ChemSpider 2D Image | Alvimopan | C25H32N2O4

Alvimopan

  • Molecular FormulaC25H32N2O4
  • Average mass424.533 Da
  • Monoisotopic mass424.236206 Da
  • ChemSpider ID4589864

  • defined stereocentres - 3 of 3 defined stereocentres

More details:

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

({(2S)-2-Benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]propanoyl}amino)acetic acid
156053-89-3 [RN]
ADL-8-2698
Alvimopan [USAN]
Alvimopan anhydrous
Glycine, N-[(2S)-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]-1-oxo-2-(phenylmethyl)propyl]- [ACD/Index Name]
LY-246736
MFCD09838268 [MDL number]
N-[(2S)-2-[[(3R,4R)-4-(3-Hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-phenylpropyl]glycine
N-{(2S)-2-Benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]propanoyl}glycin [German] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

8245 [DBID]
ADL 8-2698 [DBID]
LY246736 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Safety:

      A06AH02 Wikidata Q4738021

    • Bio Activity:

      Alvimopan(LY 246736; ADL 8-2698) is a peripherally acting mu-opioid receptor (PAM-OR, IC50= 1.7 nM) antagonist for accelerating gastrointestinal recovery after surgery. MedChem Express http://www.medchemexpress.com/alvimopan.html, HY-13243
      Alvimopan(LY 246736; ADL 8-2698) is a peripherally acting mu-opioid receptor (PAM-OR, IC50= 1.7 nM) antagonist for accelerating gastrointestinal recovery after surgery. ;IC50 Value: 1.7 nM (Mu-type opioid receptor) [1];Target: mu-opioid receptor;In vitro: The dissociation rate of alvimopan from the micro opioid receptor (t(1/2)=30--44 min) was comparable to that of the long acting partial agonist buprenorphine (t(1/2)=44 min), but was slower than those of the antagonists naloxone (t(1/2)=0.82 min) and N-methylnaltrexone (t(1/2)=0.46 min) [2].;In vivo: Alvimopan did not significantly accelerate GI-3 compared with placebo [6 mg: hazard ratio (HR) = 1.20, p = 0.080; 12 mg: HR = 1.24, p = 0.038). However, after adjustment for significant covariates (sex/surgical duration), benefits were significant for both doses (6 mg: HR = 1.24, p = 0.037; 12 mg: HR = 1.26, p = 0.028). Alvimopan also significantly accelerated time to GI-2 (6 mg: HR = 1.37, p = 0.008; 12 mg: HR = 1.33, p = 0.018) and MedChem Express HY-13243
      GPCR/G protein MedChem Express HY-13243
      GPCR/G protein; Neuronal Signaling; MedChem Express HY-13243
      Opioid Receptor MedChem Express HY-13243

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

Density: 1.2±0.1 g/cm3
Boiling Point: 684.1±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.2 mmHg at 25°C
Enthalpy of Vaporization: 105.4±3.0 kJ/mol
Flash Point: 367.5±31.5 °C
Index of Refraction: 1.572
Molar Refractivity: 119.8±0.3 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 3.38
ACD/LogD (pH 5.5): 0.68
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 4.04
ACD/LogD (pH 7.4): 0.55
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 2.98
Polar Surface Area: 90 Å2
Polarizability: 47.5±0.5 10-24cm3
Surface Tension: 48.1±3.0 dyne/cm
Molar Volume: 363.8±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) =  4.19

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  659.19  (Adapted Stein & Brown method)
    Melting Pt (deg C):  330.19  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.15E-017  (Modified Grain method)
    Subcooled liquid VP: 1.18E-013 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):  2.179
       log Kow used: 4.19 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1122 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.93E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.064E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.19  (KowWin est)
  Log Kaw used:  -18.794  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  22.984
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7377
   Biowin2 (Non-Linear Model)     :   0.4142
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1080  (months      )
   Biowin4 (Primary Survey Model) :   3.3608  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0572
   Biowin6 (MITI Non-Linear Model):   0.0048
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.2295
 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):  1.57E-011 Pa (1.18E-013 mm Hg)
  Log Koa (Koawin est  ): 22.984
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.91E+005 
       Octanol/air (Koa) model:  2.37E+010 
   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 = 219.0722 E-12 cm3/molecule-sec
      Half-Life =     0.049 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.586 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   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    :  2.631E+005
      Log Koc:  5.420 

 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: 4.19 (estimated)

 Volatilization from Water:
    Henry LC:  3.93E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  3.07E+017  hours   (1.279E+016 days)
    Half-Life from Model Lake : 3.349E+018  hours   (1.395E+017 days)

 Removal In Wastewater Treatment:
    Total removal:              39.41  percent
    Total biodegradation:        0.39  percent
    Total sludge adsorption:    39.02  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       3.75e-007       1.17         1000       
   Water     8.23            1.44e+003    1000       
   Soil      87.9            2.88e+003    1000       
   Sediment  3.91            1.3e+004     0          
     Persistence Time: 2.97e+003 hr

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