ChemSpider 2D Image | Ibuprofen | C13H18O2

Ibuprofen

  • Molecular FormulaC13H18O2
  • Average mass206.281 Da
  • Monoisotopic mass206.130676 Da
  • ChemSpider ID3544

More details:

Featured data source
The Merck Index Online

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

Ibuprofen [BAN] [INN] [JAN] [USAN] [Wiki]
(±)-2-(4-Isobutylphenyl)propanoic acid
(±)-ibuprofen
(RS)-ibuprofen
15687-27-1 [RN]
2-(4-Isobutylphenyl)propanoic acid [ACD/IUPAC Name]
2-(4-Isobutylphenyl)propansäure [German] [ACD/IUPAC Name]
2-(4-Isobutylphenyl)propionic acid [ACD/IUPAC Name]
2-[4-(2-Methylpropyl)phenyl]propansäure [German]
239-784-6 [EINECS]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

MFCD00010393 [DBID]
UNII:WK2XYI10QM [DBID]
WK2XYI10QM [DBID]
μ6640000 [DBID]
671DKG7P5S [DBID]
99W8H60N62 [DBID]
Adex 200 [DBID]
AIDS025464 [DBID]
AIDS-025464 [DBID]
Atril 300 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous

    • Appearance:

      white powder OU Chemical Safety Data (No longer updated) More details

    • Stability:

      Stable. Combustible. Incompatible with strong oxidizing agents. OU Chemical Safety Data (No longer updated) More details

    • Toxicity:

      Organic Compound; Drug; Food Toxin; Analgesic, Non-Narcotic; Anti-Inflammatory Agent; Analgesic; Anti-Inflammatory Agent, Non-Steroidal; Cyclooxygenase Inhibitor; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D2970
      ORL-RAT LD50 636 mg kg-1 OU Chemical Safety Data (No longer updated) More details

    • Safety:

      22-51/53-63 Alfa Aesar B20989
      36/37-61 Alfa Aesar B20989
      9 Alfa Aesar B20989
      C01EB16 Wikidata Q186969
      G02CC01 Wikidata Q186969
      H361-H302-H411 Alfa Aesar B20989
      M01AE01 Wikidata Q186969
      M02AA13 Wikidata Q186969
      Minimize contact. OU Chemical Safety Data (No longer updated) More details
      P281-P273-P301+P312-P308+P313-P405-P501a Alfa Aesar B20989
      Warning Alfa Aesar B20989
      WARNING: Irreversible damage risk, protect skin/eyes/lungs. Alfa Aesar B20989

    • Target Organs:

      Thrombomodulin;PPAR activator;COX inhibitor;Bcl-2 modulator TargetMol T1394

    • Chemical Class:

      A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(2-methylpropyl)phenyl group. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5855, CHEBI:5855

    • Bio Activity:

      Angiogensis; Metabolism;Neuroscience; Apoptosis TargetMol T1394
      CFTR;Thrombomodulin;PPAR??;Prostaglandin G/H synthase1;Bcl-2;Prostaglandin G/H synthase2 TargetMol T1394
      COX MedChem Express HY-78131
      Ibuprofen (Motrin) is an anti-inflammatory inhibitor targeting COX-1 and COX-2, of which is used for pain relief, fever reduction and for reducing swelling. MedChem Express
      Ibuprofen (Motrin) is an anti-inflammatory inhibitor targeting COX-1 and COX-2, of which is used for pain relief, fever reduction and for reducing swelling.; Target: COX-1; COX-2 ; Ibuprofen (INN) is a nonsteroidal anti-inflammatory drug (NSAID) used for pain relief, fever reduction, and for reducing swelling.Nonsteroidal anti-inflammatory drugs such as ibuprofen work by inhibiting the enzyme cyclooxygenase (COX), which converts arachidonic acid to prostaglandin H2 (PGH2). MedChem Express HY-78131
      Ibuprofen (Motrin) is an anti-inflammatory inhibitor targeting COX-1 and COX-2, of which is used for pain relief, fever reduction and for reducing swelling.;Target: COX-1; COX-2 ;Ibuprofen (INN) is a nonsteroidal anti-inflammatory drug (NSAID) used for pain relief, fever reduction, and for reducing swelling.Nonsteroidal anti-inflammatory drugs such as ibuprofen work by inhibiting the enzyme cyclooxygenase (COX), which converts arachidonic acid to prostaglandin H2 (PGH2). PGH2, in turn, is converted by other enzymes to several other prostaglandins (which are mediators of pain, inflammation, and fever) and to thromboxane A2 (which stimulates platelet aggregation, leading to the formation of blood clots).Like aspirin and indomethacin, ibuprofen is a nonselective COX inhibitor, in that it inhibits two isoforms of cyclooxygenase, COX-1 and COX-2. The analgesic, antipyretic, and anti-inflammatory activity of NSAIDs appears to operate mainly through inhibition of COX-2, whereas inhibiti MedChem Express HY-78131
      Immunology/Inflammation MedChem Express HY-78131
      Immunology/Inflammation; MedChem Express HY-78131
  • Gas Chromatography

