ChemSpider 2D Image | Paroxetine | C19H20FNO3

Paroxetine

  • Molecular FormulaC19H20FNO3
  • Average mass329.365 Da
  • Monoisotopic mass329.142731 Da
  • ChemSpider ID39888
  • defined stereocentres - 2 of 2 defined stereocentres


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(-)-Paroxetine
(-)-trans-4-(p-Fluorophenyl)-3-[[3,4-(methylenedioxy)phenoxy]methyl]piperidine
(3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine [ACD/IUPAC Name]
(3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)méthyl]-4-(4-fluorophényl)pipéridine [French] [ACD/IUPAC Name]
(3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorphenyl)piperidin [German] [ACD/IUPAC Name]
(3S-trans)-3-[(1,3-Benzodioxol-5-yl-oxy)methyl]-4-(4-fluorophenyl)piperidine
41VRH5220H
4327
61869-08-7 [RN]
aropax
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:7936 [DBID]
GF 74 [DBID]
BRL 29060 [DBID]
BRL-29060 [DBID]
C07415 [DBID]
D02362 [DBID]
DivK1c_006884 [DBID]
FG 7051 [DBID]
FG-7051 [DBID]
KBio1_001828 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      N06AB05 Wikidata Q408471
    • Chemical Class:

      A benzodioxole that consists of piperidine bearing 1,3-benzodioxol-5-yloxy)methyl and 4-fluorophenyl substituents at positions 3 and 4 respectively; the (3<stereo>S</stereo>,4<stereo>R</stereo>)-diast ereomer. Highly potent and selective 5-HT uptake inhibitor that binds with high affinity to the serotonin transporter (Ki = 0.05 nM). Ki values are 1.1, 350 and 1100 nM for inhibition of [3H]-5-HT, [3 H]-l-NA and [3H]-DA uptake respectively. Displays minimal affinity for <greek>alpha</greek>1-, <greek>alpha</greek>2- or <greek>beta</greek>-adrenoceptors, 5-HT<smallsub>2A</smallsub>, 5-HT<smallsub>1 A</smallsub>, D<smallsub>2</smallsub> or H<smallsub>1</smallsub> receptors at concentrations below 1000 nM, however displays weak affinity for muscarinic ACh receptors (Ki = 42 nM). Antidepressant and anxiolytic in vivo. ChEBI CHEBI:7936
    • Therapeutical Effect:

      Serotonin Uptake Inhibitors Sean Ekins

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

Density: 1.2±0.1 g/cm3
Boiling Point: 451.7±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 71.1±3.0 kJ/mol
Flash Point: 227.0±28.7 °C
Index of Refraction: 1.561
Molar Refractivity: 87.9±0.3 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 3.89
ACD/LogD (pH 5.5): 0.61
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 2.05
ACD/LogD (pH 7.4): 1.46
ACD/BCF (pH 7.4): 2.20
ACD/KOC (pH 7.4): 14.31
Polar Surface Area: 40 Å2
Polarizability: 34.9±0.5 10-24cm3
Surface Tension: 45.5±3.0 dyne/cm
Molar Volume: 271.5±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) =  2.57

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  423.77  (Adapted Stein & Brown method)
    Melting Pt (deg C):  172.51  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.49E-008  (Modified Grain method)
    Subcooled liquid VP: 2.18E-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):  537.1
       log Kow used: 2.57 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3938.3 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Vinyl/Allyl Ethers

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.91E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.237E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.57  (KowWin est)
  Log Kaw used:  -7.107  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.677
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -1.0528
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9879  (months      )
   Biowin4 (Primary Survey Model) :   3.3315  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0302
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.8566
 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):  0.000291 Pa (2.18E-006 mm Hg)
  Log Koa (Koawin est  ): 9.677
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0103 
       Octanol/air (Koa) model:  0.00117 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.272 
       Mackay model           :  0.452 
       Octanol/air (Koa) model:  0.0854 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 423.8937 E-12 cm3/molecule-sec
      Half-Life =     0.025 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    18.168 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     8.425000 E-17 cm3/molecule-sec
      Half-Life =     0.136 Days (at 7E11 mol/cm3)
      Half-Life =      3.265 Hrs
   Fraction sorbed to airborne particulates (phi): 0.362 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  432
      Log Koc:  2.635 

 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 = 1.278 (BCF = 18.97)
       log Kow used: 2.57 (estimated)

 Volatilization from Water:
    Henry LC:  1.91E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.563E+005  hours   (2.318E+004 days)
    Half-Life from Model Lake : 6.069E+006  hours   (2.529E+005 days)

 Removal In Wastewater Treatment:
    Total removal:               3.31  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     3.21  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       0.00836         0.511        1000       
   Water     16.7            1.44e+003    1000       
   Soil      83.2            2.88e+003    1000       
   Sediment  0.164           1.3e+004     0          
     Persistence Time: 1.78e+003 hr




                    

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