ChemSpider 2D Image | Sulindac | C20H17FO3S

Sulindac

  • Molecular FormulaC20H17FO3S
  • Average mass356.411 Da
  • Monoisotopic mass356.088257 Da
  • ChemSpider ID1265915
  • Double-bond stereo - Double-bond stereo


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

(Z)-5-Fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-1H-indene-3-acetic Acid
[(1Z)-5-Fluor-2-methyl-1-{[4-(methylsulfinyl)phenyl]methyliden}-1H-inden-3-yl]essigsäure [German]
[(1Z)-5-fluoro-2-methyl-1-{[4-(methylsulfinyl)phenyl]methylidene}-1H-inden-3-yl]acetic acid
{(1Z)-5-Fluor-2-methyl-1-[4-(methylsulfinyl)benzyliden]-1H-inden-3-yl}essigsäure [German] [ACD/IUPAC Name]
{(1Z)-5-Fluoro-2-methyl-1-[4-(methylsulfinyl)benzylidene]-1H-inden-3-yl}acetic acid [ACD/IUPAC Name]
184SNS8VUH
1H-Indene-3-acetic acid, 5-fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-, (1Z)- [ACD/Index Name]
1H-Indene-3-acetic acid, 5-fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-, (Z)-
253-819-2 [EINECS]
3791
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:9352 [DBID]
1LZ36959EV [DBID]
BRN 2951842 [DBID]
C01531 [DBID]
CCRIS 3305 [DBID]
D00120 [DBID]
EU-0101070 [DBID]
Lopac-S-8139 [DBID]
MK 231 [DBID]
NCGC00015970-01 [DBID]
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  • Experimental Physico-chemical Properties
    • Experimental Melting Point:

      183 °C LKT Labs [S8145]
      183 °C Jean-Claude Bradley Open Melting Point Dataset 16908
      185.3 °C Jean-Claude Bradley Open Melting Point Dataset 17338
      183.5 °C Jean-Claude Bradley Open Melting Point Dataset 28563, 28564, 28565
      128 °C Jean-Claude Bradley Open Melting Point Dataset 28563, 28564, 28565
      181-183 °C LabNetwork LN00191571
    • Experimental Solubility:

      10 mM in H2O MedChem Express HY-B0008
      Soluble in DMSO (100 mM) or ethanol (25 mM). LKT Labs [S8145]
      Soluble to 100 mM in DMSO and to 25 mM in ethanol Tocris Bioscience 1707
      Soluble to 100 mM in DMSO and to 25 mM in ethanol MedChem Express HY-B0008
  • Miscellaneous
    • Appearance:

      YELLOW POWDER NIH Clinical Collection [SMR000326718]
    • Safety:

      22-63-42/43 LKT Labs [S8145]
      H301 H317 H334 H361 LKT Labs [S8145]
      IRRITANT Matrix Scientific 093179
      M01AB02 Wikidata Q963093
      UN 2811 6.1/PG 3 LKT Labs [S8145]
      Xn LKT Labs [S8145]
    • Target Organs:

      COX inhibitor TargetMol T0459
    • Chemical Class:

      A monocarboxylic acid that is 1-benzylidene-1<element>H</element>-indene which is substituted at positions 2, 3, and 5 by methyl, carboxymethyl, and fluorine respectively, and in which the phenyl grou p of the benzylidene moiety is substituted at the <ital>para</ital> position by a methylsulfinyl group. It is a prodrug for the corresponding sulfide, a non-steroidal anti-inflammatory drug, used part icularly in the treatment of acute and chronic inflammatory conditions. ChEBI CHEBI:9352
    • Drug Status:

      approved BIONET-Key Organics KS-5153
    • Compound Source:

      synthetic Microsource [01500556]
    • Bio Activity:

