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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (12)transporters (3) Show 15 proteins XML

enzymes (12)transporters (3) Show 15 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014620

Secondary Accession Numbers

HMDB14620

Metabolite Identification

Common Name

Chlorpromazine

Description

Chlorpromazine, also known as thorazine or aminazine, belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring. A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety. Chlorpromazine is a drug which is used for the treatment of schizophrenia; to control nausea and vomiting; for relief of restlessness and apprehension before surgery; for acute intermittent porphyria; as an adjunct in the treatment of tetanus; to control the manifestations of the manic type of manic-depressive illness; for relief of intractable hiccups; for the treatment of severe behavioral problems in children (1 to 12 years of age) marked by combativeness and/or explosive hyperexcitable behavior (out of proportion to immediate provocations), and in the short-term treatment of hyperactive children who show excessive motor activity with accompanying conduct disorders consisting of some or all of the following symptoms: impulsivity, difficulty sustaining attention, aggressivity, mood lability, and poor frustration tolerance. Chlorpromazine is a very strong basic compound (based on its pKa). Chlorpromazine is a potentially toxic compound.

Structure

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

HMDB0014620
     RDKit          3D
Chlorpromazine
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.8874   -0.4892    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6168   -0.3916   -0.6613 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6597    0.7976   -1.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5703   -0.3083    0.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1995   -0.2026   -0.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1890   -0.1219    0.8474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1758   -0.0442    0.3677 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7312   -1.2651   -0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9651   -2.4379   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4361   -3.6519   -0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7063   -3.7292   -1.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4856   -2.6023   -1.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9851   -1.4113   -0.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617    0.0319   -0.7362 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1415    1.3780   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7659    2.5762   -0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1301    3.6780    0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8575    3.5431    0.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9622    4.9020    1.6193 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1887    2.3233    0.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8509    1.2022    0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7439   -0.8212    1.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3834    0.5234    0.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5717   -1.2215   -0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691    0.9193   -2.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8091    1.6561   -0.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5914    0.7194   -2.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7433    0.6373    0.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6683   -1.1606    1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9729   -0.8970   -1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2124    0.8199   -0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2925   -1.0466    1.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5395    0.7136    1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332   -2.4494    0.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8203   -4.5447   -0.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0951   -4.6720   -1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5036   -2.6185   -1.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7949    2.7386   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6209    4.6489    0.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1751    2.2781    1.2966 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
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21  7  1  0
 13  8  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 16 38  1  0
 17 39  1  0
 20 40  1  0
M  END

477
  Mrv0541 02231214422D          

 21 23  0  0  0  0            999 V2000
    6.4919   -0.7592    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6957   -2.3625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6957   -0.7784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3239    1.5978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6957    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098    0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098    1.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3817   -1.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098   -1.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3817   -1.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098   -1.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0898   -0.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3018   -0.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0898   -2.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3018   -2.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6380    1.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3239    2.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8075   -1.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841   -1.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8075   -1.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841   -1.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 10  1  0  0  0  0
  2 11  1  0  0  0  0
  3  5  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4  7  1  0  0  0  0
  4 16  1  0  0  0  0
  4 17  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8 10  2  0  0  0  0
  8 12  1  0  0  0  0
  9 11  1  0  0  0  0
  9 13  2  0  0  0  0
 10 14  1  0  0  0  0
 11 15  2  0  0  0  0
 12 18  2  0  0  0  0
 13 19  1  0  0  0  0
 14 20  2  0  0  0  0
 15 21  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014620

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C17H19ClN2S/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20/h3-4,6-9,12H,5,10-11H2,1-2H3

> <INCHI_KEY>
ZPEIMTDSQAKGNT-UHFFFAOYSA-N

> <FORMULA>
C17H19ClN2S

> <MOLECULAR_WEIGHT>
318.864

> <EXACT_MASS>
318.095747015

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
35.10071114378624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[3-(2-chloro-10H-phenothiazin-10-yl)propyl]dimethylamine

> <ALOGPS_LOGP>
5.18

> <JCHEM_LOGP>
4.535000242333334

> <ALOGPS_LOGS>
-4.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.196976785801306

