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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3)transporters (2) Show 5 proteins XML

enzymes (3)transporters (2) Show 5 proteins

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

HMDB0014619

Secondary Accession Numbers

HMDB14619

Metabolite Identification

Common Name

Duloxetine

Description

Duloxetine (brand names Cymbalta, Yentreve, and in parts of Europe, Xeristar or Ariclaim) is a drug which primarily targets major depressive disorder (MDD), generalized anxiety disorder (GAD), pain related to diabetic peripheral neuropathy and in some countries stress urinary incontinence (SUI). It is manufactured and marketed by Eli Lilly and Company. Duloxetine has not yet been FDA approved for stress urinary incontinence or for fibromyalgia. Duloxetine is a selective SNRI (selective serotonin-norepinephrine reuptake inhibitor). Duloxetine is a systemic drug therapy which affects the body as a whole. Known also under the code name LY248686, it is a potent dual reuptake inhibitor of serotonin (5-hydroxytryptamine, 5-HT) and norepinephrine (NE), possessing comparable affinities in binding to NE- and 5-HT transporter sites. It is a less potent inhibitor of dopamine reuptake.

Structure

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

HMDB0014619
     RDKit          3D
Duloxetine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -3.6753   -2.2486    0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2373   -2.2362    0.5064 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8482   -1.3648    1.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259    0.0906    1.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448    0.4838    0.0381 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0234    0.3602    0.1750 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9244   -0.3704   -0.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5554   -1.1745   -1.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5220   -1.9012   -2.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8382   -1.8180   -1.8742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2380   -1.0114   -0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5620   -0.9208   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9402   -0.1212    0.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9802    0.6018    1.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6722    0.5003    0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2544   -0.3101   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6409    1.9233   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1165    3.0513    0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5336    4.2327   -0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4514    4.2100   -1.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7006    2.5445   -1.4876 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2204   -2.1402    1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0276   -3.2097   -0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9777   -1.4362   -0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9568   -3.2072    0.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7787   -1.4756    1.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4260   -1.6921    2.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2176    0.1852    1.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386    0.7398    2.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7418   -0.1117   -0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4919   -1.2691   -1.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1910   -2.5266   -3.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6025   -2.3865   -2.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2710   -1.5152   -1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9718   -0.0670    0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3213    1.2190    2.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9490    1.0838    1.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705    2.9922    1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1847    5.2252    0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9102    5.0706   -1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  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
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  5 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 16  7  1  0
 21 17  1  0
 16 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  6
  8 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
M  END

476
  Mrv0541 02231214422D          

 21 23  0  0  1  0            999 V2000
    5.1753   -1.7207    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    0.0017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    0.0017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.4108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7934    0.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    1.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    2.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8405   -1.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    1.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743    0.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    2.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    2.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743    2.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -2.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -2.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    1.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    2.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 18  1  0  0  0  0
  4  2  1  6  0  0  0
  2  8  1  0  0  0  0
  3  6  1  0  0  0  0
  3 19  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  7 11  2  0  0  0  0
  8  9  1  0  0  0  0
  8 12  2  0  0  0  0
  9 10  1  0  0  0  0
  9 13  2  0  0  0  0
 10 14  1  0  0  0  0
 10 16  2  0  0  0  0
 11 17  1  0  0  0  0
 12 15  1  0  0  0  0
 13 20  1  0  0  0  0
 14 15  2  0  0  0  0
 16 21  1  0  0  0  0
 17 18  2  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014619

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCC[C@H](OC1=CC=CC2=CC=CC=C12)C1=CC=CS1

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NOS/c1-19-12-11-17(18-10-5-13-21-18)20-16-9-4-7-14-6-2-3-8-15(14)16/h2-10,13,17,19H,11-12H2,1H3/t17-/m0/s1

> <INCHI_KEY>
ZEUITGRIYCTCEM-KRWDZBQOSA-N

> <FORMULA>
C18H19NOS

> <MOLECULAR_WEIGHT>
297.415

> <EXACT_MASS>
297.118734925

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
33.15278651399598

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl[(3S)-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propyl]amine

