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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:04 UTC

HMDB ID

HMDB0015678

Secondary Accession Numbers

HMDB15678

Metabolite Identification

Common Name

Nepafenac

Description

Nepafenac, also known as nevanac or ahr 9434, belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. After penetrating the cornea as a prodrug, nepafenac undergoes rapid bioactivation to amfenac, which is a potent NSAID that uniformly inhibits the COX1 and COX2 activity. Nepafenac (prodrug) is deaminated to amfenac (active compound) in the ciliary body epithelium, retina, and choroid by intraocular hydrolases. Nepafenac is a drug which is used for the treatment of pain and inflammation associated with cataract surgery. Ocularly applied non-steroidal anti-inflammatory drugs may cause increased bleeding of ocular tissues (including hyphemas) in conjunction with ocular surgery. It is used to treat pain and inflammation associated with cataract surgery. The mean steady-state Cmax for nepafenac and for amfenac were 0.310 ± 0.104 ng/ml and 0.422 ± 0.121 ng/ml, respectively, following ocular administration. Nepafenac is a moderately basic compound (based on its pKa). In humans, nepafenac is involved in nepafenac action pathway. Nepafenac is only found in individuals that have used or taken this drug. Subsequently, amfenac undergoes extensive metabolism to more polar metabolites involving hydroxylation of the aromatic ring leading to glucuronide conjugate formation.

Structure

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

HMDB0015678
     RDKit          3D
Nepafenac
 33 34  0  0  0  0  0  0  0  0999 V2000
   -5.5555    0.7053    0.1215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2161    0.3176    0.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6081    0.8253    1.3028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5669   -0.6425   -0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1614   -0.9421   -0.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8124   -2.1263    0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5077   -2.3974    0.8012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5072   -1.4669    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1910   -0.2928   -0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1837    0.7226   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7281    1.8593   -0.8213 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6016    0.6680   -0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3159   -0.4730   -0.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6966   -0.4935   -0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2982    0.6508    0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5966    1.8267    0.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370    1.8345    0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1402   -0.0638   -0.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961    1.1372   -1.0780 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1729    1.1553    0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9737    0.5317   -0.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5799   -0.2702   -1.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1065   -1.6321   -0.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6121   -2.8383    0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2735   -3.3300    1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5080   -1.7359    0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8394   -1.3997   -0.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2115   -1.4264   -0.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3739    0.6227    0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0914    2.7054    0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6654    2.7551    0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6653    1.2136   -2.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974    1.9996   -0.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  9 18  2  0
 18 19  1  0
 18  5  1  0
 17 12  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
 19 33  1  0
M  END


  Mrv0541 02241214192D          

 19 20  0  0  0  0            999 V2000
    1.0717   -1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3585   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3585   -1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441   -2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296   -1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0730   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7875   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5019   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7875   -1.8562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 10 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015678

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N

> <INCHI_IDENTIFIER>
InChI=1S/C15H14N2O2/c16-13(18)9-11-7-4-8-12(14(11)17)15(19)10-5-2-1-3-6-10/h1-8H,9,17H2,(H2,16,18)

> <INCHI_KEY>
QEFAQIPZVLVERP-UHFFFAOYSA-N

> <FORMULA>
C15H14N2O2

> <MOLECULAR_WEIGHT>
254.2839

> <EXACT_MASS>
254.105527702

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.633807732217292

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-amino-3-benzoylphenyl)acetamide

