ChemSpider 2D Image | Epalrestat | C15H13NO3S2

Epalrestat

  • Molecular FormulaC15H13NO3S2
  • Average mass319.399 Da
  • Monoisotopic mass319.033691 Da
  • ChemSpider ID1266086
  • Double-bond stereo - Double-bond stereo


More details:






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

{(5Z)-5-[(2E)-2-Methyl-3-phenyl-2-propen-1-yliden]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}essigsäure [German] [ACD/IUPAC Name]
{(5Z)-5-[(2E)-2-Methyl-3-phenyl-2-propen-1-ylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}acetic acid [ACD/IUPAC Name]
{(5Z)-5-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}acetic acid
3-Thiazolidineacetic acid, 5-[(2E)-2-methyl-3-phenyl-2-propen-1-ylidene]-4-oxo-2-thioxo-, (5Z)- [ACD/Index Name]
5896
82159-09-9 [RN]
Acide {(5Z)-5-[(2E)-2-méthyl-3-phényl-2-propén-1-ylidène]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}acétique [French] [ACD/IUPAC Name]
epalrestat [Spanish] [INN]
Epalrestat [INN] [JAN] [Wiki]
épalrestat [French] [INN]
More...

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

424DV0807X [DBID]
D01688 [DBID]
ONO 2235 [DBID]
ONO-2235 [DBID]
UNII:424DV0807X [DBID]
UNII-424DV0807X [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Target Organs:

      Reductase inhibitor TargetMol T1458
    • Chemical Class:

      A monocarboxylic acid that is 1,3-thiazolidine which is substituted on the nitrogen by a carboxymethyl group, at positions 2 and 4 by thioxo and oxo groups, respectively, and at position 5 by a 2-meth yl-3-phenylprop-2-en-1-ylidene group. It is an inhibitor of aldose reductase (which catalyses the conversion of glucose to sorbitol) and is used for the treatment of some diabetic complications, inclu ding neuropathy. ChEBI CHEBI:31539
    • Bio Activity:

      Aldose reductase MedChem Express HY-66009
      Aldose reductase TargetMol T1458
      Enzyme TargetMol T1458
      Epalrestat is an aldose reductase inhibitor for the treatment of diabetic neuropathy.; Target: Aldose Reductase; Epalrestat may affect or delay progression of the underlying disease process. MedChem Express HY-66009
      Epalrestat is an aldose reductase inhibitor for the treatment of diabetic neuropathy.;Target: Aldose ReductaseEpalrestat may affect or delay progression of the underlying disease process. Data from six clinical trials were evaluated, and it was determined that epalrestat 50 mg 3 times/day may improve motor and sensory nerve conduction velocity and subjective neuropathy symptoms as compared with baseline and placebo. Epalrestat may serve as a new therapeutic option to prevent or slow the progression of diabetic neuropathy [1]. Epalrestat significantly increased the amplitude of 3 cpm waves on EGG and improved the spectral analytical parameters of heart rate variability. These findings suggest that epalrestat is useful for the treatment of diabetic gastroparesis [2]. Epalrestat is a highly effective and safe agent for the treatment of diabetic neuropathy [3]. MedChem Express HY-66009
      Metabolic Enzyme/Protease; MedChem Express HY-66009
      Others MedChem Express HY-66009
      Used against diabetic neuropathy Zerenex Molecular [ZBioX-0146]

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

Density: 1.4±0.1 g/cm3
Boiling Point: 516.8±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 83.1±3.0 kJ/mol
Flash Point: 266.4±32.9 °C
Index of Refraction: 1.706
Molar Refractivity: 86.5±0.4 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 2.02
ACD/LogD (pH 5.5): -0.09
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 2.94
ACD/LogD (pH 7.4): -1.67
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 115 Å2
Polarizability: 34.3±0.5 10-24cm3
Surface Tension: 75.3±5.0 dyne/cm
Molar Volume: 222.4±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) =  2.54

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  547.94  (Adapted Stein & Brown method)
    Melting Pt (deg C):  234.99  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.97E-012  (Modified Grain method)
    Subcooled liquid VP: 1.65E-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):  64.01
       log Kow used: 2.54 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  13822 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.33E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.889E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.54  (KowWin est)
  Log Kaw used:  -10.265  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.805
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0064
   Biowin2 (Non-Linear Model)     :   0.9736
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8258  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9828  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1730
   Biowin6 (MITI Non-Linear Model):   0.0274
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0046
 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):  2.2E-007 Pa (1.65E-009 mm Hg)
  Log Koa (Koawin est  ): 12.805
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  13.6 
       Octanol/air (Koa) model:  1.57 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.998 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  0.992 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 113.0612 E-12 cm3/molecule-sec
      Half-Life =     0.095 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.135 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    63.180000 E-17 cm3/molecule-sec
      Half-Life =     0.018 Days (at 7E11 mol/cm3)
      Half-Life =     26.120 Min
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  137.2
      Log Koc:  2.137 

 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: 2.54 (estimated)

 Volatilization from Water:
    Henry LC:  1.33E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.867E+008  hours   (3.278E+007 days)
    Half-Life from Model Lake : 8.583E+009  hours   (3.576E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               3.21  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     3.11  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       0.0132          0.365        1000       
   Water     21.4            360          1000       
   Soil      78.4            720          1000       
   Sediment  0.159           3.24e+003    0          
     Persistence Time: 612 hr




                    

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