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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (13)transporters (1) Show 14 proteins XML

enzymes (13)transporters (1) Show 14 proteins

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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:54 UTC

HMDB ID

HMDB0015202

Secondary Accession Numbers

HMDB15202

Metabolite Identification

Common Name

Promethazine

Description

Promethazine is only found in individuals that have used or taken this drug. It is a phenothiazine derivative with histamine H1-blocking, antimuscarinic, and sedative properties. It is used as an antiallergic, in pruritus, for motion sickness and sedation, and also in animals. [PubChem]Like other H1-antagonists, promethazine competes with free histamine for binding at H1-receptor sites in the GI tract, uterus, large blood vessels, and bronchial muscle. The relief of nausea appears to be related to central anticholinergic actions and may implicate activity on the medullary chemoreceptor trigger zone.

Structure

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

HMDB0242580
     RDKit          3D
(2R)-N,N-Dimethyl-1-phenothiazin-10-ylpropan-2-amine
 40 42  0  0  0  0  0  0  0  0999 V2000
    2.9783    0.0767   -1.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7864    0.3776   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6114   -0.2782   -1.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6528   -0.1044   -0.5724 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2140    1.2097   -0.6823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6164    2.1519   -1.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1714    3.4052   -1.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3087    3.7311   -1.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8902    2.8131   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3490    1.5814   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1880    0.4830    1.0846 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3371   -1.0731    0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8775   -2.0947    1.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702   -3.3279    1.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1234   -3.4882    0.9423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6080   -2.4281    0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1941   -1.1582    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1903   -0.0448    0.6248 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5169   -1.3763    0.8769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9526    0.8132    1.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5374   -0.8166   -1.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6824    0.9157   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6195   -0.1550   -2.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7579    1.4971   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4460    0.0511   -2.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8282   -1.3484   -1.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2592    1.9284   -2.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    4.1558   -2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7639    4.7267   -1.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8132    3.1240    0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7944   -1.9710    2.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6732   -4.1478    2.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6213   -4.4691    0.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2798   -2.6477   -0.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347   -1.4063    1.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5659   -2.0557    0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8504   -1.8603    1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9567    1.0513    2.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2652    0.3647    2.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5930    1.7942    1.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  2 18  1  0
 18 19  1  0
 18 20  1  0
 17  4  1  0
 10  5  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
M  END

1069
  Mrv0541 02231215132D          

 20 22  0  0  1  0            999 V2000
    3.6958   -1.9665    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6958   -0.3823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3819    1.5979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3819    0.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6958    0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0099   -0.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3819   -0.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0678    0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0099   -1.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3819   -1.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0678    1.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6958    1.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3019   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0899   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3019   -1.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0899   -1.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5842   -0.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8076   -0.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5842   -1.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8076   -1.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 10  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  1  0  0  0  0
  3 12  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 13  2  0  0  0  0
  7 10  1  0  0  0  0
  7 14  2  0  0  0  0
  9 15  2  0  0  0  0
 10 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015202

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CN1C2=CC=CC=C2SC2=CC=CC=C12)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C17H20N2S/c1-13(18(2)3)12-19-14-8-4-6-10-16(14)20-17-11-7-5-9-15(17)19/h4-11,13H,12H2,1-3H3

> <INCHI_KEY>
PWWVAXIEGOYWEE-UHFFFAOYSA-N

> <FORMULA>
C17H20N2S

> <MOLECULAR_WEIGHT>
284.419

> <EXACT_MASS>
284.13471934

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.384972456103085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
dimethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]amine

