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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8)transporters (2) Show 10 proteins XML

enzymes (8)transporters (2) Show 10 proteins

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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014850

Secondary Accession Numbers

HMDB14850

Metabolite Identification

Common Name

Flurbiprofen

Description

Flurbiprofen, a propionic acid derivative, is a nonsteroidal anti-inflammatory agent (NSAIA) with antipyretic and analgesic activity. Oral formulations of flurbiprofen may be used for the symptomatic treatment of rheumatoid arthritis, osteoarthritis and anklylosing spondylitis. Flurbiprofen may also be used topically prior to ocular surgery to prevent or reduce intraoperative miosis. Flurbiprofen is structurally and pharmacologically related to fenoprofen, ibuprofen, and ketoprofen.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0258727
     RDKit          3D
Tarenflurbil
 31 32  0  0  0  0  0  0  0  0999 V2000
    3.8540   -0.1759   -1.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3607    0.5188   -0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9835   -0.1004    1.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7244    0.5259    1.9719 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7534   -1.4420    1.4398 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8652    0.4372    0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2450   -0.7947    0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1299   -0.8926    0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9303    0.2273    0.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3798    0.0696    0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -0.8278    1.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3405   -0.9818    1.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1883   -0.2561    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6130    0.6408   -0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2360    0.7938   -0.6058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3203    1.4655    0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1172    2.5537    0.1105 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.0637    1.5607    0.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0387   -1.2666   -1.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0441   -0.1313   -2.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7815    0.2639   -1.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6840    1.5691   -0.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4696   -2.0474    1.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8756   -1.6721    0.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6203   -1.8746    0.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902   -1.3984    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7812   -1.6852    1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2663   -0.3460    0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2758    1.2203   -1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8045    1.5041   -1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209    2.5418    0.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  1  0
 16 18  2  0
 18  6  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 18 31  1  0
M  END

712
  Mrv1652305271900122D          

 18 19  0  0  1  0            999 V2000
    1.6500    0.7466    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -2.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    1.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    2.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    2.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    3.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2 13  1  0  0  0  0
  3 13  2  0  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  4 13  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  6  9  2  0  0  0  0
  6 10  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
 12 14  2  0  0  0  0
 12 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014850

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C(O)=O)C1=CC(F)=C(C=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18)

> <INCHI_KEY>
SYTBZMRGLBWNTM-UHFFFAOYSA-N

> <FORMULA>
C15H13FO2

> <MOLECULAR_WEIGHT>
244.2609

> <EXACT_MASS>
244.089957865

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
25.231700553762323

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{2-fluoro-[1,1'-biphenyl]-4-yl}propanoic acid

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
3.943907682

> <ALOGPS_LOGS>
-3.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.421757643734796

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
67.29270000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
flurbiprofen

