ChemSpider 2D Image | Retigabine | C16H18FN3O2

Retigabine

  • Molecular FormulaC16H18FN3O2
  • Average mass303.331 Da
  • Monoisotopic mass303.138306 Da
  • ChemSpider ID108740

More details:

Featured data source
The Merck Index Online

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

[2-Amino-4-(4-fluoro-benzylamino)-phenyl]-carbamic acid ethyl ester
{2-Amino-4-[(4-fluorobenzyl)amino]phényl}carbamate d'éthyle [French] [ACD/IUPAC Name]
12G01I6BBU
150812-12-7 [RN]
200-835-2 [EINECS]
2-Amino-4-(4-fluorbenzylamino)-1-ethoxycarbonylaminobenzene
Carbamic acid, N-[2-amino-4-[[(4-fluorophenyl)methyl]amino]phenyl]-, ethyl ester [ACD/Index Name]
Ethyl (2-amino-4-(((4-fluorophenyl)methyl)amino)phenyl)carbamate
Ethyl {2-amino-4-[(4-fluorobenzyl)amino]phenyl}carbamate [ACD/IUPAC Name]
ethyl N-(2-amino-4-{[(4-fluorophenyl)methyl]amino}phenyl)carbamate
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

7545 [DBID]
8072099 [DBID]
AWD21-360 [DBID]
D-23129 [DBID]
GKE-841 [DBID]
GW582892X [DBID]
WAY-143841 [DBID]
ADD-230001 [DBID]
C13826 [DBID]
CCRIS 4693 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Safety:

      N03AX21 Wikidata Q2146170

    • Target Organs:

      Potassium Channel TargetMol T2536

    • Chemical Class:

      A substituted aniline that is benzene-1,2,4-triamine bearing ethoxycarbonyl and 4-fluorobenzyl substituents at positions N-1 and N-4 respectively. An anticonvulsant used to treat seizures associated with epilepsy in adults. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:68584, CHEBI:68584

    • Bio Activity:

      Ion Channels Tocris Bioscience 6233
      KV7 (KCNQ) channel activator (EC50 values are 0.6 - 100 muM for KV7.1 - KV7.5). Anticonvulsant. Orally bioavailable. Tocris Bioscience 6233
      KV7 channel activator Tocris Bioscience 6233
      Membrane Tranporter/Ion Channel MedChem Express HY-15471
      Membrane Tranporter/Ion Channel; MedChem Express HY-15471
      Membrane Transporter/Ion Channel TargetMol T2536
      Potassium Channel TargetMol T2536
      Potassium Channels Tocris Bioscience 6233
      Potassiun Channel MedChem Express HY-15471
      Retigabine (Ezogabine; D23129) is a Kv7.2-7.5 (KCNQ2-5) neuronal potassium channel opener witrh anticonvulsant activity. MedChem Express
      Retigabine (Ezogabine; D23129) is a Kv7.2-7.5 (KCNQ2-5) neuronal potassium channel opener witrh anticonvulsant activity.; IC50 value:; Target: Kv7.2-7.5; Retigabine (D-23129) is a novel antiepileptic compound with broad spectrum and potent anticonvulsant properties, both in vitro and in vivo. MedChem Express HY-15471
      Voltage-Gated Potassium Channels Tocris Bioscience 6233

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

Density: 1.3±0.1 g/cm3
Boiling Point: 430.0±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 68.5±3.0 kJ/mol
Flash Point: 213.9±28.7 °C
Index of Refraction: 1.656
Molar Refractivity: 85.2±0.3 cm3
#H bond acceptors: 5
#H bond donors: 4
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 0.81
ACD/LogD (pH 5.5): 1.97
ACD/BCF (pH 5.5): 15.94
ACD/KOC (pH 5.5): 210.67
ACD/LogD (pH 7.4): 2.24
ACD/BCF (pH 7.4): 29.85
ACD/KOC (pH 7.4): 394.42
Polar Surface Area: 76 Å2
Polarizability: 33.8±0.5 10-24cm3
Surface Tension: 55.9±3.0 dyne/cm
Molar Volume: 232.0±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) =  2.56

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  426.52  (Adapted Stein & Brown method)
    Melting Pt (deg C):  172.07  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.62E-008  (Modified Grain method)
    Subcooled liquid VP: 1.87E-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):  75.82
       log Kow used: 2.56 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.2615 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.49E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.958E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.56  (KowWin est)
  Log Kaw used:  -13.514  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.074
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.5948
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8053  (months      )
   Biowin4 (Primary Survey Model) :   3.4004  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.4801
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4485
 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):  0.000249 Pa (1.87E-006 mm Hg)
  Log Koa (Koawin est  ): 16.074
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.012 
       Octanol/air (Koa) model:  2.91E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.303 
       Mackay model           :  0.49 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 213.3367 E-12 cm3/molecule-sec
      Half-Life =     0.050 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.602 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.397 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2.103E+004
      Log Koc:  4.323 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  3.997E-005  L/mol-sec
  Kb Half-Life at pH 8:     549.531  years  
  Kb Half-Life at pH 7:    5495.308  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.274 (BCF = 18.81)
       log Kow used: 2.56 (estimated)

 Volatilization from Water:
    Henry LC:  7.49E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.361E+012  hours   (5.673E+010 days)
    Half-Life from Model Lake : 1.485E+013  hours   (6.188E+011 days)

 Removal In Wastewater Treatment:
    Total removal:               3.28  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     3.17  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       6.61e-009       1.2          1000       
   Water     14              1.44e+003    1000       
   Soil      85.9            2.88e+003    1000       
   Sediment  0.135           1.3e+004     0          
     Persistence Time: 2.42e+003 hr

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