ChemSpider 2D Image | Piboserod | C22H31N3O2


  • Molecular FormulaC22H31N3O2
  • Average mass369.500 Da
  • Monoisotopic mass369.241638 Da
  • ChemSpider ID154413

More details:

Featured data source

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

152811-62-6 [RN]
1'-Butyl-4'-piperidinylmethyl ester
2H-[1,3]Oxazino[3,2-a]indole-10-carboxamide, N-[(1-butyl-4-piperidinyl)methyl]-3,4-dihydro- [ACD/Index Name]
N-[(1-Butyl-4-piperidinyl)methyl]-3,4-dihydro-2H-[1,3]oxazino[3,2-a]indol-10-carboxamid [German] [ACD/IUPAC Name]
N-[(1-Butyl-4-piperidinyl)methyl]-3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide [ACD/IUPAC Name]
N-[(1-Butyl-4-pipéridinyl)méthyl]-3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide [French] [ACD/IUPAC Name]

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

7587 [DBID]
SB 207256 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Target Organs:

      5-HT Receptor antagonist TargetMol T2278
    • Bio Activity:

      5-HT Receptor MedChem Express HY-15574
      5-HT(4) receptor TargetMol T2278
      GPCR/G protein MedChem Express HY-15574
      GPCR/G protein; Neuronal Signaling; MedChem Express HY-15574
      Neuroscience TargetMol T2278
      Piboserod (SB 207266) is a selective 5-HT(4) receptor antagonist. MedChem Express
      Piboserod (SB 207266) is a selective 5-HT(4) receptor antagonist.; IC50 value:; Target: 5-HT4 antagonist; in vitro: Piboserod did not modify the basal contractions but concentration-dependently antagonized the ability of 5-HT to enhance bladder strip contractions to EFS. MedChem Express HY-15574
      Piboserod (SB 207266) is a selective 5-HT(4) receptor antagonist.;IC50 value:;Target: 5-HT4 antagonist;In vitro: Piboserod did not modify the basal contractions but concentration-dependently antagonized the ability of 5-HT to enhance bladder strip contractions to EFS. In presence of 1 and 100 nM of piboserod, the maximal 5-HT-induced potentiations were reduced to 45.0+/-7.9 and 38.7+/-8.7%, respectively [1].;In vivo: Piboserod significantly increased LVEF by 1.7% vs. placebo (CI 0.3, 3.2, P = 0.020), primarily through reduced end-systolic volume from 165 to 158 mL (P = 0.060). There was a trend for greater increase in LVEF (2.7%, CI -1.1, 6.6, P = 0.15) in a small subset of patients not on chronic beta-blocker therapy. There was no significant effect on neurohormones, quality of life, or exercise tolerance. Patients on piboserod reported more adverse events, but numbers were too small to identify specific safety issues [2]. Pretreatment with potent 5-HT4 ligands dose-dependently r MedChem Express HY-15574

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.2±0.1 g/cm3
Boiling Point: 570.3±35.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 85.5±3.0 kJ/mol
Flash Point: 298.7±25.9 °C
Index of Refraction: 1.626
Molar Refractivity: 106.8±0.5 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 3.95
ACD/LogD (pH 5.5): 0.72
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 2.43
ACD/LogD (pH 7.4): 1.77
ACD/BCF (pH 7.4): 4.38
ACD/KOC (pH 7.4): 27.24
Polar Surface Area: 47 Å2
Polarizability: 42.3±0.5 10-24cm3
Surface Tension: 47.0±7.0 dyne/cm
Molar Volume: 301.8±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) =  5.19

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  546.64  (Adapted Stein & Brown method)
    Melting Pt (deg C):  234.38  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.85E-012  (Modified Grain method)
    Subcooled liquid VP: 1.78E-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):  0.1759
       log Kow used: 5.19 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  10.708 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.38E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.723E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.19  (KowWin est)
  Log Kaw used:  -13.416  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.606
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8169
   Biowin2 (Non-Linear Model)     :   0.9107
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3138  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5782  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2314
   Biowin6 (MITI Non-Linear Model):   0.0462
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.1043
 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):  2.37E-007 Pa (1.78E-009 mm Hg)
  Log Koa (Koawin est  ): 18.606
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  12.6 
       Octanol/air (Koa) model:  9.91E+005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.998 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 329.6050 E-12 cm3/molecule-sec
      Half-Life =     0.032 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    23.365 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.998 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2.198E+005
      Log Koc:  5.342 

 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 = 3.293 (BCF = 1963)
       log Kow used: 5.19 (estimated)

 Volatilization from Water:
    Henry LC:  9.38E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:   1.2E+012  hours   (4.999E+010 days)
    Half-Life from Model Lake : 1.309E+013  hours   (5.454E+011 days)

 Removal In Wastewater Treatment:
    Total removal:              82.88  percent
    Total biodegradation:        0.71  percent
    Total sludge adsorption:    82.17  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       4.13e-006       0.779        1000       
   Water     7.15            900          1000       
   Soil      68.3            1.8e+003     1000       
   Sediment  24.5            8.1e+003     0          
     Persistence Time: 2.41e+003 hr


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