      COX MedChem Express HY-B0008
      Cyclooxygenase Tocris Bioscience 1707
      Cyclooxygenase inhibitor (following metabolism to sulindac sulfide) Tocris Bioscience 1707
      Enzymes Tocris Bioscience 1707
      Immunology/Inflammation MedChem Express HY-B0008
      Immunology/Inflammation; MedChem Express HY-B0008
      Neuroscience TargetMol T0459
      Oxygenases/Oxidases Tocris Bioscience 1707
      Prodrug. Metabolizes to sulindac sulfide, a cyclooxgenase inhibitor that represses ras signaling, and sulindac sulfone, an antitumor agent, following oral administration in vivo. Widely used anti-infl ammatory agent. Tocris Bioscience 1707
      Prodrug. Metabolizes to sulindac sulfide, a cyclooxgenase inhibitor that represses ras signaling, and sulindac sulfone, an antitumor agent, following oral administration in vivo. Widely used anti-inflammatory agent. Tocris Bioscience 1707
      Prostaglandin G/H synthase TargetMol T0459
      Sulindac (Clinoril) is a non-steroidal anti-inflammatory agent of the arylalkanoic acid class; it is thought to act on enzymes COX-1 and COX-2, inhibiting prostaglandin synthesis.; IC50 value: ; Target: COX1/2; Sulindac (Clinoril) is a non-steroidal anti-inflammatory drug of the arylalkanoic acid class. MedChem Express HY-B0008
      Sulindac (Clinoril) is a non-steroidal anti-inflammatory agent of the arylalkanoic acid class; it is thought to act on enzymes COX-1 and COX-2, inhibiting prostaglandin synthesis.;IC50 value: ;Target: COX1/2Sulindac (Clinoril) is a non-steroidal anti-inflammatory drug of the arylalkanoic acid class. Like other NSAIDs, it is useful in the treatment of acute or chronic inflammatory conditions. Sulindac is a prodrug, derived from sulfinylindene that is converted in the body to an active NSAID. More specifically, the agent is converted by liver enzymes to a sulfide which is excreted in the bile and then reabsorbed from the intestine. This is thought to help maintain constant blood levels with reduced gastrointestinal side effects. MedChem Express HY-B0008

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

Density: 1.4±0.1 g/cm3
Boiling Point: 581.6±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 91.5±3.0 kJ/mol
Flash Point: 305.6±30.1 °C
Index of Refraction: 1.673
Molar Refractivity: 96.2±0.4 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 3.59
ACD/LogD (pH 5.5): 2.11
ACD/BCF (pH 5.5): 11.79
ACD/KOC (pH 5.5): 89.18
ACD/LogD (pH 7.4): 0.33
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.47
Polar Surface Area: 74 Å2
Polarizability: 38.1±0.5 10-24cm3
Surface Tension: 65.9±5.0 dyne/cm
Molar Volume: 256.7±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) =  4.28
    Log Kow (Exper. database match) =  3.42
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  512.07  (Adapted Stein & Brown method)
    Melting Pt (deg C):  218.24  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.05E-010  (Modified Grain method)
    MP  (exp database):  183 deg C
    Subcooled liquid VP: 1.36E-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):  16.89
       log Kow used: 3.42 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  3000 mg/L ( deg C)
        Exper. Ref:  MERCK INDEX (1996); pH 7

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  82.789 mg/L
    Wat Sol (Exper. database match) =  3000.00
       Exper. Ref:  MERCK INDEX (1996); pH 7

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.25E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.468E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.42  (exp database)
  Log Kaw used:  -13.292  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.712
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.1594
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3692  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7325  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0357
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.1482
 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):  1.81E-006 Pa (1.36E-008 mm Hg)
  Log Koa (Koawin est  ): 16.712
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.65 
       Octanol/air (Koa) model:  1.26E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.984 
       Mackay model           :  0.993 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 349.9680 E-12 cm3/molecule-sec
      Half-Life =     0.031 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    22.005 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant = 59136.480469 E-17 cm3/molecule-sec
      Half-Life =     0.000 Days (at 7E11 mol/cm3)
      Half-Life =      0.028 Min
   Fraction sorbed to airborne particulates (phi): 0.988 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.905E+004
      Log Koc:  4.280 

 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: 3.42 (expkow database)

 Volatilization from Water:
    Henry LC:  1.25E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 8.843E+011  hours   (3.684E+010 days)
    Half-Life from Model Lake : 9.646E+012  hours   (4.019E+011 days)

 Removal In Wastewater Treatment:
    Total removal:              11.34  percent
    Total biodegradation:        0.17  percent
    Total sludge adsorption:    11.17  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       3.41e-007       0.000465     1000       
   Water     11.8            900          1000       
   Soil      87.4            1.8e+003     1000       
   Sediment  0.71            8.1e+003     0          
     Persistence Time: 1.81e+003 hr




                    

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