> <ALOGPS_LOGP>
4.72

> <JCHEM_LOGP>
4.197729191333333

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.702576554982972

> <JCHEM_POLAR_SURFACE_AREA>
21.259999999999998

> <JCHEM_REFRACTIVITY>
87.73390000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.96e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
duloxetine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014619
     RDKit          3D
Duloxetine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -3.6753   -2.2486    0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2373   -2.2362    0.5064 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8482   -1.3648    1.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259    0.0906    1.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448    0.4838    0.0381 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0234    0.3602    0.1750 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9244   -0.3704   -0.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5554   -1.1745   -1.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5220   -1.9012   -2.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8382   -1.8180   -1.8742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2380   -1.0114   -0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5620   -0.9208   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9402   -0.1212    0.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9802    0.6018    1.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6722    0.5003    0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2544   -0.3101   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6409    1.9233   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1165    3.0513    0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5336    4.2327   -0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4514    4.2100   -1.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7006    2.5445   -1.4876 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2204   -2.1402    1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0276   -3.2097   -0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9777   -1.4362   -0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9568   -3.2072    0.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7787   -1.4756    1.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4260   -1.6921    2.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2176    0.1852    1.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386    0.7398    2.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7418   -0.1117   -0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4919   -1.2691   -1.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1910   -2.5266   -3.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6025   -2.3865   -2.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2710   -1.5152   -1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9718   -0.0670    0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3213    1.2190    2.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9490    1.0838    1.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705    2.9922    1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1847    5.2252    0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9102    5.0706   -1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  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
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  5 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 16  7  1  0
 21 17  1  0
 16 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  6
  8 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 476                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       9.661  -3.212   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       9.748   0.003   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       4.414   0.003   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.415  -0.767   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081   0.003   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747  -0.767   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415  -2.307   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.748   1.543   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.082   2.313   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.082   3.853   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.169  -3.212   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415   2.313   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.459   1.490   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.748   4.623   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415   3.853   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.459   4.677   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.645  -4.677   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.185  -4.677   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.080  -0.767   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.854   2.281   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.854   3.885   0.000  0.00  0.00           C+0
CONECT    1    7   18                                                       
CONECT    2    4    8                                                       
CONECT    3    6   19                                                       
CONECT    4    2    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    3    5                                                       
CONECT    7    1    4   11                                                  
CONECT    8    2    9   12                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   14   16                                                  
CONECT   11    7   17                                                       
CONECT   12    8   15                                                       
CONECT   13    9   20                                                       
CONECT   14   10   15                                                       
CONECT   15   12   14                                                       
CONECT   16   10   21                                                       
CONECT   17   11   18                                                       
CONECT   18    1   17                                                       
CONECT   19    3                                                            
CONECT   20   13   21                                                       
CONECT   21   16   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0014619
HETATM    1  C1  UNL     1      -3.675  -2.249   0.338  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.237  -2.236   0.506  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.848  -1.365   1.610  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.126   0.091   1.266  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.345   0.484   0.038  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.023   0.360   0.175  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.924  -0.370  -0.521  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.555  -1.174  -1.568  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.522  -1.901  -2.246  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.838  -1.818  -1.874  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.238  -1.011  -0.819  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.562  -0.921  -0.437  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.940  -0.121   0.605  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.980   0.602   1.279  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.672   0.500   0.888  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.254  -0.310  -0.175  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.641   1.923  -0.306  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.116   3.051   0.262  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.534   4.233  -0.215  1.00  0.00           C  
HETATM   20  C18 UNL     1      -2.451   4.210  -1.232  1.00  0.00           C  
HETATM   21  S1  UNL     1      -2.701   2.545  -1.488  1.00  0.00           S  
HETATM   22  H1  UNL     1      -4.220  -2.140   1.294  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.028  -3.210  -0.116  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.978  -1.436  -0.357  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.957  -3.207   0.782  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.779  -1.476   1.858  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.426  -1.692   2.493  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.218   0.185   1.121  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.839   0.740   2.105  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.742  -0.112  -0.805  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.492  -1.269  -1.898  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.191  -2.527  -3.068  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.602  -2.387  -2.404  1.00  0.00           H  
HETATM   34  H13 UNL     1       5.271  -1.515  -1.007  1.00  0.00           H  
HETATM   35  H14 UNL     1       5.972  -0.067   0.881  1.00  0.00           H  
HETATM   36  H15 UNL     1       4.321   1.219   2.095  1.00  0.00           H  
HETATM   37  H16 UNL     1       1.949   1.084   1.442  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.371   2.992   1.089  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.185   5.225   0.159  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.910   5.071  -1.750  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   17   30
CONECT    6    7
CONECT    7    8    8   16
CONECT    8    9   31
CONECT    9   10   10   32
CONECT   10   11   33
CONECT   11   12   12   16
CONECT   12   13   34
CONECT   13   14   14   35
CONECT   14   15   36
CONECT   15   16   16   37
CONECT   17   18   18   21
CONECT   18   19   38
CONECT   19   20   20   39
CONECT   20   21   40
END

