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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (27)transporters (1) Show 28 proteins XML

enzymes (27)transporters (1) Show 28 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-10-17 11:25:30 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005038

Secondary Accession Numbers

HMDB05038

Metabolite Identification

Common Name

Citalopram

Description

Citalopram is an antidepressant drug used to treat depression associated with mood disorders. It is also used on occasion in the treatment of body dysmorphic disorder and anxiety; Citalopram belongs to a class of drugs known as selective serotonin reuptake inhibitors (SSRIs). It is sold under the brand-names Celexa (U.S., Forest Laboratories, Inc.), Cipramil, Seropram (Europe and Australia) and Ciazil (Australia); A furancarbonitrile that is one of the serotonin uptake inhibitors used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from tardive dyskinesia in preference to tricyclic antidepressants, which aggravate this condition; Citalopram is an antidepressant drug used to treat depression associated with mood disorders. It is also used on occasion in the treatment of body dysmorphic disorder and anxiety. Citalopram belongs to a class of drugs known as selective serotonin reuptake inhibitors (SSRIs).

Structure

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

HMDB0243676
     RDKit          3D
(R)-Citalopram
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.6502   -1.2072   -0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3352   -0.5517   -0.2069 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4664    0.7053   -0.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0068   -0.3273    1.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6261    0.2665    1.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6678   -0.7311    0.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7777   -0.3008    0.7862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5569   -1.4101    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4209   -1.6408   -1.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1061   -2.6510   -1.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9418   -3.4291   -1.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6495   -4.4496   -1.6494 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0867   -3.2072    0.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3908   -2.1921    0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2256   -0.1186    2.0690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3355    0.6951    1.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9892    1.6233    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4075    2.8671    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9154    3.5097   -0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734    4.8282   -1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7387    5.8743   -1.3603 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9459    2.8635   -1.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5056    1.6018   -0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247    0.9857    0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0859   -1.3310    0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4962   -2.2289   -0.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2841   -0.6407   -0.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7461    0.4407   -1.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5232    1.2366   -0.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3316    1.2640   -0.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0814   -1.3077    1.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7631    0.3291    1.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5539    1.2477    0.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4149    0.4443    2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7951   -1.7023    1.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9255   -0.8966   -0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7593   -1.0314   -1.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9998   -2.8357   -2.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7696   -3.8566    0.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5310   -2.0511    1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5511    1.2328    2.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2695    0.1967    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1602    3.3515    1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5676    3.3828   -2.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2463    1.1520   -1.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  3  0
 19 22  2  0
 22 23  1  0
 23 24  2  0
 24  7  1  0
 14  8  1  0
 24 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  9 37  1  0
 10 38  1  0
 13 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 22 44  1  0
 23 45  1  0
M  END

215
  Mrv1652305271900062D          

 24 26  0  0  1  0            999 V2000
    7.9618    1.5353    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.7701   -1.0638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1681    1.5162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.3013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2886   -0.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0351    0.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2284    0.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9569    0.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2886   -1.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9748    1.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8721    0.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7100   -0.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5404    1.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3783    0.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2935    1.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9145    2.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150    0.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  2  5  1  0  0  0  0
  2 11  1  0  0  0  0
  3 12  1  0  0  0  0
  3 22  1  0  0  0  0
  3 23  1  0  0  0  0
  4 24  3  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  2  0  0  0  0
  7 13  1  0  0  0  0
  8 11  1  0  0  0  0
  8 14  1  0  0  0  0
  9 12  1  0  0  0  0
 10 15  2  0  0  0  0
 10 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 17 18  1  0  0  0  0
 18 24  1  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005038

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3

> <INCHI_KEY>
WSEQXVZVJXJVFP-UHFFFAOYSA-N

> <FORMULA>
C20H21FN2O

> <MOLECULAR_WEIGHT>
324.3919

> <EXACT_MASS>
324.163791509

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
35.29621323231018

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile

> <ALOGPS_LOGP>
3.58

> <JCHEM_LOGP>
3.764304206333334

> <ALOGPS_LOGS>
-4.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.784977656720883