    • Retention Index (Kovats):

      1632 (estimated with error: 51) NIST Spectra mainlib_352144, replib_250557, replib_312885, replib_335499, replib_233882
      1614 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 2 m; Column type: Packed; Start T: 200 C; CAS no: 15687271; Active phase: OV-101; Carrier gas: N2; Substrate: Chromosorb W HP (100-120 mesh); Data type: Kovats RI; Authors: Macek, J.; Smolkova-Keulemansova, E., Correlation of the chromatographic retention of some phenylacetic and phenylpropionic acid derivatives with molecular structure, J. Chromatogr., 333, 1985, 309-317., Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column type: Capillary; Start T: 200 C; CAS no: 15687271; Active phase: OV-101; Data type: Kovats RI; Authors: Tarjan, G.; Nyiredy, Sz.; Gyor, M.; Lombosi, E.R.; Lombosi, T.S.; Budahegyi, M.V.; Meszaros, S.Y.; Takacs, J.M., Review. Thirtieth Anniversary of the Retention Index According to Kovats in Gas-Liquid Chromatography, J. Chromatogr., 472, 1989, 1-92.) NIST Spectra nist ri
      1622 (Program type: Isothermal; Col... (show more) umn class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 15 m; Column type: Capillary; Start T: 220 C; CAS no: 15687271; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.2 um; Data type: Kovats RI; Authors: Phillips, A.M.; Logan, B.K.; Stafford, D.T., Further applications for capillary gas chromatography in routine quantitative toxicological analyses, J. Hi. Res. Chromatogr., 13, 1990, 754-758.) NIST Spectra nist ri

    • Retention Index (Normal Alkane):

      1585 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.53 mm; Column length: 10 m; Column type: Capillary; Heat rate: 5 K/min; Start T: 130 C; End T: 230 C; CAS no: 15687271; Active phase: DB-1; Carrier gas: He; Phase thickness: 2.65 um; Data type: Normal alkane RI; Authors: Anderson, W.H.; Fuller, D.C., A simplified procedure for the isolation, characterization, and identification of weak acid and neutral drugs from whole blood, J. Anal. Toxicol., 11, 1987, 198-204.) NIST Spectra nist ri
      1600 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.25 mm; Column length: 15 m; Column type: Capillary; Heat rate: 10 K/min; Start T: 130 C; End T: 290 C; End time: 10 min; Start time: 1 min; CAS no: 15687271; Active phase: DB-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Sharp, M.E., A rapid screening procedure for acidic and neutral drugs in blood by high resolution gas chromatography, J. Anal. Toxicol., 11, 1987, 8-11.) NIST Spectra nist ri
      1589 (Program type: Isothermal; Col... (show more) umn class: Semi-standard non-polar; Column length: 1.5 m; Column type: Packed; CAS no: 15687271; Active phase: Apolane; Data type: Normal alkane RI; Authors: Huggett, A.; Andrews, P.; Flanagan, R.J., Rapid Micro-Method for the Measurement of Paracetamol in Blood Plasma or Serum Using Gas-Liquid Chromatography with Flame-Ionisation Detection., J. Chromatogr., 209, 1981, 67-76.) NIST Spectra nist ri