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
2.0844785749999994

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.434407793812813

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.818239466611313

> <JCHEM_PKA_STRONGEST_BASIC>
1.8317096563071513

> <JCHEM_POLAR_SURFACE_AREA>
86.17999999999999

> <JCHEM_REFRACTIVITY>
74.4637

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nepafenac

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015678
     RDKit          3D
Nepafenac
 33 34  0  0  0  0  0  0  0  0999 V2000
   -5.5555    0.7053    0.1215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2161    0.3176    0.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6081    0.8253    1.3028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5669   -0.6425   -0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1614   -0.9421   -0.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8124   -2.1263    0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5077   -2.3974    0.8012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5072   -1.4669    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1910   -0.2928   -0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1837    0.7226   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7281    1.8593   -0.8213 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6016    0.6680   -0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3159   -0.4730   -0.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6966   -0.4935   -0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2982    0.6508    0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5966    1.8267    0.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370    1.8345    0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1402   -0.0638   -0.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961    1.1372   -1.0780 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1729    1.1553    0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9737    0.5317   -0.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5799   -0.2702   -1.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1065   -1.6321   -0.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6121   -2.8383    0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2735   -3.3300    1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5080   -1.7359    0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8394   -1.3997   -0.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2115   -1.4264   -0.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3739    0.6227    0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0914    2.7054    0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6654    2.7551    0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6653    1.2136   -2.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974    1.9996   -0.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  9 18  2  0
 18 19  1  0
 18  5  1  0
 17 12  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
 19 33  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.001  -3.465   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.001  -1.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.334  -1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.668  -1.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.668  -3.465   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.334  -4.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.002  -1.155   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.002   0.385   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.335  -1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.669  -1.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.003  -1.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.003  -3.465   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.669  -4.235   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.335  -3.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.336  -1.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.670  -1.925   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.004  -1.155   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      12.670  -3.465   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       8.669   0.385   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   10                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0015678
HETATM    1  N1  UNL     1      -5.555   0.705   0.121  1.00  0.00           N  
HETATM    2  C1  UNL     1      -4.216   0.318   0.336  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.608   0.825   1.303  1.00  0.00           O  
HETATM    4  C2  UNL     1      -3.567  -0.643  -0.541  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.161  -0.942  -0.171  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.812  -2.126   0.461  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.508  -2.397   0.801  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.507  -1.467   0.510  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.191  -0.293  -0.113  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.184   0.723  -0.386  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.728   1.859  -0.821  1.00  0.00           O  
HETATM   12  C9  UNL     1       2.602   0.668  -0.249  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.316  -0.473  -0.467  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.697  -0.494  -0.260  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.298   0.651   0.162  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.597   1.827   0.390  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.237   1.835   0.183  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.140  -0.064  -0.436  1.00  0.00           C  
HETATM   19  N2  UNL     1      -1.496   1.137  -1.078  1.00  0.00           N  
HETATM   20  H1  UNL     1      -6.173   1.155   0.826  1.00  0.00           H  
HETATM   21  H2  UNL     1      -5.974   0.532  -0.818  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.580  -0.270  -1.608  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.107  -1.632  -0.612  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.612  -2.838   0.681  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.273  -3.330   1.293  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.508  -1.736   0.838  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.839  -1.400  -0.851  1.00  0.00           H  
HETATM   28  H9  UNL     1       5.212  -1.426  -0.448  1.00  0.00           H  
HETATM   29  H10 UNL     1       6.374   0.623   0.321  1.00  0.00           H  
HETATM   30  H11 UNL     1       5.091   2.705   0.718  1.00  0.00           H  
HETATM   31  H12 UNL     1       2.665   2.755   0.359  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.665   1.214  -2.100  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.597   2.000  -0.507  1.00  0.00           H  
CONECT    1    2   20   21
CONECT    2    3    3    4
CONECT    4    5   22   23
CONECT    5    6    6   18
CONECT    6    7   24
CONECT    7    8    8   25
CONECT    8    9   26
CONECT    9   10   18   18
CONECT   10   11   11   12
CONECT   12   13   13   17
CONECT   13   14   27
CONECT   14   15   15   28
CONECT   15   16   29
CONECT   16   17   17   30
CONECT   17   31
CONECT   18   19
CONECT   19   32   33
END

HMDB0015678
     RDKit          3D
Nepafenac
 33 34  0  0  0  0  0  0  0  0999 V2000
   -5.5555    0.7053    0.1215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2161    0.3176    0.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6081    0.8253    1.3028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5669   -0.6425   -0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1614   -0.9421   -0.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8124   -2.1263    0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5077   -2.3974    0.8012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5072   -1.4669    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1910   -0.2928   -0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1837    0.7226   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7281    1.8593   -0.8213 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6016    0.6680   -0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3159   -0.4730   -0.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6966   -0.4935   -0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2982    0.6508    0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5966    1.8267    0.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370    1.8345    0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1402   -0.0638   -0.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961    1.1372   -1.0780 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1729    1.1553    0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9737    0.5317   -0.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5799   -0.2702   -1.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1065   -1.6321   -0.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6121   -2.8383    0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2735   -3.3300    1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5080   -1.7359    0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8394   -1.3997   -0.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2115   -1.4264   -0.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3739    0.6227    0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0914    2.7054    0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6654    2.7551    0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6653    1.2136   -2.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974    1.9996   -0.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  9 18  2  0
 18 19  1  0
 18  5  1  0
 17 12  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
 19 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Amino-3-benzoylbenzeneacetamide	ChEBI
AHR 9434	ChEBI
AHR-9434	ChEBI
AL 6515	ChEBI
AL-6515	ChEBI
Nepafenaco	ChEBI
Nepafenacum	ChEBI
Nevanac	ChEBI
Amfenac amide	HMDB