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
93.75630000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.17e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chlorpromazine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014620
     RDKit          3D
Chlorpromazine
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.8874   -0.4892    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6168   -0.3916   -0.6613 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6597    0.7976   -1.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5703   -0.3083    0.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1995   -0.2026   -0.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1890   -0.1219    0.8474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1758   -0.0442    0.3677 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7312   -1.2651   -0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9651   -2.4379   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4361   -3.6519   -0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7063   -3.7292   -1.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4856   -2.6023   -1.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9851   -1.4113   -0.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617    0.0319   -0.7362 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1415    1.3780   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7659    2.5762   -0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1301    3.6780    0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8575    3.5431    0.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9622    4.9020    1.6193 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1887    2.3233    0.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8509    1.2022    0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7439   -0.8212    1.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3834    0.5234    0.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5717   -1.2215   -0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691    0.9193   -2.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8091    1.6561   -0.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5914    0.7194   -2.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7433    0.6373    0.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6683   -1.1606    1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9729   -0.8970   -1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2124    0.8199   -0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2925   -1.0466    1.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5395    0.7136    1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332   -2.4494    0.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8203   -4.5447   -0.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0951   -4.6720   -1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5036   -2.6185   -1.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7949    2.7386   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6209    4.6489    0.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1751    2.2781    1.2966 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
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21  7  1  0
 13  8  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 16 38  1  0
 17 39  1  0
 20 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 477                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      12.118  -1.417   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0       6.899  -4.410   0.000  0.00  0.00           S+0
HETATM    3  N   UNK     0       6.899  -1.453   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       4.338   2.983   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.899   0.026   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.618   0.765   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.618   2.243   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.179  -2.192   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.618  -2.192   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.179  -3.671   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.618  -3.671   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.501  -1.402   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.297  -1.402   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.501  -4.461   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.297  -4.461   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.058   2.243   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.338   4.461   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.841  -2.161   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.957  -2.161   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.841  -3.702   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.957  -3.702   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2   10   11                                                       
CONECT    3    5    8    9                                                  
CONECT    4    7   16   17                                                  
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    4    6                                                       
CONECT    8    3   10   12                                                  
CONECT    9    3   11   13                                                  
CONECT   10    2    8   14                                                  
CONECT   11    2    9   15                                                  
CONECT   12    8   18                                                       
CONECT   13    9   19                                                       
CONECT   14   10   20                                                       
CONECT   15   11   21                                                       
CONECT   16    4                                                            
CONECT   17    4                                                            
CONECT   18    1   12   20                                                  
CONECT   19   13   21                                                       
CONECT   20   14   18                                                       
CONECT   21   15   19                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0014620
HETATM    1  C1  UNL     1       4.887  -0.489   0.030  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.617  -0.392  -0.661  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.660   0.798  -1.490  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.570  -0.308   0.326  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.200  -0.203  -0.293  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.189  -0.122   0.847  1.00  0.00           C  
HETATM    7  N2  UNL     1      -1.176  -0.044   0.368  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.731  -1.265  -0.142  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.965  -2.438  -0.117  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.436  -3.652  -0.584  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.706  -3.729  -1.099  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.486  -2.602  -1.139  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.985  -1.411  -0.666  1.00  0.00           C  
HETATM   14  S1  UNL     1      -4.062   0.032  -0.736  1.00  0.00           S  
HETATM   15  C12 UNL     1      -3.142   1.378  -0.052  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.766   2.576  -0.011  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.130   3.678   0.494  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.857   3.543   0.954  1.00  0.00           C  
HETATM   19 CL1  UNL     1      -0.962   4.902   1.619  1.00  0.00          CL  
HETATM   20  C16 UNL     1      -1.189   2.323   0.925  1.00  0.00           C  
HETATM   21  C17 UNL     1      -1.851   1.202   0.406  1.00  0.00           C  
HETATM   22  H1  UNL     1       4.744  -0.821   1.081  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.383   0.523   0.094  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.572  -1.221  -0.447  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.769   0.919  -2.126  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.809   1.656  -0.783  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.591   0.719  -2.104  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.743   0.637   0.910  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.668  -1.161   1.025  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.973  -0.897  -1.082  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.212   0.820  -0.811  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.292  -1.047   1.485  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.540   0.714   1.454  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.033  -2.449   0.281  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.820  -4.545  -0.552  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.095  -4.672  -1.471  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.504  -2.618  -1.541  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.795   2.739  -0.370  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.621   4.649   0.533  1.00  0.00           H  
HETATM   40  H19 UNL     1      -0.175   2.278   1.297  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4
CONECT    3   25   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8   21
CONECT    8    9    9   13
CONECT    9   10   34
CONECT   10   11   11   35
CONECT   11   12   36
CONECT   12   13   13   37
CONECT   13   14
CONECT   14   15
CONECT   15   16   16   21
CONECT   16   17   38
CONECT   17   18   18   39
CONECT   18   19   20
CONECT   20   21   21   40
END

