs: Somnolence (2 patients) Sources: Blurred vision (1 patient) Dizziness (3 patients) Agitation (1 patient) Bradyphrenia (1 patient) Disorientation (1 patient) Euphoric mood (1 patient) |
200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 37.2 years Health Status: unhealthy Age Group: 37.2 years Sex: M+F Sources: |
Disc. AE: Convulsion, Somnolence... AEs leading to discontinuation/dose reduction: Convulsion (1.4%) Sources: Somnolence (0.7%) Depression (0.6%) Dizziness (0.6%) Fatigue (0.5%) Suicidal ideation (0.5%) Suicide attempt (0.5%) |
800 mg 1 times / day steady, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: steady Dose: 800 mg, 1 times / day Sources: |
healthy, 64.1 years Health Status: healthy Age Group: 64.1 years Sources: |
Other AEs: Somnolence, Dizziness... Other AEs: Somnolence (57.1%) Sources: Dizziness (42.9%) |
2 mg/kg 2 times / day steady, oral Highest studied dose Dose: 2 mg/kg, 2 times / day Route: oral Route: steady Dose: 2 mg/kg, 2 times / day Sources: |
unhealthy, <8 years Health Status: unhealthy Age Group: <8 years Sex: M+F Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Agitation | 1 patient | 1400 mg single, oral Highest studied dose|MID |
healthy, 18-55 years |
Blurred vision | 1 patient | 1400 mg single, oral Highest studied dose|MID |
healthy, 18-55 years |
Bradyphrenia | 1 patient | 1400 mg single, oral Highest studied dose|MID |
healthy, 18-55 years |
Disorientation | 1 patient | 1400 mg single, oral Highest studied dose|MID |
healthy, 18-55 years |
Euphoric mood | 1 patient | 1400 mg single, oral Highest studied dose|MID |
healthy, 18-55 years |
Dizziness | 2 patients | 1400 mg single, oral Highest studied dose|MID |
healthy, 18-55 years |
Somnolence | severe, 2 patients | 1400 mg single, oral Highest studied dose|MID |
healthy, 18-55 years |
Agitation | 1 patient | 1000 mg single, oral MTD |
healthy, 18-55 years |
Blurred vision | 1 patient | 1000 mg single, oral MTD |
healthy, 18-55 years |
Bradyphrenia | 1 patient | 1000 mg single, oral MTD |
healthy, 18-55 years |
Disorientation | 1 patient | 1000 mg single, oral MTD |
healthy, 18-55 years |
Euphoric mood | 1 patient | 1000 mg single, oral MTD |
healthy, 18-55 years |
Somnolence | 2 patients | 1000 mg single, oral MTD |
healthy, 18-55 years |
Dizziness | 3 patients | 1000 mg single, oral MTD |
healthy, 18-55 years |
Fatigue | 0.5% Disc. AE |
200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 37.2 years Health Status: unhealthy Age Group: 37.2 years Sex: M+F Sources: |
Suicidal ideation | 0.5% Disc. AE |
200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 37.2 years Health Status: unhealthy Age Group: 37.2 years Sex: M+F Sources: |
Suicide attempt | 0.5% Disc. AE |
200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 37.2 years Health Status: unhealthy Age Group: 37.2 years Sex: M+F Sources: |
Depression | 0.6% Disc. AE |
200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 37.2 years Health Status: unhealthy Age Group: 37.2 years Sex: M+F Sources: |
Dizziness | 0.6% Disc. AE |
200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 37.2 years Health Status: unhealthy Age Group: 37.2 years Sex: M+F Sources: |
Somnolence | 0.7% Disc. AE |
200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 37.2 years Health Status: unhealthy Age Group: 37.2 years Sex: M+F Sources: |
Convulsion | 1.4% Disc. AE |
200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 37.2 years Health Status: unhealthy Age Group: 37.2 years Sex: M+F Sources: |
Dizziness | 42.9% | 800 mg 1 times / day steady, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: steady Dose: 800 mg, 1 times / day Sources: |
healthy, 64.1 years Health Status: healthy Age Group: 64.1 years Sources: |
Somnolence | 57.1% | 800 mg 1 times / day steady, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: steady Dose: 800 mg, 1 times / day Sources: |
healthy, 64.1 years Health Status: healthy Age Group: 64.1 years Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 541 uM] | ||||
no [IC50 740 uM] | ||||
no [Inhibition 200 uM] | ||||
no [Inhibition 650 uM] | ||||
no [Inhibition 650 uM] | ||||
no [Inhibition 650 uM] | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
yes [Km 70 uM] | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Discovery of 4-substituted pyrrolidone butanamides as new agents with significant antiepileptic activity. | 2004 Jan 29 |
|
