ChemSpider 2D Image | armodafinil | C15H15NO2S

armodafinil

  • Molecular FormulaC15H15NO2S
  • Average mass273.350 Da
  • Monoisotopic mass273.082336 Da
  • ChemSpider ID7962943
  • defined stereocentres - 1 of 1 defined stereocentres


More details:






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

(-)-(R)-modafinil
(-)-Modafinil
(R)-(-)-Modafinil
(R)-Modafinil
112111-43-0 [RN]
2-[(R)-(Diphenylmethyl)sulfinyl]acetamid [German] [ACD/IUPAC Name]
2-[(R)-(Diphenylmethyl)sulfinyl]acetamide [ACD/IUPAC Name]
2-[(R)-(Diphénylméthyl)sulfinyl]acétamide [French] [ACD/IUPAC Name]
8474
Acetamide, 2-[(R)-[(1R)-diphenylmethyl]sulfinyl]- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CEP-10952 [DBID]
CRL-40982 [DBID]
D03215 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A 2-[(diphenylmethyl)sulfinyl]acetamide that has <stereo>R</stereo> configuration at the sulfur atom. Like its racemate, modafinil, it is used for the treatment of sleeping disorders such as narcoleps y, obstructive sleep apnoea, and shift-work sleep disorder. Peak concentration in the blood later occurs later following administration than with modafinil, so it is thought that armodafinil may be mo re effective than modafinil in treating people with excessive daytime sleepiness. ChEBI CHEBI:77590
    • Bio Activity:

      Armodafinil(CRL 40982; CEP 10952) is an enantiopure drug consisting of just the active (-)-(R)-enantiomer of the racemic drug modafinil (Provigil). MedChem Express HY-15201
      Armodafinil(CRL 40982; CEP 10952) is an enantiopure drug consisting of just the active (-)-(R)-enantiomer of the racemic drug modafinil (Provigil). ;IC50 value:;Target: Armodafinil is approved by the FDA for the treatment of narcolepsy and shift work sleep disorder, and as an adjunctive treatment for obstructive sleep apnea. Cephalon plans to conduct one or more Phase III clinical trials evaluating the use of Nuvigil as a adjunctive treatment for bipolar depression. The drug was being considered for the first FDA-approved medicinally-specific drug for combating jet-lag. From Wikipedia MedChem Express HY-15201
      Dopamine Receptor MedChem Express HY-15201
      Dopamine Transporters Tocris Bioscience 6131
      Dopamine uptake inhibitor Tocris Bioscience 6131
      Dopamine uptake inhibitor (IC50 = 4 ?M). Increases extracellular dopamine (DA) levels in the nucleus accumbens and substitutes for cocaine in discrimination tests in mice. Tocris Bioscience 6131
      Dopamine uptake inhibitor (IC50 = 4 muM). Increases extracellular dopamine (DA) levels in the nucleus accumbens and substitutes for cocaine in discrimination tests in mice. Tocris Bioscience 6131
      GPCR/G protein MedChem Express HY-15201
      GPCR/G protein; Nueronal Signaling; MedChem Express HY-15201
      Neurotransmitter Transporters Tocris Bioscience 6131
      Transporters Tocris Bioscience 6131

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

Density: 1.3±0.1 g/cm3
Boiling Point: 559.1±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 84.1±3.0 kJ/mol
Flash Point: 292.0±30.1 °C
Index of Refraction: 1.646
Molar Refractivity: 77.3±0.3 cm3
#H bond acceptors: 3
#H bond donors: 2
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 1.17
ACD/LogD (pH 5.5): 1.37
ACD/BCF (pH 5.5): 6.44
ACD/KOC (pH 5.5): 132.07
ACD/LogD (pH 7.4): 1.37
ACD/BCF (pH 7.4): 6.44
ACD/KOC (pH 7.4): 132.07
Polar Surface Area: 79 Å2
Polarizability: 30.6±0.5 10-24cm3
Surface Tension: 63.8±3.0 dyne/cm
Molar Volume: 212.9±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) =  1.13

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  472.34  (Adapted Stein & Brown method)
    Melting Pt (deg C):  199.68  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.96E-009  (Modified Grain method)
    Subcooled liquid VP: 1.36E-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):  170.1
       log Kow used: 1.13 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  9363.5 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.91E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.144E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.13  (KowWin est)
  Log Kaw used:  -14.697  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.827
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0837
   Biowin2 (Non-Linear Model)     :   0.9956
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5849  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6686  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1474
   Biowin6 (MITI Non-Linear Model):   0.0700
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1907
 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):  1.81E-005 Pa (1.36E-007 mm Hg)
  Log Koa (Koawin est  ): 15.827
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.165 
       Octanol/air (Koa) model:  1.65E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.857 
       Mackay model           :  0.93 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  91.8478 E-12 cm3/molecule-sec
      Half-Life =     0.116 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.397 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.893 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  6226
      Log Koc:  3.794 

 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 = 0.166 (BCF = 1.467)
       log Kow used: 1.13 (estimated)

 Volatilization from Water:
    Henry LC:  4.91E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.971E+013  hours   (8.214E+011 days)
    Half-Life from Model Lake : 2.151E+014  hours   (8.961E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               1.90  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.81  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       5.95e-009       2.8          1000       
   Water     39              900          1000       
   Soil      60.9            1.8e+003     1000       
   Sediment  0.085           8.1e+003     0          
     Persistence Time: 1.08e+003 hr




                    

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