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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (10)transporters (3) Show 13 proteins XML

enzymes (10)transporters (3) Show 13 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:46 UTC

HMDB ID

HMDB0014853

Secondary Accession Numbers

HMDB14853

Metabolite Identification

Common Name

Paroxetine

Description

Paroxetine hydrochloride and paroxetine mesylate belong to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). Despite distinct structural differences between compounds in this class, SSRIs possess similar pharmacological activity. As with other antidepressant agents, several weeks of therapy may be required before a clinical effect is seen. SSRIs are potent inhibitors of neuronal serotonin reuptake. They have little to no effect on norepinephrine or dopamine reuptake and do not antagonize α- or β-adrenergic, dopamine D₂ or histamine H₁ receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT_1A and terminal autoreceptors. Chronic use leads to desensitization of somatodendritic 5-HT_1A and terminal autoreceptors. The overall clinical effect of increased mood and decreased anxiety is thought to be due to adaptive changes in neuronal function that leads to enhanced serotonergic neurotransmission. Side effects include dry mouth, nausea, dizziness, drowsiness, sexual dysfunction and headache (see Toxicity section below for a complete listing of side effects). Side effects generally occur during the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Paroxetine hydrochloride and mesylate are considered therapeutic alternatives rather than generic equivalents by the US Food and Drug Administration (FDA); both agents contain the same active moiety (i.e. paroxetine), but are formulated as different salt forms. Clinical studies establishing the efficacy of paroxetine in various conditions were performed using paroxetine hydrochloride. Since both agents contain the same active moiety, the clinical efficacy of both agents is thought to be similar. Paroxetine may be used to treat major depressive disorder (MDD), panic disorder with or without agoraphobia, obsessive-compulsive disorder (OCD), social anxiety disorder (social phobia), generalized anxiety disorder (GAD), post-traumatic stress disorder (PTSD) and premenstrual dysphoric disorder (PMDD). Paroxetine has the most evidence supporting its use for anxiety-related disorders of the SSRIs. It has the greatest anticholinergic activity of the agents in this class and compared to other SSRIs, paroxetine may cause greater weight gain, sexual dysfunction, sedation and constipation.

Structure

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

HMDB0014853
     RDKit          3D
Paroxetine
 44 47  0  0  0  0  0  0  0  0999 V2000
    3.5664    4.4912   -1.4288 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.2868    3.2514   -0.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2563    3.0560    0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9723    1.7975    0.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7252    0.7617    0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4231   -0.5792    0.6049 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4886   -1.5955    0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1434   -2.8735    0.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8585   -3.3517    0.5330 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375   -2.3952    0.9259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027   -1.1247    0.1443 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0383   -0.1626    0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115   -0.7706   -0.0888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4619   -0.1715   -0.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964    1.0932    0.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8404    1.7220    0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9739    1.0745    0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8506   -0.1864   -0.4434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5996   -0.7941   -0.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1262   -0.5742   -0.8274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0652    0.3144   -0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3034    1.4738    0.0404 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7535    0.9477   -1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0371    2.2051   -1.8137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4521    3.8756    1.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4398   -0.5560    1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4989   -1.2426    0.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3068   -1.8297   -0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9973   -2.5242    2.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9221   -3.6304    0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8618   -3.3882   -0.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1832   -2.7718    0.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9844   -2.1617    2.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1763   -1.3596   -0.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2077    0.7827   -0.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1725    0.1056    1.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7077    1.5816    0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9378    2.6997    0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4886   -1.7763   -0.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4514   -0.0950    0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8577    0.5497   -0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5540    0.1109   -2.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0621    2.3632   -2.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
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  7  8  1  0
  8  9  1  0
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 11 12  1  0
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 13 14  1  0
 14 15  2  0
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 17 18  1  0
 18 19  2  0
 18 20  1  0
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 21 22  1  0
  5 23  1  0
 23 24  2  0
 24  2  1  0
 11  6  1  0
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 22 17  1  0
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  6 27  1  1
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 19 40  1  0
 21 41  1  0
 21 42  1  0
 23 43  1  0
 24 44  1  0
M  END

