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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014642

Secondary Accession Numbers

HMDB14642

Metabolite Identification

Common Name

Flutamide

Description

Flutamide is only found in individuals that have used or taken this drug. It is an antiandrogen with about the same potency as cyproterone in rodent and canine species.Flutamide is a nonsteroidal antiandrogen that blocks the action of both endogenous and exogenous testosterone by binding to the androgen receptor. In addition Flutamide is a potent inhibitor of testosterone-stimulated prostatic DNA synthesis. Moreover, it is capable of inhibiting prostatic nuclear uptake of androgen.

Structure

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

HMDB0014642
     RDKit          3D
Flutamide
 30 30  0  0  0  0  0  0  0  0999 V2000
    3.7742   -0.4419   -0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2523   -0.1599    1.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9426   -1.1337    1.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7766   -0.4192    0.9768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3702   -1.3060    1.7669 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9255    0.2868    0.1068 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4521    0.1540   -0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2600   -0.7137    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6166   -0.7969    0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2545    0.0191   -0.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6571   -0.0925   -0.6841 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.1682   -1.2237   -0.4313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5041    0.8643   -1.1051 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.4787    0.8960   -1.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1291    1.7989   -2.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7738    1.0971   -3.1732 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8773    2.7770   -1.5904 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0919    2.5013   -2.8428 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1197    0.9581   -0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3469    0.4315   -0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9599   -0.7449   -1.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4989   -1.2888   -0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4820    0.8900    1.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8584   -0.7012    2.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2226   -1.4086    2.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2150   -2.0694    1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4102    1.0139   -0.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8431   -1.3740    1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2566   -1.4902    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5524    1.6765   -1.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 14 19  2  0
 19  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 19 30  1  0
M  CHG  2  11   1  13  -1
M  END

499
  Mrv0541 02231214432D          

 19 19  0  0  0  0            999 V2000
    2.9685    1.8563    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    1.8563    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.6813    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6188    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.0313    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2 19  1  0  0  0  0
  3 19  1  0  0  0  0
  4 11  2  0  0  0  0
  5  8  1  0  0  0  0
  6  8  2  0  0  0  0
  7 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8 16  1  0  0  0  0
  9 11  1  0  0  0  0
  9 14  1  0  0  0  0
  9 15  1  0  0  0  0
 10 13  2  0  0  0  0
 10 17  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 12 19  1  0  0  0  0
 16 18  1  0  0  0  0
 17 18  2  0  0  0  0
M  CHG  2   5  -1   8   1
M  END
> <DATABASE_ID>
HMDB0014642

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C(=O)NC1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C11H11F3N2O3/c1-6(2)10(17)15-7-3-4-9(16(18)19)8(5-7)11(12,13)14/h3-6H,1-2H3,(H,15,17)

> <INCHI_KEY>
MKXKFYHWDHIYRV-UHFFFAOYSA-N

> <FORMULA>
C11H11F3N2O3

> <MOLECULAR_WEIGHT>
276.2118

> <EXACT_MASS>
276.072176843

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.204003355292166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
3.2723109796666665