HMDB0014619
     RDKit          3D
Duloxetine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -3.6753   -2.2486    0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2373   -2.2362    0.5064 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8482   -1.3648    1.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259    0.0906    1.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448    0.4838    0.0381 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0234    0.3602    0.1750 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9244   -0.3704   -0.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5554   -1.1745   -1.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5220   -1.9012   -2.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8382   -1.8180   -1.8742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2380   -1.0114   -0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5620   -0.9208   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9402   -0.1212    0.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9802    0.6018    1.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6722    0.5003    0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2544   -0.3101   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6409    1.9233   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1165    3.0513    0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5336    4.2327   -0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4514    4.2100   -1.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7006    2.5445   -1.4876 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2204   -2.1402    1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0276   -3.2097   -0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9777   -1.4362   -0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9568   -3.2072    0.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7787   -1.4756    1.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4260   -1.6921    2.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2176    0.1852    1.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386    0.7398    2.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7418   -0.1117   -0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4919   -1.2691   -1.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1910   -2.5266   -3.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6025   -2.3865   -2.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2710   -1.5152   -1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9718   -0.0670    0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3213    1.2190    2.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9490    1.0838    1.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705    2.9922    1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1847    5.2252    0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9102    5.0706   -1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  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
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  5 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 16  7  1  0
 21 17  1  0
 16 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  6
  8 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3S)-N-Methyl-3-(1-naphthyloxy)-3-(2-thienyl)propan-1-amine	ChEBI
LY 248686	ChEBI
Yentreve	Kegg
Duloxetine HCL	HMDB
Hydrochloride, duloxetine	HMDB
Duloxetine hydrochloride	HMDB
Duloxetine ethanedioate (1:1), (+-)-isomer - T353987	HMDB
N-Methyl-3-(1-naphthalenyloxy)-2-thiophenepropanamine	HMDB
Cymbalta	HMDB
HCL, Duloxetine	HMDB
N-Methyl-3-(1-naphthalenyloxy)-3-(2-thiophene)propanamide	HMDB
Duloxetine, (+)-isomer	HMDB
Duloxetine	MeSH

Chemical Formula

C₁₈H₁₉NOS

Average Molecular Weight

297.415

Monoisotopic Molecular Weight

297.118734925

IUPAC Name

methyl[(3S)-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propyl]amine

Traditional Name

duloxetine

CAS Registry Number

136434-34-9

SMILES

CNCC[C@H](OC1=CC=CC2=CC=CC=C12)C1=CC=CS1

InChI Identifier

InChI=1S/C18H19NOS/c1-19-12-11-17(18-10-5-13-21-18)20-16-9-4-7-14-6-2-3-8-15(14)16/h2-10,13,17,19H,11-12H2,1H3/t17-/m0/s1