HMDB0014620
     RDKit          3D
Chlorpromazine
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.8874   -0.4892    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6168   -0.3916   -0.6613 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6597    0.7976   -1.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5703   -0.3083    0.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1995   -0.2026   -0.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1890   -0.1219    0.8474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1758   -0.0442    0.3677 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7312   -1.2651   -0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9651   -2.4379   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4361   -3.6519   -0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7063   -3.7292   -1.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4856   -2.6023   -1.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9851   -1.4113   -0.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617    0.0319   -0.7362 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1415    1.3780   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7659    2.5762   -0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1301    3.6780    0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8575    3.5431    0.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9622    4.9020    1.6193 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1887    2.3233    0.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8509    1.2022    0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7439   -0.8212    1.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3834    0.5234    0.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5717   -1.2215   -0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691    0.9193   -2.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8091    1.6561   -0.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5914    0.7194   -2.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7433    0.6373    0.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6683   -1.1606    1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9729   -0.8970   -1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2124    0.8199   -0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2925   -1.0466    1.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5395    0.7136    1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332   -2.4494    0.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8203   -4.5447   -0.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0951   -4.6720   -1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5036   -2.6185   -1.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7949    2.7386   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6209    4.6489    0.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1751    2.2781    1.2966 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
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21  7  1  0
 13  8  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 16 38  1  0
 17 39  1  0
 20 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(2-Chloro-10H-phenothiazin-10-yl)-N,N-dimethyl-1-propanamine	ChEBI
3-(2-Chlorophenothiazin-10-yl)-N,N-dimethyl-propan-1-amine	ChEBI
Aminazine	ChEBI
Chlorderazin	ChEBI
Chloropromazine	ChEBI
Chlorpromados	ChEBI
Chlorpromazinum	ChEBI
Clorpromazina	ChEBI
Contomin	ChEBI
CPZ	ChEBI
Largactil	ChEBI
N-(3-Dimethylaminopropyl)-3-chlorophenothiazine	ChEBI
Thorazine	ChEBI
Chlorazine	HMDB
Propaphenin	HMDB
Chlorpromazine hydrochloride	HMDB
Fenactil	HMDB
Chlordelazine	HMDB
Hydrochloride, chlorpromazine	HMDB

Chemical Formula

C₁₇H₁₉ClN₂S

Average Molecular Weight

318.864

Monoisotopic Molecular Weight

318.095747015

IUPAC Name

[3-(2-chloro-10H-phenothiazin-10-yl)propyl]dimethylamine

Traditional Name

chlorpromazine

CAS Registry Number

50-53-3

SMILES

CN(C)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2

InChI Identifier

InChI=1S/C17H19ClN2S/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20/h3-4,6-9,12H,5,10-11H2,1-2H3

InChI Key

ZPEIMTDSQAKGNT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Phenothiazines