715
  Mrv0541 02231214572D          

 24 27  0  0  1  0            999 V2000
    2.3645   -2.7308    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.9818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4321    0.8206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4321   -0.5071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.2193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.5693    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0791    0.9818    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6500    0.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9136    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 11  1  0  0  0  0
  2 17  1  0  0  0  0
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  8 10  1  0  0  0  0
 12 13  2  0  0  0  0
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 16 18  1  0  0  0  0
 17 19  2  0  0  0  0
 17 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 23  2  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014853

> <DATABASE_NAME>
hmdb

> <SMILES>
FC1=CC=C(C=C1)[C@@H]1CCNC[C@H]1COC1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H20FNO3/c20-15-3-1-13(2-4-15)17-7-8-21-10-14(17)11-22-16-5-6-18-19(9-16)24-12-23-18/h1-6,9,14,17,21H,7-8,10-12H2/t14-,17-/m0/s1

> <INCHI_KEY>
AHOUBRCZNHFOSL-YOEHRIQHSA-N

> <FORMULA>
C19H20FNO3

> <MOLECULAR_WEIGHT>
329.3654

> <EXACT_MASS>
329.142721716

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.482378819581655

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4R)-3-[(2H-1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
3.1482486886666656

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.774978204323723

> <JCHEM_POLAR_SURFACE_AREA>
39.72

> <JCHEM_REFRACTIVITY>
88.02370000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.53e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
paroxetine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014853
     RDKit          3D
Paroxetine
 44 47  0  0  0  0  0  0  0  0999 V2000
    3.5664    4.4912   -1.4288 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.2868    3.2514   -0.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2563    3.0560    0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9723    1.7975    0.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7252    0.7617    0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4231   -0.5792    0.6049 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4886   -1.5955    0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1434   -2.8735    0.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8585   -3.3517    0.5330 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375   -2.3952    0.9259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027   -1.1247    0.1443 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0383   -0.1626    0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115   -0.7706   -0.0888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4619   -0.1715   -0.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964    1.0932    0.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8404    1.7220    0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9739    1.0745    0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8506   -0.1864   -0.4434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5996   -0.7941   -0.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1262   -0.5742   -0.8274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0652    0.3144   -0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3034    1.4738    0.0404 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7535    0.9477   -1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0371    2.2051   -1.8137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4521    3.8756    1.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9516    1.6571    2.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4398   -0.5560    1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4989   -1.2426    0.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3068   -1.8297   -0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9973   -2.5242    2.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9221   -3.6304    0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8618   -3.3882   -0.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9844   -2.1617    2.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1763   -1.3596   -0.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2077    0.7827   -0.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1725    0.1056    1.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7077    1.5816    0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9378    2.6997    0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4886   -1.7763   -0.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4514   -0.0950    0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8577    0.5497   -0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5540    0.1109   -2.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0621    2.3632   -2.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
  5 23  1  0
 23 24  2  0
 24  2  1  0
 11  6  1  0
 19 14  1  0
 22 17  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  1
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  6
 12 36  1  0
 12 37  1  0
 15 38  1  0
 16 39  1  0
 19 40  1  0
 21 41  1  0
 21 42  1  0
 23 43  1  0
 24 44  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 715                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       4.414  -5.097   0.000  0.00  0.00           F+0