InChI Key

ZEUITGRIYCTCEM-KRWDZBQOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Alkyl aryl ether
Aralkylamine
Thiophene
Heteroaromatic compound
Secondary aliphatic amine
Ether
Secondary amine
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

duloxetine (CHEBI:36795 )

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

Membrane (HMDB: HMDB0014619)

Source

Exogenous

Exogenous (HMDB: HMDB0014619)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Antidepressant (HMDB: HMDB0014619)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.003 g/L	Not Available
LogP	4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	171.0	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.003 g/L	ALOGPS
logP	4.72	ALOGPS
logP	4.2	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	9.7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	21.26 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	87.73 m³·mol⁻¹	ChemAxon
Polarizability	33.15 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	169.384	31661259
DarkChem	[M-H]-	168.941	31661259
DeepCCS	[M-2H]-	196.363	30932474
DeepCCS	[M+Na]+	171.59	30932474
AllCCS	[M+H]+	170.4	32859911
AllCCS	[M+H-H2O]+	167.0	32859911
AllCCS	[M+NH4]+	173.6	32859911
AllCCS	[M+Na]+	174.5	32859911
AllCCS	[M-H]-	173.5	32859911
AllCCS	[M+Na-2H]-	173.0	32859911
AllCCS	[M+HCOO]-	172.6	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.	7.06 minutes	32390414
Predicted by Siyang on May 30, 2022	13.2861 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.68 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	38.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1730.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	328.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	196.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	203.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	187.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	523.4 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	496.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	264.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1092.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	494.3 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	1510.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	305.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	374.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	332.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	195.1 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	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Duloxetine	CNCC[C@H](OC1=CC=CC2=CC=CC=C12)C1=CC=CS1	3264.9	Standard polar	33892256
Duloxetine	CNCC[C@H](OC1=CC=CC2=CC=CC=C12)C1=CC=CS1	2458.3	Standard non polar	33892256
Duloxetine	CNCC[C@H](OC1=CC=CC2=CC=CC=C12)C1=CC=CS1	2430.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Duloxetine,1TMS,isomer #1	CN(CC[C@H](OC1=CC=CC2=CC=CC=C12)C1=CC=CS1)[Si](C)(C)C	2618.3	Semi standard non polar	33892256
Duloxetine,1TMS,isomer #1	CN(CC[C@H](OC1=CC=CC2=CC=CC=C12)C1=CC=CS1)[Si](C)(C)C	2644.0	Standard non polar	33892256
Duloxetine,1TMS,isomer #1	CN(CC[C@H](OC1=CC=CC2=CC=CC=C12)C1=CC=CS1)[Si](C)(C)C	3370.2	Standard polar	33892256
Duloxetine,1TBDMS,isomer #1	CN(CC[C@H](OC1=CC=CC2=CC=CC=C12)C1=CC=CS1)[Si](C)(C)C(C)(C)C	2847.1	Semi standard non polar	33892256
Duloxetine,1TBDMS,isomer #1	CN(CC[C@H](OC1=CC=CC2=CC=CC=C12)C1=CC=CS1)[Si](C)(C)C(C)(C)C	2854.9	Standard non polar	33892256
Duloxetine,1TBDMS,isomer #1	CN(CC[C@H](OC1=CC=CC2=CC=CC=C12)C1=CC=CS1)[Si](C)(C)C(C)(C)C	3440.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Duloxetine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9530000000-49ea61eaf551272fdf2b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Duloxetine 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 - Duloxetine LC-ESI-qTof , Positive-QTOF	splash10-0002-0890000000-a1b4d59cc0496fb3b755	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Duloxetine LC-ESI-qTof , Positive-QTOF	splash10-0002-0970000000-5a3d39a5afda39a4ec23	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Duloxetine , positive-QTOF	splash10-0002-0890000000-a1b4d59cc0496fb3b755	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Duloxetine , positive-QTOF	splash10-0002-0970000000-5a3d39a5afda39a4ec23	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Duloxetine LC-ESI-QFT , positive-QTOF	splash10-0002-0590000000-894e0be7451e63140e89	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Duloxetine 35V, Positive-QTOF	splash10-0006-9000000000-f8c67ea645eec49b2c3e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Duloxetine 35V, Positive-QTOF	splash10-0002-0590000000-894e0be7451e63140e89	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Duloxetine 10V, Positive-QTOF	splash10-00kb-0090000000-79dbcab4853aa7d19624	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Duloxetine 20V, Positive-QTOF	splash10-014m-4290000000-a13b02643710fd4db48f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Duloxetine 40V, Positive-QTOF	splash10-05tf-5910000000-9993fd40535267373a45	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Duloxetine 10V, Negative-QTOF	splash10-0002-1390000000-1f24878e7debb65a5c43	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Duloxetine 20V, Negative-QTOF	splash10-0005-3390000000-39a64a08f599b40173a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Duloxetine 40V, Negative-QTOF	splash10-0a4l-8910000000-3949e7d24fa4c4d4757a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Duloxetine 10V, Positive-QTOF	splash10-0002-0890000000-1a0428116fbabd8d95d4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Duloxetine 20V, Positive-QTOF	splash10-0002-1960000000-91680eff5f6acae59b5a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Duloxetine 40V, Positive-QTOF	splash10-00ov-2910000000-664e6f8f3a608f6cb53f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Duloxetine 10V, Negative-QTOF	splash10-0002-0190000000-1263586eab6bc5fb17ff	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Duloxetine 20V, Negative-QTOF	splash10-000x-6910000000-78b5f700d18c7c60b0bb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Duloxetine 40V, Negative-QTOF	splash10-0006-1900000000-df1c429b62c077911edf	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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 DB00476	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00476	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

