ChemSpider 2D Image | Azilsartan | C25H20N4O5

Azilsartan

  • Molecular FormulaC25H20N4O5
  • Average mass456.450 Da
  • Monoisotopic mass456.143372 Da
  • ChemSpider ID8001032

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

147403-03-0 [RN]
1H-Benzimidazole-7-carboxylic acid, 1-[[2'-(4,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]methyl]-2-ethoxy- [ACD/Index Name]
2-ethoxy-1-((2'-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-biphenyl-4-yl)methyl)-1H-benzimidazole-7-carboxylic acid
2-Ethoxy-1-{[2'-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-4-biphenylyl]methyl}-1H-benzimidazol-7-carbonsäure [German] [ACD/IUPAC Name]
2-Ethoxy-1-{[2'-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-4-biphenylyl]methyl}-1H-benzimidazole-7-carboxylic acid [ACD/IUPAC Name]
8724
Acide 2-éthoxy-1-{[2'-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-4-biphénylyl]méthyl}-1H-benzimidazole-7-carboxylique [French] [ACD/IUPAC Name]
azilsartan [French] [INN]
azilsartán [Spanish] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

F9NUX55P23 [DBID]
TAK-536 [DBID]
CCRIS 4693 [DBID]
TAK 536 [DBID]
UNII:F9NUX55P23 [DBID]
UNII-F9NUX55P23 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Target Organs:

      AGTR antagonist TargetMol T1057
    • Chemical Class:

      A benzimidazolecarboxylic acid that is benzimidazole-7-carboxylic acid substituted at position 2 by a methoxy group and at position 1 by a 2'-[(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]met hyl group. Used (as the prodrug, azilsartan medoxomil) for treatment of hypertension. ChEBI CHEBI:68850
    • Bio Activity:

      7-TM Receptors Tocris Bioscience 4553
      AGTR1 TargetMol T1057
      Angiogenesis TargetMol T1057
      Angiotensin Receptor MedChem Express HY-14914
      Angiotensin Receptors Tocris Bioscience 4553
      Azilsartan(TAK-536) is a specific and potent angiotensin II type 1 receptor antagonist with IC50 of 2.6 nM. MedChem Express
      Azilsartan(TAK-536) is a specific and potent angiotensin II type 1 receptor antagonist with IC50 of 2.6 nM.; IC50 Value: 2.6 nM [1]; Target: AT1 receptor; in vitro: Azilsartan inhibited the specific binding of 125I-Sar1-Ile8-AII to human angiotensin type 1 receptors with an IC50 of 2.6 nM. MedChem Express HY-14914
      Azilsartan(TAK-536) is a specific and potent angiotensin II type 1 receptor antagonist with IC50 of 2.6 nM.;IC50 Value: 2.6 nM [1];Target: AT1 receptor;In vitro: Azilsartan inhibited the specific binding of 125I-Sar1-Ile8-AII to human angiotensin type 1 receptors with an IC50 of 2.6 nM. The inhibitory effect of AZL persisted after washout of the free compound (IC(50) value of 7.4 nM). AZL also inhibited the accumulation of AII-induced inositol 1-phosphate (IP1) in the cell-based assay with an IC50 value of 9.2 nmol; this effect was resistant to washout (IC50 value of 81.3 nM). Olmesartan and valsartan inhibited IP1 accumulation with IC50 values of 12.2 and 59.8 nM, respectively [1]. Azilsartan is not readily biodegradable. Results of the water sediment study demonstrated significant shifting of azilsartan metabolites to sediment. Based on the equilibrium partitioning method, metabolites are unlikely to pose a risk to sediment-dwelling organisms [2].;In vivo: In 4 randomized con MedChem Express HY-14914
      GPCR/G protein MedChem Express HY-14914
      GPCR/G protein; MedChem Express HY-14914
      Peptide Receptors Tocris Bioscience 4553
      Potent angiotensin II type 1 (AT1) receptor inverse agonist (IC50 = 2.6 nM at the human AT1 receptor). Inhibits angiotensin II-induced IP1 accumulation in COS-7 cells; decreases maximal contraction of rabbit aortic strips in a concentration-dependent manner (pD'2 = 9.9). Antihypertensive; prevents vascular cell proliferation and expression of PAI-1. Tocris Bioscience 4553
      Potent angiotensin II type 1 (AT1) receptor inverse agonist (IC50 = 2.6 nM at the human AT1 receptor). Inhibits angiotensin II-induced IP1 accumulation in COS-7 cells; decreases maximal contraction of rabbit aortic strips in a concentration-dependent manner (pD'2 = 9.9). Antihypertensive; prevents vascular cell proliferation and expression of PAI-1. Tocris Bioscience 4553
      Potent AT1 receptor inverse agonist; antihypertensive Tocris Bioscience 4553

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

Density: 1.4±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.695
Molar Refractivity: 123.3±0.5 cm3
#H bond acceptors: 9
#H bond donors: 2
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 4.21
ACD/LogD (pH 5.5): 1.63
ACD/BCF (pH 5.5): 3.10
ACD/KOC (pH 5.5): 19.21
ACD/LogD (pH 7.4): 0.26
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 115 Å2
Polarizability: 48.9±0.5 10-24cm3
Surface Tension: 58.3±7.0 dyne/cm
Molar Volume: 320.9±7.0 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) =  4.30

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  823.43  (Adapted Stein & Brown method)
    Melting Pt (deg C):  349.84  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.45E-020  (Modified Grain method)
    Subcooled liquid VP: 7.44E-017 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):  0.2859
       log Kow used: 4.30 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.22052 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.45E-020  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.046E-020 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.30  (KowWin est)
  Log Kaw used:  -17.652  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  21.952
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8390
   Biowin2 (Non-Linear Model)     :   0.7681
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2202  (months      )
   Biowin4 (Primary Survey Model) :   3.2740  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0109
   Biowin6 (MITI Non-Linear Model):   0.0053
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.1690
 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):  9.92E-015 Pa (7.44E-017 mm Hg)
  Log Koa (Koawin est  ): 21.952
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.02E+008 
       Octanol/air (Koa) model:  2.2E+009 
   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 = 114.1576 E-12 cm3/molecule-sec
      Half-Life =     0.094 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.124 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    :  8.662E+005
      Log Koc:  5.938 

 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: 4.30 (estimated)

 Volatilization from Water:
    Henry LC:  5.45E-020 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.295E+016  hours   (9.563E+014 days)
    Half-Life from Model Lake : 2.504E+017  hours   (1.043E+016 days)

 Removal In Wastewater Treatment:
    Total removal:              45.27  percent
    Total biodegradation:        0.44  percent
    Total sludge adsorption:    44.83  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       0.00796         2.25         1000       
   Water     8.67            1.44e+003    1000       
   Soil      86              2.88e+003    1000       
   Sediment  5.35            1.3e+004     0          
     Persistence Time: 2.74e+003 hr




                    

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