> <JCHEM_POLAR_SURFACE_AREA>
36.26

> <JCHEM_REFRACTIVITY>
94.0202

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
recital

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0243676
     RDKit          3D
(R)-Citalopram
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.6502   -1.2072   -0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3352   -0.5517   -0.2069 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4664    0.7053   -0.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0068   -0.3273    1.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6261    0.2665    1.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6678   -0.7311    0.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7777   -0.3008    0.7862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5569   -1.4101    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4209   -1.6408   -1.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1061   -2.6510   -1.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9418   -3.4291   -1.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6495   -4.4496   -1.6494 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0867   -3.2072    0.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3908   -2.1921    0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2256   -0.1186    2.0690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3355    0.6951    1.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9892    1.6233    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4075    2.8671    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9154    3.5097   -0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734    4.8282   -1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7387    5.8743   -1.3603 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9459    2.8635   -1.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5056    1.6018   -0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247    0.9857    0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0859   -1.3310    0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4962   -2.2289   -0.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2841   -0.6407   -0.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7461    0.4407   -1.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5232    1.2366   -0.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3316    1.2640   -0.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0814   -1.3077    1.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7631    0.3291    1.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5539    1.2477    0.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4149    0.4443    2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7951   -1.7023    1.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9255   -0.8966   -0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7593   -1.0314   -1.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9998   -2.8357   -2.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7696   -3.8566    0.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5310   -2.0511    1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5511    1.2328    2.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2695    0.1967    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1602    3.3515    1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5676    3.3828   -2.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2463    1.1520   -1.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  3  0
 19 22  2  0
 22 23  1  0
 23 24  2  0
 24  7  1  0
 14  8  1  0
 24 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  9 37  1  0
 10 38  1  0
 13 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 22 44  1  0
 23 45  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 215                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  F   UNK     0      14.862   2.866   0.000  0.00  0.00           F+0
HETATM    2  O   UNK     0      10.771  -1.986   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.914   2.830   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       3.080  -4.296   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       9.872  -0.746   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.399   0.719   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415  -1.216   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415  -2.756   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.893   1.042   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.120   0.157   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.872  -3.225   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.420   2.507   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -0.446   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -3.526   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.961   1.689   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.525  -0.472   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.747  -1.216   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.747  -2.756   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.209   2.591   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.773   0.431   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.615   1.963   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.440   4.296   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.881   1.688   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.414  -3.526   0.000  0.00  0.00           C+0
CONECT    1   21                                                            
CONECT    2    5   11                                                       
CONECT    3   12   22   23                                                  
CONECT    4   24                                                            
CONECT    5    2    6    7   10                                             
CONECT    6    5    9                                                       
CONECT    7    5    8   13                                                  
CONECT    8    7   11   14                                                  
CONECT    9    6   12                                                       
CONECT   10    5   15   16                                                  
CONECT   11    2    8                                                       
CONECT   12    3    9                                                       
CONECT   13    7   17                                                       
CONECT   14    8   18                                                       
CONECT   15   10   19                                                       
CONECT   16   10   20                                                       
CONECT   17   13   18                                                       
CONECT   18   14   17   24                                                  
CONECT   19   15   21                                                       
CONECT   20   16   21                                                       
CONECT   21    1   19   20                                                  
CONECT   22    3                                                            
CONECT   23    3                                                            
CONECT   24    4   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0243676
HETATM    1  C1  UNL     1       4.650  -1.207  -0.308  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.335  -0.552  -0.207  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.466   0.705  -0.942  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.007  -0.327   1.189  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.626   0.266   1.325  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.668  -0.731   0.721  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.778  -0.301   0.786  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.557  -1.410   0.151  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.421  -1.641  -1.194  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.106  -2.651  -1.833  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.942  -3.429  -1.064  1.00  0.00           C  
HETATM   12  F1  UNL     1      -3.650  -4.450  -1.649  1.00  0.00           F  
HETATM   13  C11 UNL     1      -3.087  -3.207   0.287  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.391  -2.192   0.899  1.00  0.00           C  
HETATM   15  O1  UNL     1      -1.226  -0.119   2.069  1.00  0.00           O  
HETATM   16  C13 UNL     1      -2.335   0.695   1.993  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.989   1.623   0.876  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.407   2.867   0.480  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.915   3.510  -0.624  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.373   4.828  -1.024  1.00  0.00           C  
HETATM   21  N2  UNL     1      -2.739   5.874  -1.360  1.00  0.00           N  
HETATM   22  C18 UNL     1      -0.946   2.864  -1.372  1.00  0.00           C  
HETATM   23  C19 UNL     1      -0.506   1.602  -0.990  1.00  0.00           C  
HETATM   24  C20 UNL     1      -1.025   0.986   0.129  1.00  0.00           C  
HETATM   25  H1  UNL     1       5.086  -1.331   0.724  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.496  -2.229  -0.717  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.284  -0.641  -0.991  1.00  0.00           H  
HETATM   28  H4  UNL     1       3.746   0.441  -1.991  1.00  0.00           H  
HETATM   29  H5  UNL     1       2.523   1.237  -0.938  1.00  0.00           H  
HETATM   30  H6  UNL     1       4.332   1.264  -0.510  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.081  -1.308   1.694  1.00  0.00           H  
HETATM   32  H8  UNL     1       3.763   0.329   1.672  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.554   1.248   0.822  1.00  0.00           H  
HETATM   34  H10 UNL     1       1.415   0.444   2.401  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.795  -1.702   1.239  1.00  0.00           H  
HETATM   36  H12 UNL     1       0.925  -0.897  -0.338  1.00  0.00           H  
HETATM   37  H13 UNL     1      -0.759  -1.031  -1.823  1.00  0.00           H  
HETATM   38  H14 UNL     1      -2.000  -2.836  -2.900  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.770  -3.857   0.871  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.531  -2.051   1.973  1.00  0.00           H  
HETATM   41  H17 UNL     1      -2.551   1.233   2.940  1.00  0.00           H  
HETATM   42  H18 UNL     1      -3.270   0.197   1.689  1.00  0.00           H  
HETATM   43  H19 UNL     1      -3.160   3.352   1.073  1.00  0.00           H  
HETATM   44  H20 UNL     1      -0.568   3.383  -2.240  1.00  0.00           H  
HETATM   45  H21 UNL     1       0.246   1.152  -1.614  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4
CONECT    3   28   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7   35   36
CONECT    7    8   15   24
CONECT    8    9    9   14
CONECT    9   10   37
CONECT   10   11   11   38
CONECT   11   12   13
CONECT   13   14   14   39
CONECT   14   40
CONECT   15   16
CONECT   16   17   41   42
CONECT   17   18   18   24
CONECT   18   19   43
CONECT   19   20   22   22
CONECT   20   21   21   21
CONECT   22   23   44
CONECT   23   24   24   45
END