DB00476

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54822

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Duloxetine

METLIN ID

Not Available

PubChem Compound

60835

PDB ID

Not Available

ChEBI ID

36795

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

Carter NJ, McCormack PL: Duloxetine: a review of its use in the treatment of generalized anxiety disorder. CNS Drugs. 2009;23(6):523-41. doi: 10.2165/00023210-200923060-00006. [PubMed:19480470 ]
Karpa KD, Cavanaugh JE, Lakoski JM: Duloxetine pharmacology: profile of a dual monoamine modulator. CNS Drug Rev. 2002 Winter;8(4):361-76. [PubMed:12481192 ]
van Groeningen CJ, Peters GJ, Pinedo HM: Lack of effectiveness of combined 5-fluorouracil and leucovorin in patients with 5-fluorouracil-resistant advanced colorectal cancer. Eur J Cancer Clin Oncol. 1989 Jan;25(1):45-9. [PubMed:2784100 ]
Jost W, Marsalek P: Duloxetine: mechanism of action at the lower urinary tract and Onuf's nucleus. Clin Auton Res. 2004 Aug;14(4):220-7. [PubMed:15316838 ]
Turcotte JE, Debonnel G, de Montigny C, Hebert C, Blier P: Assessment of the serotonin and norepinephrine reuptake blocking properties of duloxetine in healthy subjects. Neuropsychopharmacology. 2001 May;24(5):511-21. [PubMed:11282251 ]
Anttila S, Leinonen E: Duloxetine Eli Lilly. Curr Opin Investig Drugs. 2002 Aug;3(8):1217-21. [PubMed:12211418 ]