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.172859943644383

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6999384565398477

> <JCHEM_POLAR_SURFACE_AREA>
74.92

> <JCHEM_REFRACTIVITY>
63.4208

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
flutamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014642
     RDKit          3D
Flutamide
 30 30  0  0  0  0  0  0  0  0999 V2000
    3.7742   -0.4419   -0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2523   -0.1599    1.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9426   -1.1337    1.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7766   -0.4192    0.9768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3702   -1.3060    1.7669 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9255    0.2868    0.1068 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4521    0.1540   -0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2600   -0.7137    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6166   -0.7969    0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2545    0.0191   -0.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6571   -0.0925   -0.6841 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.1682   -1.2237   -0.4313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5041    0.8643   -1.1051 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.4787    0.8960   -1.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1291    1.7989   -2.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7738    1.0971   -3.1732 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8773    2.7770   -1.5904 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0919    2.5013   -2.8428 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1197    0.9581   -0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3469    0.4315   -0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9599   -0.7449   -1.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4989   -1.2888   -0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4820    0.8900    1.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8584   -0.7012    2.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2226   -1.4086    2.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2150   -2.0694    1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4102    1.0139   -0.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8431   -1.3740    1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2566   -1.4902    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5524    1.6765   -1.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 14 19  2  0
 19  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 19 30  1  0
M  CHG  2  11   1  13  -1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 499                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       5.541   3.465   0.000  0.00  0.00           F+0
HETATM    2  F   UNK     0       8.621   3.465   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       7.081   5.005   0.000  0.00  0.00           F+0
HETATM    4  O   UNK     0       8.415  -3.465   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.080   1.155   0.000  0.00  0.00           O-1
HETATM    6  O   UNK     0       4.414   3.465   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       9.748  -1.155   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       4.414   1.925   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0      11.082  -3.465   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.748  -2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081   1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415   1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.416  -2.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.082  -5.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748   1.155   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081  -1.155   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748  -0.385   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.081   3.465   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2   19                                                            
CONECT    3   19                                                            
CONECT    4   11                                                            
CONECT    5    8                                                            
CONECT    6    8                                                            
CONECT    7   10   11                                                       
CONECT    8    5    6   16                                                  
CONECT    9   11   14   15                                                  
CONECT   10    7   13   17                                                  
CONECT   11    4    7    9                                                  
CONECT   12   13   16   19                                                  
CONECT   13   10   12                                                       
CONECT   14    9                                                            
CONECT   15    9                                                            
CONECT   16    8   12   18                                                  
CONECT   17   10   18                                                       
CONECT   18   16   17                                                       
CONECT   19    1    2    3   12                                             
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0014642
HETATM    1  C1  UNL     1       3.774  -0.442  -0.375  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.252  -0.160   1.024  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.943  -1.134   1.949  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.777  -0.419   0.977  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.370  -1.306   1.767  1.00  0.00           O  
HETATM    6  N1  UNL     1       0.925   0.287   0.107  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.452   0.154  -0.046  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.260  -0.714   0.641  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.617  -0.797   0.443  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.254   0.019  -0.491  1.00  0.00           C  
HETATM   11  N2  UNL     1      -4.657  -0.093  -0.684  1.00  0.00           N1+
HETATM   12  O2  UNL     1      -5.168  -1.224  -0.431  1.00  0.00           O  
HETATM   13  O3  UNL     1      -5.504   0.864  -1.105  1.00  0.00           O1-
HETATM   14  C9  UNL     1      -2.479   0.896  -1.193  1.00  0.00           C  
HETATM   15  C10 UNL     1      -3.129   1.799  -2.204  1.00  0.00           C  
HETATM   16  F1  UNL     1      -3.774   1.097  -3.173  1.00  0.00           F  
HETATM   17  F2  UNL     1      -3.877   2.777  -1.590  1.00  0.00           F  
HETATM   18  F3  UNL     1      -2.092   2.501  -2.843  1.00  0.00           F  
HETATM   19  C11 UNL     1      -1.120   0.958  -0.974  1.00  0.00           C  
HETATM   20  H1  UNL     1       4.347   0.432  -0.785  1.00  0.00           H  
HETATM   21  H2  UNL     1       2.960  -0.745  -1.080  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.499  -1.289  -0.397  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.482   0.890   1.263  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.858  -0.701   2.409  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.223  -1.409   2.758  1.00  0.00           H  
HETATM   26  H7  UNL     1       4.215  -2.069   1.381  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.410   1.014  -0.510  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.843  -1.374   1.376  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.257  -1.490   0.993  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.552   1.676  -1.564  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4   23
CONECT    3   24   25   26
CONECT    4    5    5    6
CONECT    6    7   27
CONECT    7    8    8   19
CONECT    8    9   28
CONECT    9   10   10   29
CONECT   10   11   14
CONECT   11   12   12   13
CONECT   14   15   19   19
CONECT   15   16   17   18
CONECT   19   30
END

