ChemSpider 2D Image | (-)-etodolac | C17H21NO3

(-)-etodolac

  • Molecular FormulaC17H21NO3
  • Average mass287.353 Da
  • Monoisotopic mass287.152130 Da
  • ChemSpider ID580901
  • defined stereocentres - 1 of 1 defined stereocentres


More details:






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

(-)-etodolac
(R)-etodolac
[(1R)-1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl]acetic acid [ACD/IUPAC Name]
[(1R)-1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl]essigsäure [German] [ACD/IUPAC Name]
87226-41-3 [RN]
Acide [(1R)-1,8-diéthyl-1,3,4,9-tétrahydropyrano[3,4-b]indol-1-yl]acétique [French] [ACD/IUPAC Name]
Pyrano(3,4-b)indole-1-acetic acid, 1,3,4,9-tetrahydro-1,8-diethyl-, (R)-
Pyrano[3,4-b]indole-1-acetic acid, 1,8-diethyl-1,3,4,9-tetrahydro-, (1R)- [ACD/Index Name]
(-)-[1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl]acetic acid
(+)-(S)-Etodolac
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

Y1RAH31T6K [DBID]
NCGC00016849-01 [DBID]
UNII:Y1RAH31T6K [DBID]
UNII-Y1RAH31T6K [DBID]
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 047889
    • Chemical Class:

      The <stereo>R</stereo>-enantiomer of etodolac. It is inactive, in contrast to the enantiomer, (<stereo>S</stereo>)-etodolac, which is a preferential inhibitor of cyclo-oxygenase 2 and a non-steroidal anti-inflammatory. The racemate is commonly used for the treatment of rheumatoid arthritis and osteoarthritis, and for the alleviation of postoperative pain. ChEBI CHEBI:60370
      The R-enantiomer of etodolac. It is inactive, in contrast to the enantiomer, (S)-etodolac, which is a preferential inhibitor of cyclo-oxygenase 2 and a non-steroidal ; anti-inflammatory. The racemate is commonly used for the treatment of rheumatoid arthritis and osteoarthritis, and for the alleviation of postoperative pain. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:60370

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

Density: 1.2±0.1 g/cm3
Boiling Point: 507.9±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 81.9±3.0 kJ/mol
Flash Point: 261.0±28.7 °C
Index of Refraction: 1.597
Molar Refractivity: 82.0±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 3.59
ACD/LogD (pH 5.5): 2.23
ACD/BCF (pH 5.5): 15.01
ACD/KOC (pH 5.5): 110.86
ACD/LogD (pH 7.4): 0.44
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.79
Polar Surface Area: 62 Å2
Polarizability: 32.5±0.5 10-24cm3
Surface Tension: 54.0±3.0 dyne/cm
Molar Volume: 240.8±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) =  3.93

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  456.20  (Adapted Stein & Brown method)
    Melting Pt (deg C):  192.14  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.02E-008  (Modified Grain method)
    MP  (exp database):  146.5 deg C
    Subcooled liquid VP: 3.45E-007 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):  16.01
       log Kow used: 3.93 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  30.87 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.42E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.771E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.93  (KowWin est)
  Log Kaw used:  -11.236  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.166
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2615
   Biowin2 (Non-Linear Model)     :   0.0118
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5583  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5185  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1401
   Biowin6 (MITI Non-Linear Model):   0.0432
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3257
 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):  4.6E-005 Pa (3.45E-007 mm Hg)
  Log Koa (Koawin est  ): 15.166
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0652 
       Octanol/air (Koa) model:  360 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.702 
       Mackay model           :  0.839 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 217.7861 E-12 cm3/molecule-sec
      Half-Life =     0.049 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.589 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.771 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  962.1
      Log Koc:  2.983 

 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 = 0.500 (BCF = 3.162)
       log Kow used: 3.93 (estimated)

 Volatilization from Water:
    Henry LC:  1.42E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.989E+009  hours   (2.912E+008 days)
    Half-Life from Model Lake : 7.625E+010  hours   (3.177E+009 days)

 Removal In Wastewater Treatment:
    Total removal:              26.97  percent
    Total biodegradation:        0.30  percent
    Total sludge adsorption:    26.68  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       2.05e-006       1.18         1000       
   Water     11              900          1000       
   Soil      86.8            1.8e+003     1000       
   Sediment  2.21            8.1e+003     0          
     Persistence Time: 1.88e+003 hr




                    

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