Enzymes

Enzyme Details

1. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Knadler MP, Lobo E, Chappell J, Bergstrom R: Duloxetine: clinical pharmacokinetics and drug interactions. Clin Pharmacokinet. 2011 May;50(5):281-94. doi: 10.2165/11539240-000000000-00000. [PubMed:21366359 ]
Preskorn SH, Nichols AI, Paul J, Patroneva AL, Helzner EC, Guico-Pabia CJ: Effect of desvenlafaxine on the cytochrome P450 2D6 enzyme system. J Psychiatr Pract. 2008 Nov;14(6):368-78. doi: 10.1097/01.pra.0000341891.43501.6b. [PubMed:19057238 ]
Authors unspecified: Duloxetine: new indication. Depression and diabetic neuropathy: too many adverse effects. Prescrire Int. 2006 Oct;15(85):168-72. [PubMed:17121211 ]
Carter NJ, McCormack PL: Duloxetine: a review of its use in the treatment of generalized anxiety disorder. CNS Drugs. 2009;23(6):523-41. doi: 10.2165/00023210-200923060-00006. [PubMed:19480470 ]

Enzyme Details

2. 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

Knadler MP, Lobo E, Chappell J, Bergstrom R: Duloxetine: clinical pharmacokinetics and drug interactions. Clin Pharmacokinet. 2011 May;50(5):281-94. doi: 10.2165/11539240-000000000-00000. [PubMed:21366359 ]
Lobo ED, Bergstrom RF, Reddy S, Quinlan T, Chappell J, Hong Q, Ring B, Knadler MP: In vitro and in vivo evaluations of cytochrome P450 1A2 interactions with duloxetine. Clin Pharmacokinet. 2008;47(3):191-202. [PubMed:18307373 ]
Authors unspecified: Duloxetine: new indication. Depression and diabetic neuropathy: too many adverse effects. Prescrire Int. 2006 Oct;15(85):168-72. [PubMed:17121211 ]
Carter NJ, McCormack PL: Duloxetine: a review of its use in the treatment of generalized anxiety disorder. CNS Drugs. 2009;23(6):523-41. doi: 10.2165/00023210-200923060-00006. [PubMed:19480470 ]

Enzyme Details

3. Sodium-dependent dopamine transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A3
Uniprot ID:: Q01959
Molecular weight:: 68494.255

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Carter NJ, McCormack PL: Duloxetine: a review of its use in the treatment of generalized anxiety disorder. CNS Drugs. 2009;23(6):523-41. doi: 10.2165/00023210-200923060-00006. [PubMed:19480470 ]
Pereira P, Gianesini J, da Silva Barbosa C, Cassol GF, Von Borowski RG, Kahl VF, Cappelari SE, Picada JN: Neurobehavioral and genotoxic parameters of duloxetine in mice using the inhibitory avoidance task and comet assay as experimental models. Pharmacol Res. 2009 Jan;59(1):57-61. doi: 10.1016/j.phrs.2008.09.014. Epub 2008 Oct 5. [PubMed:18973814 ]
Hunziker ME, Suehs BT, Bettinger TL, Crismon ML: Duloxetine hydrochloride: a new dual-acting medication for the treatment of major depressive disorder. Clin Ther. 2005 Aug;27(8):1126-43. [PubMed:16199241 ]