HMDB0243676
     RDKit          3D
(R)-Citalopram
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.6502   -1.2072   -0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3352   -0.5517   -0.2069 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4664    0.7053   -0.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0068   -0.3273    1.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6261    0.2665    1.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6678   -0.7311    0.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7777   -0.3008    0.7862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5569   -1.4101    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4209   -1.6408   -1.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1061   -2.6510   -1.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9418   -3.4291   -1.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6495   -4.4496   -1.6494 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0867   -3.2072    0.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3908   -2.1921    0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2256   -0.1186    2.0690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3355    0.6951    1.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9892    1.6233    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4075    2.8671    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9154    3.5097   -0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734    4.8282   -1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7387    5.8743   -1.3603 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9459    2.8635   -1.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5056    1.6018   -0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247    0.9857    0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0859   -1.3310    0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4962   -2.2289   -0.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2841   -0.6407   -0.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7461    0.4407   -1.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5232    1.2366   -0.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3316    1.2640   -0.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0814   -1.3077    1.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7631    0.3291    1.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5539    1.2477    0.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4149    0.4443    2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7951   -1.7023    1.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9255   -0.8966   -0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7593   -1.0314   -1.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9998   -2.8357   -2.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7696   -3.8566    0.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5310   -2.0511    1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5511    1.2328    2.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2695    0.1967    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1602    3.3515    1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5676    3.3828   -2.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2463    1.1520   -1.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  3  0
 19 22  2  0
 22 23  1  0
 23 24  2  0
 24  7  1  0
 14  8  1  0
 24 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  9 37  1  0
 10 38  1  0
 13 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 22 44  1  0
 23 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Citadur	Kegg
Bonitrile	HMDB
Celexa	HMDB
Citalopram hydrobromide	HMDB
Nitalapram	HMDB
Escitalopram	HMDB
Cytalopram	HMDB
Lexapro	HMDB
Escitalopram oxalate	HMDB
Seropram	HMDB