Chemical Formula

C₁₅H₁₄N₂O₂

Average Molecular Weight

254.2839

Monoisotopic Molecular Weight

254.105527702

IUPAC Name

2-(2-amino-3-benzoylphenyl)acetamide

Traditional Name

nepafenac

CAS Registry Number

78281-72-8

SMILES

NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N

InChI Identifier

InChI=1S/C15H14N2O2/c16-13(18)9-11-7-4-8-12(14(11)17)15(19)10-5-2-1-3-6-10/h1-8H,9,17H2,(H2,16,18)

InChI Key

QEFAQIPZVLVERP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzophenones

Direct Parent

Benzophenones

Alternative Parents

Substituents

Benzophenone
Aryl-phenylketone
Diphenylmethane
Phenylacetamide
Benzoyl
Aniline or substituted anilines
Aryl ketone
Vinylogous amide
Amino acid or derivatives
Carboxamide group
Primary carboxylic acid amide
Ketone
Carboxylic acid derivative
Amine
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:75922 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015678)
Membrane (HMDB: HMDB0015678)

Source

Exogenous

Exogenous (HMDB: HMDB0015678)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Nepafenac Action Pathway (PathBank: SMP0000702)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	1.53	ALOGPS
logP	2.08	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	15.82	ChemAxon
pKa (Strongest Basic)	1.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	86.18 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.46 m³·mol⁻¹	ChemAxon
Polarizability	26.63 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	160.057	31661259
DarkChem	[M-H]-	158.115	31661259
DeepCCS	[M+H]+	158.482	30932474
DeepCCS	[M-H]-	156.124	30932474
DeepCCS	[M-2H]-	189.356	30932474
DeepCCS	[M+Na]+	164.575	30932474
AllCCS	[M+H]+	159.1	32859911
AllCCS	[M+H-H2O]+	155.3	32859911
AllCCS	[M+NH4]+	162.7	32859911
AllCCS	[M+Na]+	163.8	32859911
AllCCS	[M-H]-	161.2	32859911
AllCCS	[M+Na-2H]-	161.0	32859911
AllCCS	[M+HCOO]-	160.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.52 minutes	32390414
Predicted by Siyang on May 30, 2022	11.7824 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.87 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	35.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1605.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	311.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	138.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	188.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	103.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	379.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	453.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	128.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	983.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	372.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1137.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	307.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	340.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	301.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	310.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	92.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nepafenac	NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N	4024.5	Standard polar	33892256
Nepafenac	NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N	2501.2	Standard non polar	33892256
Nepafenac	NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N	2699.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nepafenac,1TMS,isomer #1	C[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N	2521.5	Semi standard non polar	33892256
Nepafenac,1TMS,isomer #1	C[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N	2614.2	Standard non polar	33892256
Nepafenac,1TMS,isomer #1	C[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N	3483.4	Standard polar	33892256
Nepafenac,1TMS,isomer #2	C[Si](C)(C)NC1=C(CC(N)=O)C=CC=C1C(=O)C1=CC=CC=C1	2529.4	Semi standard non polar	33892256
Nepafenac,1TMS,isomer #2	C[Si](C)(C)NC1=C(CC(N)=O)C=CC=C1C(=O)C1=CC=CC=C1	2492.6	Standard non polar	33892256
Nepafenac,1TMS,isomer #2	C[Si](C)(C)NC1=C(CC(N)=O)C=CC=C1C(=O)C1=CC=CC=C1	3444.3	Standard polar	33892256
Nepafenac,2TMS,isomer #1	C[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N[Si](C)(C)C	2553.5	Semi standard non polar	33892256
Nepafenac,2TMS,isomer #1	C[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N[Si](C)(C)C	2634.7	Standard non polar	33892256
Nepafenac,2TMS,isomer #1	C[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N[Si](C)(C)C	3089.1	Standard polar	33892256
Nepafenac,2TMS,isomer #2	C[Si](C)(C)N(C(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N)[Si](C)(C)C	2579.6	Semi standard non polar	33892256
Nepafenac,2TMS,isomer #2	C[Si](C)(C)N(C(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N)[Si](C)(C)C	2676.5	Standard non polar	33892256
Nepafenac,2TMS,isomer #2	C[Si](C)(C)N(C(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N)[Si](C)(C)C	3359.2	Standard polar	33892256
Nepafenac,2TMS,isomer #3	C[Si](C)(C)N(C1=C(CC(N)=O)C=CC=C1C(=O)C1=CC=CC=C1)[Si](C)(C)C	2529.4	Semi standard non polar	33892256
Nepafenac,2TMS,isomer #3	C[Si](C)(C)N(C1=C(CC(N)=O)C=CC=C1C(=O)C1=CC=CC=C1)[Si](C)(C)C	2538.5	Standard non polar	33892256
Nepafenac,2TMS,isomer #3	C[Si](C)(C)N(C1=C(CC(N)=O)C=CC=C1C(=O)C1=CC=CC=C1)[Si](C)(C)C	3262.3	Standard polar	33892256
Nepafenac,3TMS,isomer #1	C[Si](C)(C)NC1=C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C=CC=C1C(=O)C1=CC=CC=C1	2631.8	Semi standard non polar	33892256
Nepafenac,3TMS,isomer #1	C[Si](C)(C)NC1=C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C=CC=C1C(=O)C1=CC=CC=C1	2700.4	Standard non polar	33892256
Nepafenac,3TMS,isomer #1	C[Si](C)(C)NC1=C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C=CC=C1C(=O)C1=CC=CC=C1	2980.6	Standard polar	33892256