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0258727
     RDKit          3D
Tarenflurbil
 31 32  0  0  0  0  0  0  0  0999 V2000
    3.8540   -0.1759   -1.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3607    0.5188   -0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9835   -0.1004    1.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7244    0.5259    1.9719 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7534   -1.4420    1.4398 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8652    0.4372    0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2450   -0.7947    0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1299   -0.8926    0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9303    0.2273    0.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3798    0.0696    0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -0.8278    1.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3405   -0.9818    1.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1883   -0.2561    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6130    0.6408   -0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2360    0.7938   -0.6058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3203    1.4655    0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1172    2.5537    0.1105 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.0637    1.5607    0.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0387   -1.2666   -1.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0441   -0.1313   -2.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7815    0.2639   -1.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6840    1.5691   -0.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4696   -2.0474    1.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8756   -1.6721    0.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6203   -1.8746    0.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902   -1.3984    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7812   -1.6852    1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2663   -0.3460    0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2758    1.2203   -1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8045    1.5041   -1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209    2.5418    0.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  1  0
 16 18  2  0
 18  6  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 18 31  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 712                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  F   UNK     0       3.080   1.394   0.000  0.00  0.00           F+0
HETATM    2  O   UNK     0       7.081  -5.536   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.415  -3.226   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.747  -3.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.747  -1.686   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747   1.394   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414  -0.916   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -0.916   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414   0.624   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081   0.624   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -3.996   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.747   2.934   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -3.996   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414   3.704   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   3.704   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414   5.244   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081   5.244   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.747   6.014   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   13                                                            
CONECT    3   13                                                            
CONECT    4    5   11   13                                                  
CONECT    5    4    7    8                                                  
CONECT    6    9   10   12                                                  
CONECT    7    5    9                                                       
CONECT    8    5   10                                                       
CONECT    9    1    6    7                                                  
CONECT   10    6    8                                                       
CONECT   11    4                                                            
CONECT   12    6   14   15                                                  
CONECT   13    2    3    4                                                  
CONECT   14   12   16                                                       
CONECT   15   12   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   18                                                       
CONECT   18   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0014850
HETATM    1  C1  UNL     1       3.849  -1.251  -1.075  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.276  -0.757   0.215  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.954   0.519   0.570  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.652   0.637   1.613  1.00  0.00           O  
HETATM    5  O2  UNL     1       3.814   1.603  -0.270  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.816  -0.491   0.150  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.299   0.379  -0.781  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.073   0.591  -0.794  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.940  -0.021   0.069  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.381   0.219   0.035  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.097   0.239  -1.147  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.457   0.465  -1.175  1.00  0.00           C  
HETATM   13  C11 UNL     1      -5.161   0.682  -0.011  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.455   0.663   1.173  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.090   0.436   1.202  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.380  -0.893   0.994  1.00  0.00           C  
HETATM   17  F1  UNL     1      -1.231  -1.510   1.861  1.00  0.00           F  
HETATM   18  C15 UNL     1       0.974  -1.134   1.046  1.00  0.00           C  
HETATM   19  H1  UNL     1       3.214  -2.084  -1.443  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.857  -1.643  -0.877  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.948  -0.441  -1.825  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.485  -1.532   1.009  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.508   2.331  -0.264  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.961   0.882  -1.484  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.448   1.284  -1.541  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.524   0.065  -2.067  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.999   0.477  -2.114  1.00  0.00           H  
HETATM   28  H10 UNL     1      -6.228   0.857  -0.061  1.00  0.00           H  
HETATM   29  H11 UNL     1      -4.995   0.832   2.096  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.522   0.420   2.137  1.00  0.00           H  
HETATM   31  H13 UNL     1       1.373  -1.823   1.783  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    6   22
CONECT    3    4    4    5
CONECT    5   23
CONECT    6    7    7   18
CONECT    7    8   24
CONECT    8    9    9   25
CONECT    9   10   16
CONECT   10   11   11   15
CONECT   11   12   26
CONECT   12   13   13   27
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   30
CONECT   16   17   18   18
CONECT   18   31
END

