ChemSpider 2D Image | Duloxetine | C18H19NOS

Duloxetine

  • Molecular FormulaC18H19NOS
  • Average mass297.415 Da
  • Monoisotopic mass297.118744 Da
  • ChemSpider ID54822
  • defined stereocentres - 1 of 1 defined stereocentres


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Duloxetine [Wiki]
(+)-(S)-N-methyl-g-(1-naphthyloxy)-2-thiophenepropylamine
(3S)-N-Methyl-3-(1-naphthyloxy)-3-(2-thienyl)-1-propanamin [German] [ACD/IUPAC Name]
(3S)-N-Methyl-3-(1-naphthyloxy)-3-(2-thienyl)-1-propanamine [ACD/IUPAC Name]
(3S)-N-Methyl-3-(1-naphthyloxy)-3-(2-thienyl)propan-1-amine
(3S)-N-Méthyl-3-(1-naphtyloxy)-3-(2-thiényl)-1-propanamine [French] [ACD/IUPAC Name]
(3S)-N-methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amine
(S)-duloxetine
(S)-N-Methyl-g-(1-naphthalenyloxy)-2-thiophenepropanamine
(S)-N-Methyl-γ-(1-naphthalenyloxy)-2-thiophenepropanamine
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:36795 [DBID]
LY 248686 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 094812
      N06AX21 Wikidata Q411932
    • Bio Activity:

      Duloxetine is a serotonin-norepinephrine reuptake inhibitor with Ki of 4.6 nM, used for treatment of major depressive disorder and generalized anxiety disorder (GAD). MedChem Express http://www.medchemexpress.com/detomidine.html, HY-B0161
      Duloxetine is a serotonin-norepinephrine reuptake inhibitor with Ki of 4.6 nM, used for treatment of major depressive disorder and generalized anxiety disorder (GAD). ;Target: SNRIsDuloxetine inhibits the reuptake of serotonin and norepinephrine in the central nervous system. Duloxetine is also considered a less potent inhibitor of dopamine reuptake. However, duloxetine has no significant affinity for dopaminergic, adrenergic, cholinergic, histaminergic, opioid, glutamate, and GABA receptors and can therefore be considered to be a selective reuptake inhibitor at the 5-HT and NA transporters. Duloxetine undergoes extensive metabolism, but the major circulating metabolites do not contribute significantly to the pharmacologic activity. Major depressive disorder is believed to be due in part to an increase in pro-inflammatory cytokines within the central nervous system. Antidepressants including ones with a similar mechanism of action as duloxetine, i.e. serotonin metabolism inhibition MedChem Express HY-B0161
      Others MedChem Express HY-B0161

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

Density: 1.2±0.1 g/cm3
Boiling Point: 466.2±40.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 72.8±3.0 kJ/mol
Flash Point: 235.7±27.3 °C
Index of Refraction: 1.628
Molar Refractivity: 91.1±0.3 cm3
#H bond acceptors: 2
#H bond donors: 1
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 3.73
ACD/LogD (pH 5.5): 0.94
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 3.05
ACD/LogD (pH 7.4): 1.53
ACD/BCF (pH 7.4): 2.16
ACD/KOC (pH 7.4): 11.78
Polar Surface Area: 50 Å2
Polarizability: 36.1±0.5 10-24cm3
Surface Tension: 46.1±3.0 dyne/cm
Molar Volume: 256.8±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) =  4.68

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  420.44  (Adapted Stein & Brown method)
    Melting Pt (deg C):  156.99  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.18E-007  (Modified Grain method)
    Subcooled liquid VP: 2.64E-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):  13.01
       log Kow used: 4.68 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2.1862 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.43E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.549E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.68  (KowWin est)
  Log Kaw used:  -7.654  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.334
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8917
   Biowin2 (Non-Linear Model)     :   0.8951
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5082  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5390  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2275
   Biowin6 (MITI Non-Linear Model):   0.0642
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2426
 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):  0.000352 Pa (2.64E-006 mm Hg)
  Log Koa (Koawin est  ): 12.334
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00852 
       Octanol/air (Koa) model:  0.53 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.235 
       Mackay model           :  0.405 
       Octanol/air (Koa) model:  0.977 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 313.5273 E-12 cm3/molecule-sec
      Half-Life =     0.034 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    24.563 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.32 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.786E+005
      Log Koc:  5.252 

 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 = 2.905 (BCF = 803.1)
       log Kow used: 4.68 (estimated)

 Volatilization from Water:
    Henry LC:  5.43E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  1.86E+006  hours   (7.748E+004 days)
    Half-Life from Model Lake : 2.029E+007  hours   (8.452E+005 days)

 Removal In Wastewater Treatment:
    Total removal:              65.05  percent
    Total biodegradation:        0.59  percent
    Total sludge adsorption:    64.46  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       0.00427         0.819        1000       
   Water     10.1            900          1000       
   Soil      78.5            1.8e+003     1000       
   Sediment  11.4            8.1e+003     0          
     Persistence Time: 1.89e+003 hr




                    

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