Nepafenac,3TMS,isomer #2	C[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N([Si](C)(C)C)[Si](C)(C)C	2563.2	Semi standard non polar	33892256
Nepafenac,3TMS,isomer #2	C[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N([Si](C)(C)C)[Si](C)(C)C	2585.5	Standard non polar	33892256
Nepafenac,3TMS,isomer #2	C[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N([Si](C)(C)C)[Si](C)(C)C	2906.3	Standard polar	33892256
Nepafenac,4TMS,isomer #1	C[Si](C)(C)N(C(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2641.7	Semi standard non polar	33892256
Nepafenac,4TMS,isomer #1	C[Si](C)(C)N(C(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2720.9	Standard non polar	33892256
Nepafenac,4TMS,isomer #1	C[Si](C)(C)N(C(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2809.1	Standard polar	33892256
Nepafenac,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N	2726.8	Semi standard non polar	33892256
Nepafenac,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N	2805.7	Standard non polar	33892256
Nepafenac,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N	3523.1	Standard polar	33892256
Nepafenac,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=C(CC(N)=O)C=CC=C1C(=O)C1=CC=CC=C1	2748.6	Semi standard non polar	33892256
Nepafenac,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=C(CC(N)=O)C=CC=C1C(=O)C1=CC=CC=C1	2713.9	Standard non polar	33892256
Nepafenac,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=C(CC(N)=O)C=CC=C1C(=O)C1=CC=CC=C1	3519.9	Standard polar	33892256
Nepafenac,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N[Si](C)(C)C(C)(C)C	2961.4	Semi standard non polar	33892256
Nepafenac,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N[Si](C)(C)C(C)(C)C	3024.6	Standard non polar	33892256
Nepafenac,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N[Si](C)(C)C(C)(C)C	3263.5	Standard polar	33892256
Nepafenac,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N)[Si](C)(C)C(C)(C)C	3012.2	Semi standard non polar	33892256
Nepafenac,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N)[Si](C)(C)C(C)(C)C	3078.7	Standard non polar	33892256
Nepafenac,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N)[Si](C)(C)C(C)(C)C	3398.9	Standard polar	33892256
Nepafenac,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=C(CC(N)=O)C=CC=C1C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2979.8	Semi standard non polar	33892256
Nepafenac,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=C(CC(N)=O)C=CC=C1C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2930.4	Standard non polar	33892256
Nepafenac,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=C(CC(N)=O)C=CC=C1C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3351.4	Standard polar	33892256
Nepafenac,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=CC=C1C(=O)C1=CC=CC=C1	3227.5	Semi standard non polar	33892256
Nepafenac,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=CC=C1C(=O)C1=CC=CC=C1	3287.7	Standard non polar	33892256
Nepafenac,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=CC=C1C(=O)C1=CC=CC=C1	3241.8	Standard polar	33892256
Nepafenac,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3171.0	Semi standard non polar	33892256
Nepafenac,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3192.8	Standard non polar	33892256
Nepafenac,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3179.0	Standard polar	33892256
Nepafenac,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3473.8	Semi standard non polar	33892256
Nepafenac,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3477.0	Standard non polar	33892256
Nepafenac,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3126.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nepafenac GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-1490000000-472a61bcbe3904de6ac4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nepafenac GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nepafenac 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 - Nepafenac , positive-QTOF	splash10-03dr-1490000000-433d63cd52e5b86417da	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepafenac 10V, Positive-QTOF	splash10-0a4r-0190000000-b6c2bf9435ad635d30bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepafenac 20V, Positive-QTOF	splash10-0a4r-0890000000-1c148620fd1183334640	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepafenac 40V, Positive-QTOF	splash10-0a4i-2900000000-de52c273376f27e1aec8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepafenac 10V, Negative-QTOF	splash10-0udi-0090000000-1410eafe17e767b3cc39	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepafenac 20V, Negative-QTOF	splash10-0w2c-3290000000-3604d63c0fc47c406ecc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepafenac 40V, Negative-QTOF	splash10-0006-9200000000-0ccf405a700b155ba243	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepafenac 10V, Positive-QTOF	splash10-0a4i-0090000000-3060c6f1d3f25782b5f6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepafenac 20V, Positive-QTOF	splash10-06si-0970000000-521792df462056dc0554	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepafenac 40V, Positive-QTOF	splash10-004i-9400000000-b292dc56c56def4c3cc1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepafenac 10V, Negative-QTOF	splash10-0ik9-0090000000-db943419dc26289ab4fe	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepafenac 20V, Negative-QTOF	splash10-03di-0090000000-409cecc16290d2050d37	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepafenac 40V, Negative-QTOF	splash10-0006-9540000000-5ae94d44ecaaabdcabf9	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Nepafenac 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 DB06802	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06802	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06802