HMDB0014642
     RDKit          3D
Flutamide
 30 30  0  0  0  0  0  0  0  0999 V2000
    3.7742   -0.4419   -0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2523   -0.1599    1.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9426   -1.1337    1.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7766   -0.4192    0.9768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3702   -1.3060    1.7669 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9255    0.2868    0.1068 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4521    0.1540   -0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2600   -0.7137    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6166   -0.7969    0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2545    0.0191   -0.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6571   -0.0925   -0.6841 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.1682   -1.2237   -0.4313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5041    0.8643   -1.1051 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.4787    0.8960   -1.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1291    1.7989   -2.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7738    1.0971   -3.1732 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8773    2.7770   -1.5904 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0919    2.5013   -2.8428 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1197    0.9581   -0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3469    0.4315   -0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9599   -0.7449   -1.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4989   -1.2888   -0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4820    0.8900    1.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8584   -0.7012    2.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2226   -1.4086    2.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2150   -2.0694    1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4102    1.0139   -0.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8431   -1.3740    1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2566   -1.4902    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5524    1.6765   -1.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 14 19  2  0
 19  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 19 30  1  0
M  CHG  2  11   1  13  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4'-Nitro-3'-trifluoromethylisobutyranilide	ChEBI
alpha,alpha,alpha-Trifluoro-2-methyl-4'-nitro-m-propionotoluidide	ChEBI
Eulexin	ChEBI
Flutamida	ChEBI
Flutamidum	ChEBI
Niftolid	ChEBI
Niftolide	ChEBI
a,a,a-Trifluoro-2-methyl-4'-nitro-m-propionotoluidide	Generator
Α,α,α-trifluoro-2-methyl-4'-nitro-m-propionotoluidide	Generator
Flutamide usp25	HMDB
Euflex	HMDB
Eulexine	HMDB
Fluken	HMDB
Flulem	HMDB
Fluta cell	HMDB
Fluta-gry	HMDB
Flutaplex	HMDB
Fugerel	HMDB
Juta brand OF flutamide	HMDB
Novo flutamide	HMDB
PMS-Flutamide	HMDB
Pharmascience brand OF flutamide	HMDB
Prasfarma brand OF flutamide	HMDB
Prostica	HMDB
Schering brand OF flutamide	HMDB
Schering-plough brand OF flutamide	HMDB
TAD brand OF flutamide	HMDB
Cell pharm brand OF flutamide	HMDB
1a Brand OF flutamide	HMDB
Apo flutamide	HMDB
Apogepha brand OF flutamide	HMDB
Chimax	HMDB
Cytamid	HMDB
Fluta gry	HMDB
Fluta-cell	HMDB
Flutacell	HMDB
Grisetin	HMDB
Gry brand OF flutamide	HMDB
Lemery brand OF flutamide	HMDB
Q Pharm brand OF flutamide	HMDB
Apo-flutamide	HMDB
Ciclum brand OF flutamide	HMDB
Drogenil	HMDB
Flumid	HMDB
FlutaGRY	HMDB
Flutexin	HMDB
Inibsa brand OF flutamide	HMDB
Ipsen brand OF flutamide	HMDB
PMS Flutamide	HMDB
Prostacur	HMDB
Prostogenat	HMDB
Testotard	HMDB
Esparma brand OF flutamide	HMDB
Alphapharm brand OF flutamide	HMDB
Apimid	HMDB
ApoFlutamide	HMDB
Apotex brand OF flutamide	HMDB
Azupharma brand OF flutamide	HMDB
Chephasaar brand OF flutamide	HMDB
Chiron brand OF flutamide	HMDB
Essex brand OF flutamide	HMDB
Fluta 1a pharma	HMDB
Flutamin	HMDB
Flutandrona	HMDB
Hexal brand OF flutamide	HMDB
Kendrick brand OF flutamide	HMDB
Novo-flutamide	HMDB
NovoFlutamide	HMDB
Novopharm brand OF flutamide	HMDB
Oncosal	HMDB
Q-Pharm brand OF flutamide	HMDB
Schering plough brand OF flutamide	HMDB
Tedec meiji brand OF flutamide	HMDB

Chemical Formula

C₁₁H₁₁F₃N₂O₃

Average Molecular Weight

276.2118

Monoisotopic Molecular Weight

276.072176843

IUPAC Name

2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

Traditional Name

flutamide

CAS Registry Number

13311-84-7

SMILES

CC(C)C(=O)NC1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F

InChI Identifier

InChI=1S/C11H11F3N2O3/c1-6(2)10(17)15-7-3-4-9(16(18)19)8(5-7)11(12,13)14/h3-6H,1-2H3,(H,15,17)

InChI Key

MKXKFYHWDHIYRV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Trifluoromethylbenzenes

Direct Parent

Trifluoromethylbenzenes

Alternative Parents

Substituents

Trifluoromethylbenzene
Nitrobenzene
Anilide
N-arylamide
Nitroaromatic compound
Carboxamide group
C-nitro compound
Organic nitro compound
Secondary carboxylic acid amide
Carboxylic acid derivative
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Alkyl halide
Organooxygen compound
Organonitrogen compound
Organofluoride
Organic oxygen compound
Organohalogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Alkyl fluoride
Organic zwitterion
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:5132 )
(trifluoromethyl)benzenes (CHEBI:5132 )

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: HMDB0014642)
Membrane (HMDB: HMDB0014642)

Source

Exogenous

Exogenous (HMDB: HMDB0014642)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	111 - 113 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0057 g/L	Not Available
LogP	2.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	160.022	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000829