Chemical Formula

C₂₀H₂₁FN₂O

Average Molecular Weight

324.3919

Monoisotopic Molecular Weight

324.163791509

IUPAC Name

1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile

Traditional Name

recital

CAS Registry Number

59729-33-8

SMILES

CN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

InChI Identifier

InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3

InChI Key

WSEQXVZVJXJVFP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylbutylamines

Direct Parent

Phenylbutylamines

Alternative Parents

Substituents

Phenylbutylamine
Isocoumaran
Fluorobenzene
Halobenzene
Aralkylamine
Aryl halide
Aryl fluoride
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Dialkyl ether
Ether
Carbonitrile
Nitrile
Organoheterocyclic compound
Organic oxygen compound
Organopnictogen compound
Amine
Organohalogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:77397 )
tertiary amino compound (CHEBI:77397 )
2-benzofurans (CHEBI:77397 )
nitrile (CHEBI:77397 )
cyclic ether (CHEBI:77397 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Gastrointestinal disorder

Vomiting (HMDB: HMDB0005038)
Nausea (HMDB: HMDB0005038)

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Insomnia (HMDB: HMDB0005038)
Confusion (HMDB: HMDB0005038)

Tremor (HMDB: HMDB0005038)

Renal system and urinary system

Renal disorder

Renal failure (HMDB: HMDB0005038)

Circulatory system disorder

Cardiac disorder

Sinus tachycardia (HMDB: HMDB0005038)

Disposition

Biological location

Cellular element

Platelet (HMDB: HMDB0005038)

Organ

Brain (HMDB: HMDB0005038)
Liver (HMDB: HMDB0005038)

Cell

Hematocyte

Platelet (HMDB: HMDB0005038)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Cellular substructure

Membrane (HMDB: HMDB0005038)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0005038)

Source

Exogenous

Environmental

Wastewater (HMDB: HMDB0005038)

Process

Naturally occurring process

Biological process

Biochemical pathway

Citalopram Action Pathway (HMDB: HMDB0005038)

Drug action pathway

Citalopram Action Pathway (PathBank: SMP0000424)

Metabolic pathway

Citalopram Metabolism Pathway (PathBank: SMP0000627)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	178 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	180.1	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0059 g/L	ALOGPS
logP	3.58	ALOGPS
logP	3.76	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	9.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	36.26 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	94.02 m³·mol⁻¹	ChemAxon
Polarizability	35.3 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	182.758	30932474
DeepCCS	[M-H]-	180.4	30932474
DeepCCS	[M-2H]-	213.567	30932474
DeepCCS	[M+Na]+	188.944	30932474
AllCCS	[M+H]+	176.9	32859911
AllCCS	[M+H-H2O]+	173.7	32859911
AllCCS	[M+NH4]+	179.9	32859911
AllCCS	[M+Na]+	180.8	32859911
AllCCS	[M-H]-	183.7	32859911
AllCCS	[M+Na-2H]-	183.5	32859911
AllCCS	[M+HCOO]-	183.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citalopram	CN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1	3391.0	Standard polar	33892256
Citalopram	CN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1	2504.7	Standard non polar	33892256
Citalopram	CN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1	2397.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Citalopram GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-6190000000-9c092c583199a2a486ef	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citalopram GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citalopram GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citalopram GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9110000000-5b1fde1b7a58929c7f2d	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 - Citalopram LC-ESI-QTOF , positive-QTOF	splash10-004i-0009000000-589e7ae88aee7da0e0bd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-QTOF , positive-QTOF	splash10-004i-0029000000-8fd40dc922da5ab2c8b0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-QTOF , positive-QTOF	splash10-03di-0291000000-c60cbea4e4e6acbb4599	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-QTOF , positive-QTOF	splash10-00l2-0290000000-f2131534473e56b3c8a7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-QTOF , positive-QTOF	splash10-00mk-0390000000-e6cd61150feeca1d2867	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-ITFT , positive-QTOF	splash10-03di-0291000000-ff658bd6b54adccbaf03	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-ITFT , positive-QTOF	splash10-004i-0009000000-67fa40aabd862948aaf3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-ITFT , positive-QTOF	splash10-004i-0129000000-60abdaff2f5d8f72e271	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-ITFT , positive-QTOF	splash10-0bt9-0981000000-1eba423765a46f1dd6b9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0980000000-514f2e0bb73903b25b90	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0970000000-f27f46e3a573498d9f9b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0980000000-5ba355c707bc5008c067	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-ITFT , positive-QTOF	splash10-004i-0009000000-a115136f2084cc2a6a47	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-ITFT , positive-QTOF	splash10-004i-0129000000-474ae50db9e74e5a31be	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-ITFT , positive-QTOF	splash10-0bt9-0981000000-011dbb85d8e791486397	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0970000000-99aedc452f996b9c9113	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0980000000-c8734dde2a469350af7c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0970000000-cff11d70160f94e8fc2e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Citalopram LC-ESI-ITFT , positive-QTOF	splash10-03di-0391000000-e7862ea10a18e5771adc	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram 10V, Positive-QTOF	splash10-004i-1029000000-b0f10b0f7897ca083ed5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram 20V, Positive-QTOF	splash10-003r-2294000000-5935fccdd160458bb836	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram 40V, Positive-QTOF	splash10-00di-9740000000-7a3a98de78c385feae56	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram 10V, Negative-QTOF	splash10-00di-0019000000-84c6ddc8fad411d8541f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram 20V, Negative-QTOF	splash10-00di-1029000000-d4716f92fec4a098ef2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram 40V, Negative-QTOF	splash10-0005-5290000000-45334fd57d41c1fadf1a	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Brain
Liver
Platelet