> <ALOGPS_LOGP>
4.52

> <JCHEM_LOGP>
4.287570851666667

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.046575852890253

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
88.50490000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
promethazine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0242580
     RDKit          3D
(2R)-N,N-Dimethyl-1-phenothiazin-10-ylpropan-2-amine
 40 42  0  0  0  0  0  0  0  0999 V2000
    2.9783    0.0767   -1.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7864    0.3776   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6114   -0.2782   -1.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6528   -0.1044   -0.5724 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2140    1.2097   -0.6823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6164    2.1519   -1.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1714    3.4052   -1.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3087    3.7311   -1.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8902    2.8131   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3490    1.5814   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1880    0.4830    1.0846 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3371   -1.0731    0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8775   -2.0947    1.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702   -3.3279    1.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1234   -3.4882    0.9423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6080   -2.4281    0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1941   -1.1582    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1903   -0.0448    0.6248 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5169   -1.3763    0.8769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9526    0.8132    1.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5374   -0.8166   -1.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6824    0.9157   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6195   -0.1550   -2.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7579    1.4971   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4460    0.0511   -2.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8282   -1.3484   -1.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2592    1.9284   -2.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    4.1558   -2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7639    4.7267   -1.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8132    3.1240    0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7944   -1.9710    2.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6732   -4.1478    2.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6213   -4.4691    0.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2798   -2.6477   -0.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347   -1.4063    1.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5659   -2.0557    0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8504   -1.8603    1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9567    1.0513    2.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2652    0.3647    2.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5930    1.7942    1.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  2 18  1  0
 18 19  1  0
 18 20  1  0
 17  4  1  0
 10  5  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1069                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       6.899  -3.671   0.000  0.00  0.00           S+0
HETATM    2  N   UNK     0       6.899  -0.714   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       8.179   2.983   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.179   1.504   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.899   0.765   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.618  -1.453   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.179  -1.453   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.460   0.765   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.618  -2.931   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.179  -2.931   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.460   3.722   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.899   3.722   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.297  -0.662   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.501  -0.662   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.297  -3.722   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.501  -3.722   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.957  -1.422   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.841  -1.422   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.957  -2.962   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.841  -2.962   0.000  0.00  0.00           C+0
CONECT    1    9   10                                                       
CONECT    2    5    6    7                                                  
CONECT    3    4   11   12                                                  
CONECT    4    3    5    8                                                  
CONECT    5    2    4                                                       
CONECT    6    2    9   13                                                  
CONECT    7    2   10   14                                                  
CONECT    8    4                                                            
CONECT    9    1    6   15                                                  
CONECT   10    1    7   16                                                  
CONECT   11    3                                                            
CONECT   12    3                                                            
CONECT   13    6   17                                                       
CONECT   14    7   18                                                       
CONECT   15    9   19                                                       
CONECT   16   10   20                                                       
CONECT   17   13   19                                                       
CONECT   18   14   20                                                       
CONECT   19   15   17                                                       
CONECT   20   16   18                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0015202
HETATM    1  C1  UNL     1      -1.710   0.830  -1.049  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.556  -0.305  -0.113  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.544  -0.192   0.973  1.00  0.00           C  
HETATM    4  N1  UNL     1       0.820  -0.003   0.543  1.00  0.00           N  
HETATM    5  C4  UNL     1       1.331   1.316   0.325  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.546   2.434   0.580  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.995   3.733   0.402  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.262   3.960  -0.042  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.044   2.871  -0.296  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.596   1.591  -0.119  1.00  0.00           C  
HETATM   11  S1  UNL     1       3.759   0.306  -0.487  1.00  0.00           S  
HETATM   12  C10 UNL     1       2.885  -1.222  -0.124  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.563  -2.385  -0.321  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.980  -3.610  -0.085  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.688  -3.618   0.355  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.007  -2.425   0.552  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.586  -1.188   0.319  1.00  0.00           C  
HETATM   18  N2  UNL     1      -2.796  -0.773   0.486  1.00  0.00           N  
HETATM   19  C16 UNL     1      -3.719  -1.306  -0.516  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.503   0.276   1.190  1.00  0.00           C  
HETATM   21  H1  UNL     1      -0.721   0.974  -1.562  1.00  0.00           H  
HETATM   22  H2  UNL     1      -2.118   1.761  -0.648  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.436   0.509  -1.850  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.277  -1.179  -0.801  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.867   0.656   1.674  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.694  -1.035   1.685  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.449   2.359   0.939  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.354   4.592   0.612  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.594   4.986  -0.175  1.00  0.00           H  
HETATM   30  H10 UNL     1       4.057   3.091  -0.652  1.00  0.00           H  
HETATM   31  H11 UNL     1       4.600  -2.356  -0.676  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.486  -4.541  -0.230  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.218  -4.579   0.544  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.009  -2.558   0.889  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.239  -1.316  -1.517  1.00  0.00           H  
HETATM   36  H16 UNL     1      -4.681  -0.779  -0.507  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.846  -2.401  -0.265  1.00  0.00           H  
HETATM   38  H18 UNL     1      -2.868   0.901   1.825  1.00  0.00           H  
HETATM   39  H19 UNL     1      -4.114   0.859   0.466  1.00  0.00           H  
HETATM   40  H20 UNL     1      -4.225  -0.235   1.864  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   18   24
CONECT    3    4   25   26
CONECT    4    5   17
CONECT    5    6    6   10
CONECT    6    7   27
CONECT    7    8    8   28
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11
CONECT   11   12
CONECT   12   13   13   17
CONECT   13   14   31
CONECT   14   15   15   32
CONECT   15   16   33
CONECT   16   17   17   34
CONECT   18   19   20
CONECT   19   35   36   37
CONECT   20   38   39   40
END

