ChemSpider 2D Image | felbamate | C11H14N2O4

felbamate

  • Molecular FormulaC11H14N2O4
  • Average mass238.240 Da
  • Monoisotopic mass238.095352 Da
  • ChemSpider ID3214

More details:



Featured data source



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

1,3-Propanediol, 2-phenyl-, dicarbamate [ACD/Index Name]
247-001-4 [EINECS]
25451-15-4 [RN]
2-Phenyl-1,3-propandiyldicarbamat [German] [ACD/IUPAC Name]
2-Phenyl-1,3-propanediyl dicarbamate [ACD/IUPAC Name]
2-Phenylpropane-1,3-diyl dicarbamate
5686
Dicarbamate de 2-phényl-1,3-propanediyle [French] [ACD/IUPAC Name]
Felbamato [Spanish]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

ADD 03055 [DBID]
BRN 3345236 [DBID]
C07501 [DBID]
D00536 [DBID]
EU-0100524 [DBID]
F0778_SIGMA [DBID]
Lopac-F-0778 [DBID]
LS-120706 [DBID]
MLS000028465 [DBID]
NCGC00015429-01 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      N03AX10 Wikidata Q421301
      P261; P262 Biosynth Q-100326
    • Target Organs:

      NMDAR TargetMol T1946
    • Chemical Class:

      The bis(carbamate ester) of 2-phenylpropane-1,3-diol. An anticonvulsant, it is used in the treatment of epilepsy. ChEBI CHEBI:4995
    • Therapeutical Effect:

      anticonvulsant, antiepileptic Microsource [01505600]
    • Drug Status:

      approved BIONET-Key Organics KS-1171
      USAN, INN Microsource [01505600]
    • Compound Source:

      synthetic; W-554 Microsource [01505600]
    • Bio Activity:

      Anticonvulsant, acting as an antagonist at the NMDA-associated glycine binding site. Tocris Bioscience 0869, 869
      Felbamate (FBM) is a potent nonsedative anticonvulsant whose clinical effect may be related to the inhibition of N-methyl-D-aspartate (NMDA) . MedChem Express
      Felbamate (FBM) is a potent nonsedative anticonvulsant whose clinical effect may be related to the inhibition of N-methyl-D-aspartate (NMDA) .; Target: NMDA Receptor; Felbamate (marketed under the brand name Felbatol by MedPointe) is an anti-epileptic drug used in the treatment of epilepsy. MedChem Express HY-B0184
      Felbamate (FBM) is a potent nonsedative anticonvulsant whose clinical effect may be related to the inhibition of N-methyl-D-aspartate (NMDA) .;Target: NMDA ReceptorFelbamate (marketed under the brand name Felbatol by MedPointe) is an anti-epileptic drug used in the treatment of epilepsy. It is used to treat partial seizures (with and without generalization) in adults and partial and generalized seizures associated with Lennox-Gastaut syndrome in children. However, an increased risk of potentially fatal aplastic anemia and/or liver failure limit the drugs usage to severe refractory epilepsy.Felbamate has been proposed to a unique dual mechanism of action as a positive modulator of GABAA receptors and as a blocker of NMDA receptors, particularly isoforms containing the NR2B subunit. Although it is clear that felbamate does cause pharmacological inhibition of NMDA receptor of relevance of NMDA receptor blockade as a strategy for the treatment of human epilepsy has been questioned. T MedChem Express HY-B0184
      Glutamate (Ionotropic) Receptors Tocris Bioscience 869
      Ion Channels Tocris Bioscience 869
      Ligand-gated Ion Channels Tocris Bioscience 869
      Membrane Tranporter/Ion Channel MedChem Express HY-B0184
      Membrane Tranporter/Ion Channel; Neuronal Signaling; MedChem Express HY-B0184
      Neuroscience TargetMol T1946
      NMDA antagonist, acts glycine site Tocris Bioscience 0869, 869
      NMDA Receptor MedChem Express HY-B0184
      NMDA Receptor TargetMol T1946
  • Gas Chromatography

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

Density: 1.3±0.1 g/cm3
Boiling Point: 511.9±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 78.3±3.0 kJ/mol
Flash Point: 288.4±26.4 °C
Index of Refraction: 1.559
Molar Refractivity: 60.3±0.3 cm3
#H bond acceptors: 6
#H bond donors: 4
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 1.20
ACD/LogD (pH 5.5): 1.04
ACD/BCF (pH 5.5): 3.64
ACD/KOC (pH 5.5): 87.71
ACD/LogD (pH 7.4): 1.04
ACD/BCF (pH 7.4): 3.64
ACD/KOC (pH 7.4): 87.71
Polar Surface Area: 105 Å2
Polarizability: 23.9±0.5 10-24cm3
Surface Tension: 55.3±3.0 dyne/cm
Molar Volume: 186.8±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) =  0.76

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  334.22  (Adapted Stein & Brown method)
    Melting Pt (deg C):  77.33  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.6E-005  (Modified Grain method)
    MP  (exp database):  151.5 deg C
    Subcooled liquid VP: 0.000311 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):  6116
       log Kow used: 0.76 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3748.5 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.80E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.201E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.76  (KowWin est)
  Log Kaw used:  -9.707  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.467
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9760
   Biowin2 (Non-Linear Model)     :   0.9824
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5264  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.8276  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0466
   Biowin6 (MITI Non-Linear Model):   0.1428
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5477
 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):  0.0415 Pa (0.000311 mm Hg)
  Log Koa (Koawin est  ): 10.467
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  7.23E-005 
       Octanol/air (Koa) model:  0.00719 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00261 
       Mackay model           :  0.00575 
       Octanol/air (Koa) model:  0.365 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  23.9896 E-12 cm3/molecule-sec
      Half-Life =     0.446 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     5.350 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.00418 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  752.4
      Log Koc:  2.876 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  1.320E-004  L/mol-sec
  Kb Half-Life at pH 8:     166.327  years  
  Kb Half-Life at pH 7:    1663.267  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 0.76 (estimated)

 Volatilization from Water:
    Henry LC:  4.8E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.883E+008  hours   (7.845E+006 days)
    Half-Life from Model Lake : 2.054E+009  hours   (8.558E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               1.87  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.78  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       6.52e-005       10.7         1000       
   Water     42.9            900          1000       
   Soil      57.1            1.8e+003     1000       
   Sediment  0.087           8.1e+003     0          
     Persistence Time: 1.02e+003 hr




                    

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