HETATM    2  O   UNK     0       8.415   1.833   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.873   1.532   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.873  -0.947   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       4.414   4.143   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.414   1.063   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748   1.833   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080   1.833   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748   3.373   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080   3.373   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   1.063   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -0.477   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748  -1.247   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -1.247   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.748  -2.787   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080  -2.787   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748   1.063   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414  -3.557   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.082   1.833   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.748  -0.477   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.416   1.063   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.416  -0.477   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.082  -1.247   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.772   0.293   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2   11   17                                                       
CONECT    3   21   24                                                       
CONECT    4   22   24                                                       
CONECT    5    9   10                                                       
CONECT    6    7    8   12                                                  
CONECT    7    6    9   11                                                  
CONECT    8    6   10                                                       
CONECT    9    5    7                                                       
CONECT   10    5    8                                                       
CONECT   11    2    7                                                       
CONECT   12    6   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   18                                                       
CONECT   16   14   18                                                       
CONECT   17    2   19   20                                                  
CONECT   18    1   15   16                                                  
CONECT   19   17   21                                                       
CONECT   20   17   23                                                       
CONECT   21    3   19   22                                                  
CONECT   22    4   21   23                                                  
CONECT   23   20   22                                                       
CONECT   24    3    4                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0014853
HETATM    1  F1  UNL     1       3.566   4.491  -1.429  1.00  0.00           F  
HETATM    2  C1  UNL     1       3.287   3.251  -0.932  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.256   3.056   0.433  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.972   1.797   0.912  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.725   0.762   0.048  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.423  -0.579   0.605  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.489  -1.595   0.198  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.143  -2.873   0.974  1.00  0.00           C  
HETATM    9  N1  UNL     1       1.859  -3.352   0.533  1.00  0.00           N  
HETATM   10  C8  UNL     1       0.837  -2.395   0.926  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.103  -1.125   0.144  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.038  -0.163   0.375  1.00  0.00           C  
HETATM   13  O1  UNL     1      -1.212  -0.771  -0.089  1.00  0.00           O  
HETATM   14  C11 UNL     1      -2.462  -0.171  -0.036  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.596   1.093   0.496  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.840   1.722   0.562  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.974   1.074   0.088  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.851  -0.186  -0.443  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.600  -0.794  -0.500  1.00  0.00           C  
HETATM   20  O2  UNL     1      -6.126  -0.574  -0.827  1.00  0.00           O  
HETATM   21  C17 UNL     1      -7.065   0.314  -0.257  1.00  0.00           C  
HETATM   22  O3  UNL     1      -6.303   1.474   0.040  1.00  0.00           O  
HETATM   23  C18 UNL     1       2.754   0.948  -1.318  1.00  0.00           C  
HETATM   24  C19 UNL     1       3.037   2.205  -1.814  1.00  0.00           C  
HETATM   25  H1  UNL     1       3.452   3.876   1.135  1.00  0.00           H  
HETATM   26  H2  UNL     1       2.952   1.657   2.008  1.00  0.00           H  
HETATM   27  H3  UNL     1       2.440  -0.556   1.712  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.499  -1.243   0.408  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.307  -1.830  -0.877  1.00  0.00           H  
HETATM   30  H6  UNL     1       2.997  -2.524   2.037  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.922  -3.630   0.898  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.862  -3.388  -0.492  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.183  -2.772   0.733  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.984  -2.162   2.010  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.176  -1.360  -0.925  1.00  0.00           H  
HETATM   36  H12 UNL     1       0.208   0.783  -0.180  1.00  0.00           H  
HETATM   37  H13 UNL     1      -0.172   0.106   1.423  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.708   1.582   0.859  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.938   2.700   0.974  1.00  0.00           H  
HETATM   40  H16 UNL     1      -3.489  -1.776  -0.912  1.00  0.00           H  
HETATM   41  H17 UNL     1      -7.451  -0.095   0.699  1.00  0.00           H  
HETATM   42  H18 UNL     1      -7.858   0.550  -0.983  1.00  0.00           H  
HETATM   43  H19 UNL     1       2.554   0.111  -2.009  1.00  0.00           H  
HETATM   44  H20 UNL     1       3.062   2.363  -2.886  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3   24
CONECT    3    4   25
CONECT    4    5    5   26
CONECT    5    6   23
CONECT    6    7   11   27
CONECT    7    8   28   29
CONECT    8    9   30   31
CONECT    9   10   32
CONECT   10   11   33   34
CONECT   11   12   35
CONECT   12   13   36   37
CONECT   13   14
CONECT   14   15   15   19
CONECT   15   16   38
CONECT   16   17   17   39
CONECT   17   18   22
CONECT   18   19   19   20
CONECT   19   40
CONECT   20   21
CONECT   21   22   41   42
CONECT   23   24   24   43
CONECT   24   44
END

