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enzymes (3) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:56 UTC

HMDB ID

HMDB0015307

Secondary Accession Numbers

HMDB15307

Metabolite Identification

Common Name

Cyclizine

Description

Cyclizine is only found in individuals that have used or taken this drug. It is a histamine H1 antagonist given by mouth or parenterally for the control of postoperative and drug-induced vomiting and in motion sickness. (From Martindale, The Extra Pharmacopoeia, 30th ed, p935)Vomiting (emesis) is essentially a protective mechanism for removing irritant or otherwise harmful substances from the upper GI tract. Emesis or vomiting is controlled by the vomiting centre in the medulla region of the brain, an important part of which is the chemotrigger zone (CTZ). The vomiting centre possesses neurons which are rich in muscarinic cholinergic and histamine containing synapses. These types of neurons are especially involved in transmission from the vestibular apparatus to the vomiting centre. Motion sickness principally involves overstimulation of these pathways due to various sensory stimuli. Hence the action of cyclizine which acts to block the histamine receptors in the vomiting centre and thus reduce activity along these pathways. Furthermore since cyclizine possesses anti-cholinergic properties as well, the muscarinic receptors are similarly blocked.

Structure

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

HMDB0015307
     RDKit          3D
Cyclizine
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.6937    0.3157   -0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -0.4052    0.2316 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988    0.5343    0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5168    0.8556   -0.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6378   -0.2939   -0.7295 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4126   -0.2656    0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0435    1.1185    0.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3157    1.7324    1.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909    2.9977    1.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1987    3.6593    0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9262    3.0447   -0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547    1.7877   -0.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4454   -1.2871    0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2923   -2.6446    0.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3605   -3.5456    0.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6416   -3.0791   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8344   -1.7171   -0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7781   -0.8638    0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4806   -1.4476   -0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9403   -1.1156   -0.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4190    0.6467   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9178    1.1753    0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5067   -0.4347   -0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0399    1.4906    0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9883    0.2368    1.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0938    1.1461   -1.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9679    1.7392   -0.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0868   -0.3838    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0898    1.2479    2.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1146    3.5015    2.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6534    4.6591    0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1590    3.5442   -1.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1515    1.3284   -1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3167   -3.0673    0.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1591   -4.6069    0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4978   -3.7679   -0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8655   -1.3731   -0.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9817    0.1867   -0.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1751   -2.2715   -1.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5300   -1.6887    0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4561   -2.0958   -0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0237   -0.5933   -1.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  5 19  1  0
 19 20  1  0
 20  2  1  0
 12  7  1  0
 18 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
M  END

1176
  Mrv0541 02231215182D          

 20 22  0  0  0  0            999 V2000
    3.7935    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  2 10  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  8 11  2  0  0  0  0
  8 13  1  0  0  0  0
  9 12  2  0  0  0  0
  9 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  2  0  0  0  0
 15 19  2  0  0  0  0
 16 20  2  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015307

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H22N2/c1-19-12-14-20(15-13-19)18(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18H,12-15H2,1H3

> <INCHI_KEY>
UVKZSORBKUEBAZ-UHFFFAOYSA-N

> <FORMULA>
C18H22N2

> <MOLECULAR_WEIGHT>
266.3807

> <EXACT_MASS>
266.178298714

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
31.52958976297503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(diphenylmethyl)-4-methylpiperazine

