ChemSpider 2D Image | Brivaracetam | C11H20N2O2

Brivaracetam

  • Molecular FormulaC11H20N2O2
  • Average mass212.289 Da
  • Monoisotopic mass212.152481 Da
  • ChemSpider ID8012964

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

Featured data source
The Merck Index Online

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(2S)-2-[(4R)-2-Oxo-4-propyl-1-pyrrolidinyl]butanamid [German] [ACD/IUPAC Name]
(2S)-2-[(4R)-2-Oxo-4-propyl-1-pyrrolidinyl]butanamide [ACD/IUPAC Name]
(2S)-2-[(4R)-2-Oxo-4-propyl-1-pyrrolidinyl]butanamide [French] [ACD/IUPAC Name]
1-Pyrrolidineacetamide, α-ethyl-2-oxo-4-propyl-, (αS,4R)- [ACD/Index Name]
357336-20-0 [RN]
Brivaracetam [INN] [USAN] [Wiki]
Briviact [Trade name]
Rikelta [Trade name]
U863JGG2IA
UCB 34714
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

8642 [DBID]
UCB-34714 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A non-proteinogenic amino acid derivative that is butanamide in which the pro-S hydrogen at position 2 is replaced by a (4R)-2-oxo-4-propylpyrrolidin-1-; yl. Used for treatment of partial onset seizu res related to epilepsy. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:133013
      A non-proteinogenic amino acid derivative that is butanamide in which the <ital> pro-<stereo>S</stereo></ital> hydrogen at position 2 is replaced by a (4<stereo>R</stereo>)-2-oxo-4-propylpyrrolidin-1- yl. Used for treatment of partial onset seizures related to epilepsy. ChEBI CHEBI:133013
      A non-proteinogenic amino acid derivative that is butanamide in which the pro-S hydrogen at position 2 is replaced by a (4R)-2-oxo-4-propylpyrrolidin-1-yl. Used for treatment of partial onset seizures related to epilepsy. ChEBI CHEBI:133013

    • Bio Activity:

      Brivaracetam(UCB-34714) is a 4-substituted pyrrolidone butanamide as agent with significant antiepileptic activity; high affinity SV2A ligand and also shows an ability to inhibit Na+ channels. MedChem Express
      Brivaracetam(UCB-34714) is a 4-substituted pyrrolidone butanamide as agent with significant antiepileptic activity; high affinity SV2A ligand and also shows an ability to inhibit Na+ channels.; IC50 value:; Target: SV2A ligand; in vitro: Brivaracetam has been tested in a comprehensive safety pharmacology, toxicology, developmental toxicology, and genotoxicity program. MedChem Express HY-14449
      Brivaracetam(UCB-34714) is a 4-substituted pyrrolidone butanamide as agent with significant antiepileptic activity; high affinity SV2A ligand and also shows an ability to inhibit Na+ channels.;IC50 value:;Target: SV2A ligand;In vitro: Brivaracetam has been tested in a comprehensive safety pharmacology, toxicology, developmental toxicology, and genotoxicity program. It is of low acute toxicity, target organ for toxic effects is the hepatobiliary tract. Carcinogenicity studies are ongoing. Human pharmacology studies have shown that brivaracetam has a half-life of 8 h and nearly complete bioavailability [1]. CSD episodes were regularly elicited on slices upon delivery of calibrated KCl drops and were recorded via two micropipette electrodes. After control CSDs, the drug was added to the perfusion and five subsequent CSDs were elicited during drug perfusion. Effects were assessed via CSD amplitude (Ampl) and duration at half-amplitude (D(1/2)). BRV, 10 and 32 microM reduced the Ampl an MedChem Express HY-14449
      Others MedChem Express HY-14449

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.1±0.1 g/cm3
Boiling Point: 409.3±28.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 66.1±3.0 kJ/mol
Flash Point: 201.3±24.0 °C
Index of Refraction: 1.494
Molar Refractivity: 58.2±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 0.88
ACD/LogD (pH 5.5): 0.61
ACD/BCF (pH 5.5): 1.70
ACD/KOC (pH 5.5): 50.92
ACD/LogD (pH 7.4): 0.61
ACD/BCF (pH 7.4): 1.70
ACD/KOC (pH 7.4): 50.92
Polar Surface Area: 63 Å2
Polarizability: 23.1±0.5 10-24cm3
Surface Tension: 40.3±3.0 dyne/cm
Molar Volume: 199.8±3.0 cm3

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™ 

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  0.91

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  398.48  (Adapted Stein & Brown method)
    Melting Pt (deg C):  161.40  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.6E-007  (Modified Grain method)
    Subcooled liquid VP: 9.05E-006 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  6344
       log Kow used: 0.91 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.1182e+005 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.25E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.585E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.91  (KowWin est)
  Log Kaw used:  -7.593  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.503
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0668
   Biowin2 (Non-Linear Model)     :   0.9954
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6216  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.9523  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4841
   Biowin6 (MITI Non-Linear Model):   0.4353
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.7473
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.00121 Pa (9.05E-006 mm Hg)
  Log Koa (Koawin est  ): 8.503
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00249 
       Octanol/air (Koa) model:  7.82E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0824 
       Mackay model           :  0.166 
       Octanol/air (Koa) model:  0.00621 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  41.7684 E-12 cm3/molecule-sec
      Half-Life =     0.256 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.073 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.124 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  335.4
      Log Koc:  2.526 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 0.91 (estimated)

 Volatilization from Water:
    Henry LC:  6.25E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.365E+006  hours   (5.687E+004 days)
    Half-Life from Model Lake : 1.489E+007  hours   (6.204E+005 days)

 Removal In Wastewater Treatment:
    Total removal:               1.88  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.79  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.00893         6.15         1000       
   Water     41.7            900          1000       
   Soil      58.2            1.8e+003     1000       
   Sediment  0.0866          8.1e+003     0          
     Persistence Time: 1.03e+003 hr

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