ChemSpider 2D Image | acemetacin | C21H18ClNO6

acemetacin

  • Molecular FormulaC21H18ClNO6
  • Average mass415.824 Da
  • Monoisotopic mass415.082275 Da
  • ChemSpider ID1904

More details:



Featured data source



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

({[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl}oxy)acetic acid
[({1-[(4-chlorophenyl)carbonyl]-2-methyl-5-(methyloxy)-1H-indol-3-yl}acetyl)oxy]acetic acid
[({1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetyl)oxy]acetic acid
{2-[1-(4-Chlorbenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetoxy}essigsäure [German] [ACD/IUPAC Name]
{2-[1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetoxy}acetic acid [ACD/IUPAC Name]
1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-, carboxymethyl ester [ACD/Index Name]
258-403-4 [EINECS]
3664
53164-05-9 [RN]
5V141XK28X
More...

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

A1674_SIGMA [DBID]
BRN 0501672 [DBID]
D01582 [DBID]
DivK1c_000490 [DBID]
K 708 [DBID]
K-708 [DBID]
KBio1_000490 [DBID]
KBio2_000908 [DBID]
KBio2_003476 [DBID]
KBio2_006044 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      26/27/28 LKT Labs [A0816]
      H300 H310 H330 LKT Labs [A0816]
      T+ LKT Labs [A0816]
      UN 2811 6.1/PG 2 LKT Labs [A0816]
    • Target Organs:

      COX inhibitor TargetMol T1467
    • Chemical Class:

      A carboxylic ester that is the carboxymethyl ester of indometacin. A non-steroidal anti-inflammatory drug, it is used in the treatment of rheumatoid arthritis, osteoarthritis, and low back pain, as we ll as for postoperative pain and inflammation. Its activity is due to both acemetacin and its major metabolite, indometacin. ChEBI CHEBI:31162
    • Therapeutical Effect:

      antiinflammatory Microsource [01500666]
    • Drug Status:

      INN, BAN, JAN Microsource [01500666]
    • Compound Source:

      synthetic Microsource [01500666]
    • Bio Activity:

      Acemetacin is a non-steroidal anti-inflammatory drug and a glycolic acid ester of indometacin that is a cyclooxygenase inhibitor. MedChem Express
      Acemetacin is a non-steroidal anti-inflammatory drug and a glycolic acid ester of indometacin that is a cyclooxygenase inhibitor.; Target: COX; Acemetacin is a non-steroidal anti-inflammatory drug, used for the treatment of osteoarthritis, rheumatoid arthritis, lower back pain, and relieving post-operative pain. MedChem Express HY-B0482
      Acemetacin is a non-steroidal anti-inflammatory drug and a glycolic acid ester of indometacin that is a cyclooxygenase inhibitor.;Target: COXAcemetacin is a non-steroidal anti-inflammatory drug, used for the treatment of osteoarthritis, rheumatoid arthritis, lower back pain, and relieving post-operative pain. Acemetacin, a glycolic acid ester of indometacin, acts as a prodrug; in the body, it is metabolized to indometacin, which then acts as an inhibitor of cyclooxygenase, producing the anti-inflammatory effects. An advantage of acemetacin is that it reduces gastric damage when compared to indometacin. From Wikipedia. MedChem Express HY-B0482
      COX MedChem Express HY-B0482
      Immunology/Inflammation MedChem Express HY-B0482
      Immunology/Inflammation; MedChem Express HY-B0482
      Neuroscience TargetMol T1467
      Prostaglandin G/H synthase TargetMol T1467

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

Density: 1.4±0.1 g/cm3
Boiling Point: 565.5±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 89.4±3.0 kJ/mol
Flash Point: 295.8±30.1 °C
Index of Refraction: 1.611
Molar Refractivity: 106.1±0.5 cm3
#H bond acceptors: 7
#H bond donors: 1
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 3.20
ACD/LogD (pH 5.5): 0.89
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 3.66
ACD/LogD (pH 7.4): 0.02
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 95 Å2
Polarizability: 42.0±0.5 10-24cm3
Surface Tension: 49.4±7.0 dyne/cm
Molar Volume: 305.4±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) =  4.13

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  563.88  (Adapted Stein & Brown method)
    Melting Pt (deg C):  242.44  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.29E-011  (Modified Grain method)
    MP  (exp database):  151.5 deg C
    Subcooled liquid VP: 6.39E-010 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):  1.788
       log Kow used: 4.13 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.0328 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.28E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.007E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.13  (KowWin est)
  Log Kaw used:  -13.666  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.796
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8553
   Biowin2 (Non-Linear Model)     :   0.9613
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3706  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6370  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2945
   Biowin6 (MITI Non-Linear Model):   0.0348
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2447
 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):  8.52E-008 Pa (6.39E-010 mm Hg)
  Log Koa (Koawin est  ): 17.796
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  35.2 
       Octanol/air (Koa) model:  1.53E+005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 204.1463 E-12 cm3/molecule-sec
      Half-Life =     0.052 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.629 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  1159
      Log Koc:  3.064 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.960E+001  L/mol-sec
  Kb Half-Life at pH 8:       6.504  hours  
  Kb Half-Life at pH 7:       2.710  days   

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 4.13 (estimated)

 Volatilization from Water:
    Henry LC:  5.28E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.261E+012  hours   (9.422E+010 days)
    Half-Life from Model Lake : 2.467E+013  hours   (1.028E+012 days)

 Removal In Wastewater Treatment:
    Total removal:              36.33  percent
    Total biodegradation:        0.37  percent
    Total sludge adsorption:    35.96  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       7.34e-007       1.26         1000       
   Water     10.8            900          1000       
   Soil      85.8            1.8e+003     1000       
   Sediment  3.44            8.1e+003     0          
     Persistence Time: 1.91e+003 hr




                    

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