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0057 g/L	ALOGPS
logP	2.55	ALOGPS
logP	3.27	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	13.17	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	63.42 m³·mol⁻¹	ChemAxon
Polarizability	23.2 Å³	ChemAxon
Number of Rings	1	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
DeepCCS	[M+H]+	163.901	30932474
DeepCCS	[M-H]-	161.156	30932474
DeepCCS	[M-2H]-	195.945	30932474
DeepCCS	[M+Na]+	172.154	30932474
AllCCS	[M+H]+	157.0	32859911
AllCCS	[M+H-H2O]+	153.5	32859911
AllCCS	[M+NH4]+	160.2	32859911
AllCCS	[M+Na]+	161.1	32859911
AllCCS	[M-H]-	156.3	32859911
AllCCS	[M+Na-2H]-	156.1	32859911
AllCCS	[M+HCOO]-	156.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Flutamide	CC(C)C(=O)NC1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F	2269.6	Standard polar	33892256
Flutamide	CC(C)C(=O)NC1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F	1959.3	Standard non polar	33892256
Flutamide	CC(C)C(=O)NC1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F	1927.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Flutamide,1TMS,isomer #1	CC(C)C(=O)N(C1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)[Si](C)(C)C	1708.9	Semi standard non polar	33892256
Flutamide,1TMS,isomer #1	CC(C)C(=O)N(C1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)[Si](C)(C)C	1797.7	Standard non polar	33892256
Flutamide,1TMS,isomer #1	CC(C)C(=O)N(C1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)[Si](C)(C)C	1842.8	Standard polar	33892256
Flutamide,1TBDMS,isomer #1	CC(C)C(=O)N(C1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)[Si](C)(C)C(C)(C)C	1984.1	Semi standard non polar	33892256
Flutamide,1TBDMS,isomer #1	CC(C)C(=O)N(C1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)[Si](C)(C)C(C)(C)C	1996.3	Standard non polar	33892256
Flutamide,1TBDMS,isomer #1	CC(C)C(=O)N(C1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)[Si](C)(C)C(C)(C)C	1961.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Flutamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9280000000-95879ab49ae3474dd134	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flutamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flutamide 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 - Flutamide LC-ESI-qTof , Positive-QTOF	splash10-004i-0290000000-cca4c08f2a9bb3fc6f57	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide LC-ESI-qTof , Positive-QTOF	splash10-004i-0190000000-df05faf7e38e6d6da203	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide LC-ESI-qTof , Positive-QTOF	splash10-000i-3900000000-8b7e5888950eed07b29b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide LC-ESI-QFT , negative-QTOF	splash10-004i-0090000000-983edf51e9c479db69a5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide , positive-QTOF	splash10-004i-0190000000-df05faf7e38e6d6da203	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide , positive-QTOF	splash10-004i-0290000000-cca4c08f2a9bb3fc6f57	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide , positive-QTOF	splash10-03di-2940000000-170008eb50a63f0664d0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide 90V, Negative-QTOF	splash10-0gx0-1900000000-c322f29e305a6d10044c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide 50V, Positive-QTOF	splash10-014i-0940000000-8c0e8ce0c0167f824210	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide 10V, Negative-QTOF	splash10-004i-0090000000-3ec575077e4f9903d0af	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide 50V, Positive-QTOF	splash10-014i-0940000000-5a90366233a810251923	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide 30V, Negative-QTOF	splash10-0udi-0390000000-bb6d9f3ab642b5c061ba	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide 20V, Negative-QTOF	splash10-004i-0090000000-cdcab2cffbd217c82fad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide 40V, Positive-QTOF	splash10-014i-0920000000-3d0edd4f5b6b7545a7f3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide 60V, Negative-QTOF	splash10-0udi-0890000000-9c05c9f4c668a596f70e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide 30V, Positive-QTOF	splash10-014i-0910000000-abf238316a2db628c154	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide 40V, Positive-QTOF	splash10-014i-0920000000-9eb906d56b8ae34b4681	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide 75V, Negative-QTOF	splash10-0il0-0920000000-a14d1afe6adfae49f6ab	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flutamide 45V, Negative-QTOF	splash10-0ufr-0190000000-0c4cfbc09b7620965ab5	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flutamide 10V, Positive-QTOF	splash10-004i-0090000000-7122c7547dc4f518e9fa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flutamide 20V, Positive-QTOF	splash10-00kf-8090000000-02b603738815e91326c2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flutamide 40V, Positive-QTOF	splash10-006x-9010000000-19ee080aa7e8861af1ff	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flutamide 10V, Negative-QTOF	splash10-004i-0090000000-e5a1eaa719d4f63bf6f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flutamide 20V, Negative-QTOF	splash10-004i-2090000000-13768fb84641e8448d75	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flutamide 40V, Negative-QTOF	splash10-0076-9000000000-10b226e4bd1f69316fa1	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB00499	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00499	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

