ChemSpider 2D Image | ambrisentan | C22H22N2O4

ambrisentan

  • Molecular FormulaC22H22N2O4
  • Average mass378.421 Da
  • Monoisotopic mass378.157959 Da
  • ChemSpider ID5293690
  • defined stereocentres - 1 of 1 defined stereocentres


More details:



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

(2S)-2-[(4,6-Dimethyl-2-pyrimidinyl)oxy]-3-methoxy-3,3-diphenylpropanoic acid [ACD/IUPAC Name]
(2S)-2-[(4,6-Dimethyl-2-pyrimidinyl)oxy]-3-methoxy-3,3-diphenylpropansäure [German] [ACD/IUPAC Name]
(2S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropanoic acid
177036-94-1 [RN]
8128
Acide (2S)-2-[(4,6-diméthyl-2-pyrimidinyl)oxy]-3-méthoxy-3,3-diphénylpropanoïque [French] [ACD/IUPAC Name]
acide (2S)-2-[(4,6-diméthylpyrimidin-2-yl)oxy]-3-méthoxy-3,3-diphénylpropanoïque [French]
ambrisentan [INN] [Wiki]
ambrisentan [French] [INN]
ambrisentán [Spanish] [INN]
More...

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

BSF-208075 [DBID]
CCRIS 4693 [DBID]
LU 208075 [DBID]
LU-208075 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      Not Available Novochemy [NC-01698]
    • Safety:

      20/21/22 Novochemy [NC-01698]
      20/21/36/37/39 Novochemy [NC-01698]
      5 Axon Medchem 1648
      GHS07; GHS09 Novochemy [NC-01698]
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1648
      H332; H403 Novochemy [NC-01698]
      no pictogram Axon Medchem 1648
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1648
      P301+P310; P337+P313 Novochemy [NC-01698]
      R22 Novochemy [NC-01698]
      Warning Novochemy [NC-01698]
      Warning Axon Medchem 1648
    • Drug Status:

      approved BIONET-Key Organics DE-0223
    • Bio Activity:

      Ambrisentan(BSF 208075; LU 208075) is an oral, once-daily endothelin receptor antagonist that is selective for the endothelin type A receptor. MedChem Express http://www.medchemexpress.com/Zanamivir.html, HY-13209
      Ambrisentan(BSF 208075; LU 208075) is an oral, once-daily endothelin receptor antagonist that is selective for the endothelin type A receptor. ;IC50 value:;Target: ETA receptorAmbrisentan is indicated for the treatment of pulmonary arterial hypertension (PAH). Once daily oral ambrisentan 2.5 to 10 mg/day significantly improved exercise capacity (6-minute walk distance) compared with placebo in two double-blind, multicenter trials (ARIES-1 & ARIES-2). A decrease in dyspnea and a delay in clinical worsening were among the improvements in secondary outcomes generally observed with ambrisentan versus placebo. In ARIES-E, a 2-year extension of ARIES-1 and -2, approved dosages of ambrisentan (5 and 10mg/day) were associated with a sustained improvement in 6MWD, a generally sustained improvement in dyspnea, and a low risk of clinical worsening and of death. Six months' treatment with ambrisentan 5mg/day significantly improved 6MWD (primary outcome measure) and dyspnea relative to baselin MedChem Express HY-13209
      Endothelin Receptor MedChem Express HY-13209
      GPCR/G protein MedChem Express HY-13209
      GPCR/G protein; MedChem Express HY-13209

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

Density: 1.2±0.1 g/cm3
Boiling Point: 551.1±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 87.5±3.0 kJ/mol
Flash Point: 287.1±32.9 °C
Index of Refraction: 1.593
Molar Refractivity: 104.4±0.3 cm3
#H bond acceptors: 6
#H bond donors: 1
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 1
ACD/LogP: 6.24
ACD/LogD (pH 5.5): 2.04
ACD/BCF (pH 5.5): 3.62
ACD/KOC (pH 5.5): 10.94
ACD/LogD (pH 7.4): 1.48
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 3.01
Polar Surface Area: 82 Å2
Polarizability: 41.4±0.5 10-24cm3
Surface Tension: 51.2±3.0 dyne/cm
Molar Volume: 308.0±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) =  4.22

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  511.65  (Adapted Stein & Brown method)
    Melting Pt (deg C):  218.04  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.21E-010  (Modified Grain method)
    Subcooled liquid VP: 1.39E-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):  2.561
       log Kow used: 4.22 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  87.524 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 :   1.02E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.353E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.22  (KowWin est)
  Log Kaw used:  -12.380  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.600
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6062
   Biowin2 (Non-Linear Model)     :   0.5315
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3429  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4740  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1548
   Biowin6 (MITI Non-Linear Model):   0.0220
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.9929
 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):  1.85E-006 Pa (1.39E-008 mm Hg)
  Log Koa (Koawin est  ): 16.600
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.62 
       Octanol/air (Koa) model:  9.77E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.983 
       Mackay model           :  0.992 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  58.5647 E-12 cm3/molecule-sec
      Half-Life =     0.183 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.192 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.988 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1449
      Log Koc:  3.161 

 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: 4.22 (estimated)

 Volatilization from Water:
    Henry LC:  1.02E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.117E+011  hours   (4.653E+009 days)
    Half-Life from Model Lake : 1.218E+012  hours   (5.076E+010 days)

 Removal In Wastewater Treatment:
    Total removal:              40.99  percent
    Total biodegradation:        0.41  percent
    Total sludge adsorption:    40.58  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       6.71e-006       4.38         1000       
   Water     10.6            900          1000       
   Soil      85.2            1.8e+003     1000       
   Sediment  4.18            8.1e+003     0          
     Persistence Time: 1.92e+003 hr




                    

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