HMDB0258727
     RDKit          3D
Tarenflurbil
 31 32  0  0  0  0  0  0  0  0999 V2000
    3.8540   -0.1759   -1.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3607    0.5188   -0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9835   -0.1004    1.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7244    0.5259    1.9719 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7534   -1.4420    1.4398 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8652    0.4372    0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2450   -0.7947    0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1299   -0.8926    0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9303    0.2273    0.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3798    0.0696    0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -0.8278    1.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3405   -0.9818    1.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1883   -0.2561    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6130    0.6408   -0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2360    0.7938   -0.6058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3203    1.4655    0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1172    2.5537    0.1105 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.0637    1.5607    0.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0387   -1.2666   -1.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0441   -0.1313   -2.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7815    0.2639   -1.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6840    1.5691   -0.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4696   -2.0474    1.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8756   -1.6721    0.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6203   -1.8746    0.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902   -1.3984    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7812   -1.6852    1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2663   -0.3460    0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2758    1.2203   -1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8045    1.5041   -1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209    2.5418    0.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  1  0
 16 18  2  0
 18  6  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 18 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-2-Fluoro-alpha-methyl-4-biphenylacetic acid	ChEBI
2-(2-Fluorobiphenyl-4-yl)propanoic acid	ChEBI
2-Fluoro-alpha-methyl-(1,1'-biphenyl)-4-acetic acid	ChEBI
3-Fluoro-4-phenylhydratropic acid	ChEBI
Ansaid	ChEBI
(+-)-2-Fluoro-a-methyl-4-biphenylacetate	Generator
(+-)-2-Fluoro-a-methyl-4-biphenylacetic acid	Generator
(+-)-2-Fluoro-alpha-methyl-4-biphenylacetate	Generator
(+-)-2-Fluoro-α-methyl-4-biphenylacetate	Generator
(+-)-2-Fluoro-α-methyl-4-biphenylacetic acid	Generator
2-(2-Fluorobiphenyl-4-yl)propanoate	Generator
2-Fluoro-a-methyl-(1,1'-biphenyl)-4-acetate	Generator
2-Fluoro-a-methyl-(1,1'-biphenyl)-4-acetic acid	Generator
2-Fluoro-alpha-methyl-(1,1'-biphenyl)-4-acetate	Generator
2-Fluoro-α-methyl-(1,1'-biphenyl)-4-acetate	Generator
2-Fluoro-α-methyl-(1,1'-biphenyl)-4-acetic acid	Generator
3-Fluoro-4-phenylhydratropate	Generator
FLP	HMDB
Allergan brand OF flurbiprofen sodium	MeSH, HMDB
Apotex brand OF flurbiprofen	MeSH, HMDB
Klosterfrau brand OF flurbiprofen	MeSH, HMDB
Knoll brand OF flurbiprofen	MeSH, HMDB
Nu flurbiprofen	MeSH, HMDB
Ratiopharm brand OF flurbiprofen	MeSH, HMDB
Recordati brand OF flurbiprofen	MeSH, HMDB
Dobrofen	MeSH, HMDB
Flugalin	MeSH, HMDB
neo Artrol	MeSH, HMDB
novo Flurprofen	MeSH, HMDB
novo-Flurprofen	MeSH, HMDB
Nu-pharm brand OF flurbiprofen	MeSH, HMDB
Ocuflur	MeSH, HMDB
Cebutid	MeSH, HMDB
Flubiprofen	MeSH, HMDB
Flurbiprofen pfizer brand	MeSH, HMDB
Flurbiprofen sodium	MeSH, HMDB
Froben	MeSH, HMDB
Froben SR	MeSH, HMDB
Novopharm brand OF flurbiprofen	MeSH, HMDB
Nu-flurbiprofen	MeSH, HMDB
Ocufen	MeSH, HMDB
Pharm allergan brand OF flurbiprofen sodium	MeSH, HMDB
Pharm-allergan brand OF flurbiprofen sodium	MeSH, HMDB
Shire brand OF flurbiprofen	MeSH, HMDB
Sodium, flurbiprofen	MeSH, HMDB
ratio Flurbiprofen	MeSH, HMDB
Abbott brand OF flurbiprofen	MeSH, HMDB
apo Flurbiprofen	MeSH, HMDB
apo-Flurbiprofen	MeSH, HMDB
Cantabria brand OF flurbiprofen	MeSH, HMDB
Crookes brand OF flurbiprofen	MeSH, HMDB
Fluriproben	MeSH, HMDB
Nu pharm brand OF flurbiprofen	MeSH, HMDB
Pfizer brand OF flurbiprofen	MeSH, HMDB
Strefen	MeSH, HMDB
ratio-Flurbiprofen	MeSH, HMDB

Chemical Formula

C₁₅H₁₃FO₂

Average Molecular Weight

244.2609

Monoisotopic Molecular Weight

244.089957865

IUPAC Name

2-{2-fluoro-[1,1'-biphenyl]-4-yl}propanoic acid

Traditional Name

flurbiprofen

CAS Registry Number

5104-49-4

SMILES

CC(C(O)=O)C1=CC(F)=C(C=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18)