Pathways

Name	SMPDB/PathBank	KEGG
Citalopram Action Pathway		Not Available
Citalopram Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

DB00215

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023605

KNApSAcK ID

Not Available

Chemspider ID

2669

KEGG Compound ID

C07572

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Citalopram

METLIN ID

1781

PubChem Compound

2771

PDB ID

Not Available

ChEBI ID

77397

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Petersen, Hans; Bogeso, Klaus Peter; Bech Sommer, Michael. Lundbeck A/S, Method for the preparation of citalopram. PCT Int. Appl. (1998), 16 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Horak EL, Jenkins AJ: Postmortem tissue distribution of olanzapine and citalopram in a drug intoxication. J Forensic Sci. 2005 May;50(3):679-81. [PubMed:15932107 ]
Gleason OC, Yates WR, Isbell MD, Philipsen MA: An open-label trial of citalopram for major depression in patients with hepatitis C. J Clin Psychiatry. 2002 Mar;63(3):194-8. [PubMed:11926717 ]
Blardi P, de Lalla A, Urso R, Auteri A, Dell'Erba A, Bossini L, Castrogiovanni P: Activity of citalopram on adenosine and serotonin circulating levels in depressed patients. J Clin Psychopharmacol. 2005 Jun;25(3):262-6. [PubMed:15876907 ]
Bhagwagar Z, Hafizi S, Cowen PJ: Acute citalopram administration produces correlated increases in plasma and salivary cortisol. Psychopharmacology (Berl). 2002 Aug;163(1):118-20. Epub 2002 Jun 27. [PubMed:12185409 ]
Nikisch G, Mathe AA, Czernik A, Eap CB, Jimenez-Vasquez P, Brawand-Amey M, Baumann P: Stereoselective metabolism of citalopram in plasma and cerebrospinal fluid of depressive patients: relationship with 5-HIAA in CSF and clinical response. J Clin Psychopharmacol. 2004 Jun;24(3):283-90. [PubMed:15118482 ]
Anastos N, McIntyre IM, Lynch MJ, Drummer OH: Postmortem concentrations of citalopram. J Forensic Sci. 2002 Jul;47(4):882-4. [PubMed:12137000 ]
Lapatto-Reiniluoto O, Kivisto KT, Neuvonen PJ: Effect of activated charcoal alone or given after gastric lavage in reducing the absorption of diazepam, ibuprofen and citalopram. Br J Clin Pharmacol. 1999 Aug;48(2):148-53. [PubMed:10417490 ]
Worm K, Dragsholt C, Simonsen KW, Kringsholm B: [Citalopram in forensic samples. Citalopram concentrations in samples from legal autopsies and from living persons in connection with traffic accidents or cases of violence in Denmark 1989-1996]. Ugeskr Laeger. 1999 Jul 26;161(30):4291-2. [PubMed:10439690 ]
Jensen PN, Olesen OV, Bertelsen A, Linnet K: Citalopram and desmethylcitalopram concentrations in breast milk and in serum of mother and infant. Ther Drug Monit. 1997 Apr;19(2):236-9. [PubMed:9108657 ]
Schmidt K, Olesen OV, Jensen PN: Citalopram and breast-feeding: serum concentration and side effects in the infant. Biol Psychiatry. 2000 Jan 15;47(2):164-5. [PubMed:10664835 ]
Rochat B, Kosel M, Boss G, Testa B, Gillet M, Baumann P: Stereoselective biotransformation of the selective serotonin reuptake inhibitor citalopram and its demethylated metabolites by monoamine oxidases in human liver. Biochem Pharmacol. 1998 Jul 1;56(1):15-23. [PubMed:9698084 ]
Kristoffersen L, Bugge A, Lundanes E, Slordal L: Simultaneous determination of citalopram, fluoxetine, paroxetine and their metabolites in plasma and whole blood by high-performance liquid chromatography with ultraviolet and fluorescence detection. J Chromatogr B Biomed Sci Appl. 1999 Nov 12;734(2):229-46. [PubMed:10595721 ]
Nordeng H, Bergsholm YK, Bohler E, Spigset O: [The transfer of selective serotonin reuptake inhibitors to human milk]. Tidsskr Nor Laegeforen. 2001 Jan 20;121(2):199-203. [PubMed:11475200 ]
Plenge P, Mellerup ET: [3H]citalopram binding to brain and platelet membranes of human and rat. J Neurochem. 1991 Jan;56(1):248-52. [PubMed:1824783 ]
Nikisch G, Mathe AA, Czernik A, Thiele J, Bohner J, Eap CB, Agren H, Baumann P: Long-term citalopram administration reduces responsiveness of HPA axis in patients with major depression: relationship with S-citalopram concentrations in plasma and cerebrospinal fluid (CSF) and clinical response. Psychopharmacology (Berl). 2005 Oct;181(4):751-60. Epub 2005 Sep 29. [PubMed:15988572 ]
Spigset O, Hagg S, Stegmayr B, Dahlqvist R: Citalopram pharmacokinetics in patients with chronic renal failure and the effect of haemodialysis. Eur J Clin Pharmacol. 2000 Dec;56(9-10):699-703. [PubMed:11214779 ]
Anderer P, Saletu B, Semlitsch HV, Pascual-Marqui RD: Perceptual and cognitive event-related potentials in neuropsychopharmacology: methodological aspects and clinical applications (pharmaco-ERP topography and tomography). Methods Find Exp Clin Pharmacol. 2002;24 Suppl C:121-37. [PubMed:12575494 ]
Kosel M, Gnerre C, Voirol P, Amey M, Rochat B, Bouras C, Testa B, Baumann P: In vitro biotransformation of the selective serotonin reuptake inhibitor citalopram, its enantiomers and demethylated metabolites by monoamine oxidase in rat and human brain preparations. Mol Psychiatry. 2002;7(2):181-8. [PubMed:11840311 ]
Spigset O, Wilhelmsson C, Mjorndal T, Eriksson S: Low serum sodium concentrations during treatment with citalopram in elderly patients: relationship to serum citalopram levels and to platelet serotonin 5-HT2A receptor status. J Clin Psychopharmacol. 2000 Oct;20(5):582-4. [PubMed:11001247 ]