HMDB0242580
     RDKit          3D
(2R)-N,N-Dimethyl-1-phenothiazin-10-ylpropan-2-amine
 40 42  0  0  0  0  0  0  0  0999 V2000
    2.9783    0.0767   -1.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7864    0.3776   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6114   -0.2782   -1.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6528   -0.1044   -0.5724 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2140    1.2097   -0.6823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6164    2.1519   -1.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1714    3.4052   -1.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3087    3.7311   -1.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8902    2.8131   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3490    1.5814   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1880    0.4830    1.0846 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3371   -1.0731    0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8775   -2.0947    1.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702   -3.3279    1.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1234   -3.4882    0.9423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6080   -2.4281    0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1941   -1.1582    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1903   -0.0448    0.6248 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5169   -1.3763    0.8769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9526    0.8132    1.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5374   -0.8166   -1.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6824    0.9157   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6195   -0.1550   -2.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7579    1.4971   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4460    0.0511   -2.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8282   -1.3484   -1.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2592    1.9284   -2.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    4.1558   -2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7639    4.7267   -1.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8132    3.1240    0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7944   -1.9710    2.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6732   -4.1478    2.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6213   -4.4691    0.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2798   -2.6477   -0.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347   -1.4063    1.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5659   -2.0557    0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8504   -1.8603    1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9567    1.0513    2.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2652    0.3647    2.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5930    1.7942    1.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  2 18  1  0
 18 19  1  0
 18 20  1  0
 17  4  1  0
 10  5  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2-Dimethylamino-2-methyl)ethyl-N-dibenzoparathiazine	ChEBI
10-(2-Dimethylaminopropyl)phenothiazine	ChEBI
10-[2-(Dimethylamino)propyl]phenothiazine	ChEBI
N,N,alpha-Trimethyl-10H-phenothiazine-10-ethanamine	ChEBI
N-(2'-Dimethylamino-2'-methyl)ethylphenothiazine	ChEBI
Proazamine	ChEBI
Prometazina	ChEBI
Promethazinum	ChEBI
N,N,a-Trimethyl-10H-phenothiazine-10-ethanamine	Generator
N,N,Α-trimethyl-10H-phenothiazine-10-ethanamine	Generator
Isopromethazine	HMDB
Lilly 1516	HMDB
Proazaimine	HMDB
Promazinamide	HMDB
Prometazine	HMDB
Promethazin	HMDB
Promethiazine	HMDB
Promezathine	HMDB
Prothazin	HMDB
Prothazine	HMDB
Diprazin	HMDB
Rumergan	HMDB
Phenargan	HMDB
Phensedyl	HMDB
Promet	HMDB
Promethazine hydrochloride	HMDB
Remsed	HMDB
Prometazin	HMDB
Pyrethia	HMDB
Atosil	HMDB
Diphergan	HMDB
Hydrochloride, promethazine	HMDB
Phenergan	HMDB
Pipolfen	HMDB
Pipolphen	HMDB

Chemical Formula

C₁₇H₂₀N₂S

Average Molecular Weight

284.419

Monoisotopic Molecular Weight

284.13471934

IUPAC Name

dimethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]amine

Traditional Name

promethazine

CAS Registry Number

60-87-7

SMILES

CC(CN1C2=CC=CC=C2SC2=CC=CC=C12)N(C)C

InChI Identifier

InChI=1S/C17H20N2S/c1-13(18(2)3)12-19-14-8-4-6-10-16(14)20-17-11-7-5-9-15(17)19/h4-11,13H,12H2,1-3H3