InChI Key

SYTBZMRGLBWNTM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Biphenyls and derivatives

Alternative Parents

Substituents

Biphenyl
2-phenylpropanoic-acid
P-cymene
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Fluorobenzene
Halobenzene
Aryl halide
Aryl fluoride
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organofluoride
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

fluorobiphenyl (CHEBI:5130 )

Ontology

Not Available

Exogenous (HMDB: HMDB0014850)

Food

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	110 - 111 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.025 g/L	Not Available
LogP	3.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	3.57	ALOGPS
logP	3.94	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.42	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	67.29 m³·mol⁻¹	ChemAxon
Polarizability	25.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	157.769	30932474
DeepCCS	[M-H]-	155.373	30932474
DeepCCS	[M-2H]-	188.308	30932474
DeepCCS	[M+Na]+	163.786	30932474
AllCCS	[M+H]+	154.7	32859911
AllCCS	[M+H-H2O]+	150.6	32859911
AllCCS	[M+NH4]+	158.4	32859911
AllCCS	[M+Na]+	159.5	32859911
AllCCS	[M-H]-	156.3	32859911
AllCCS	[M+Na-2H]-	155.9	32859911
AllCCS	[M+HCOO]-	155.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Flurbiprofen	CC(C(O)=O)C1=CC(F)=C(C=C1)C1=CC=CC=C1	3317.2	Standard polar	33892256
Flurbiprofen	CC(C(O)=O)C1=CC(F)=C(C=C1)C1=CC=CC=C1	1935.5	Standard non polar	33892256
Flurbiprofen	CC(C(O)=O)C1=CC(F)=C(C=C1)C1=CC=CC=C1	1954.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Flurbiprofen,1TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C1=CC=C(C2=CC=CC=C2)C(F)=C1	1984.0	Semi standard non polar	33892256
Flurbiprofen,1TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(C2=CC=CC=C2)C(F)=C1	2264.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Flurbiprofen GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2940000000-9f5fff7c7dd3930840ab	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flurbiprofen GC-MS (1 TMS) - 70eV, Positive	splash10-0fft-9531000000-d8e1afedb8496d7ccae1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flurbiprofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flurbiprofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flurbiprofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flurbiprofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flurbiprofen LC-ESI-qTof , Positive-QTOF	splash10-002b-0900000000-1c9889f5fc33443c7b3b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flurbiprofen LC-ESI-qTof , Positive-QTOF	splash10-002b-0900000000-1791423706be24cc354b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flurbiprofen LC-ESI-qTof , Positive-QTOF	splash10-0229-3920000000-b822873abe0cc77b6500	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flurbiprofen , positive-QTOF	splash10-002b-0900000000-1791423706be24cc354b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flurbiprofen , positive-QTOF	splash10-002b-0900000000-1c9889f5fc33443c7b3b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flurbiprofen , positive-QTOF	splash10-004i-2900000000-d74a9b309815da3ba05d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flurbiprofen 35V, Negative-QTOF	splash10-0002-0900000000-be4ed0fe252134b8d5d0	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurbiprofen 10V, Positive-QTOF	splash10-0002-0290000000-a84327eef03dc68e08c6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurbiprofen 20V, Positive-QTOF	splash10-0002-0890000000-8fb4c7dcd6ef32ab325b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurbiprofen 40V, Positive-QTOF	splash10-00ba-2910000000-570b59a950d65dd4631e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurbiprofen 10V, Negative-QTOF	splash10-0006-0390000000-68c52b6d3396c526a75c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurbiprofen 20V, Negative-QTOF	splash10-0005-1950000000-7014af9c0d6f2fc23c18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurbiprofen 40V, Negative-QTOF	splash10-00fr-5910000000-9a60410e16b662ddcff0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurbiprofen 10V, Positive-QTOF	splash10-0002-0090000000-cbd4141a005693f2c6aa	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurbiprofen 20V, Positive-QTOF	splash10-0002-0940000000-f30f7aa21a68a7f1ab95	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurbiprofen 40V, Positive-QTOF	splash10-004i-0900000000-2bf6ee99259baef46083	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurbiprofen 10V, Negative-QTOF	splash10-002b-0910000000-b3fba75f1be1c305f3d6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurbiprofen 20V, Negative-QTOF	splash10-004i-0900000000-f48dedd82d182cffdfbf	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurbiprofen 40V, Negative-QTOF	splash10-0fi0-0900000000-150de333ffe505b0359d	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Flurbiprofen Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00712	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00712	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00712

