ChemSpider 2D Image | Gabapentin enacarbil | C16H27NO6

Gabapentin enacarbil

  • Molecular FormulaC16H27NO6
  • Average mass329.389 Da
  • Monoisotopic mass329.183838 Da
  • ChemSpider ID8059607

More details:

Featured data source
The Merck Index Online

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

Gabapentin enacarbil [USAN] [Wiki]
{1-[({[1-(Isobutyryloxy)ethoxy]carbonyl}amino)methyl]cyclohexyl}acetic acid [ACD/IUPAC Name]
{1-[({[1-(Isobutyryloxy)ethoxy]carbonyl}amino)methyl]cyclohexyl}essigsäure [German] [ACD/IUPAC Name]
478296-72-9 [RN]
75OCL1SPBQ
Acide {1-[({[1-(isobutyryloxy)éthoxy]carbonyl}amino)méthyl]cyclohexyl}acétique [French] [ACD/IUPAC Name]
Cyclohexaneacetic acid, 1-[[[[1-(2-methyl-1-oxopropoxy)ethoxy]carbonyl]amino]methyl]- [ACD/Index Name]
Gabapentin Enacarbil, (R)-
Gabapentin Enacarbil, (S)-
gabapentina enacarbilo [Spanish] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

8611 [DBID]
XP13512 [DBID]
8TFE968DGA [DBID]
ASP-8825 [DBID]
D94N45262W [DBID]
XP 13512 [DBID]
XP-053 [DBID]
XP-13512 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A carbamate ester that is the <element>N</element>-[1-(isobutyryloxy)ethoxy]carbonyl derivative of [1-(aminomethyl)cyclohexyl]acetic acid. The prodrug for gabapentin, used for treatment of neuropathic pain and restless legs syndrome. ChEBI CHEBI:68840
      A carbamate ester that is the N-[1-(isobutyryloxy)ethoxy]carbonyl derivative of [1-(aminomethyl)cyclohexyl]acetic acid. The prodrug for gabapentin, used for treatment of neuropathic pain and restless legs syndrome. ChEBI CHEBI:68840
      A carbamate ester that is the N-[1-(isobutyryloxy)ethoxy]carbonyl derivative of [1-(aminomethyl)cyclohexyl]acetic acid. The prodrug for gabapentin, used for treatment of neuropathic; pain and restles s legs syndrome. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:68840

    • Bio Activity:

      Calcium Channel MedChem Express HY-16216
      Gabapentin enacarbil (XP-13512) is a prodrug for the anticonvulsant and analgesic drug gabapentin. MedChem Express
      Gabapentin enacarbil (XP-13512) is a prodrug for the anticonvulsant and analgesic drug gabapentin.; IC50 Value: ; Target: Calcium Channel; Gabapentin enacarbil is an actively transported prodrug of gabapentin that provides sustained dose-proportional exposure to gabapentin and predictable bioavailability.; in vitro: The prodrug (XP-13512) demonstrated active apical to basolateral transport across Caco-2 cell monolayers and pH-dependent passive permeability across artificial membranes. MedChem Express HY-16216
      Gabapentin enacarbil (XP-13512) is a prodrug for the anticonvulsant and analgesic drug gabapentin.;IC50 Value: ;Target: Calcium ChannelGabapentin enacarbil is an actively transported prodrug of gabapentin that provides sustained dose-proportional exposure to gabapentin and predictable bioavailability.;In vitro: The prodrug (XP-13512) demonstrated active apical to basolateral transport across Caco-2 cell monolayers and pH-dependent passive permeability across artificial membranes. XP13512 inhibited uptake of (14)C-lactate by human embryonic kidney cells expressing monocarboxylate transporter type-1, and direct uptake of prodrug by these cells was confirmed using liquid chromatography-tandem mass spectrometry. XP13512 inhibited uptake of (3)H-biotin into Chinese hamster ovary cells overexpressing human sodium-dependent multivitamin transporter (SMVT) [1].;In vivo: In 4 studies of healthy volunteers (136 subjects total), the pharmacokinetics of XP13512 immediate- and extended-rel MedChem Express HY-16216
      Membrane Transporter/Ion Channel MedChem Express HY-16216
      Membrane Transporter/Ion Channel; MedChem Express HY-16216

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

Density: 1.1±0.1 g/cm3
Boiling Point: 482.0±20.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.6 mmHg at 25°C
Enthalpy of Vaporization: 81.8±6.0 kJ/mol
Flash Point: 245.3±21.8 °C
Index of Refraction: 1.481
Molar Refractivity: 82.7±0.3 cm3
#H bond acceptors: 7
#H bond donors: 2
#Freely Rotating Bonds: 9
#Rule of 5 Violations: 0
ACD/LogP: 3.07
ACD/LogD (pH 5.5): 1.96
ACD/BCF (pH 5.5): 11.32
ACD/KOC (pH 5.5): 113.93
ACD/LogD (pH 7.4): 0.16
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.81
Polar Surface Area: 102 Å2
Polarizability: 32.8±0.5 10-24cm3
Surface Tension: 43.5±3.0 dyne/cm
Molar Volume: 290.2±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) =  3.29

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  401.16  (Adapted Stein & Brown method)
    Melting Pt (deg C):  135.76  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.99E-007  (Modified Grain method)
    Subcooled liquid VP: 7.79E-006 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):  31.63
       log Kow used: 3.29 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1785.9 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.15E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.208E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.29  (KowWin est)
  Log Kaw used:  -12.328  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.618
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7332
   Biowin2 (Non-Linear Model)     :   0.9121
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7172  (weeks-months)
   Biowin4 (Primary Survey Model) :   4.0272  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3786
   Biowin6 (MITI Non-Linear Model):   0.3352
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2580
 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):  0.00104 Pa (7.79E-006 mm Hg)
  Log Koa (Koawin est  ): 15.618
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00289 
       Octanol/air (Koa) model:  1.02E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0945 
       Mackay model           :  0.188 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  35.7654 E-12 cm3/molecule-sec
      Half-Life =     0.299 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.589 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.141 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  133.1
      Log Koc:  2.124 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  6.387E-001  L/mol-sec
  Kb Half-Life at pH 8:      12.560  days   
  Kb Half-Life at pH 7:     125.598  days   

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 3.29 (estimated)

 Volatilization from Water:
    Henry LC:  1.15E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  9.24E+010  hours   (3.85E+009 days)
    Half-Life from Model Lake : 1.008E+012  hours   (4.2E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               9.07  percent
    Total biodegradation:        0.15  percent
    Total sludge adsorption:     8.91  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       9.66e-008       7.18         1000       
   Water     12              900          1000       
   Soil      87.5            1.8e+003     1000       
   Sediment  0.53            8.1e+003     0          
     Persistence Time: 1.82e+003 hr

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