ChemSpider 2D Image | Ketorolac | C15H13NO3

Ketorolac

  • Molecular FormulaC15H13NO3
  • Average mass255.269 Da
  • Monoisotopic mass255.089539 Da
  • ChemSpider ID3694

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1H-Pyrrolizine-1-carboxylic acid, 5-benzoyl-2,3-dihydro- [ACD/Index Name]
5-(Phenylcarbonyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid
5-Benzoyl-2,3-dihydro-1H-pyrrolizin-1-carbonsäure [German] [ACD/IUPAC Name]
5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid [ACD/IUPAC Name]
5-Benzoyl-2,3-dihydro-1H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid [ACD/IUPAC Name]
74103-06-3 [RN]
Acide 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylique [French] [ACD/IUPAC Name]
Ketorolaco [Spanish] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

UNII:YZI5105V0L [DBID]
YZI5105V0L [DBID]
10A5O25ILE [DBID]
5558 [DBID]
5H3TJ0A81K [DBID]
Acular LS;RS37619;Sprix;Toradol [DBID]
C07062 [DBID]
D020910 [DBID]
RS 37619 [DBID]
RS37619 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      M01AB15 Wikidata Q2014797
      S01BC05 Wikidata Q2014797
      TBC SynQuest 4H58-1-PV
    • Chemical Class:

      A member of the class of pyrrolizines that is 2,3-dihydro-1<element>H</element>-pyrrolizine which is substituted at positions 1 and 5 by carboxy and benzoyl groups, respectively. ChEBI CHEBI:6129, CHEBI:76223
      A member of the class of pyrrolizines that is 2,3-dihydro-1H-pyrrolizine which is substituted at positions 1 and 5 by carboxy and benzoyl groups, respectively. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:76223
      A racemate comprising equimolar amounts of (<stereo>R</stereo>)-(+)- and (<stereo>S</stereo>)-(<minus/>)-5-benzoyl-2,3-dihydro-1<element>H</element>-pyrrolizine-1-carboxylic acid. While only the (<ste reo>S</stereo>)-(<minus/>) enantiomer is a COX1 and COX2 inhibitor, the (<stereo>R</stereo>)-(+) enantiomer exhibits potent analgesic activity. A non-steroidal anti-inflammatory drug, ketorolac is mai nly used (generally as the tromethamine salt) for its potent analgesic properties in the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with se asonal allergic conjunctivitis. It was withdrawn from the market in many countries in 1993 following association with haemorrhage and renal failure. ChEBI CHEBI:6129, CHEBI:76223
      A racemate comprising equimolar amounts of (R)-(+)- and (S)-(-)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid. While only the (S)-(-) enantiomer is a COX1 and COX2 inhibitor, the (R)-(+) enan tiomer exhibits potent analgesic activity. A non-steroidal anti-inflammatory drug, ketorolac is mainly used (generally as the tromethamine salt) for its potent analgesic properties in the short-term m anagement of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis. It was withdrawn from the market in many countries in 1993 following association with haemorrhage and renal failure. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6129
    • Bio Activity:

      COX MedChem Express HY-B0580
      Immunology/Inflammation MedChem Express HY-B0580
      Immunology/Inflammation; MedChem Express HY-B0580
      Ketorolac(RS37619), a non-selective COX inhibitor, is a non-steroidal anti-inflammatory drug. MedChem Express http://www.medchemexpress.com/dexrazoxane.html, HY-B0580
  • Gas Chromatography

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

Density: 1.3±0.1 g/cm3
Boiling Point: 493.2±40.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 80.1±3.0 kJ/mol
Flash Point: 252.1±27.3 °C
Index of Refraction: 1.659
Molar Refractivity: 70.5±0.5 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 2.08
ACD/LogD (pH 5.5): 1.34
ACD/BCF (pH 5.5): 3.12
ACD/KOC (pH 5.5): 34.99
ACD/LogD (pH 7.4): -0.44
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 59 Å2
Polarizability: 28.0±0.5 10-24cm3
Surface Tension: 54.8±7.0 dyne/cm
Molar Volume: 191.2±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) =  2.32

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  414.83  (Adapted Stein & Brown method)
    Melting Pt (deg C):  170.41  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.47E-007  (Modified Grain method)
    MP  (exp database):  160.5 deg C
    Subcooled liquid VP: 3.61E-006 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):  572.3
       log Kow used: 2.32 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1852.9 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.35E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.628E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.32  (KowWin est)
  Log Kaw used:  -10.863  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.183
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8883
   Biowin2 (Non-Linear Model)     :   0.8755
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9243  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7791  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3388
   Biowin6 (MITI Non-Linear Model):   0.2143
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1403
 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):  0.000481 Pa (3.61E-006 mm Hg)
  Log Koa (Koawin est  ): 13.183
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00623 
       Octanol/air (Koa) model:  3.74 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.184 
       Mackay model           :  0.333 
       Octanol/air (Koa) model:  0.997 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 203.3050 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
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.258 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  321
      Log Koc:  2.507 

 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: 2.32 (estimated)

 Volatilization from Water:
    Henry LC:  3.35E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.792E+009  hours   (1.163E+008 days)
    Half-Life from Model Lake : 3.046E+010  hours   (1.269E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               2.68  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.58  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       7.55e-006       1.26         1000       
   Water     19.8            360          1000       
   Soil      80.1            720          1000       
   Sediment  0.105           3.24e+003    0          
     Persistence Time: 740 hr




                    

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