Transporters

Enzyme Details

1. Sodium-dependent noradrenaline transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular weight:: 69331.42

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Gould GG, Javors MA, Frazer A: Effect of chronic administration of duloxetine on serotonin and norepinephrine transporter binding sites in rat brain. Biol Psychiatry. 2007 Jan 15;61(2):210-5. Epub 2006 May 2. [PubMed:16650830 ]
Vaishnavi SN, Nemeroff CB, Plott SJ, Rao SG, Kranzler J, Owens MJ: Milnacipran: a comparative analysis of human monoamine uptake and transporter binding affinity. Biol Psychiatry. 2004 Feb 1;55(3):320-2. [PubMed:14744476 ]
Beique JC, Lavoie N, de Montigny C, Debonnel G: Affinities of venlafaxine and various reuptake inhibitors for the serotonin and norepinephrine transporters. Eur J Pharmacol. 1998 May 15;349(1):129-32. [PubMed:9669506 ]
Vincent S, Bieck PR, Garland EM, Loghin C, Bymaster FP, Black BK, Gonzales C, Potter WZ, Robertson D: Clinical assessment of norepinephrine transporter blockade through biochemical and pharmacological profiles. Circulation. 2004 Jun 29;109(25):3202-7. Epub 2004 Jun 7. [PubMed:15184278 ]
Schou M, Halldin C, Pike VW, Mozley PD, Dobson D, Innis RB, Farde L, Hall H: Post-mortem human brain autoradiography of the norepinephrine transporter using (S,S)-[18F]FMeNER-D2. Eur Neuropsychopharmacol. 2005 Oct;15(5):517-20. Epub 2005 Apr 7. [PubMed:16139169 ]
Mirza NR, Nielsen EO, Troelsen KB: Serotonin transporter density and anxiolytic-like effects of antidepressants in mice. Prog Neuropsychopharmacol Biol Psychiatry. 2007 May 9;31(4):858-66. Epub 2007 Jan 30. [PubMed:17335951 ]
Karpa KD, Cavanaugh JE, Lakoski JM: Duloxetine pharmacology: profile of a dual monoamine modulator. CNS Drug Rev. 2002 Winter;8(4):361-76. [PubMed:12481192 ]
van Groeningen CJ, Peters GJ, Pinedo HM: Lack of effectiveness of combined 5-fluorouracil and leucovorin in patients with 5-fluorouracil-resistant advanced colorectal cancer. Eur J Cancer Clin Oncol. 1989 Jan;25(1):45-9. [PubMed:2784100 ]
Jost W, Marsalek P: Duloxetine: mechanism of action at the lower urinary tract and Onuf's nucleus. Clin Auton Res. 2004 Aug;14(4):220-7. [PubMed:15316838 ]
Trivedi MH, Desaiah D, Ossanna MJ, Pritchett YL, Brannan SK, Detke MJ: Clinical evidence for serotonin and norepinephrine reuptake inhibition of duloxetine. Int Clin Psychopharmacol. 2008 May;23(3):161-9. doi: 10.1097/YIC.0b013e3282f41d7e. [PubMed:18408530 ]
Bymaster FP, Lee TC, Knadler MP, Detke MJ, Iyengar S: The dual transporter inhibitor duloxetine: a review of its preclinical pharmacology, pharmacokinetic profile, and clinical results in depression. Curr Pharm Des. 2005;11(12):1475-93. [PubMed:15892657 ]
Khullar V, Cardozo L, Dmochowski R: Mixed incontinence: current evidence and future perspectives. Neurourol Urodyn. 2010 Apr;29(4):618-22. doi: 10.1002/nau.20907. [PubMed:20432324 ]
Carter NJ, McCormack PL: Duloxetine: a review of its use in the treatment of generalized anxiety disorder. CNS Drugs. 2009;23(6):523-41. doi: 10.2165/00023210-200923060-00006. [PubMed:19480470 ]
Hunziker ME, Suehs BT, Bettinger TL, Crismon ML: Duloxetine hydrochloride: a new dual-acting medication for the treatment of major depressive disorder. Clin Ther. 2005 Aug;27(8):1126-43. [PubMed:16199241 ]

Enzyme Details

2. Sodium-dependent serotonin transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:: SLC6A4
Uniprot ID:: P31645
Molecular weight:: 70324.165

