ChemSpider 2D Image | Vanoxerine | C28H32F2N2O

Vanoxerine

  • Molecular FormulaC28H32F2N2O
  • Average mass450.563 Da
  • Monoisotopic mass450.248260 Da
  • ChemSpider ID3337

More details:

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

1-(2-(Bis(p-fluorophenyl)methoxy)ethyl)-4-(3-phenylpropyl)piperazine
1-{2-[Bis(4-fluorophenyl)methoxy]ethyl}-4-(3-phenylpropyl)piperazine [ACD/IUPAC Name]
1-{2-[Bis(4-fluorophényl)méthoxy]éthyl}-4-(3-phénylpropyl)pipérazine [French] [ACD/IUPAC Name]
1-{2-[Bis(4-fluorphenyl)methoxy]ethyl}-4-(3-phenylpropyl)piperazin [German] [ACD/IUPAC Name]
67469-69-6 [RN]
Piperazine, 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)- [ACD/Index Name]
vanoxerina
Vanoxerina [Spanish] [INN]
Vanoxerine [INN] [Wiki]
Vanoxerine [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

6307 [DBID]
90X28IKH43 [DBID]
CHEBI:64089 [DBID]
Biomol-NT_000010 [DBID]
BPBio1_000629 [DBID]
BPBio1_001141 [DBID]
BSPBio_000571 [DBID]
DivK1c_006996 [DBID]
Gbr 12909 [DBID]
GBR12909 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      An <element>N</element>-alkylpiperazine that consists of piperazine bearing 2-bis(4-fluorophenyl)methoxy]ethyl and 3-phenylpropyl groups at positions 1 and 4 respectively. Potent, competitive inhibito r of dopamine uptake (Ki = 1 nM for inhibition of striatal dopamine uptake). Has <greaterthan/> 100-fold lower affinity for the noradrenalin and 5-HT uptake carriers. Also a potent sigma ligand (IC<sm allsub>50</smallsub> = 48 nM). Centrally active following systemic administration. ChEBI CHEBI:64089
      An N-alkylpiperazine that consists of piperazine bearing 2-bis(4-fluorophenyl)methoxy]ethyl and 3-phenylpropyl groups at positions 1 and 4 respectively. Potent, competitive inhibito; r of dopamine upt ake (Ki = 1 nM for inhibition of striatal dopamine uptake). Has > 100-fold lower affinity for the noradrenalin and 5-HT uptake carriers. Also a potent sigma ligand (IC50 = 48 nM). Centrally active fol lowing systemic administration. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:64089
      An N-alkylpiperazine that consists of piperazine bearing 2-bis(4-fluorophenyl)methoxy]ethyl and 3-phenylpropyl groups at positions 1 and 4 respectively. Potent, competitive inhibitor of dopamine uptak e (Ki = 1 nM for inhibition of striatal dopamine uptake). Has > 100-fold lower affinity for the noradrenalin and 5-HT uptake carriers. Also a potent sigma ligand (IC50 = 48 nM). Centrally active follo wing systemic administration. ChEBI CHEBI:64089

    • Bio Activity:

      Dopamine reuptake inhibitor MedChem Express HY-13217A
      Neuronal Signaling MedChem Express HY-13217A
      Neuronal Signaling; MedChem Express HY-13217A
      Vanoxerine (GBR12909) is a potent and selective DRI (Dopamine reuptake inhibitor). MedChem Express
      Vanoxerine (GBR12909) is a potent and selective DRI (Dopamine reuptake inhibitor).; IC50 value:; Target: Dopamine reuptake inhibitor; At a cellular level, vanoxerine acts to block cardiac ion channels. MedChem Express HY-13217A
      Vanoxerine (GBR12909) is a potent and selective DRI (Dopamine reuptake inhibitor).;IC50 value:;Target: Dopamine reuptake inhibitorAt a cellular level, vanoxerine acts to block cardiac ion channels. Vanoxerine is a multichannel blocker, acting on IKr (potassium), L-type calcium and sodium ion channels.[14] By blocking these specific channels, there is a prolongation of the action potential of the cell, preventing reactivation by a reentrant circuit. The block is strongly frequency dependant: as the pacing of the heart increases so does the frequency of ion channel blocking by vanoxerine. Vanoxerine is a potentially effective treatment for cardiac arrhythmias. A significant cause of cardiac arrhythmias is reentry, an electrophysiologic event in which the proliferating signal that refuses to terminate, and endures to reexcite the heart after the refractory period. MedChem Express HY-13217A

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

Density: 1.1±0.1 g/cm3
Boiling Point: 542.7±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 82.1±3.0 kJ/mol
Flash Point: 282.0±30.1 °C
Index of Refraction: 1.562
Molar Refractivity: 128.6±0.3 cm3
#H bond acceptors: 3
#H bond donors: 0
#Freely Rotating Bonds: 10
#Rule of 5 Violations: 1
ACD/LogP: 5.24
ACD/LogD (pH 5.5): 3.61
ACD/BCF (pH 5.5): 103.42
ACD/KOC (pH 5.5): 247.70
ACD/LogD (pH 7.4): 5.26
ACD/BCF (pH 7.4): 4681.55
ACD/KOC (pH 7.4): 11212.78
Polar Surface Area: 16 Å2
Polarizability: 51.0±0.5 10-24cm3
Surface Tension: 41.7±3.0 dyne/cm
Molar Volume: 396.8±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) =  5.78

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  506.21  (Adapted Stein & Brown method)
    Melting Pt (deg C):  215.50  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.79E-010  (Modified Grain method)
    Subcooled liquid VP: 1.91E-008 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):  0.1737
       log Kow used: 5.78 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.61515 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.08E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.110E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.78  (KowWin est)
  Log Kaw used:  -11.070  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.850
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -1.6621
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   0.8185  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.5752  (weeks-months)
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.4438
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -3.0581
 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):  2.55E-006 Pa (1.91E-008 mm Hg)
  Log Koa (Koawin est  ): 16.850
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.18 
       Octanol/air (Koa) model:  1.74E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.977 
       Mackay model           :  0.99 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 247.9489 E-12 cm3/molecule-sec
      Half-Life =     0.043 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.518 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.983 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.628E+007
      Log Koc:  7.212 

 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 = 3.752 (BCF = 5650)
       log Kow used: 5.78 (estimated)

 Volatilization from Water:
    Henry LC:  2.08E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.975E+009  hours   (2.49E+008 days)
    Half-Life from Model Lake : 6.518E+010  hours   (2.716E+009 days)

 Removal In Wastewater Treatment:
    Total removal:              90.94  percent
    Total biodegradation:        0.76  percent
    Total sludge adsorption:    90.18  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       1.55e-005       1.04         1000       
   Water     1.49            4.32e+003    1000       
   Soil      64.5            8.64e+003    1000       
   Sediment  34              3.89e+004    0          
     Persistence Time: 1.22e+004 hr

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