HMDB0014853
     RDKit          3D
Paroxetine
 44 47  0  0  0  0  0  0  0  0999 V2000
    3.5664    4.4912   -1.4288 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.2868    3.2514   -0.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2563    3.0560    0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9723    1.7975    0.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7252    0.7617    0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4231   -0.5792    0.6049 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4886   -1.5955    0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1434   -2.8735    0.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8585   -3.3517    0.5330 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375   -2.3952    0.9259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027   -1.1247    0.1443 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0383   -0.1626    0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115   -0.7706   -0.0888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4619   -0.1715   -0.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964    1.0932    0.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8404    1.7220    0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9739    1.0745    0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8506   -0.1864   -0.4434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5996   -0.7941   -0.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1262   -0.5742   -0.8274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0652    0.3144   -0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3034    1.4738    0.0404 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7535    0.9477   -1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0371    2.2051   -1.8137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4521    3.8756    1.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9516    1.6571    2.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4398   -0.5560    1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4989   -1.2426    0.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3068   -1.8297   -0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9973   -2.5242    2.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9221   -3.6304    0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8618   -3.3882   -0.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1832   -2.7718    0.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9844   -2.1617    2.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1763   -1.3596   -0.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2077    0.7827   -0.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1725    0.1056    1.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7077    1.5816    0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9378    2.6997    0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4886   -1.7763   -0.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4514   -0.0950    0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8577    0.5497   -0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5540    0.1109   -2.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0621    2.3632   -2.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
  5 23  1  0
 23 24  2  0
 24  2  1  0
 11  6  1  0
 19 14  1  0
 22 17  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  1
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  6
 12 36  1  0
 12 37  1  0
 15 38  1  0
 16 39  1  0
 19 40  1  0
 21 41  1  0
 21 42  1  0
 23 43  1  0
 24 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-(3S,4R)-4-(p-Fluorophenyl)-3-((3,4-(methylenedioxy)phenoxy)methyl)piperidine	ChEBI
(3S-trans)-3-((1,3-Benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine	ChEBI
Paroxetina	ChEBI
Paroxetinum	ChEBI
Hydrochloride hemihydrate, paroxetine	HMDB
Hydrochloride, hemihydrate paroxetine	HMDB
Acetate, paroxetine	HMDB
Maleate, paroxetine	HMDB
Paroxetine acetate	HMDB
Paroxetine hydrochloride hemihydrate	HMDB
Paroxetine, trans-(+)-isomer	HMDB
Seroxat	HMDB
Aropax	HMDB
Hemihydrate paroxetine hydrochloride	HMDB
Paroxetine hydrochloride anhydrous	HMDB
Paroxetine, cis-(+)-isomer	HMDB
Paxil	HMDB
Anhydrous, paroxetine hydrochloride	HMDB
Hemihydrate, paroxetine hydrochloride	HMDB
Hydrochloride anhydrous, paroxetine	HMDB
Hydrochloride, paroxetine	HMDB
Paroxetine hydrochloride	HMDB
Paroxetine hydrochloride, hemihydrate	HMDB
Paroxetine maleate	HMDB
Paroxetine, cis-(-)-isomer	HMDB

Chemical Formula

C₁₉H₂₀FNO₃

Average Molecular Weight

329.3654

Monoisotopic Molecular Weight

329.142721716

IUPAC Name

(3S,4R)-3-[(2H-1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine

Traditional Name

paroxetine

CAS Registry Number

61869-08-7

SMILES

FC1=CC=C(C=C1)[C@@H]1CCNC[C@H]1COC1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C19H20FNO3/c20-15-3-1-13(2-4-15)17-7-8-21-10-14(17)11-22-16-5-6-18-19(9-16)24-12-23-18/h1-6,9,14,17,21H,7-8,10-12H2/t14-,17-/m0/s1

InChI Key

AHOUBRCZNHFOSL-YOEHRIQHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Phenylpiperidines

Direct Parent

Phenylpiperidines

Alternative Parents

Substituents

Phenylpiperidine
Benzodioxole
Alkyl aryl ether
Fluorobenzene
Halobenzene
Aralkylamine
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Ether
Secondary aliphatic amine
Acetal
Oxacycle
Secondary amine
Azacycle
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

piperidines (CHEBI:7936 )
organofluorine compound (CHEBI:7936 )
aromatic ether (CHEBI:7936 )
benzodioxoles (CHEBI:7936 )

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: HMDB0014853)

Source

Exogenous

Exogenous (HMDB: HMDB0014853)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Antidepressant (HMDB: HMDB0014853)

Pharmaceutical industry

Anxiolytic drug (HMDB: HMDB0014853)

Biological role

Hepatotoxic agent (HMDB: HMDB0014853)
Serotonin uptake inhibitor (HMDB: HMDB0014853)

Modulator

Inhibitor

P450 inhibitor (HMDB: HMDB0014853)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	129 - 131 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0085 g/L	Not Available
LogP	3.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	183.2	30932474
[M+H]+	Not Available	181.07	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001065