InChI Key

PWWVAXIEGOYWEE-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
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Thioether
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:8461 )
tertiary amine (CHEBI:8461 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	60 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.024 g/L	Not Available
LogP	4.4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	163.7	30932474
[M+H]+	Not Available	162.657	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000924

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
logP	4.52	ALOGPS
logP	4.29	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	9.05	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	3	ChemAxon
Refractivity	88.5 m³·mol⁻¹	ChemAxon
Polarizability	32.38 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
DarkChem	[M+H]+	165.869	31661259
DarkChem	[M-H]-	163.499	31661259
DeepCCS	[M-2H]-	190.768	30932474
DeepCCS	[M+Na]+	166.272	30932474
AllCCS	[M+H]+	166.1	32859911
AllCCS	[M+H-H2O]+	162.7	32859911
AllCCS	[M+NH4]+	169.2	32859911
AllCCS	[M+Na]+	170.1	32859911
AllCCS	[M-H]-	169.6	32859911
AllCCS	[M+Na-2H]-	169.0	32859911
AllCCS	[M+HCOO]-	168.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Promethazine	CC(CN1C2=CC=CC=C2SC2=CC=CC=C12)N(C)C	3254.1	Standard polar	33892256
Promethazine	CC(CN1C2=CC=CC=C2SC2=CC=CC=C12)N(C)C	2242.0	Standard non polar	33892256
Promethazine	CC(CN1C2=CC=CC=C2SC2=CC=CC=C12)N(C)C	2258.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Promethazine CI-B (Non-derivatized)	splash10-000i-0090000000-f1fe9756bed13819bbb4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Promethazine EI-B (Non-derivatized)	splash10-00di-9000000000-abbdf5514dccef4821b2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Promethazine EI-B (Non-derivatized)	splash10-00di-9100000000-9bef9a6b83d662fc7e2c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Promethazine CI-B (Non-derivatized)	splash10-0079-8290000000-fe5d6b4e9f62b7270798	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Promethazine CI-B (Non-derivatized)	splash10-000i-0090000000-f1fe9756bed13819bbb4	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Promethazine EI-B (Non-derivatized)	splash10-00di-9000000000-abbdf5514dccef4821b2	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Promethazine EI-B (Non-derivatized)	splash10-00di-9100000000-9bef9a6b83d662fc7e2c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Promethazine CI-B (Non-derivatized)	splash10-0079-8290000000-fe5d6b4e9f62b7270798	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Promethazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0229-9150000000-19753aa755aa19143e9b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Promethazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Promethazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Promethazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-9210000000-7167670dff3395a6ade2	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 - Promethazine , positive-QTOF	splash10-000j-0690000000-0b4dfbac9712d2e36046	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Promethazine LC-ESI-QFT , positive-QTOF	splash10-000i-9220000000-9d761be1437f10dcc94b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Promethazine 35V, Positive-QTOF	splash10-000i-9120000000-53ae2d83de014d922ec7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Promethazine 30V, Positive-QTOF	splash10-0002-0920000000-c051699dc72e950f2e98	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Promethazine 50V, Positive-QTOF	splash10-0002-0910000000-e92aacd8ca86df8a0e18	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Promethazine 40V, Positive-QTOF	splash10-0002-0910000000-0ce89af1c9b2c4633eda	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Promethazine 20V, Positive-QTOF	splash10-0002-0950000000-70d959c63d9e713a865a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Promethazine 10V, Positive-QTOF	splash10-000i-0090000000-842e411dfa4c9fad1f7f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promethazine 10V, Positive-QTOF	splash10-000i-2090000000-76a910470a52a47a6757	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promethazine 20V, Positive-QTOF	splash10-000f-8090000000-d597b4b7604e8276f449	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promethazine 40V, Positive-QTOF	splash10-00dr-9110000000-cbed4a551fc77cf0e5b9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promethazine 10V, Negative-QTOF	splash10-001i-0090000000-e24a248a31f0e31f1ec5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promethazine 20V, Negative-QTOF	splash10-009t-0940000000-afb556a81c40edffb9a1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promethazine 40V, Negative-QTOF	splash10-0002-3910000000-3daef27d94a5cac7d4a7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promethazine 10V, Positive-QTOF	splash10-000i-9070000000-e74135a63711b2ca001f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promethazine 20V, Positive-QTOF	splash10-000i-9020000000-25ad7e0e10410cbe88c3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promethazine 40V, Positive-QTOF	splash10-000j-9610000000-32a1e6113f4291e6a186	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promethazine 10V, Negative-QTOF	splash10-001i-0090000000-a26692bb509bb9fc8701	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promethazine 20V, Negative-QTOF	splash10-000t-0590000000-3a84419d780b185fa21a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promethazine 40V, Negative-QTOF	splash10-01ot-0940000000-7c01990eb3e291008595	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Promethazine H1-Antihistamine Action		Not Available

