ChemSpider 2D Image | prucalopride | C18H26ClN3O3

prucalopride

  • Molecular FormulaC18H26ClN3O3
  • Average mass367.870 Da
  • Monoisotopic mass367.166260 Da
  • ChemSpider ID2314539

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

179474-81-8 [RN]
4-Amino-5-chlor-N-[1-(3-methoxypropyl)-4-piperidinyl]-2,3-dihydro-1-benzofuran-7-carboxamid [German] [ACD/IUPAC Name]
4-Amino-5-chloro-N-[1-(3-methoxypropyl)-4-piperidinyl]-2,3-dihydro-1-benzofuran-7-carboxamide [ACD/IUPAC Name]
4-Amino-5-chloro-N-[1-(3-méthoxypropyl)-4-pipéridinyl]-2,3-dihydro-1-benzofurane-7-carboxamide [French] [ACD/IUPAC Name]
4-Amino-5-chloro-N-[1-(3-methoxypropyl)piperidin-4-yl]-2,3-dihydro-1-benzofuran-7-carboxamide
7702
7-Benzofurancarboxamide, 4-amino-5-chloro-2,3-dihydro-N-[1-(3-methoxypropyl)-4-piperidinyl]- [ACD/Index Name]
Prucaloprida [Spanish] [INN]
prucalopride [INN] [Wiki]
prucalopride [French] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

0A09IUW5TP [DBID]
R-093877 [DBID]
R-108512 [DBID]
R-93877 [DBID]
UNII:0A09IUW5TP [DBID]
UNII-0A09IUW5TP [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1479
      A06AX05 Wikidata Q68484
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1479
      no pictogram Axon Medchem 1479
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1479
      Warning Axon Medchem 1479
    • Target Organs:

      5-HT Receptor agonist TargetMol T2542
    • Bio Activity:

      5-HT Receptor MedChem Express HY-14151
      5-HT4A/B;5-HT3;5-HT1A TargetMol T2542
      GPCR/G protein MedChem Express HY-14151
      GPCR/G protein; Neuronal Signaling; MedChem Express HY-14151
      Neuroscience TargetMol T2542
      Prucalopride (R093877) is a drug acting as a selective, high affinity 5-HT4 receptor agonist(pKi=8.6/8.1 for 5-HT4a/4b); MedChem Express http://www.medchemexpress.com/Tegaserod-maleate.html
      Prucalopride (R093877) is a drug acting as a selective, high affinity 5-HT4 receptor agonist(pKi=8.6/8.1 for 5-HT4a/4b); >150-fold higher affinity for 5-HT4 receptors than for other receptors.; IC50 value: 8.6/8.1 for 5-HT4a/4b(pKi); Target: 5-HT4 receptor; Prucalopride is a novel enterokinetic compound and is the first representative of the benzofuran class. MedChem Express HY-14151
      Prucalopride (R093877) is a drug acting as a selective, high affinity 5-HT4 receptor agonist(pKi=8.6/8.1 for 5-HT4a/4b); >150-fold higher affinity for 5-HT4 receptors than for other receptors.;IC50 value: 8.6/8.1 for 5-HT4a/4b(pKi);Target: 5-HT4 receptorPrucalopride is a novel enterokinetic compound and is the first representative of the benzofuran class. Receptor binding data have demonstrated prucalopride's high affinity to both investigated 5-HT(4) receptor isoforms, with mean pK(i) estimates of 8.60 and 8.10 for the human 5-HT(4a) and 5-HT(4b) receptor, respectively. From the 50 other binding assays investigated in this study only the human D(4) receptor (pK(i) 5.63), the mouse 5-HT(3) receptor (pK(i) 5.41) and the human sigma(1) (pK(i) 5.43) have shown measurable affinity, resulting in at least 290-fold selectivity for the 5-HT(4) receptor [1]. MedChem Express HY-14151

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

Density: 1.3±0.1 g/cm3
Boiling Point: 481.4±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 74.6±3.0 kJ/mol
Flash Point: 244.9±28.7 °C
Index of Refraction: 1.599
Molar Refractivity: 97.8±0.4 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 1.44
ACD/LogD (pH 5.5): -0.45
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): 1.23
ACD/BCF (pH 7.4): 3.00
ACD/KOC (pH 7.4): 41.48
Polar Surface Area: 77 Å2
Polarizability: 38.8±0.5 10-24cm3
Surface Tension: 56.7±5.0 dyne/cm
Molar Volume: 286.2±5.0 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) =  1.52

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  519.36  (Adapted Stein & Brown method)
    Melting Pt (deg C):  221.64  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.99E-011  (Modified Grain method)
    Subcooled liquid VP: 8.86E-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):  238.8
       log Kow used: 1.52 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  27518 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.75E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.421E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.52  (KowWin est)
  Log Kaw used:  -16.949  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.469
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.0548
   Biowin2 (Non-Linear Model)     :   0.0010
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.6666  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.0266  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0106
   Biowin6 (MITI Non-Linear Model):   0.0037
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.3436
 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):  1.18E-006 Pa (8.86E-009 mm Hg)
  Log Koa (Koawin est  ): 18.469
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.54 
       Octanol/air (Koa) model:  7.23E+005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.989 
       Mackay model           :  0.995 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 136.8472 E-12 cm3/molecule-sec
      Half-Life =     0.078 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.938 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.992 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  395.9
      Log Koc:  2.598 

 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 = 0.471 (BCF = 2.961)
       log Kow used: 1.52 (estimated)

 Volatilization from Water:
    Henry LC:  2.75E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.089E+015  hours   (1.704E+014 days)
    Half-Life from Model Lake : 4.461E+016  hours   (1.859E+015 days)

 Removal In Wastewater Treatment:
    Total removal:               1.98  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.89  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       2.64e-010       1.88         1000       
   Water     36.8            4.32e+003    1000       
   Soil      63.1            8.64e+003    1000       
   Sediment  0.0974          3.89e+004    0          
     Persistence Time: 2.09e+003 hr




                    

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