Direct Parent

Phenothiazines

Alternative Parents

Substituents

Phenothiazine
Alkyldiarylamine
Diarylthioether
Aryl thioether
Tertiary aliphatic/aromatic amine
Para-thiazine
Aryl chloride
Aryl halide
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Azacycle
Thioether
Organic nitrogen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:3647 )
tertiary amine (CHEBI:3647 )
organochlorine compound (CHEBI:3647 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0042 g/L	Not Available
LogP	4.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	170.6	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0042 g/L	ALOGPS
logP	5.18	ALOGPS
logP	4.54	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	9.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.76 m³·mol⁻¹	ChemAxon
Polarizability	35.1 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]+	167.798	30932474
DeepCCS	[M-H]-	165.44	30932474
DeepCCS	[M-2H]-	198.326	30932474
DeepCCS	[M+Na]+	173.891	30932474
AllCCS	[M+H]+	170.5	32859911
AllCCS	[M+H-H2O]+	167.5	32859911
AllCCS	[M+NH4]+	173.4	32859911
AllCCS	[M+Na]+	174.2	32859911
AllCCS	[M-H]-	170.9	32859911
AllCCS	[M+Na-2H]-	170.2	32859911
AllCCS	[M+HCOO]-	169.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chlorpromazine	CN(C)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2	3562.6	Standard polar	33892256
Chlorpromazine	CN(C)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2	2478.0	Standard non polar	33892256
Chlorpromazine	CN(C)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2	2499.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Chlorpromazine EI-B (Non-derivatized)	splash10-0a4r-9053000000-9e1cc1d4fc6be5bc73b8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Chlorpromazine CI-B (Non-derivatized)	splash10-014i-2019000000-54e008f9fc11d7f45b68	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Chlorpromazine CI-B (Non-derivatized)	splash10-000i-9070000000-9bbe6c5123c891b9489b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Chlorpromazine EI-B (Non-derivatized)	splash10-0a4r-9053000000-9e1cc1d4fc6be5bc73b8	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Chlorpromazine CI-B (Non-derivatized)	splash10-014i-2019000000-54e008f9fc11d7f45b68	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Chlorpromazine CI-B (Non-derivatized)	splash10-000i-9070000000-9bbe6c5123c891b9489b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorpromazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-9161000000-fb3a39cba2075363c833	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorpromazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorpromazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9231000000-ed14fee152701eacf689	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 - Chlorpromazine LC-ESI-QTOF , positive-QTOF	splash10-014i-0019000000-0028b3984b4c35e44def	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine LC-ESI-QTOF , positive-QTOF	splash10-0002-0090000000-800bf68c2158920c3f30	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine LC-ESI-QTOF , positive-QTOF	splash10-03dj-0090000000-649e773296a3ecec2b04	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine LC-ESI-QTOF , positive-QTOF	splash10-03di-0190000000-7404aac4e28621b4f60a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine , positive-QTOF	splash10-01b9-0019000000-993566c51e802e754da2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine 15V, Positive-QTOF	splash10-014i-1009000000-9e085e0019e6d749bec7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine 30V, Positive-QTOF	splash10-000i-9001000000-63215388b62ecefa2319	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine 60V, Positive-QTOF	splash10-0a4r-9000000000-0a622181e8ef22e69347	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine 75V, Negative-QTOF	splash10-07vi-9100000000-c781f19efbf7f5bc080e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine 90V, Negative-QTOF	splash10-014i-9000000000-a19b19eaa8aa053f7de7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine 45V, Positive-QTOF	splash10-052r-9000000000-7c7616a9c48b6deec4ce	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine 40V, Positive-QTOF	splash10-03dj-0090000000-649e773296a3ecec2b04	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine 60V, Negative-QTOF	splash10-066r-9200000000-6c03747eb04ed227c0fc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine 45V, Negative-QTOF	splash10-0a4i-0390000000-3ba26439eefecf96a16d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine 50V, Positive-QTOF	splash10-03di-0190000000-911db04bc44a18aa9bcc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine 30V, Positive-QTOF	splash10-0002-0090000000-800bf68c2158920c3f30	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine 20V, Positive-QTOF	splash10-014i-0009000000-ed71cd0c4716568b4ed8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine 50V, Positive-QTOF	splash10-03di-0190000000-7404aac4e28621b4f60a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpromazine 15V, Negative-QTOF	splash10-0a4l-0890000000-0864e24ac7a3c6e8e6c1	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpromazine 10V, Positive-QTOF	splash10-014i-1029000000-7e34879597957c9ee39f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpromazine 20V, Positive-QTOF	splash10-01bi-9076000000-5e7e6025c08ddac427f2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpromazine 40V, Positive-QTOF	splash10-059f-9320000000-af8b418201e78097c537	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpromazine 10V, Negative-QTOF	splash10-014i-0019000000-86aa9bde1ce82c180318	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpromazine 20V, Negative-QTOF	splash10-0aor-0393000000-613da71e073b4dd78512	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpromazine 40V, Negative-QTOF	splash10-001j-3890000000-a4243a809dea08eb0af6	2016-08-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
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 DB00477	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00477	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00477

