ChemSpider 2D Image | Dabigatran | C25H25N7O3

Dabigatran

  • Molecular FormulaC25H25N7O3
  • Average mass471.511 Da
  • Monoisotopic mass471.201874 Da
  • ChemSpider ID187412

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211914-51-1 [RN]
8027
dabigatran [French] [INN]
dabigatrán [Spanish] [INN]
dabigatranum [Latin] [INN]
I0VM4M70GC
N-[(2-{[(4-Carbamimidoylphenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-yl)carbonyl]-N-2-pyridinyl-β-alanin [German] [ACD/IUPAC Name]
N-[(2-{[(4-Carbamimidoylphenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-yl)carbonyl]-N-2-pyridinyl-β-alanine [ACD/IUPAC Name]
N-[(2-{[(4-Carbamimidoylphényl)amino]méthyl}-1-méthyl-1H-benzimidazol-5-yl)carbonyl]-N-2-pyridinyl-β-alanine [French] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BIBR 953 ZW [DBID]
BIBR953 [DBID]
BIBR 953 [DBID]
BIBR-953 [DBID]
BIBR-953ZW [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      P261; P262 Biosynth Q-102529
    • Chemical Class:

      An aromatic amide obtained by formal condensation of the carboxy group of 2-{[(4-carbamimidoylphenyl)amino]methyl}-1-methyl-1<element>H</element>-benzimidazole-5-carboxylic acid with the secondary amo ino group of <element>N</element>-pyridin-2-yl-<locant>beta</locant>-alanine. The active metabolite of the prodrug dabigatran etexilate, it acts as an anticoagulant which is used for the prevention o f stroke and systemic embolism. ChEBI CHEBI:70752
    • Bio Activity:

      Dabigatran(BIB-953; BIBR 953ZW) is a reversible and selective, direct thrombin inhibitor (DTI) with Ki value of 4.5 nM. MedChem Express
      Dabigatran(BIB-953; BIBR 953ZW) is a reversible and selective, direct thrombin inhibitor (DTI) with Ki value of 4.5 nM.; IC50 Value: 4.5 nM (Ki); 10 nM(Thrombin-induced platelet aggregation) [1]; Target: thrombin; in vitro: Dabigatran selectively and reversibly inhibited human thrombin(Ki: 4.5 nM) as well as thrombin-induced platelet aggregation (IC(50): 10 nM), while showing no inhibitory effect on other platelet-stimulating agents.Thrombin generation in platelet-poor plasma (PPP), measured as the endogenous thrombin potential (ETP) was inhibited concentration-dependently (IC(50): 0.56 microM). MedChem Express HY-10163
      Dabigatran(BIB-953; BIBR 953ZW) is a reversible and selective, direct thrombin inhibitor (DTI) with Ki value of 4.5 nM.;IC50 Value: 4.5 nM (Ki); 10 nM(Thrombin-induced platelet aggregation) [1];Target: thrombin;In vitro: Dabigatran selectively and reversibly inhibited human thrombin(Ki: 4.5 nM) as well as thrombin-induced platelet aggregation (IC(50): 10 nM), while showing no inhibitory effect on other platelet-stimulating agents.Thrombin generation in platelet-poor plasma (PPP), measured as the endogenous thrombin potential (ETP) was inhibited concentration-dependently (IC(50): 0.56 microM). Dabigatran demonstrated concentration-dependent anticoagulant effects in various species in vitro, doubling the activated partial thromboplastin time (aPTT), prothrombin time (PT) and ecarin clotting time (ECT) in human PPP at concentrations of 0.23, 0.83 and 0.18 microM, respectively [1]. ;In vivo: Dabigatran prolonged the aPTT dose-dependently after intravenous administration in rats (0.3, MedChem Express HY-10163
      Metabolism/Protease MedChem Express HY-10163
      Metabolism/Protease; MedChem Express HY-10163
      Thrombin MedChem Express HY-10163

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

Density: 1.4±0.1 g/cm3
Boiling Point: 797.1±70.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.9 mmHg at 25°C
Enthalpy of Vaporization: 121.6±3.0 kJ/mol
Flash Point: 435.9±35.7 °C
Index of Refraction: 1.694
Molar Refractivity: 130.8±0.5 cm3
#H bond acceptors: 10
#H bond donors: 5
#Freely Rotating Bonds: 9
#Rule of 5 Violations: 2
ACD/LogP: 0.79
ACD/LogD (pH 5.5): -1.08
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.08
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 150 Å2
Polarizability: 51.9±0.5 10-24cm3
Surface Tension: 60.9±7.0 dyne/cm
Molar Volume: 340.8±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) =  1.95

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  763.09  (Adapted Stein & Brown method)
    Melting Pt (deg C):  335.49  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.93E-019  (Modified Grain method)
    Subcooled liquid VP: 3.32E-015 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):  23.46
       log Kow used: 1.95 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  353.81 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.00E-028  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.626E-020 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.95  (KowWin est)
  Log Kaw used:  -26.388  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  28.338
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4176
   Biowin2 (Non-Linear Model)     :   0.0199
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1184  (months      )
   Biowin4 (Primary Survey Model) :   3.6313  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.4401
   Biowin6 (MITI Non-Linear Model):   0.0002
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2664
 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):  4.43E-013 Pa (3.32E-015 mm Hg)
  Log Koa (Koawin est  ): 28.338
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  6.78E+006 
       Octanol/air (Koa) model:  5.35E+015 
   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 = 128.2722 E-12 cm3/molecule-sec
      Half-Life =     0.083 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.001 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    :  3.206E+004
      Log Koc:  4.506 

 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: 1.95 (estimated)

 Volatilization from Water:
    Henry LC:  1E-028 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.271E+025  hours   (5.297E+023 days)
    Half-Life from Model Lake : 1.387E+026  hours   (5.779E+024 days)

 Removal In Wastewater Treatment:
    Total removal:               2.20  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.11  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       5.69e-013       2            1000       
   Water     24.2            1.44e+003    1000       
   Soil      75.7            2.88e+003    1000       
   Sediment  0.0904          1.3e+004     0          
     Persistence Time: 1.85e+003 hr




                    

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