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002154

KNApSAcK ID

Not Available

Chemspider ID

3277

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Flurbiprofen

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

5130

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Geerts H: Drug evaluation: (R)-flurbiprofen--an enantiomer of flurbiprofen for the treatment of Alzheimer's disease. IDrugs. 2007 Feb;10(2):121-33. [PubMed:17285465 ]
Mironov GG, Logie J, Okhonin V, Renaud JB, Mayer PM, Berezovski MV: Comparative study of three methods for affinity measurements: capillary electrophoresis coupled with UV detection and mass spectrometry, and direct infusion mass spectrometry. J Am Soc Mass Spectrom. 2012 Jul;23(7):1232-40. doi: 10.1007/s13361-012-0386-y. Epub 2012 Apr 28. [PubMed:22544663 ]
Calapai G, Imbesi S, Cafeo V, Ventura Spagnolo E, Minciullo PL, Caputi AP, Gangemi S, Milone L: Fatal hypersensitivity reaction to an oral spray of flurbiprofen: a case report. J Clin Pharm Ther. 2013 Aug;38(4):337-8. doi: 10.1111/jcpt.12073. Epub 2013 May 13. [PubMed:23668805 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:: UGT2B4
Uniprot ID:: P06133
Molecular weight:: 60512.035

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

2. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

3. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

4. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

5. UDP-glucuronosyltransferase 1-3

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT1A3
Uniprot ID:: P35503
Molecular weight:: 60337.835

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

6. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

References

Bayly CI, Black WC, Leger S, Ouimet N, Ouellet M, Percival MD: Structure-based design of COX-2 selectivity into flurbiprofen. Bioorg Med Chem Lett. 1999 Feb 8;9(3):307-12. [PubMed:10091674 ]
van Haeringen NJ, van Sorge AA, Carballosa Core-Bodelier VM: Constitutive cyclooxygenase-1 and induced cyclooxygenase-2 in isolated human iris inhibited by S(+) flurbiprofen. J Ocul Pharmacol Ther. 2000 Aug;16(4):353-61. [PubMed:10977131 ]
Smith T, McCracken J, Shin YK, DeWitt D: Arachidonic acid and nonsteroidal anti-inflammatory drugs induce conformational changes in the human prostaglandin endoperoxide H2 synthase-2 (cyclooxygenase-2). J Biol Chem. 2000 Dec 22;275(51):40407-15. [PubMed:11006278 ]
Hinz B, Brune K, Rau T, Pahl A: Flurbiprofen enantiomers inhibit inducible nitric oxide synthase expression in RAW 264.7 macrophages. Pharm Res. 2001 Feb;18(2):151-6. [PubMed:11405284 ]
Hewett SJ, Uliasz TF, Vidwans AS, Hewett JA: Cyclooxygenase-2 contributes to N-methyl-D-aspartate-mediated neuronal cell death in primary cortical cell culture. J Pharmacol Exp Ther. 2000 May;293(2):417-25. [PubMed:10773011 ]
Basselin M, Villacreses NE, Lee HJ, Bell JM, Rapoport SI: Flurbiprofen, a cyclooxygenase inhibitor, reduces the brain arachidonic acid signal in response to the cholinergic muscarinic agonist, arecoline, in awake rats. Neurochem Res. 2007 Nov;32(11):1857-67. Epub 2007 Jun 12. [PubMed:17562170 ]
Nivsarkar M, Banerjee A, Padh H: Cyclooxygenase inhibitors: a novel direction for Alzheimer's management. Pharmacol Rep. 2008 Sep-Oct;60(5):692-8. [PubMed:19066416 ]