Only showing the first 10 proteins. There are 28 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Reactions

Citalopram + Oxygen + Water → Citalopram aldehyde + Dimethylamine + Hydrogen peroxide	details

Enzyme Details

2. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Reactions

Citalopram + Oxygen + Water → Citalopram aldehyde + Dimethylamine + Hydrogen peroxide	details

Enzyme Details

3. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Enzyme Details

4. 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

Enzyme Details

5. Cytochrome P450 2C19

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

Enzyme Details

6. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

Enzyme Details

7. Cytochrome P450 3A43

General function:: Involved in monooxygenase activity
Specific function:: Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:: CYP3A43
Uniprot ID:: Q9HB55
Molecular weight:: 57756.285

Enzyme Details

8. Cytochrome P450 1B1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:: CYP1B1
Uniprot ID:: Q16678
Molecular weight:: 60845.33

Enzyme Details

9. 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

Enzyme Details

10. Cytochrome P450 2C18

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP2C18
Uniprot ID:: P33260
Molecular weight:: 55710.075

Transporters

Enzyme Details

1. 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

Only showing the first 10 proteins. There are 28 proteins in total.

Show all enzymes and transporters

Showing metabocard for Citalopram (HMDB0005038)

MOL for HMDB0005038 (Citalopram)

3D MOL for HMDB0005038 (Citalopram)

3D SDF for HMDB0005038 (Citalopram)

3D-SDF for HMDB0005038 (Citalopram)

PDB for HMDB0005038 (Citalopram)

3D PDB for HMDB0005038 (Citalopram)

SMILES for HMDB0005038 (Citalopram)

INCHI for HMDB0005038 (Citalopram)

Structure for HMDB0005038 (Citalopram)

3D Structure for HMDB0005038 (Citalopram)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Transporters