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0085 g/L	ALOGPS
logP	3.1	ALOGPS
logP	3.15	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	9.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	39.72 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.02 m³·mol⁻¹	ChemAxon
Polarizability	34.48 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	178.745	30932474
DeepCCS	[M-H]-	176.387	30932474
DeepCCS	[M-2H]-	210.265	30932474
DeepCCS	[M+Na]+	185.493	30932474
AllCCS	[M+H]+	177.6	32859911
AllCCS	[M+H-H2O]+	174.5	32859911
AllCCS	[M+NH4]+	180.5	32859911
AllCCS	[M+Na]+	181.4	32859911
AllCCS	[M-H]-	180.7	32859911
AllCCS	[M+Na-2H]-	180.3	32859911
AllCCS	[M+HCOO]-	179.9	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.	5.44 minutes	32390414
Predicted by Siyang on May 30, 2022	11.5681 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.75 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	75.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1533.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	245.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	176.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	189.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	124.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	430.3 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	440.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	457.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	951.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	421.6 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	1266.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	312.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	318.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	380.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	250.5 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	30.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Paroxetine	FC1=CC=C(C=C1)[C@@H]1CCNC[C@H]1COC1=CC2=C(OCO2)C=C1	3569.6	Standard polar	33892256
Paroxetine	FC1=CC=C(C=C1)[C@@H]1CCNC[C@H]1COC1=CC2=C(OCO2)C=C1	2626.4	Standard non polar	33892256
Paroxetine	FC1=CC=C(C=C1)[C@@H]1CCNC[C@H]1COC1=CC2=C(OCO2)C=C1	2653.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Paroxetine,1TMS,isomer #1	C[Si](C)(C)N1CC[C@@H](C2=CC=C(F)C=C2)[C@H](COC2=CC=C3OCOC3=C2)C1	2699.6	Semi standard non polar	33892256
Paroxetine,1TMS,isomer #1	C[Si](C)(C)N1CC[C@@H](C2=CC=C(F)C=C2)[C@H](COC2=CC=C3OCOC3=C2)C1	2813.8	Standard non polar	33892256
Paroxetine,1TMS,isomer #1	C[Si](C)(C)N1CC[C@@H](C2=CC=C(F)C=C2)[C@H](COC2=CC=C3OCOC3=C2)C1	3559.2	Standard polar	33892256
Paroxetine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CC[C@@H](C2=CC=C(F)C=C2)[C@H](COC2=CC=C3OCOC3=C2)C1	2950.8	Semi standard non polar	33892256
Paroxetine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CC[C@@H](C2=CC=C(F)C=C2)[C@H](COC2=CC=C3OCOC3=C2)C1	3011.1	Standard non polar	33892256
Paroxetine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CC[C@@H](C2=CC=C(F)C=C2)[C@H](COC2=CC=C3OCOC3=C2)C1	3702.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Paroxetine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f9i-1911000000-12c3e68d4fb152fcf19a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Paroxetine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-8900000000-0a273deac3c7836cdc76	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paroxetine LC-ESI-QTOF , positive-QTOF	splash10-001i-3709000000-7d029049c2e6d638ecbe	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paroxetine LC-ESI-QFT , positive-QTOF	splash10-001i-2409000000-077fb077fbf0e4210f51	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paroxetine 10V, Positive-QTOF	splash10-001i-0009000000-56cd88a7bae65159b40e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paroxetine 40V, Positive-QTOF	splash10-00di-9300000000-95d57654f38599951250	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paroxetine -1V, Positive-QTOF	splash10-001i-3609000000-814e80528f9dde6c33a5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paroxetine 20V, Positive-QTOF	splash10-001l-6809000000-6461647e2077c359be2e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paroxetine 35V, Positive-QTOF	splash10-001l-2906000000-a8c78adc02d4f098ec53	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paroxetine 35V, Positive-QTOF	splash10-001i-2309000000-dae2fa8b8f5f0d2d9c83	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paroxetine 10V, Positive-QTOF	splash10-001i-0409000000-034c664e49ac69cc6701	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paroxetine 20V, Positive-QTOF	splash10-0uel-1915000000-1cceed9b83dba502dc39	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paroxetine 40V, Positive-QTOF	splash10-0006-6900000000-a45d96d1002ba6a0049e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paroxetine 10V, Negative-QTOF	splash10-004i-0409000000-7b0c408204b05629f155	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paroxetine 20V, Negative-QTOF	splash10-002r-1829000000-c76de0eff9bcad218ff4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paroxetine 40V, Negative-QTOF	splash10-000i-4900000000-77810e81d9b6e4cb0cf7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paroxetine 10V, Positive-QTOF	splash10-001i-0409000000-52ccb63e39824262697a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paroxetine 20V, Positive-QTOF	splash10-001r-0915000000-6663900bf83beabe3f50	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paroxetine 40V, Positive-QTOF	splash10-004r-0901000000-7e65658f2aa91b98e293	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paroxetine 10V, Negative-QTOF	splash10-000i-0903000000-8712cfe4d48fe9ccd484	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paroxetine 20V, Negative-QTOF	splash10-004r-0927000000-031f43eecdb967cf56ae	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paroxetine 40V, Negative-QTOF	splash10-0a4i-1900000000-6adcbe9a9b2a0603a1ce	2021-10-11	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 DB00715	21059682	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00715	21059682	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

