ChemSpider 2D Image | Ramatroban | C21H21FN2O4S

Ramatroban

  • Molecular FormulaC21H21FN2O4S
  • Average mass416.466 Da
  • Monoisotopic mass416.120605 Da
  • ChemSpider ID110413
  • defined stereocentres - 1 of 1 defined stereocentres


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(+)-(3R)-3-(p-Fluorobenzenesulfonamido)-1,2,3,4-tetrahydrocarbazole-9-propionic acid
116649-85-5 [RN]
3-((3R)-3-(((4-Fluorophenyl)sulfonyl)amino)-1,2,3,4-tetrahydro-9H-carbazol-9-yl)propanoic Acid
3-[(3R)-3-{[(4-Fluorophenyl)sulfonyl]amino}-1,2,3,4-tetrahydro-9H-carbazol-9-yl]propanoic acid [ACD/IUPAC Name]
3-[(3R)-3-{[(4-Fluorphenyl)sulfonyl]amino}-1,2,3,4-tetrahydro-9H-carbazol-9-yl]propansäure [German] [ACD/IUPAC Name]
7273
9H-Carbazole-9-propanoic acid, 3-[[(4-fluorophenyl)sulfonyl]amino]-1,2,3,4-tetrahydro-, (3R)- [ACD/Index Name]
Acide 3-[(3R)-3-{[(4-fluorophényl)sulfonyl]amino}-1,2,3,4-tétrahydro-9H-carbazol-9-yl]propanoïque [French] [ACD/IUPAC Name]
BAY u 3405
BAY u-3405
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

EN 137774 [DBID]
D01128 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 094731
    • Target Organs:

      TXA2 receptor antagonist TargetMol T2396
    • Drug Status:

      approved BIONET-Key Organics KS-1310
    • Bio Activity:

      7-TM Receptors Tocris Bioscience 2732
      Angiogenesis TargetMol T2396
      Dual TP/DP2 (CRTH2) receptor antagonist Tocris Bioscience 2732
      Others MedChem Express HY-B0745
      Potent dual antagonist of TP/DP2 (CRTH2) prostanoid receptors (Ki values are 4.3, 4.5 and > 10000 nM for hDP2, hTP and hDP1 receptors respectively). Suppresses PGD2-induced migration of human eosinoph ils (IC50 = 170 nM). Tocris Bioscience 2732
      Potent dual antagonist of TP/DP2 (CRTH2) prostanoid receptors (Ki values are 4.3, 4.5 and > 10000 nM for hDP2, hTP and hDP1 receptors respectively). Suppresses PGD2-induced migration of human eosinophils (IC50 = 170 nM). Tocris Bioscience 2732
      Prostanoid Receptors Tocris Bioscience 2732
      Ramatroban (BAY u3405) is a thromboxane A(2) (TxA(2)) antagonist marketed for allergic rhinitis. MedChem Express
      Ramatroban (BAY u3405) is a thromboxane A(2) (TxA(2)) antagonist marketed for allergic rhinitis.; Target: TXA2 receptor; CRTh2; Ramatroban (Baynas, BAY u3405), a thromboxane A(2) (TxA(2)) antagonist marketed for allergic rhinitis, has been shown to partially attenuate prostaglandin (PG)D(2)-induced bronchial hyperresponsiveness in humans, as well as reduce antigen-induced early- and late-phase inflammatory responses in mice, guinea pigs, and rats. MedChem Express HY-B0745
      Ramatroban (BAY u3405) is a thromboxane A(2) (TxA(2)) antagonist marketed for allergic rhinitis.;Target: TXA2 receptor; CRTh2Ramatroban (Baynas, BAY u3405), a thromboxane A(2) (TxA(2)) antagonist marketed for allergic rhinitis, has been shown to partially attenuate prostaglandin (PG)D(2)-induced bronchial hyperresponsiveness in humans, as well as reduce antigen-induced early- and late-phase inflammatory responses in mice, guinea pigs, and rats. PGD(2)-stimulated human eosinophil migration was shown to be mediated exclusively through activation of CRTH2, and surprisingly, these effects were completely inhibited by ramatroban. This is also the first report detailing an orally bioavailable small molecule CRTH2 antagonist. Our findings suggest that clinical efficacy of ramatroban may be in part mediated through its action on this Th2-, eosinophil-, and basophil-specific chemoattractant receptor [1]. Ramatroban can block the newly identified PGD2 receptor, chemoattractant receptor-homol MedChem Express HY-B0745
      TXA2 receptor; CRTh2 TargetMol T2396

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

Density: 1.4±0.1 g/cm3
Boiling Point: 654.7±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 101.3±3.0 kJ/mol
Flash Point: 349.7±34.3 °C
Index of Refraction: 1.664
Molar Refractivity: 107.5±0.5 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 4.09
ACD/LogD (pH 5.5): 2.79
ACD/BCF (pH 5.5): 46.11
ACD/KOC (pH 5.5): 288.58
ACD/LogD (pH 7.4): 0.99
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 4.53
Polar Surface Area: 97 Å2
Polarizability: 42.6±0.5 10-24cm3
Surface Tension: 56.0±7.0 dyne/cm
Molar Volume: 289.7±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) =  4.44

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  588.56  (Adapted Stein & Brown method)
    Melting Pt (deg C):  253.97  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.68E-013  (Modified Grain method)
    Subcooled liquid VP: 1.47E-010 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):  0.9656
       log Kow used: 4.44 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.3571 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 :   2.59E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.656E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.44  (KowWin est)
  Log Kaw used:  -12.975  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.415
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.0787
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0868  (months      )
   Biowin4 (Primary Survey Model) :   3.5088  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2430
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0127
 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):  1.96E-008 Pa (1.47E-010 mm Hg)
  Log Koa (Koawin est  ): 17.415
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  153 
       Octanol/air (Koa) model:  6.38E+004 
   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 = 234.0591 E-12 cm3/molecule-sec
      Half-Life =     0.046 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.548 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    :  1.627E+005
      Log Koc:  5.211 

 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: 4.44 (estimated)

 Volatilization from Water:
    Henry LC:  2.59E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.613E+011  hours   (1.922E+010 days)
    Half-Life from Model Lake : 5.033E+012  hours   (2.097E+011 days)

 Removal In Wastewater Treatment:
    Total removal:              52.84  percent
    Total biodegradation:        0.50  percent
    Total sludge adsorption:    52.34  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       0.00012         1.1          1000       
   Water     7.82            1.44e+003    1000       
   Soil      85.5            2.88e+003    1000       
   Sediment  6.71            1.3e+004     0          
     Persistence Time: 3.06e+003 hr




                    

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