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 DB01069	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01069	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

DB01069

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4758

KEGG Compound ID

C07404

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Promethazine

METLIN ID

Not Available

PubChem Compound

4927

PDB ID

Not Available

ChEBI ID

8461

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1799771

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Peters RJ Jr, Kelder SH, Markham CM, Yacoubian GS Jr, Peters LA, Ellis A: Beliefs and social norms about codeine and promethazine hydrochloride cough syrup (CPHCS) onset and perceived addiction among urban Houstonian adolescents: an addiction trend in the city of lean. J Drug Educ. 2003;33(4):415-25. [PubMed:15237866 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 2C9

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

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2D6

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

References

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 ]
Platts SH, Shi SJ, Meck JV: Akathisia with combined use of midodrine and promethazine. JAMA. 2006 May 3;295(17):2000-1. [PubMed:16670408 ]

Enzyme Details

3. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. 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

Golembiewski JA, O'Brien D: A systematic approach to the management of postoperative nausea and vomiting. J Perianesth Nurs. 2002 Dec;17(6):364-76. [PubMed:12476402 ]

Enzyme Details

5. Calmodulin

General function:: Involved in calcium ion binding
Specific function:: Calmodulin mediates the control of a large number of enzymes and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number of protein kinases and phosphatases. Together with CEP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis
Gene Name:: CALM1
Uniprot ID:: P62158
Molecular weight:: 16837.5

References

Cohen ME, Sharp GW, Donowitz M: Suggestion of a role for calmodulin and phosphorylation in regulation of rabbit ileal electrolyte transport: effects of promethazine. Am J Physiol. 1986 Nov;251(5 Pt 1):G710-7. [PubMed:3022601 ]
Scott JA, Khaw BA, Fallon JT, Locke E, Rabito CA, Peto CA, Homcy CJ: The effect of phenothiazines upon maintenance of membrane integrity in the cultured myocardial cell. J Mol Cell Cardiol. 1986 Dec;18(12):1243-54. [PubMed:3820316 ]
Lohr KM, Feix JB, Kurth C: Chlorpromazine inhibits neutrophil chemotaxis beyond the chemotactic receptor-ligand interaction. J Infect Dis. 1984 Nov;150(5):643-52. [PubMed:6092486 ]
DiPaola M, Keith CH, Feldman D, Tycko B, Maxfield FR: Loss of alpha 2-macroglobulin and epidermal growth factor surface binding induced by phenothiazines and naphthalene sulfonamides. J Cell Physiol. 1984 Feb;118(2):193-202. [PubMed:6319437 ]
Luchowski EM, Yousif F, Triggle DJ, Maurer SC, Sarmiento JG, Janis RA: Effects of metal cations and calmodulin antagonists on [3H] nitrendipine binding in smooth and cardiac muscle. J Pharmacol Exp Ther. 1984 Sep;230(3):607-13. [PubMed:6433001 ]