DB00499

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3280

KEGG Compound ID

C07653

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Flutamide

METLIN ID

Not Available

PubChem Compound

3397

PDB ID

Not Available

ChEBI ID

5132

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

BC Cancer Agency [Link]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

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 ]

Enzyme Details

2. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

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 ]

Enzyme Details

3. Cytochrome P450 1B1

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. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:: CYP1B1
Uniprot ID:: Q16678
Molecular weight:: 60845.33

References

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 ]

Enzyme Details

4. Cytochrome P450 3A5

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.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

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 ]

Enzyme Details

5. Cytochrome P450 1A1

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.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

References

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 ]

Enzyme Details

6. Cytochrome P450 1A2

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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423 ]
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 ]
Shet MS, McPhaul M, Fisher CW, Stallings NR, Estabrook RW: Metabolism of the antiandrogenic drug (Flutamide) by human CYP1A2. Drug Metab Dispos. 1997 Nov;25(11):1298-303. [PubMed:9351907 ]

Enzyme Details

7. Androgen receptor

General function:: Involved in DNA binding
Specific function:: Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3
Gene Name:: AR
Uniprot ID:: P10275
Molecular weight:: 98987.9

References

Chang HC, Miyamoto H, Marwah P, Lardy H, Yeh S, Huang KE, Chang C: Suppression of Delta(5)-androstenediol-induced androgen receptor transactivation by selective steroids in human prostate cancer cells. Proc Natl Acad Sci U S A. 1999 Sep 28;96(20):11173-7. [PubMed:10500149 ]
Martelli A, Campart GB, Carrozzino R, Ghia M, Mattioli F, Mereto E, Orsi P, Puglia CP: Evaluation of flutamide genotoxicity in rats and in primary human hepatocytes. Pharmacol Toxicol. 2000 Mar;86(3):129-34. [PubMed:10752671 ]
Montalvo L, Carmena MJ, Solano RM, Clemente C, Roman ID, Sanchez-Chapado M, Prieto JC: Effect of flutamide-induced androgen-receptor blockade on adenylate cyclase activation through G-protein coupled receptors in rat prostate. Cell Signal. 2000 May;12(5):311-6. [PubMed:10822172 ]
Pazos F, Sanchez-Franco F, Balsa JA, Escalada J, Palacios N, Cacicedo L: Mechanisms of reduced body growth in the pubertal feminized male rat: unbalanced estrogen and androgen action on the somatotropic axis. Pediatr Res. 2000 Jul;48(1):96-103. [PubMed:10879806 ]
Shilling AD, Williams DE: The non-aromatizable androgen, dihydrotestosterone, induces antiestrogenic responses in the rainbow trout. J Steroid Biochem Mol Biol. 2000 Nov 15;74(4):187-94. [PubMed:11162924 ]
Balk SP: Androgen receptor as a target in androgen-independent prostate cancer. Urology. 2002 Sep;60(3 Suppl 1):132-8; discussion 138-9. [PubMed:12231070 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

8. Aryl hydrocarbon receptor

General function:: Involved in transcription regulator activity
Specific function:: Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:: AHR
Uniprot ID:: P35869
Molecular weight:: 96146.7

References

Hu W, Sorrentino C, Denison MS, Kolaja K, Fielden MR: Induction of cyp1a1 is a nonspecific biomarker of aryl hydrocarbon receptor activation: results of large scale screening of pharmaceuticals and toxicants in vivo and in vitro. Mol Pharmacol. 2007 Jun;71(6):1475-86. Epub 2007 Feb 27. [PubMed:17327465 ]

Showing metabocard for Flutamide (HMDB0014642)

MOL for HMDB0014642 (Flutamide)

3D MOL for HMDB0014642 (Flutamide)

3D SDF for HMDB0014642 (Flutamide)

3D-SDF for HMDB0014642 (Flutamide)

PDB for HMDB0014642 (Flutamide)

3D PDB for HMDB0014642 (Flutamide)

SMILES for HMDB0014642 (Flutamide)

INCHI for HMDB0014642 (Flutamide)

Structure for HMDB0014642 (Flutamide)

3D Structure for HMDB0014642 (Flutamide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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