ChemSpider 2D Image | Levetiracetam | C8H14N2O2

Levetiracetam

  • Molecular FormulaC8H14N2O2
  • Average mass170.209 Da
  • Monoisotopic mass170.105530 Da
  • ChemSpider ID4447633
  • defined stereocentres - 1 of 1 defined stereocentres


More details:



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

(-)-(S)-α-Ethyl-2-oxo-1-pyrrolidineacetamide
(2S)-2-(2-Oxo-1-pyrrolidinyl)butanamid [German] [ACD/IUPAC Name]
(2S)-2-(2-Oxo-1-pyrrolidinyl)butanamide [ACD/IUPAC Name]
(2S)-2-(2-Oxo-1-pyrrolidinyl)butanamide [French] [ACD/IUPAC Name]
(2S)-2-(2-Oxopyrrolidin-1-yl)butanamid [German]
(2S)-2-(2-Oxopyrrolidin-1-yl)butanamide
(aS)-a-Ethyl-2-oxo-1-pyrrolidineacetamide
(S)-Etiracetam
102767-28-2 [RN]
1-pyrrolidineacetamide, a-ethyl-2-oxo-, (aS)-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:6437 [DBID]
L-059 [DBID]
LS-137054 [DBID]
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1110
      GHS07 Biosynth Q-201292
      H302; H319 Biosynth Q-201292
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1110
      IRRITANT Matrix Scientific 076097
      no pictogram Axon Medchem 1110
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1110
      P305+P351+P338 Biosynth Q-201292
      Warning Biosynth Q-201292
      Warning Axon Medchem 1110
    • Chemical Class:

      A pyrrolidinone and carboxamide that is <element>N</element>-methylpyrrolidin-2-one in which one of the methyl hydrogens is replaced by an aminocarbonyl group, while another is replaced by an ethyl gr oup (the <stereo>S</stereo> enantiomer). An anticonvulsant, it is used for the treatment of epilepsy in both human and veterinary medicine. ChEBI CHEBI:6437
    • Drug Status:

      approved BIONET-Key Organics KS-1176
    • Bio Activity:

      Antiepileptic that displays distinctive properties from conventional antiepileptic drugs. Displays potent seizure protection in animal models of chronic epilepsy but lacks activity in acute seizure mo dels. Binds synaptic vesicle protein 2A (SV2A) and inhibits Na+-dependent Cl-/HCO3- exchange. Tocris Bioscience 2839
      Antiepileptic that displays distinctive properties from conventional antiepileptic drugs. Displays potent seizure protection in animal models of chronic epilepsy but lacks activity in acute seizure models. Binds synaptic vesicle protein 2A (SV2A) and inhibits Na+-dependent Cl-/HCO3- exchange. Tocris Bioscience 2839
      Antiepileptic that displays distinctive properties from conventional antiepileptic drugs. Displays potent seizure protection in animal models of chronic epilepsy but lacks activity in acute seizure models. Binds synaptic vesicle protein 2A (SV2A) and inhibits Na+-dependent Cl-/HCO3- exchange. Deuterated analog also available. Tocris Bioscience 2839
      Antiepileptic; binds SV2A Tocris Bioscience 2839
      Cell Biology Tocris Bioscience 2839
      Levetiracetam(UCB L059) is a novel anticonvulsant with antihyperalgesic efficacy in inflammatory pain. MedChem Express
      Levetiracetam(UCB L059) is a novel anticonvulsant with antihyperalgesic efficacy in inflammatory pain.; Target: Calcium Channel; Levetiracetam is used to control some types of seizures in patients with epilepsy. MedChem Express HY-B0106
      Levetiracetam(UCB L059) is a novel anticonvulsant with antihyperalgesic efficacy in inflammatory pain.;Target: Calcium ChannelLevetiracetam is used to control some types of seizures in patients with epilepsy. This medicine cannot cure epilepsy and will only work to control seizures for as long as you continue to use it. The exact mechanism for levetiracetam is unknown. However, the drug binds to a synaptic vesicle protein, SV2A, which is believed to impede nerve conduction across synapses [1].Levetiracetam (10-200 mg/kg), ibuprofen (12.5-100 mg/kg), celecoxib (3.75-30 mg/kg), paracetamol (50-200 mg/kg), caffeine (15-100 mg/kg), and 2-drug combinations of levetiracetam with analgesics/caffeine produced a significant, dose-dependent reduction of inflammatory hyperalgesia. Isobolographic analysis revealed that levetiracetam exerts a synergistic interaction with analgesics, with approximately 7-, 9-, and 11-fold reduction of doses of both drugs in combination of levetiracetam with pa MedChem Express HY-B0106
      Others MedChem Express HY-B0106
      Signal Transduction Tocris Bioscience 2839
      Translocation, Exocytosis & Endocytosis Tocris Bioscience 2839

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.2±0.1 g/cm3
Boiling Point: 395.9±25.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.9 mmHg at 25°C
Enthalpy of Vaporization: 64.6±3.0 kJ/mol
Flash Point: 193.2±23.2 °C
Index of Refraction: 1.519
Molar Refractivity: 44.2±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: -0.67
ACD/LogD (pH 5.5): -0.74
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 9.43
ACD/LogD (pH 7.4): -0.74
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 9.43
Polar Surface Area: 63 Å2
Polarizability: 17.5±0.5 10-24cm3
Surface Tension: 48.9±3.0 dyne/cm
Molar Volume: 145.7±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) =  -0.49

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  367.03  (Adapted Stein & Brown method)
    Melting Pt (deg C):  140.80  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.51E-006  (Modified Grain method)
    Subcooled liquid VP: 5.19E-005 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):  7910
       log Kow used: -0.49 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.67E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.938E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.49  (KowWin est)
  Log Kaw used:  -7.962  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.472
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0868
   Biowin2 (Non-Linear Model)     :   0.9975
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7146  (weeks-months)
   Biowin4 (Primary Survey Model) :   4.0130  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5174
   Biowin6 (MITI Non-Linear Model):   0.6088
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.8791
 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):  0.00692 Pa (5.19E-005 mm Hg)
  Log Koa (Koawin est  ): 7.472
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000434 
       Octanol/air (Koa) model:  7.28E-006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0154 
       Mackay model           :  0.0335 
       Octanol/air (Koa) model:  0.000582 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  34.5808 E-12 cm3/molecule-sec
      Half-Life =     0.309 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.712 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.0245 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  58.12
      Log Koc:  1.764 

 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: -0.49 (estimated)

 Volatilization from Water:
    Henry LC:  2.67E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.861E+006  hours   (1.192E+005 days)
    Half-Life from Model Lake : 3.121E+007  hours   (1.3E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       0.00378         7.42         1000       
   Water     46.3            900          1000       
   Soil      53.6            1.8e+003     1000       
   Sediment  0.0891          8.1e+003     0          
     Persistence Time: 971 hr




                    

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