Enzyme Details

6. 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

Bileviciute I, Stenfors C, Theodorsson E, Lundeberg T: Unilateral injection of calcitonin gene-related peptide (CGRP) induces bilateral oedema formation and release of CGRP-like immunoreactivity in the rat hindpaw. Br J Pharmacol. 1998 Nov;125(6):1304-12. [PubMed:9863661 ]
Kelley BM, Porter JH: The role of muscarinic cholinergic receptors in the discriminative stimulus properties of clozapine in rats. Pharmacol Biochem Behav. 1997 Aug;57(4):707-19. [PubMed:9258998 ]
Hoenicke EM, Vanecek SA, Woods JH: The discriminative stimulus effects of clozapine in pigeons: involvement of 5-hydroxytryptamine1C and 5-hydroxytryptamine2 receptors. J Pharmacol Exp Ther. 1992 Oct;263(1):276-84. [PubMed:1403790 ]
Martinez F, Coleman JW: A comparison of the effects of chlorpromazine and more selective histamine and 5-hydroxytryptamine antagonists on human IgG synthesis in vitro. Int J Immunopharmacol. 1990;12(2):185-91. [PubMed:2329012 ]
Fiorella D, Rabin RA, Winter JC: The role of the 5-HT2A and 5-HT2C receptors in the stimulus effects of hallucinogenic drugs. I: Antagonist correlation analysis. Psychopharmacology (Berl). 1995 Oct;121(3):347-56. [PubMed:8584617 ]

Enzyme Details

7. 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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Suzuki A, Yasui-Furukori N, Mihara K, Kondo T, Furukori H, Inoue Y, Kaneko S, Otani K: Histamine H1-receptor antagonists, promethazine and homochlorcyclizine, increase the steady-state plasma concentrations of haloperidol and reduced haloperidol. Ther Drug Monit. 2003 Apr;25(2):192-6. [PubMed:12657913 ]
Smith BN, Armstrong WE: Histamine enhances the depolarizing afterpotential of immunohistochemically identified vasopressin neurons in the rat supraoptic nucleus via H1-receptor activation. Neuroscience. 1993 Apr;53(3):855-64. [PubMed:8098142 ]
Miller RA, Tu AT: Factors in snake venoms that increase capillary permeability. J Pharm Pharmacol. 1989 Nov;41(11):792-4. [PubMed:2576052 ]
Claro E, Arbones L, Garcia A, Picatoste F: Phosphoinositide hydrolysis mediated by histamine H1-receptors in rat brain cortex. Eur J Pharmacol. 1986 Apr 16;123(2):187-96. [PubMed:3011460 ]
Ikeda H, Kubo N, Nakamura A, Harada N, Minamino M, Yamashita T: Histamine-induced calcium released from cultured human mucosal microvascular endothelial cells from nasal inferior turbinate. Acta Otolaryngol. 1997 Nov;117(6):864-70. [PubMed:9442829 ]
Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [PubMed:2866055 ]

Enzyme Details

8. 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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

9. Muscarinic acetylcholine receptor M3

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

References

Golembiewski JA, O'Brien D: A systematic approach to the management of postoperative nausea and vomiting. J Perianesth Nurs. 2002 Dec;17(6):364-76. [PubMed:12476402 ]

Enzyme Details

10. Muscarinic acetylcholine receptor M1

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

References

Golembiewski JA, O'Brien D: A systematic approach to the management of postoperative nausea and vomiting. J Perianesth Nurs. 2002 Dec;17(6):364-76. [PubMed:12476402 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

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

References

Ibrahim S, Peggins J, Knapton A, Licht T, Aszalos A: Influence of antipsychotic, antiemetic, and Ca(2+) channel blocker drugs on the cellular accumulation of the anticancer drug daunorubicin: P-glycoprotein modulation. J Pharmacol Exp Ther. 2000 Dec;295(3):1276-83. [PubMed:11082465 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Showing metabocard for Promethazine (HMDB0015202)

MOL for HMDB0015202 (Promethazine)

3D MOL for HMDB0015202 (Promethazine)

3D SDF for HMDB0015202 (Promethazine)

3D-SDF for HMDB0015202 (Promethazine)

PDB for HMDB0015202 (Promethazine)

3D PDB for HMDB0015202 (Promethazine)

SMILES for HMDB0015202 (Promethazine)

INCHI for HMDB0015202 (Promethazine)

Structure for HMDB0015202 (Promethazine)

3D Structure for HMDB0015202 (Promethazine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

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Transporters

References