ChemSpider 2D Image | Apremilast | C22H24N2O7S

Apremilast

  • Molecular FormulaC22H24N2O7S
  • Average mass460.500 Da
  • Monoisotopic mass460.130432 Da
  • ChemSpider ID9736448
  • defined stereocentres - 1 of 1 defined stereocentres


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

608141-41-9 [RN]
8872
Acetamide, N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]- [ACD/Index Name]
apremilast [Spanish] [INN]
aprémilast [French] [INN]
apremilastum [Latin] [INN]
N-{2-[(1S)-1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamid [German] [ACD/IUPAC Name]
N-{2-[(1S)-1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide [ACD/IUPAC Name]
N-{2-[(1S)-1-(3-Éthoxy-4-méthoxyphényl)-2-(méthylsulfonyl)éthyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acétamide [French] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CC-10004 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1957
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1957
      no pictogram Axon Medchem 1957
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1957
      Warning Axon Medchem 1957
    • Chemical Class:

      A member of the class of isoindoles that is isoindole-1,3-dione substituted at position 4 by an acetamido group and at position 1 by a 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl group. Used for treatment of psoriatic arthritis. ChEBI CHEBI:78540
    • Bio Activity:

      Apremilast(CC10004) is a novel small molecule inhibitor of PDE4 with an IC50 value of 74 nM. MedChem Express http://www.medchemexpress.com/Apremilast.html, HY-12085
      Apremilast(CC10004) is a novel small molecule inhibitor of PDE4 with an IC50 value of 74 nM. ;IC50 value: 74 nM;Target: PDE 4Apremilast has profound anti-inflammatory properties in animal models of inflammatory disease, as well as human chronic inflammatory diseases such as psoriasis and psoriatic arthritis. Apremilast blocks the synthesis of several pro-inflammatory cytokines and chemokines, such as tumor necrosis factor alpha, interleukin 23, CXCL9, and CXCL10 in multiple cell types. As this novel PDE4 inhibitor interferes with several key processes of inflammation, Apremilast may emerge as a promising new drug for the treatment of chronic inflammatory diseases such as those of the skin and the joints. MedChem Express HY-12085
      Immunology/Inflammation MedChem Express HY-12085
      Immunology/Inflammation; Metabolic Enzyme/Protease; MedChem Express HY-12085
      PDE4 MedChem Express HY-12085

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

Density: 1.4±0.1 g/cm3
Boiling Point: 741.3±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.5 mmHg at 25°C
Enthalpy of Vaporization: 108.1±3.0 kJ/mol
Flash Point: 402.1±32.9 °C
Index of Refraction: 1.612
Molar Refractivity: 115.9±0.4 cm3
#H bond acceptors: 9
#H bond donors: 1
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 1.75
ACD/LogD (pH 5.5): 1.71
ACD/BCF (pH 5.5): 11.81
ACD/KOC (pH 5.5): 203.82
ACD/LogD (pH 7.4): 1.71
ACD/BCF (pH 7.4): 11.81
ACD/KOC (pH 7.4): 203.82
Polar Surface Area: 127 Å2
Polarizability: 45.9±0.5 10-24cm3
Surface Tension: 60.6±3.0 dyne/cm
Molar Volume: 333.3±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) =  0.38

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  732.78  (Adapted Stein & Brown method)
    Melting Pt (deg C):  321.33  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1E-017  (Modified Grain method)
    Subcooled liquid VP: 2.19E-014 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):  610.8
       log Kow used: 0.38 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  10.819 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.08E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.920E-021 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.38  (KowWin est)
  Log Kaw used:  -19.355  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.735
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0023
   Biowin2 (Non-Linear Model)     :   0.9748
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0111  (months      )
   Biowin4 (Primary Survey Model) :   3.5430  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0007
   Biowin6 (MITI Non-Linear Model):   0.0049
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1816
 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):  2.92E-012 Pa (2.19E-014 mm Hg)
  Log Koa (Koawin est  ): 19.735
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.03E+006 
       Octanol/air (Koa) model:  1.33E+007 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  90.8115 E-12 cm3/molecule-sec
      Half-Life =     0.118 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.413 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  174.6
      Log Koc:  2.242 

 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: 0.38 (estimated)

 Volatilization from Water:
    Henry LC:  1.08E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.163E+018  hours   (4.847E+016 days)
    Half-Life from Model Lake : 1.269E+019  hours   (5.288E+017 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       1.3e-006        2.83         1000       
   Water     47.8            1.44e+003    1000       
   Soil      52.1            2.88e+003    1000       
   Sediment  0.0951          1.3e+004     0          
     Persistence Time: 1.2e+003 hr




                    

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