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ChemSpider 2D Image | indometacin | C19H16ClNO4

indometacin

  • Molecular FormulaC19H16ClNO4
  • Average mass357.788 Da
  • Monoisotopic mass357.076782 Da
  • ChemSpider ID3584

More details:



Featured data source



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

[1-(4-Chlorbenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]essigsäure [German] [ACD/IUPAC Name]
[1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid [ACD/IUPAC Name]
{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid
{1-[(4-Chlorphenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}essigsäure [German]
1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetic acid
1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl- [ACD/Index Name]
1-p-Cloro-benzoil-5-metoxi-2-metilindol-3-acido acetico [Spanish]
200-186-5 [EINECS]
74252-25-8 [RN]
More...

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

1524 [DBID]
NL3500000 [DBID]
XXE1CET956 [DBID]
AIDS025351 [DBID]
AIDS-025351 [DBID]
AIDS028381 [DBID]
AIDS-028381 [DBID]
Bio2_000405 [DBID]
Bio2_000885 [DBID]
BPBio1_000160 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Toxicity:

      Organic Compound; Organochloride; Amine; Ether; Amide; Ester; Drug; Anti-Inflammatory Agent; Anti-Inflammatory Agent, Non-Steroidal; Cyclooxygenase Inhibitor; Cardiovascular Agent; Gout Suppressant; Tocolytic Agent; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D2753
    • Safety:

      20-28-36/37-45 Alfa Aesar A19910
      28 LKT Labs [I5315]
      28-68 Alfa Aesar A19910
      6.1 Alfa Aesar A19910
      C01EB03 Wikidata Q409231
      Danger Alfa Aesar A19910
      Danger Biosynth Q-201239
      DANGER: POISON, teratogen, mutagen, GI/liver/kidney damage Alfa Aesar A19910
      GHS06 Biosynth Q-201239
      H300 Biosynth Q-201239
      H300 LKT Labs [I5315]
      H300-H341 Alfa Aesar A19910
      M01AB01 Wikidata Q409231
      M02AA23 Wikidata Q409231
      P264; P301+P310 Biosynth Q-201239
      P281-P301+P310-P308+P313-P321-P405-P501a Alfa Aesar A19910
      S01BC01 Wikidata Q409231
      T+ Abblis Chemicals AB1009492
      T+ LKT Labs [I5315]
      UN number: 2811, Class: 6.1, Packing group: 1Proper shipping name: Toxic solids, organic, n.o.s. (Indometacin)Marine pollutant: No; Poison inhalation hazard: No LKT Labs [I5315]
    • Target Organs:

      COX inhibitor;PPAR agonist TargetMol T0458
    • Chemical Class:

      A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by <ital>p</ital>-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis. ChEBI CHEBI:49662
      A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups,; respective ly. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:49662
    • Compound Source:

      synthetic Microsource [01500350]
    • Bio Activity:

      Antiinflammatories; Zerenex Molecular [ZBioX-0572]
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio [HB4422]
      COX MedChem Express HY-14397
      Cyclooxgenase (COX) inhibitor; displays selectivity for COX-1 (IC50 values are 230 and 630 nM for human COX-1 and COX-2 respectively). Widely used anti-inflammatory agent. Tocris Bioscience 1708
      Cyclooxygenase Tocris Bioscience 1708
      Cyclooxygenase inhibitor Hello Bio [HB4422]
      Cyclooxygenase inhibitor (COX-1 > COX-2) Tocris Bioscience 1708
      Enzymes Tocris Bioscience 1708
      Enzymes/Oxygenase/COX Hello Bio [HB4422]
      Immunology/Inflammation MedChem Express HY-14397
      Immunology/Inflammation; MedChem Express HY-14397
      Indomethacin is a non-steroidal anti-inflammatory compound commonly used to reduce fever, pain, stiffness, and swelling. MedChem Express
      Indomethacin is a non-steroidal anti-inflammatory compound commonly used to reduce fever, pain, stiffness, and swelling.; Target: COX1; COX2; Indomethacin is a nonselective inhibitor of cyclooxygenase (COX) 1 and 2, enzymes that participate in prostaglandin synthesis from arachidonic acid. MedChem Express HY-14397
      Indomethacin is a non-steroidal anti-inflammatory compound commonly used to reduce fever, pain, stiffness, and swelling.;Target: COX1; COX2;Indomethacin is a nonselective inhibitor of cyclooxygenase (COX) 1 and 2, enzymes that participate in prostaglandin synthesis from arachidonic acid. Prostaglandins are hormone-like molecules normally found in the body, where they have a wide variety of effects, some of which lead to pain, fever, and inflammation. Prostaglandins also cause uterine contractions in pregnant women. Indomethacin is an effective tocolytic agent,[6] able to delay premature labor by reducing uterine contractions through inhibition of PG synthesis in the uterus and possibly through calcium channel blockade [1]. MedChem Express HY-14397
      Neuroscience TargetMol T0458
      Oxygenases/Oxidases Tocris Bioscience 1708
      Prostaglandin G/H synthase 1,2;PTGR1;PPAR??;PPAR?? TargetMol T0458
  • Gas Chromatography

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

Density: 1.3±0.1 g/cm3
Boiling Point: 499.4±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 80.8±3.0 kJ/mol
Flash Point: 255.8±28.7 °C
Index of Refraction: 1.619
Molar Refractivity: 94.6±0.5 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 3.11
ACD/LogD (pH 5.5): 2.47
ACD/BCF (pH 5.5): 18.84
ACD/KOC (pH 5.5): 103.31
ACD/LogD (pH 7.4): 0.75
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.98
Polar Surface Area: 69 Å2
Polarizability: 37.5±0.5 10-24cm3
Surface Tension: 47.5±7.0 dyne/cm
Molar Volume: 269.6±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) =  4.23
    Log Kow (Exper. database match) =  4.27
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  514.50  (Adapted Stein & Brown method)
    Melting Pt (deg C):  219.37  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.12E-010  (Modified Grain method)
    MP  (exp database):  158 deg C
    Subcooled liquid VP: 1.18E-008 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):  3.114
       log Kow used: 4.27 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  0.937 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.81285 mg/L
    Wat Sol (Exper. database match) =  0.94
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.13E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.741E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.27  (exp database)
  Log Kaw used:  -11.893  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.163
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7087
   Biowin2 (Non-Linear Model)     :   0.4895
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3587  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4918  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0740
   Biowin6 (MITI Non-Linear Model):   0.0107
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4425
 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-006 Pa (1.18E-008 mm Hg)
  Log Koa (Koawin est  ): 16.163
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.91 
       Octanol/air (Koa) model:  3.57E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.986 
       Mackay model           :  0.993 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 203.4365 E-12 cm3/molecule-sec
      Half-Life =     0.053 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.631 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.99 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2323
      Log Koc:  3.366 

 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: 4.27 (expkow database)

 Volatilization from Water:
    Henry LC:  3.13E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.538E+010  hours   (1.474E+009 days)
    Half-Life from Model Lake :  3.86E+011  hours   (1.608E+010 days)

 Removal In Wastewater Treatment:
    Total removal:              43.65  percent
    Total biodegradation:        0.43  percent
    Total sludge adsorption:    43.22  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       4.87e-006       1.26         1000       
   Water     10.5            900          1000       
   Soil      84.8            1.8e+003     1000       
   Sediment  4.65            8.1e+003     0          
     Persistence Time: 1.93e+003 hr




                    

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