Enzyme Details

7. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Rieke CJ, Mulichak AM, Garavito RM, Smith WL: The role of arginine 120 of human prostaglandin endoperoxide H synthase-2 in the interaction with fatty acid substrates and inhibitors. J Biol Chem. 1999 Jun 11;274(24):17109-14. [PubMed:10358065 ]
Hewett SJ, Uliasz TF, Vidwans AS, Hewett JA: Cyclooxygenase-2 contributes to N-methyl-D-aspartate-mediated neuronal cell death in primary cortical cell culture. J Pharmacol Exp Ther. 2000 May;293(2):417-25. [PubMed:10773011 ]
Kurahashi K, Shirahase H, Nakamura S, Tarumi T, Koshino Y, Wang AM, Nishihashi T, Shimizu Y: Nicotine-induced contraction in the rat coronary artery: possible involvement of the endothelium, reactive oxygen species and COX-1 metabolites. J Cardiovasc Pharmacol. 2001 Oct;38 Suppl 1:S21-5. [PubMed:11811354 ]
Klegeris A, McGeer PL: Cyclooxygenase and 5-lipoxygenase inhibitors protect against mononuclear phagocyte neurotoxicity. Neurobiol Aging. 2002 Sep-Oct;23(5):787-94. [PubMed:12392782 ]
Droge MJ, van Sorge AA, van Haeringen NJ, Quax WJ, Zaagsma J: Alternative splicing of cyclooxygenase-1 mRNA in the human iris. Ophthalmic Res. 2003 May-Jun;35(3):160-3. [PubMed:12711844 ]
Basselin M, Villacreses NE, Lee HJ, Bell JM, Rapoport SI: Flurbiprofen, a cyclooxygenase inhibitor, reduces the brain arachidonic acid signal in response to the cholinergic muscarinic agonist, arecoline, in awake rats. Neurochem Res. 2007 Nov;32(11):1857-67. Epub 2007 Jun 12. [PubMed:17562170 ]
Nivsarkar M, Banerjee A, Padh H: Cyclooxygenase inhibitors: a novel direction for Alzheimer's management. Pharmacol Rep. 2008 Sep-Oct;60(5):692-8. [PubMed:19066416 ]

Enzyme Details

8. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Mo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. [PubMed:20167001 ]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Lin Y, Lu P, Tang C, Mei Q, Sandig G, Rodrigues AD, Rushmore TH, Shou M: Substrate inhibition kinetics for cytochrome P450-catalyzed reactions. Drug Metab Dispos. 2001 Apr;29(4 Pt 1):368-74. [PubMed:11259318 ]

Transporters

Enzyme Details

1. Multidrug resistance-associated protein 4

General function:: Involved in ATP binding
Specific function:: May be an organic anion pump relevant to cellular detoxification
Gene Name:: ABCC4
Uniprot ID:: O15439
Molecular weight:: 149525.3

References

Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [PubMed:12835412 ]

Enzyme Details

2. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. [PubMed:10991954 ]
Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [PubMed:10220563 ]

Showing metabocard for Flurbiprofen (HMDB0014850)

MOL for HMDB0014850 (Flurbiprofen)

3D MOL for HMDB0014850 (Flurbiprofen)

3D SDF for HMDB0014850 (Flurbiprofen)

3D-SDF for HMDB0014850 (Flurbiprofen)

PDB for HMDB0014850 (Flurbiprofen)

3D PDB for HMDB0014850 (Flurbiprofen)

SMILES for HMDB0014850 (Flurbiprofen)

INCHI for HMDB0014850 (Flurbiprofen)

Structure for HMDB0014850 (Flurbiprofen)

3D Structure for HMDB0014850 (Flurbiprofen)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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Transporters

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