References

Chen F, Larsen MB, Sanchez C, Wiborg O: The S-enantiomer of R,S-citalopram, increases inhibitor binding to the human serotonin transporter by an allosteric mechanism. Comparison with other serotonin transporter inhibitors. Eur Neuropsychopharmacol. 2005 Mar;15(2):193-8. [PubMed:15695064 ]
Troelsen KB, Nielsen EO, Mirza NR: Chronic treatment with duloxetine is necessary for an anxiolytic-like response in the mouse zero maze: the role of the serotonin transporter. Psychopharmacology (Berl). 2005 Oct;181(4):741-50. Epub 2005 Sep 29. [PubMed:16032412 ]
Gould GG, Javors MA, Frazer A: Effect of chronic administration of duloxetine on serotonin and norepinephrine transporter binding sites in rat brain. Biol Psychiatry. 2007 Jan 15;61(2):210-5. Epub 2006 May 2. [PubMed:16650830 ]
Mirza NR, Nielsen EO, Troelsen KB: Serotonin transporter density and anxiolytic-like effects of antidepressants in mice. Prog Neuropsychopharmacol Biol Psychiatry. 2007 May 9;31(4):858-66. Epub 2007 Jan 30. [PubMed:17335951 ]
Vaishnavi SN, Nemeroff CB, Plott SJ, Rao SG, Kranzler J, Owens MJ: Milnacipran: a comparative analysis of human monoamine uptake and transporter binding affinity. Biol Psychiatry. 2004 Feb 1;55(3):320-2. [PubMed:14744476 ]
Beique JC, Lavoie N, de Montigny C, Debonnel G: Affinities of venlafaxine and various reuptake inhibitors for the serotonin and norepinephrine transporters. Eur J Pharmacol. 1998 May 15;349(1):129-32. [PubMed:9669506 ]
Karpa KD, Cavanaugh JE, Lakoski JM: Duloxetine pharmacology: profile of a dual monoamine modulator. CNS Drug Rev. 2002 Winter;8(4):361-76. [PubMed:12481192 ]
van Groeningen CJ, Peters GJ, Pinedo HM: Lack of effectiveness of combined 5-fluorouracil and leucovorin in patients with 5-fluorouracil-resistant advanced colorectal cancer. Eur J Cancer Clin Oncol. 1989 Jan;25(1):45-9. [PubMed:2784100 ]
Jost W, Marsalek P: Duloxetine: mechanism of action at the lower urinary tract and Onuf's nucleus. Clin Auton Res. 2004 Aug;14(4):220-7. [PubMed:15316838 ]
Trivedi MH, Desaiah D, Ossanna MJ, Pritchett YL, Brannan SK, Detke MJ: Clinical evidence for serotonin and norepinephrine reuptake inhibition of duloxetine. Int Clin Psychopharmacol. 2008 May;23(3):161-9. doi: 10.1097/YIC.0b013e3282f41d7e. [PubMed:18408530 ]
Bymaster FP, Lee TC, Knadler MP, Detke MJ, Iyengar S: The dual transporter inhibitor duloxetine: a review of its preclinical pharmacology, pharmacokinetic profile, and clinical results in depression. Curr Pharm Des. 2005;11(12):1475-93. [PubMed:15892657 ]
Khullar V, Cardozo L, Dmochowski R: Mixed incontinence: current evidence and future perspectives. Neurourol Urodyn. 2010 Apr;29(4):618-22. doi: 10.1002/nau.20907. [PubMed:20432324 ]
Carter NJ, McCormack PL: Duloxetine: a review of its use in the treatment of generalized anxiety disorder. CNS Drugs. 2009;23(6):523-41. doi: 10.2165/00023210-200923060-00006. [PubMed:19480470 ]
Hunziker ME, Suehs BT, Bettinger TL, Crismon ML: Duloxetine hydrochloride: a new dual-acting medication for the treatment of major depressive disorder. Clin Ther. 2005 Aug;27(8):1126-43. [PubMed:16199241 ]

Showing metabocard for Duloxetine (HMDB0014619)

MOL for HMDB0014619 (Duloxetine)

3D MOL for HMDB0014619 (Duloxetine)

3D SDF for HMDB0014619 (Duloxetine)

3D-SDF for HMDB0014619 (Duloxetine)

PDB for HMDB0014619 (Duloxetine)

3D PDB for HMDB0014619 (Duloxetine)

SMILES for HMDB0014619 (Duloxetine)

INCHI for HMDB0014619 (Duloxetine)

Structure for HMDB0014619 (Duloxetine)

3D Structure for HMDB0014619 (Duloxetine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

Transporters

References

References