ChemSpider 2D Image | Rupatadine | C26H26ClN3

Rupatadine

  • Molecular FormulaC26H26ClN3
  • Average mass415.958 Da
  • Monoisotopic mass415.181519 Da
  • ChemSpider ID117388

More details:



Featured data source



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

158876-82-5 [RN]
2AE8M83G3E
5H-Benzo(5,6)cyclohepta(1,2-b)pyridine, 8-chloro-6,11-dihydro-11-(1-((5-methyl-3-pyridinyl)methyl)-4-piperidinylidene)-
5H-Benzo[5,6]cyclohepta[1,2-b]pyridine, 8-chloro-6,11-dihydro-11-[1-[(5-methyl-3-pyridinyl)methyl]-4-piperidinylidene]- [ACD/Index Name]
7443
8-Chlor-11-{1-[(5-methyl-3-pyridinyl)methyl]-4-piperidinyliden}-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin [German] [ACD/IUPAC Name]
8-Chloro-11-{1-[(5-methyl-3-pyridinyl)methyl]-4-piperidinylidene}-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine [ACD/IUPAC Name]
8-Chloro-11-{1-[(5-méthyl-3-pyridinyl)méthyl]-4-pipéridinylidène}-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine [French] [ACD/IUPAC Name]
8-Chloro-11-{1-[(5-methylpyridin-3-yl)methyl]piperidin-4-ylidene}-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine
8-Chloro-6,11-dihydro-11-(1-((5-methyl-3-pyridinyl)methyl)-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

UR 12592 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 093670
      P261; P262 Biosynth Q-201687
    • Bio Activity:

      5-HT Receptor MedChem Express HY-13511
      GPCR/G protein MedChem Express HY-13511
      GPCR/G protein; Neuronal Signaling; MedChem Express HY-13511
      Rupatadine (UR-12592) is a potent dual PAF/H1 antagonist with Ki of 0.55/0.1 uM(rabbit platelet membranes/guinea pig cerebellum membranes). MedChem Express
      Rupatadine (UR-12592) is a potent dual PAF/H1 antagonist with Ki of 0.55/0.1 uM(rabbit platelet membranes/guinea pig cerebellum membranes).; IC50 value:; Target: PAF/H1 antagonist; in vitro: Rupatadine competitively inhibited histamine-induced guinea pig ileum contraction (pA2 = 9.29 +/- 0.06) without affecting contraction induced by ACh, serotonin or leukotriene D4 (LTD4). MedChem Express HY-13511
      Rupatadine (UR-12592) is a potent dual PAF/H1 antagonist with Ki of 0.55/0.1 uM(rabbit platelet membranes/guinea pig cerebellum membranes).;IC50 value:;Target: PAF/H1 antagonist;In vitro: Rupatadine competitively inhibited histamine-induced guinea pig ileum contraction (pA2 = 9.29 +/- 0.06) without affecting contraction induced by ACh, serotonin or leukotriene D4 (LTD4). It also competitively inhibited PAF-induced platelet aggregation in washed rabbit platelets (WRP) (pA2 = 6.68 +/- 0.08) and in human platelet-rich plasma (HPRP) (IC50 = 0.68 microM), while not affecting ADP- or arachidonic acid-induced platelet aggregation [1]. The IC50 for rupatadine in A23187, concanavalin A and anti-IgE induced histamine release was 0.7+/-0.4 microM, 3.2+/-0.7 microM and 1.5+/-0.4 microM, respectively whereas for loratadine the IC50 was 2.1+/-0.9 microM, 4.0+/-1.3 M and 1.7+/-0.5 microM. SR-27417A exhibited no inhibitory effect [2].;In vivo: Rupatadine blocked histamine- and PAF-induced effects MedChem Express HY-13511

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

Density: 1.2±0.1 g/cm3
Boiling Point: 586.4±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 87.6±3.0 kJ/mol
Flash Point: 308.4±30.1 °C
Index of Refraction: 1.646
Molar Refractivity: 122.4±0.3 cm3
#H bond acceptors: 3
#H bond donors: 0
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 1
ACD/LogP: 6.11
ACD/LogD (pH 5.5): 4.10
ACD/BCF (pH 5.5): 339.47
ACD/KOC (pH 5.5): 849.44
ACD/LogD (pH 7.4): 5.46
ACD/BCF (pH 7.4): 7787.83
ACD/KOC (pH 7.4): 19487.04
Polar Surface Area: 29 Å2
Polarizability: 48.5±0.5 10-24cm3
Surface Tension: 56.0±3.0 dyne/cm
Molar Volume: 337.2±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) =  5.55

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  527.36  (Adapted Stein & Brown method)
    Melting Pt (deg C):  225.38  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.94E-011  (Modified Grain method)
    Subcooled liquid VP: 5.54E-009 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):  0.6999
       log Kow used: 5.55 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.29558 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.36E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.081E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.55  (KowWin est)
  Log Kaw used:  -12.659  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.209
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.0167
   Biowin2 (Non-Linear Model)     :   0.0002
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.1656  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.5512  (weeks-months)
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.6438
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.3205
 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):  7.39E-007 Pa (5.54E-009 mm Hg)
  Log Koa (Koawin est  ): 18.209
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.06 
       Octanol/air (Koa) model:  3.97E+005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.993 
       Mackay model           :  0.997 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 217.2544 E-12 cm3/molecule-sec
      Half-Life =     0.049 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.591 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =  1064.699951 E-17 cm3/molecule-sec
      Half-Life =     0.001 Days (at 7E11 mol/cm3)
      Half-Life =      1.550 Min
   Fraction sorbed to airborne particulates (phi): 0.995 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.124E+008
      Log Koc:  8.051 

 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 = 3.574 (BCF = 3746)
       log Kow used: 5.55 (estimated)

 Volatilization from Water:
    Henry LC:  5.36E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.228E+011  hours   (9.283E+009 days)
    Half-Life from Model Lake :  2.43E+012  hours   (1.013E+011 days)

 Removal In Wastewater Treatment:
    Total removal:              88.88  percent
    Total biodegradation:        0.75  percent
    Total sludge adsorption:    88.13  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       1.53e-006       0.0253       1000       
   Water     1.88            4.32e+003    1000       
   Soil      69.6            8.64e+003    1000       
   Sediment  28.6            3.89e+004    0          
     Persistence Time: 1.13e+004 hr




                    

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