DB00715

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

39888

KEGG Compound ID

C07415

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Paroxetine

METLIN ID

Not Available

PubChem Compound

43815

PDB ID

Not Available

ChEBI ID

7936

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

Baldwin DS, Anderson IM, Nutt DJ, Bandelow B, Bond A, Davidson JR, den Boer JA, Fineberg NA, Knapp M, Scott J, Wittchen HU: Evidence-based guidelines for the pharmacological treatment of anxiety disorders: recommendations from the British Association for Psychopharmacology. J Psychopharmacol. 2005 Nov;19(6):567-96. [PubMed:16272179 ]
Yonkers KA, Gullion C, Williams A, Novak K, Rush AJ: Paroxetine as a treatment for premenstrual dysphoric disorder. J Clin Psychopharmacol. 1996 Feb;16(1):3-8. [PubMed:8834412 ]
Waldinger MD, Hengeveld MW, Zwinderman AH, Olivier B: Effect of SSRI antidepressants on ejaculation: a double-blind, randomized, placebo-controlled study with fluoxetine, fluvoxamine, paroxetine, and sertraline. J Clin Psychopharmacol. 1998 Aug;18(4):274-81. [PubMed:9690692 ]
Baldwin D, Bobes J, Stein DJ, Scharwachter I, Faure M: Paroxetine in social phobia/social anxiety disorder. Randomised, double-blind, placebo-controlled study. Paroxetine Study Group. Br J Psychiatry. 1999 Aug;175:120-6. [PubMed:10627793 ]
Waldinger MD, Zwinderman AH, Olivier B: SSRIs and ejaculation: a double-blind, randomized, fixed-dose study with paroxetine and citalopram. J Clin Psychopharmacol. 2001 Dec;21(6):556-60. [PubMed:11763001 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 2C9

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

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. 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

Urichuk L, Prior TI, Dursun S, Baker G: Metabolism of atypical antipsychotics: involvement of cytochrome p450 enzymes and relevance for drug-drug interactions. Curr Drug Metab. 2008 Jun;9(5):410-8. [PubMed:18537577 ]
Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. [PubMed:8968657 ]
Ozdemir V, Naranjo CA, Herrmann N, Reed K, Sellers EM, Kalow W: Paroxetine potentiates the central nervous system side effects of perphenazine: contribution of cytochrome P4502D6 inhibition in vivo. Clin Pharmacol Ther. 1997 Sep;62(3):334-47. [PubMed:9333110 ]
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 2B6

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. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

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 2C8

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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

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. 5-hydroxytryptamine receptor 2A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

References

Bixo M, Allard P, Backstrom T, Mjorndal T, Nyberg S, Spigset O, Sundstrom-Poromaa I: Binding of [3H]paroxetine to serotonin uptake sites and of [3H]lysergic acid diethylamide to 5-HT2A receptors in platelets from women with premenstrual dysphoric disorder during gonadotropin releasing hormone treatment. Psychoneuroendocrinology. 2001 Aug;26(6):551-64. [PubMed:11403977 ]
Meyer JH, Kapur S, Eisfeld B, Brown GM, Houle S, DaSilva J, Wilson AA, Rafi-Tari S, Mayberg HS, Kennedy SH: The effect of paroxetine on 5-HT(2A) receptors in depression: an [(18)F]setoperone PET imaging study. Am J Psychiatry. 2001 Jan;158(1):78-85. [PubMed:11136637 ]