    • Retention Index (Linear):

      1594 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.25 mm; Column length: 15 m; Column type: Capillary; Heat rate: 8 K/min; Start T: 120 C; End T: 280 C; End time: 5 min; CAS no: 15687271; Active phase: DB-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Perrigo, B.J.; Ballantyne, D.J.; Peel, H.W., Condierations in developing a data base for drugs on a DBI capillary column, J. Can. Soc. Forensic Sci., 17(2), 1984, 41-49., Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.32 mm; Column length: 15 m; Column type: Capillary; Heat rate: 8 K/min; Start T: 120 C; End T: 280 C; End time: 5 min; CAS no: 15687271; Active phase: DB-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Perrigo, B.J.; Peel, H.W.; Ballantyne, D.J., Use of Dual-Column Fused-Silica Capillary Gas Chromatography in Combination with Detector Response Factors for Analytical Toxicology., J. Chromatogr., 341, 1985, 81-88.) NIST Spectra nist ri
      1630.2 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: Multi-step temperature program; T(initial)=60C; T(final)=270C; CAS no: 15687271; Active phase: VF-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., 2008.) NIST Spectra nist ri

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.0±0.1 g/cm3
Boiling Point: 319.6±11.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.7 mmHg at 25°C
Enthalpy of Vaporization: 59.3±3.0 kJ/mol
Flash Point: 216.7±14.4 °C
Index of Refraction: 1.519
Molar Refractivity: 60.8±0.3 cm3
#H bond acceptors: 2
#H bond donors: 1
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 3.72
ACD/LogD (pH 5.5): 2.25
ACD/BCF (pH 5.5): 16.17
ACD/KOC (pH 5.5): 122.42
ACD/LogD (pH 7.4): 0.45
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.95
Polar Surface Area: 37 Å2
Polarizability: 24.1±0.5 10-24cm3
Surface Tension: 38.1±3.0 dyne/cm
Molar Volume: 200.3±3.0 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) =  3.79
    Log Kow (Exper. database match) =  3.97
       Exper. Ref:  Avdeef,A (1997)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  323.11  (Adapted Stein & Brown method)
    Melting Pt (deg C):  94.22  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.000186  (Modified Grain method)
    MP  (exp database):  76 deg C
    Subcooled liquid VP: 0.000567 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):  41.05
       log Kow used: 3.97 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  21 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  57.974 mg/L
    Wat Sol (Exper. database match) =  21.00
       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 :   1.52E-007  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.230E-006 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.97  (exp database)
  Log Kaw used:  -5.207  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.177
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8314
   Biowin2 (Non-Linear Model)     :   0.8672
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9582  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7986  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1976
   Biowin6 (MITI Non-Linear Model):   0.1521
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0334
 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):  0.0756 Pa (0.000567 mm Hg)
  Log Koa (Koawin est  ): 9.177
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.97E-005 
       Octanol/air (Koa) model:  0.000369 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00143 
       Mackay model           :  0.00316 
       Octanol/air (Koa) model:  0.0287 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  11.8423 E-12 cm3/molecule-sec
      Half-Life =     0.903 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    10.838 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.0023 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  394.3
      Log Koc:  2.596 

 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: 3.97 (expkow database)

 Volatilization from Water:
    Henry LC:  1.52E-007 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:       5534  hours   (230.6 days)
    Half-Life from Model Lake : 6.049E+004  hours   (2520 days)

 Removal In Wastewater Treatment:
    Total removal:              28.72  percent
    Total biodegradation:        0.31  percent
    Total sludge adsorption:    28.40  percent
    Total to Air:                0.01  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.977           21.7         1000       
   Water     20.5            360          1000       
   Soil      76.1            720          1000       
   Sediment  2.45            3.24e+003    0          
     Persistence Time: 572 hr

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