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

133160

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nepafenac

METLIN ID

Not Available

PubChem Compound

151075

PDB ID

Not Available

ChEBI ID

75922

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

Gamache DA, Graff G, Brady MT, Spellman JM, Yanni JM: Nepafenac, a unique nonsteroidal prodrug with potential utility in the treatment of trauma-induced ocular inflammation: I. Assessment of anti-inflammatory efficacy. Inflammation. 2000 Aug;24(4):357-70. [PubMed:10850857 ]
Ke TL, Graff G, Spellman JM, Yanni JM: Nepafenac, a unique nonsteroidal prodrug with potential utility in the treatment of trauma-induced ocular inflammation: II. In vitro bioactivation and permeation of external ocular barriers. Inflammation. 2000 Aug;24(4):371-84. [PubMed:10850858 ]
Lane SS, Modi SS, Lehmann RP, Holland EJ: Nepafenac ophthalmic suspension 0.1% for the prevention and treatment of ocular inflammation associated with cataract surgery. J Cataract Refract Surg. 2007 Jan;33(1):53-8. [PubMed:17189793 ]
Walters T, Raizman M, Ernest P, Gayton J, Lehmann R: In vivo pharmacokinetics and in vitro pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac. J Cataract Refract Surg. 2007 Sep;33(9):1539-45. [PubMed:17720067 ]
Bucci FA Jr, Waterbury LD: Re: Pharmacokinetics and pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac. J Cataract Refract Surg. 2008 Aug;34(8):1226; author reply 1226-7. doi: 10.1016/j.jcrs.2008.05.019. [PubMed:18655957 ]
Summary Basis of Decision (SBD): NEVANAC. [Link]

Enzymes

Enzyme Details

1. 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

Gamache DA, Graff G, Brady MT, Spellman JM, Yanni JM: Nepafenac, a unique nonsteroidal prodrug with potential utility in the treatment of trauma-induced ocular inflammation: I. Assessment of anti-inflammatory efficacy. Inflammation. 2000 Aug;24(4):357-70. [PubMed:10850857 ]

Enzyme Details

2. 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

Gamache DA, Graff G, Brady MT, Spellman JM, Yanni JM: Nepafenac, a unique nonsteroidal prodrug with potential utility in the treatment of trauma-induced ocular inflammation: I. Assessment of anti-inflammatory efficacy. Inflammation. 2000 Aug;24(4):357-70. [PubMed:10850857 ]

Showing metabocard for Nepafenac (HMDB0015678)

MOL for HMDB0015678 (Nepafenac)

3D MOL for HMDB0015678 (Nepafenac)

3D SDF for HMDB0015678 (Nepafenac)

3D-SDF for HMDB0015678 (Nepafenac)

PDB for HMDB0015678 (Nepafenac)

3D PDB for HMDB0015678 (Nepafenac)

SMILES for HMDB0015678 (Nepafenac)

INCHI for HMDB0015678 (Nepafenac)

Structure for HMDB0015678 (Nepafenac)

3D Structure for HMDB0015678 (Nepafenac)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References