ChemSpider 2D Image | Roflumilast | C17H14Cl2F2N2O3

Roflumilast

  • Molecular FormulaC17H14Cl2F2N2O3
  • Average mass403.207 Da
  • Monoisotopic mass402.034943 Da
  • ChemSpider ID395793

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Featured data source



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

0P6C6ZOP5U
162401-32-3 [RN]
3-(Cyclopropylmethoxy)-N-(3,5-dichlor-4-pyridinyl)-4-(difluormethoxy)benzamid [German] [ACD/IUPAC Name]
3-(Cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-(difluoromethoxy)benzamide [ACD/IUPAC Name]
3-(CYCLOPROPYLMETHOXY)-N-(3,5-DICHLOROPYRIDIN-4-YL)-4-(DIFLUOROMETHOXY)BENZAMIDE
7598
Benzamide, 3-(cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-(difluoromethoxy)- [ACD/Index Name]
Daliresp [Trade name]
Daxas [Trade name]
roflumilast [French] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

B9302-107 [DBID]
BY217 [DBID]
BYK20869 [DBID]
APTA-2217 [DBID]
BY-217 [DBID]
CCRIS 4693 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      Not Available Novochemy [NC-09544]
    • Safety:

      20/21/22 Novochemy [NC-09544]
      20/21/36/37/39 Novochemy [NC-09544]
      5 Axon Medchem 2352
      GHS07; GHS09 Novochemy [NC-09544]
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 2352
      H332; H403 Novochemy [NC-09544]
      IRRITANT Matrix Scientific 097736
      no pictogram Axon Medchem 2352
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 2352
      P102; P210; P262; P270; P302+P352; P308+P313 Novochemy [NC-09544]
      R03DX07 Wikidata Q693482
      R52/53 Novochemy [NC-09544]
      Warning Novochemy [NC-09544]
      Warning Axon Medchem 2352
    • Target Organs:

      PDE inhibitor TargetMol T1024
    • Chemical Class:

      A benzamide obtained by formal condensation of the carboxy group of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid with the amino group of 3,5-dichloropyridin-4-amine. Used for treatment of br onchial asthma and chronic obstructive pulmonary disease. ChEBI CHEBI:47657
    • Bio Activity:

      Immunology/Inflammation MedChem Express HY-15455
      Immunology/Inflammation; Metabolic Enzyme/Protease; MedChem Express HY-15455
      Metabolism TargetMol T1024
      PDE4 MedChem Express HY-15455
      PDE4 TargetMol T1024
      Roflumilast(Daliresp) is a drug which acts as a selective, long-acting inhibitor of the enzyme PDE-4 with an IC50 of 0.8 nM. MedChem Express http://www.medchemexpress.com/CTEP.html, HY-15455
      Roflumilast(Daliresp) is a drug which acts as a selective, long-acting inhibitor of the enzyme PDE-4 with an IC50 of 0.8 nM. ;IC50 value: 0.8 nM;Target: PDE 4Roflumilast has antiinflammatory effects and is under development as an orally administered drug for the treatment of inflammatory conditions of the lungs such as asthma, and chronic obstructive pulmonary disease (COPD). While Roflumilast was found to be effective in clinical trials, it produced several dose-limiting side effects including nausea, diarrhoea and headache, and development is continuing in an attempt to minimise the incidence of side effects while retaining clinical efficacy. MedChem Express HY-15455

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

Density: 1.5±0.1 g/cm3
Boiling Point: 430.6±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 68.6±3.0 kJ/mol
Flash Point: 214.2±28.7 °C
Index of Refraction: 1.604
Molar Refractivity: 94.2±0.3 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 4.84
ACD/LogD (pH 5.5): 4.06
ACD/BCF (pH 5.5): 714.40
ACD/KOC (pH 5.5): 3840.99
ACD/LogD (pH 7.4): 4.05
ACD/BCF (pH 7.4): 710.27
ACD/KOC (pH 7.4): 3818.80
Polar Surface Area: 60 Å2
Polarizability: 37.3±0.5 10-24cm3
Surface Tension: 51.8±3.0 dyne/cm
Molar Volume: 274.0±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) =  3.53

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  500.68  (Adapted Stein & Brown method)
    Melting Pt (deg C):  212.92  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.64E-010  (Modified Grain method)
    Subcooled liquid VP: 2.64E-008 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):  2.842
       log Kow used: 3.53 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.5492 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.25E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.928E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.53  (KowWin est)
  Log Kaw used:  -12.292  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.822
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5101
   Biowin2 (Non-Linear Model)     :   0.2318
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5103  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.2762  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1350
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3568
 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):  3.52E-006 Pa (2.64E-008 mm Hg)
  Log Koa (Koawin est  ): 15.822
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.852 
       Octanol/air (Koa) model:  1.63E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.969 
       Mackay model           :  0.986 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  24.4268 E-12 cm3/molecule-sec
      Half-Life =     0.438 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     5.255 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.977 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  9384
      Log Koc:  3.972 

 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 = 2.016 (BCF = 103.8)
       log Kow used: 3.53 (estimated)

 Volatilization from Water:
    Henry LC:  1.25E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.405E+010  hours   (3.919E+009 days)
    Half-Life from Model Lake : 1.026E+012  hours   (4.275E+010 days)

 Removal In Wastewater Treatment:
    Total removal:              13.73  percent
    Total biodegradation:        0.19  percent
    Total sludge adsorption:    13.54  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       1.08e-006       10.5         1000       
   Water     4.74            4.32e+003    1000       
   Soil      94.7            8.64e+003    1000       
   Sediment  0.561           3.89e+004    0          
     Persistence Time: 7.62e+003 hr




                    

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