Enzyme Details

6. Muscarinic acetylcholine receptor M3

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM3
Uniprot ID:: P20309
Molecular weight:: 66127.4

References

Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]

Enzyme Details

7. Muscarinic acetylcholine receptor M1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM1
Uniprot ID:: P11229
Molecular weight:: 51420.4

References

Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]

Enzyme Details

8. Muscarinic acetylcholine receptor M2

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
Gene Name:: CHRM2
Uniprot ID:: P08172
Molecular weight:: 51714.6

References

Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]

Enzyme Details

9. Muscarinic acetylcholine receptor M4

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase
Gene Name:: CHRM4
Uniprot ID:: P08173
Molecular weight:: 53048.7

References

Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]

Enzyme Details

10. Muscarinic acetylcholine receptor M5

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM5
Uniprot ID:: P08912
Molecular weight:: 60073.2

References

Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Weiss J, Dormann SM, Martin-Facklam M, Kerpen CJ, Ketabi-Kiyanvash N, Haefeli WE: Inhibition of P-glycoprotein by newer antidepressants. J Pharmacol Exp Ther. 2003 Apr;305(1):197-204. [PubMed:12649369 ]

Enzyme Details

2. 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

Rubin RT: Paroxetine binding to the rat norepinephrine transporter in vivo. Biol Psychiatry. 2000 Nov 1;48(9):954-6. [PubMed:11203183 ]
Gilmor ML, Owens MJ, Nemeroff CB: Inhibition of norepinephrine uptake in patients with major depression treated with paroxetine. Am J Psychiatry. 2002 Oct;159(10):1702-10. [PubMed:12359676 ]
Nemeroff CB, Owens MJ: Neuropharmacology of paroxetine. Psychopharmacol Bull. 2003 Spring;37 Suppl 1:8-18. [PubMed:14566196 ]
Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]

Enzyme Details

3. 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

Scholze P, Zwach J, Kattinger A, Pifl C, Singer EA, Sitte HH: Transporter-mediated release: a superfusion study on human embryonic kidney cells stably expressing the human serotonin transporter. J Pharmacol Exp Ther. 2000 Jun;293(3):870-8. [PubMed:10869387 ]
Preuss UW, Soyka M, Bahlmann M, Wenzel K, Behrens S, de Jonge S, Kruger M, Bondy B: Serotonin transporter gene regulatory region polymorphism (5-HTTLPR), [3H]paroxetine binding in healthy control subjects and alcohol-dependent patients and their relationships to impulsivity. Psychiatry Res. 2000 Sep 25;96(1):51-61. [PubMed:10980326 ]
Haughey HM, Fleckenstein AE, Metzger RR, Hanson GR: The effects of methamphetamine on serotonin transporter activity: role of dopamine and hyperthermia. J Neurochem. 2000 Oct;75(4):1608-17. [PubMed:10987842 ]
Pollock BG, Ferrell RE, Mulsant BH, Mazumdar S, Miller M, Sweet RA, Davis S, Kirshner MA, Houck PR, Stack JA, Reynolds CF, Kupfer DJ: Allelic variation in the serotonin transporter promoter affects onset of paroxetine treatment response in late-life depression. Neuropsychopharmacology. 2000 Nov;23(5):587-90. [PubMed:11027924 ]
Wihlback AC, Sundstrom-Poromaa I, Allard P, Mjorndal T, Spigset O, Backstrom T: Influence of postmenopausal hormone replacement therapy on platelet serotonin uptake site and serotonin 2A receptor binding. Obstet Gynecol. 2001 Sep;98(3):450-7. [PubMed:11530128 ]
Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Showing metabocard for Paroxetine (HMDB0014853)

MOL for HMDB0014853 (Paroxetine)

3D MOL for HMDB0014853 (Paroxetine)

3D SDF for HMDB0014853 (Paroxetine)

3D-SDF for HMDB0014853 (Paroxetine)

PDB for HMDB0014853 (Paroxetine)

3D PDB for HMDB0014853 (Paroxetine)

SMILES for HMDB0014853 (Paroxetine)

INCHI for HMDB0014853 (Paroxetine)

Structure for HMDB0014853 (Paroxetine)

3D Structure for HMDB0014853 (Paroxetine)

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

References

References

References

References

References

References

References

Transporters

References

References

References