ChemSpider 2D Image | Flupirtine | C15H17FN4O2

Flupirtine

  • Molecular FormulaC15H17FN4O2
  • Average mass304.319 Da
  • Monoisotopic mass304.133545 Da
  • ChemSpider ID48119

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

[2-Amino-6-[[(4-fluorophenyl)methyl]amino]-3-pyridinyl]carbamic Acid Ethyl Ester
{2-Amino-6-[(4-fluorobenzyl)amino]-3-pyridinyl}carbamate d'éthyle [French] [ACD/IUPAC Name]
260-503-8 [EINECS]
278-225-0 [EINECS]
2-Amino-6-[(p-fluorobenzyl)amino]-3-pyridinecarbamic Acid Ethyl Ester
3976
56995-20-1 [RN]
Carbamic acid, N-[2-amino-6-[[(4-fluorophenyl)methyl]amino]-3-pyridinyl]-, ethyl ester [ACD/Index Name]
D 9998 [Trade name]
Ethyl {2-amino-6-[(4-fluorobenzyl)amino]-3-pyridinyl}carbamate [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

Lopac-F-8927 [DBID]
NCGC00015451-01 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      N02BG07 Wikidata Q415403
    • Bio Activity:

      Flupirtine(D 9998) is a selective neuronal potassium channel opener that also has NMDA receptor antagonist properties. MedChem Express
      Flupirtine(D 9998) is a selective neuronal potassium channel opener that also has NMDA receptor antagonist properties.; IC50 Value: ; Target: Potassium channel; NMDA receptor; in vitro: High concentrations of flupirtine antagonized inward currents to NMDA(200 microM) at -70 mV with an lC50 against steady-state responses of 182.1+/-12.1 microM. MedChem Express HY-17001A
      Flupirtine(D 9998) is a selective neuronal potassium channel opener that also has NMDA receptor antagonist properties.;IC50 Value: ;Target: Potassium channel; NMDA receptor;In vitro: High concentrations of flupirtine antagonized inward currents to NMDA(200 microM) at -70 mV with an lC50 against steady-state responses of 182.1+/-12.1 microM. The effects of flupirtine were voltage-independent and not associated with receptor desensitization making actions within the NMDA receptor channel or at the glycine modulatory site unlikely. NMDA receptor antagonism probably has little relevance for the clinical efficacy of flupirtine as the concentrations needed were far higher than those achieved in clinical practice. However, the activation of a G-protein-regulated inwardly rectifying K+ channel was identified as an interesting molecular target site of flupirtine. In the next stage, the central nervous spectrum of action of experimental K+ channel openers (PCO) was considered. As far as they MedChem Express HY-17001A
      Ion Channels Tocris Bioscience 2867
      KV7 channel activator Tocris Bioscience 2867
      Membrane Tranporter/Ion Channel MedChem Express HY-17001A
      Membrane Tranporter/Ion Channel; MedChem Express HY-17001A
      Non-opioid analgesic with muscle relaxant properties. Activates KV7 potassium channels, indirectly antagonizes NMDA receptors and modulates GABAA receptors. Exhibits neuroprotective actions in a model of cerebral ischemia in mice and reduces apoptosis and necrosis induced by noxious stimuli. Tocris Bioscience 2867
      Non-opioid analgesic with muscle relaxant properties. Activates KV7 potassium channels, indirectly antagonizes NMDA receptors and modulates GABAA receptors. Exhibits neuroprotective actions in a model of cerebral ischemia in mice and reduces apoptosis and necrosis induced by noxious stimuli. Tocris Bioscience 2867
      Potassium Channels Tocris Bioscience 2867
      Potassiun Channel MedChem Express HY-17001A
      Voltage-Gated Potassium Channels Tocris Bioscience 2867

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

Density: 1.4±0.1 g/cm3
Boiling Point: 435.0±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 69.1±3.0 kJ/mol
Flash Point: 216.9±28.7 °C
Index of Refraction: 1.662
Molar Refractivity: 83.3±0.3 cm3
#H bond acceptors: 6
#H bond donors: 4
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 1.99
ACD/LogD (pH 5.5): 2.37
ACD/BCF (pH 5.5): 35.06
ACD/KOC (pH 5.5): 414.69
ACD/LogD (pH 7.4): 2.47
ACD/BCF (pH 7.4): 44.42
ACD/KOC (pH 7.4): 525.43
Polar Surface Area: 89 Å2
Polarizability: 33.0±0.5 10-24cm3
Surface Tension: 60.6±3.0 dyne/cm
Molar Volume: 225.3±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) =  2.66

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  431.96  (Adapted Stein & Brown method)
    Melting Pt (deg C):  180.81  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.75E-007  (Modified Grain method)
    MP  (exp database):  115.5 deg C
    Subcooled liquid VP: 1.37E-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):  61.99
       log Kow used: 2.66 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  231.05 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 :   9.80E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.130E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.66  (KowWin est)
  Log Kaw used:  -16.397  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.057
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.7499
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5889  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.3803  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.5248
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2880
 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):  0.000183 Pa (1.37E-006 mm Hg)
  Log Koa (Koawin est  ): 19.057
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0164 
       Octanol/air (Koa) model:  2.8E+006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.372 
       Mackay model           :  0.568 
       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): 0.47 (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 :  2.616E-004  L/mol-sec
  Kb Half-Life at pH 8:      83.944  years  
  Kb Half-Life at pH 7:     839.445  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.348 (BCF = 22.29)
       log Kow used: 2.66 (estimated)

 Volatilization from Water:
    Henry LC:  9.8E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.042E+015  hours   (4.343E+013 days)
    Half-Life from Model Lake : 1.137E+016  hours   (4.737E+014 days)

 Removal In Wastewater Treatment:
    Total removal:               3.64  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     3.54  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       2.88e-012       1.2          1000       
   Water     9.98            4.32e+003    1000       
   Soil      89.9            8.64e+003    1000       
   Sediment  0.126           3.89e+004    0          
     Persistence Time: 5.32e+003 hr




                    

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