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2625

KEGG Compound ID

C06906

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chlorpromazine

METLIN ID

Not Available

PubChem Compound

2726

PDB ID

Z80

ChEBI ID

3647

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)

Download (PDF)

General References

Leucht S, Wahlbeck K, Hamann J, Kissling W: New generation antipsychotics versus low-potency conventional antipsychotics: a systematic review and meta-analysis. Lancet. 2003 May 10;361(9369):1581-9. [PubMed:12747876 ]

Only showing the first 10 proteins. There are 15 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:: BCHE
Uniprot ID:: P06276
Molecular weight:: 68417.575

References

Nasello AG, Gidali D, Felicio LF: A comparative study of the anticholinesterase activity of several antipsychotic agents. Pharmacol Biochem Behav. 2003 Jul;75(4):895-901. [PubMed:12957233 ]
Muraoka S, Miura T: Inactivation of cholinesterase induced by chlorpromazine cation radicals. Pharmacol Toxicol. 2003 Feb;92(2):100-4. [PubMed:12747580 ]
Spinedi A, Pacini L, Limatola C, Luly P, Farias RN: A study of human erythrocyte acetylcholinesterase inhibition by chlorpromazine. Biochem J. 1991 Sep 1;278 ( Pt 2):461-3. [PubMed:1654884 ]

Enzyme Details

2. Cytochrome P450 3A4

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

References

Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015 ]
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 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

References

Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015 ]
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 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

Micallef J, Fakra E, Blin O: [Use of antidepressant drugs in schizophrenic patients with depression]. Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9. [PubMed:16910628 ]
Otani K, Aoshima T: Pharmacogenetics of classical and new antipsychotic drugs. Ther Drug Monit. 2000 Feb;22(1):118-21. [PubMed:10688273 ]
Yoshii K, Kobayashi K, Tsumuji M, Tani M, Shimada N, Chiba K: Identification of human cytochrome P450 isoforms involved in the 7-hydroxylation of chlorpromazine by human liver microsomes. Life Sci. 2000;67(2):175-84. [PubMed:10901285 ]
Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Yoshii K, Kobayashi K, Tsumuji M, Tani M, Shimada N, Chiba K: Identification of human cytochrome P450 isoforms involved in the 7-hydroxylation of chlorpromazine by human liver microsomes. Life Sci. 2000;67(2):175-84. [PubMed:10901285 ]
Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. D(2) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD2
Uniprot ID:: P14416
Molecular weight:: 50618.9

References

Oades RD, Rao ML, Bender S, Sartory G, Muller BW: Neuropsychological and conditioned blocking performance in patients with schizophrenia: assessment of the contribution of neuroleptic dose, serum levels and dopamine D2-receptor occupancy. Behav Pharmacol. 2000 Jun;11(3-4):317-30. [PubMed:11103886 ]
Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]
Wu S, Xing Q, Gao R, Li X, Gu N, Feng G, He L: Response to chlorpromazine treatment may be associated with polymorphisms of the DRD2 gene in Chinese schizophrenic patients. Neurosci Lett. 2005 Mar 7;376(1):1-4. Epub 2004 Dec 2. [PubMed:15694263 ]
Wu SN, Gao R, Xing QH, Li HF, Shen YF, Gu NF, Feng GY, He L: Association of DRD2 polymorphisms and chlorpromazine-induced extrapyramidal syndrome in Chinese schizophrenic patients. Acta Pharmacol Sin. 2006 Aug;27(8):966-70. [PubMed:16867246 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Seeman P: Dopamine D2 receptors as treatment targets in schizophrenia. Clin Schizophr Relat Psychoses. 2010 Apr;4(1):56-73. doi: 10.3371/CSRP.4.1.5. [PubMed:20643630 ]

Enzyme Details

7. 5-hydroxytryptamine receptor 1A

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. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1A
Uniprot ID:: P08908
Molecular weight:: 46106.3

