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]
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
200-186-5 [EINECS]
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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]
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  • Experimental Physico-chemical Properties
    • Experimental Melting Point:

      160 °C TCI I0655
      158-161 °C Alfa Aesar
      159.8 °C Jean-Claude Bradley Open Melting Point Dataset 16854, 17154
      158 °C Jean-Claude Bradley Open Melting Point Dataset 16854, 17154, 21831
      159 °C Jean-Claude Bradley Open Melting Point Dataset 28192, 28193
      160 °C Jean-Claude Bradley Open Melting Point Dataset 7341
      158-161 °C Alfa Aesar A19910
      155 °C Oakwood 358171
    • Experimental Solubility:

      10 mM in DMSO MedChem Express HY-14397
      DMSO 72 mg/mL; Water <1 mg/mL MedChem Express HY-14397
      Soluble to 50 mM in ethanol and to 100 mM in DMSO Tocris Bioscience 1708
      Soluble to 50 mM in ethanol with gentle warming and to 100 mM in DMSO Tocris Bioscience 1708
  • 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
      28-68 Alfa Aesar A19910
      6.1 Alfa Aesar A19910
      C01EB03 Wikidata Q409231
      Danger Alfa Aesar A19910
      DANGER: POISON, teratogen, mutagen, GI/liver/kidney damage Alfa Aesar A19910
      H300-H341 Alfa Aesar A19910
      M01AB01 Wikidata Q409231
      M02AA23 Wikidata Q409231
      P281-P301+P310-P308+P313-P321-P405-P501a Alfa Aesar A19910
      S01BC01 Wikidata Q409231
    • 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, 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
    • Bio Activity:

      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, version: 14.00

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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