Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C11H20N2O2 |
Molecular Weight | 212.2891 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC[C@]1([H])CC(=O)N(C1)[C@@]([H])(CC)C(=N)O
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
Molecular Formula | C11H20N2O2 |
Molecular Weight | 212.2891 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 Date1.46301125E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
7.7 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 |
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 n = 6 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 6 Sources: |
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 n = 6 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 6 Sources: |
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 (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 37.2 years n = 2186 Health Status: unhealthy Age Group: 37.2 years Sex: M+F Population Size: 2186 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: Page: p. 28 |
healthy, 64.1 years n = 7 Health Status: healthy Age Group: 64.1 years Population Size: 7 Sources: Page: p. 28 |
Other AEs: Somnolence, Dizziness... Other AEs: Somnolence (57.1%) Sources: Page: p. 28Dizziness (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 Condition: generalized epilepsy 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 n = 6 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 6 Sources: |
Blurred vision | 1 patient | 1400 mg single, oral Highest studied dose|MID |
healthy, 18-55 years n = 6 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 6 Sources: |
Bradyphrenia | 1 patient | 1400 mg single, oral Highest studied dose|MID |
healthy, 18-55 years n = 6 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 6 Sources: |
Disorientation | 1 patient | 1400 mg single, oral Highest studied dose|MID |
healthy, 18-55 years n = 6 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 6 Sources: |
Euphoric mood | 1 patient | 1400 mg single, oral Highest studied dose|MID |
healthy, 18-55 years n = 6 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 6 Sources: |
Dizziness | 2 patients | 1400 mg single, oral Highest studied dose|MID |
healthy, 18-55 years n = 6 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 6 Sources: |
Somnolence | severe, 2 patients | 1400 mg single, oral Highest studied dose|MID |
healthy, 18-55 years n = 6 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 6 Sources: |
Agitation | 1 patient | 1000 mg single, oral MTD |
healthy, 18-55 years n = 6 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 6 Sources: |
Blurred vision | 1 patient | 1000 mg single, oral MTD |
healthy, 18-55 years n = 6 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 6 Sources: |
Bradyphrenia | 1 patient | 1000 mg single, oral MTD |
healthy, 18-55 years n = 6 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 6 Sources: |
Disorientation | 1 patient | 1000 mg single, oral MTD |
healthy, 18-55 years n = 6 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 6 Sources: |
Euphoric mood | 1 patient | 1000 mg single, oral MTD |
healthy, 18-55 years n = 6 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 6 Sources: |
Somnolence | 2 patients | 1000 mg single, oral MTD |
healthy, 18-55 years n = 6 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 6 Sources: |
Dizziness | 3 patients | 1000 mg single, oral MTD |
healthy, 18-55 years n = 6 Health Status: healthy Age Group: 18-55 years Sex: M Population Size: 6 Sources: |
Fatigue | 0.5% Disc. AE |
200 mg 1 times / day steady, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 37.2 years n = 2186 Health Status: unhealthy Age Group: 37.2 years Sex: M+F Population Size: 2186 Sources: |
Suicidal ideation | 0.5% Disc. AE |
200 mg 1 times / day steady, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 37.2 years n = 2186 Health Status: unhealthy Age Group: 37.2 years Sex: M+F Population Size: 2186 Sources: |
Suicide attempt | 0.5% Disc. AE |
200 mg 1 times / day steady, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 37.2 years n = 2186 Health Status: unhealthy Age Group: 37.2 years Sex: M+F Population Size: 2186 Sources: |
Depression | 0.6% Disc. AE |
200 mg 1 times / day steady, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 37.2 years n = 2186 Health Status: unhealthy Age Group: 37.2 years Sex: M+F Population Size: 2186 Sources: |
Dizziness | 0.6% Disc. AE |
200 mg 1 times / day steady, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 37.2 years n = 2186 Health Status: unhealthy Age Group: 37.2 years Sex: M+F Population Size: 2186 Sources: |
Somnolence | 0.7% Disc. AE |
200 mg 1 times / day steady, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 37.2 years n = 2186 Health Status: unhealthy Age Group: 37.2 years Sex: M+F Population Size: 2186 Sources: |
Convulsion | 1.4% Disc. AE |
200 mg 1 times / day steady, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 37.2 years n = 2186 Health Status: unhealthy Age Group: 37.2 years Sex: M+F Population Size: 2186 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: Page: p. 28 |
healthy, 64.1 years n = 7 Health Status: healthy Age Group: 64.1 years Population Size: 7 Sources: Page: p. 28 |
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: Page: p. 28 |
healthy, 64.1 years n = 7 Health Status: healthy Age Group: 64.1 years Population Size: 7 Sources: Page: p. 28 |
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 |
---|---|---|
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 |
|
Gateways to clinical trials. | 2007 Dec |
|
Pharmacological management of epilepsy: recent advances and future prospects. | 2008 |
|
Gateways to clinical trials. | 2008 Apr |
|
Treatment of Lennox-Gastaut syndrome: overview and recent findings. | 2008 Dec |
|
New molecular targets for antiepileptic drugs: alpha(2)delta, SV2A, and K(v)7/KCNQ/M potassium channels. | 2008 Jul |
|
Gateways to clinical trials. | 2008 Mar |
|
SVOP is a nucleotide binding protein. | 2009 |
|
Brivaracetam inhibits spreading depression in rat neocortical slices in vitro. | 2009 Jul |
|
Third-generation antiepileptic drugs: mechanisms of action, pharmacokinetics and interactions. | 2009 Mar-Apr |
|
Adjunctive brivaracetam for refractory partial-onset seizures: a randomized, controlled trial. | 2010 Aug 10 |
|
New drugs for pediatric epilepsy. | 2010 Dec |
|
Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders. | 2010 Feb 12 |
|
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).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 21:35:16 UTC 2021
by
admin
on
Fri Jun 25 21:35:16 UTC 2021
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Record UNII |
U863JGG2IA
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Record Status |
Validated (UNII)
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Record Version |
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-
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Common Name | English |
Classification Tree | Code System | Code | ||
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EU-Orphan Drug |
EU/3/05/315
Created by
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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
Created by
admin on Fri Jun 25 21:35:16 UTC 2021 , Edited by admin on Fri Jun 25 21:35:16 UTC 2021
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Code System | Code | Type | Description | ||
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BRIVARACETAM
Created by
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PRIMARY | |||
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5068
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PRIMARY | |||
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9837243
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PRIMARY | |||
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CHEMBL607400
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PRIMARY | |||
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8642
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PRIMARY | |||
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N0000192345
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PRIMARY | Epoxide Hydrolase Inhibitors [MoA] | ||
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C65270
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PRIMARY | |||
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SUB25397
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PRIMARY | |||
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DB05541
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Brivaracetam
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PRIMARY | |||
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1739745
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PRIMARY | |||
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U863JGG2IA
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PRIMARY | |||
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357336-20-0
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PRIMARY | |||
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M2654
Created by
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PRIMARY | Merck Index |
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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METABOLIC ENZYME -> SUBSTRATE | |||
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
URINE
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BINDER->LIGAND |
BINDING
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TARGET->LIGAND |
Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
AMOUNT EXCRETED
URINE
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METABOLITE INACTIVE -> PARENT |
MAJOR
PLASMA
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METABOLITE INACTIVE -> PARENT |
AMOUNT EXCRETED
URINE
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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