Antiepileptic drug discovery: lessons from the past and future challenges. | 2005 |
|
Gateways to clinical trials. | 2005 Jan-Feb |
|
Brivaracetam UCB. | 2005 Jul |
|
New antiepileptic drugs that are second generation to existing antiepileptic drugs. | 2006 Jun |
|
Diverse mechanisms of antiepileptic drugs in the development pipeline. | 2006 Jun |
|
Brivaracetam is superior to levetiracetam in a rat model of post-hypoxic myoclonus. | 2007 |
|
Gateways to clinical trials. | 2007 Dec |
|
Progress report on new antiepileptic drugs: a summary of the Eigth Eilat Conference (EILAT VIII). | 2007 Jan |
|
The pharmacokinetics, CNS pharmacodynamics and adverse event profile of brivaracetam after single increasing oral doses in healthy males. | 2007 Jun |
|
Evaluation of brivaracetam, a novel SV2A ligand, in the photosensitivity model. | 2007 Sep 4 |
|
Pharmacological management of epilepsy: recent advances and future prospects. | 2008 |
|
The effectiveness of anticonvulsants in psychiatric disorders. | 2008 |
|
Effect of brivaracetam on cardiac repolarisation--a thorough QT study. | 2008 Aug |
|
Brivaracetam: a rational drug discovery success story. | 2008 Aug |
|
Anti-convulsive and anti-epileptic properties of brivaracetam (ucb 34714), a high-affinity ligand for the synaptic vesicle protein, SV2A. | 2008 Aug |
|
Debate: Does genetic information in humans help us treat patients? PRO--genetic information in humans helps us treat patients. CON--genetic information does not help at all. | 2008 Dec |
|
Pharmacokinetics and metabolism of 14C-brivaracetam, a novel SV2A ligand, in healthy subjects. | 2008 Jan |
|
The pharmacokinetics, CNS pharmacodynamics and adverse event profile of brivaracetam after multiple increasing oral doses in healthy men. | 2008 Jul |
|
Gateways to clinical trials. | 2008 Mar |
|
Brivaracetam: a new drug in development for epilepsy and neuropathic pain. | 2008 Mar |
|
Brivaracetam inhibits spreading depression in rat neocortical slices in vitro. | 2009 Jul |
|
Recent advances in adjunctive therapy for epilepsy: focus on sodium channel blockers as third-generation antiepileptic drugs. | 2010 Apr |
|
Physiologically based pharmacokinetic/pharmacodynamic animal-to-man prediction of therapeutic dose in a model of epilepsy. | 2010 Mar |
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19914041
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).
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Classification Tree | Code System | Code | ||
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EU-Orphan Drug |
EU/3/05/315
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WHO-ATC |
N03AX23
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FDA ORPHAN DRUG |
207305
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FDA ORPHAN DRUG |
724019
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FDA ORPHAN DRUG |
711119
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Code System | Code | Type | Description | ||
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BRIVARACETAM
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5068
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9837243
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133013
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DTXSID00905081
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CHEMBL607400
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8642
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N0000192345
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PRIMARY | Epoxide Hydrolase Inhibitors [MoA] | ||
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U863JGG2IA
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C65270
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SUB25397
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DB05541
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Brivaracetam
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QQ-109
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1739745
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U863JGG2IA
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357336-20-0
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100000089410
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m2654
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PRIMARY | Merck Index |
ACTIVE MOIETY
METABOLITE INACTIVE (PARENT)
METABOLITE INACTIVE (PARENT)
METABOLITE INACTIVE (PARENT)