References

Cosi C, Koek W: Agonist, antagonist, and inverse agonist properties of antipsychotics at human recombinant 5-HT(1A) receptors expressed in HeLa cells. Eur J Pharmacol. 2001 Dec 14;433(1):55-62. [PubMed:11755134 ]
Newman-Tancredi A, Gavaudan S, Conte C, Chaput C, Touzard M, Verriele L, Audinot V, Millan MJ: Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study. Eur J Pharmacol. 1998 Aug 21;355(2-3):245-56. [PubMed:9760039 ]

Enzyme Details

8. 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

Kusumi I, Takahashi Y, Suzuki K, Kameda K, Koyama T: Differential effects of subchronic treatments with atypical antipsychotic drugs on dopamine D2 and serotonin 5-HT2A receptors in the rat brain. J Neural Transm (Vienna). 2000;107(3):295-302. [PubMed:10821438 ]
Yamada J, Sugimoto Y, Horisaka K: Serotonin2 (5-HT2) receptor agonist 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) inhibits chlorpromazine- and haloperidol-induced hypothermia in mice. Biol Pharm Bull. 1995 Nov;18(11):1580-3. [PubMed:8593484 ]

Enzyme Details

9. Histamine H1 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:: HRH1
Uniprot ID:: P35367
Molecular weight:: 55783.6

References

Hals PA, Hall H, Dahl SG: Muscarinic cholinergic and histamine H1 receptor binding of phenothiazine drug metabolites. Life Sci. 1988;43(5):405-12. [PubMed:2899826 ]
Church MK, Young KD: The characteristics of inhibition of histamine release from human lung fragments by sodium cromoglycate, salbutamol and chlorpromazine. Br J Pharmacol. 1983 Apr;78(4):671-9. [PubMed:6189542 ]
Johnson HG, Miller MD: Inhibition of histamine release and ionophore-induced calcium flux in rat mast cells by lidocaine and chlorpromazine. Agents Actions. 1979 Aug;9(3):239-43. [PubMed:91313 ]
Palmer GC, Wagner HR, Palmer SJ, Manian AA: Histamine-, norepinephrine-, and dopamine-sensitive central adenylate cyclases: effects of chlorpromazine derivatives and butaclamol. Arch Int Pharmacodyn Ther. 1978 Jun;233(2):314-25. [PubMed:687395 ]
Ruffolo RR, Patil PN: Kinetics of blockade of different receptors by chlorpromazine in rabbit stomach strips. Eur J Pharmacol. 1978 Mar 15;48(2):151-7. [PubMed:25190 ]

Enzyme Details

10. Alpha-1A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular weight:: 51486.0

References

Cahir M, King DJ: Antipsychotics lack alpha 1A/B adrenoceptor subtype selectivity in the rat. Eur Neuropsychopharmacol. 2005 Mar;15(2):231-4. [PubMed:15695070 ]

Transporters

Enzyme Details

1. Bile salt export pump

General function:: Involved in ATP binding
Specific function:: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:: ABCB11
Uniprot ID:: O95342
Molecular weight:: 146405.8

References

Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [PubMed:12739759 ]

Enzyme Details

2. 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

Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]
Boulton DW, DeVane CL, Liston HL, Markowitz JS: In vitro P-glycoprotein affinity for atypical and conventional antipsychotics. Life Sci. 2002 May 31;71(2):163-9. [PubMed:12031686 ]

Enzyme Details

3. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. [PubMed:12606755 ]

Only showing the first 10 proteins. There are 15 proteins in total.

Show all enzymes and transporters

Showing metabocard for Chlorpromazine (HMDB0014620)

MOL for HMDB0014620 (Chlorpromazine)

3D MOL for HMDB0014620 (Chlorpromazine)

3D SDF for HMDB0014620 (Chlorpromazine)

3D-SDF for HMDB0014620 (Chlorpromazine)

PDB for HMDB0014620 (Chlorpromazine)

3D PDB for HMDB0014620 (Chlorpromazine)

SMILES for HMDB0014620 (Chlorpromazine)

INCHI for HMDB0014620 (Chlorpromazine)

Structure for HMDB0014620 (Chlorpromazine)

3D Structure for HMDB0014620 (Chlorpromazine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Transporters

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