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
3.546002349333333

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.51019411332531

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
84.93360000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyclizine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015307
     RDKit          3D
Cyclizine
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.6937    0.3157   -0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -0.4052    0.2316 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988    0.5343    0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5168    0.8556   -0.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6378   -0.2939   -0.7295 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4126   -0.2656    0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0435    1.1185    0.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3157    1.7324    1.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909    2.9977    1.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1987    3.6593    0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9262    3.0447   -0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547    1.7877   -0.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4454   -1.2871    0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2923   -2.6446    0.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3605   -3.5456    0.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6416   -3.0791   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8344   -1.7171   -0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7781   -0.8638    0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4806   -1.4476   -0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9403   -1.1156   -0.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4190    0.6467   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9178    1.1753    0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5067   -0.4347   -0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0399    1.4906    0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9883    0.2368    1.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0938    1.1461   -1.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9679    1.7392   -0.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0868   -0.3838    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0898    1.2479    2.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1146    3.5015    2.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6534    4.6591    0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1590    3.5442   -1.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1515    1.3284   -1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3167   -3.0673    0.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1591   -4.6069    0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4978   -3.7679   -0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8655   -1.3731   -0.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9817    0.1867   -0.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1751   -2.2715   -1.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5300   -1.6887    0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4561   -2.0958   -0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0237   -0.5933   -1.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  5 19  1  0
 19 20  1  0
 20  2  1  0
 12  7  1  0
 18 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1176                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       7.081   0.000   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       7.081   3.080   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.748   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.415   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.748  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.082  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.082  -3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080  -3.850   0.000  0.00  0.00           C+0
CONECT    1    3    4    5                                                  
CONECT    2    6    7   10                                                  
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    1    8    9                                                  
CONECT    6    2    3                                                       
CONECT    7    2    4                                                       
CONECT    8    5   11   13                                                  
CONECT    9    5   12   14                                                  
CONECT   10    2                                                            
CONECT   11    8   15                                                       
CONECT   12    9   16                                                       
CONECT   13    8   17                                                       
CONECT   14    9   18                                                       
CONECT   15   11   19                                                       
CONECT   16   12   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    HMDB0015307
HETATM    1  C1  UNL     1       4.694   0.316  -0.262  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.511  -0.405   0.232  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.499   0.534   0.676  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.517   0.856  -0.429  1.00  0.00           C  
HETATM    5  N2  UNL     1       0.638  -0.294  -0.730  1.00  0.00           N  
HETATM    6  C4  UNL     1      -0.413  -0.266   0.246  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.044   1.118   0.273  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.316   1.732   1.478  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.891   2.998   1.533  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.199   3.659   0.365  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.926   3.045  -0.846  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.355   1.788  -0.894  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.445  -1.287   0.173  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.292  -2.645   0.212  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.361  -3.546   0.113  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.642  -3.079  -0.032  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.834  -1.717  -0.075  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.778  -0.864   0.023  1.00  0.00           C  
HETATM   19  C17 UNL     1       1.481  -1.448  -0.535  1.00  0.00           C  
HETATM   20  C18 UNL     1       2.940  -1.116  -0.899  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.419   0.647  -1.297  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.918   1.175   0.392  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.507  -0.435  -0.309  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.040   1.491   0.880  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.988   0.237   1.596  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.094   1.146  -1.341  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.968   1.739  -0.114  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.087  -0.384   1.252  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.090   1.248   2.416  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.115   3.501   2.462  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.653   4.659   0.375  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.159   3.544  -1.793  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.151   1.328  -1.852  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.317  -3.067   0.342  1.00  0.00           H  
HETATM   35  H15 UNL     1      -2.159  -4.607   0.153  1.00  0.00           H  
HETATM   36  H16 UNL     1      -4.498  -3.768  -0.112  1.00  0.00           H  
HETATM   37  H17 UNL     1      -4.866  -1.373  -0.191  1.00  0.00           H  
HETATM   38  H18 UNL     1      -2.982   0.187  -0.014  1.00  0.00           H  
HETATM   39  H19 UNL     1       1.175  -2.272  -1.201  1.00  0.00           H  
HETATM   40  H20 UNL     1       1.530  -1.689   0.540  1.00  0.00           H  
HETATM   41  H21 UNL     1       3.456  -2.096  -0.957  1.00  0.00           H  
HETATM   42  H22 UNL     1       3.024  -0.593  -1.850  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   20
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   19
CONECT    6    7   13   28
CONECT    7    8    8   12
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11   31
CONECT   11   12   12   32
CONECT   12   33
CONECT   13   14   14   18
CONECT   14   15   34
CONECT   15   16   16   35
CONECT   16   17   36
CONECT   17   18   18   37
CONECT   18   38
CONECT   19   20   39   40
CONECT   20   41   42
END

HMDB0015307
     RDKit          3D
Cyclizine
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.6937    0.3157   -0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -0.4052    0.2316 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988    0.5343    0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5168    0.8556   -0.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6378   -0.2939   -0.7295 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4126   -0.2656    0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0435    1.1185    0.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3157    1.7324    1.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909    2.9977    1.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1987    3.6593    0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9262    3.0447   -0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547    1.7877   -0.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4454   -1.2871    0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2923   -2.6446    0.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3605   -3.5456    0.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6416   -3.0791   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8344   -1.7171   -0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7781   -0.8638    0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4806   -1.4476   -0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9403   -1.1156   -0.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4190    0.6467   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9178    1.1753    0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5067   -0.4347   -0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0399    1.4906    0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9883    0.2368    1.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0938    1.1461   -1.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9679    1.7392   -0.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0868   -0.3838    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0898    1.2479    2.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1146    3.5015    2.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6534    4.6591    0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1590    3.5442   -1.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1515    1.3284   -1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3167   -3.0673    0.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1591   -4.6069    0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4978   -3.7679   -0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8655   -1.3731   -0.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9817    0.1867   -0.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1751   -2.2715   -1.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5300   -1.6887    0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4561   -2.0958   -0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0237   -0.5933   -1.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  5 19  1  0
 19 20  1  0
 20  2  1  0
 12  7  1  0
 18 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-1-Diphenylmethyl-4-methylpiperazine	ChEBI
(N-Benzhydryl)(n'-methyl)diethylenediamine	ChEBI
1-(Diphenylmethyl)-4-methylpiperazine	ChEBI
1-Benzhydryl-4-methylpiperazin	ChEBI
Ciclizina	ChEBI
Cyclizinum	ChEBI
N-Benzhydryl-n'-methylpiperazine	ChEBI
N-Methyl-n'-benzhydrylpiperazine	ChEBI
Cyclizine chloride	HMDB
Cyclizine hydrochloride	HMDB
HCL, Cyclizine	HMDB
Marezine	HMDB
Cyclizine HCL	HMDB
Hydrochloride, cyclizine	HMDB

Chemical Formula

C₁₈H₂₂N₂

Average Molecular Weight

266.3807

Monoisotopic Molecular Weight

266.178298714

IUPAC Name

1-(diphenylmethyl)-4-methylpiperazine

Traditional Name

cyclizine

CAS Registry Number

82-92-8

SMILES

CN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H22N2/c1-19-12-14-20(15-13-19)18(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18H,12-15H2,1H3

InChI Key

UVKZSORBKUEBAZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Aralkylamine
N-alkylpiperazine
N-methylpiperazine
1,4-diazinane
Piperazine
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

N-alkylpiperazine (CHEBI:3994 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015307)
Membrane (HMDB: HMDB0015307)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Cyclizine H1-Antihistamine Action (PathBank: SMP0058923)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.075 g/L	Not Available
LogP	3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	166.7	30932474
[M+H]+	Not Available	164.803	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000792

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.075 g/L	ALOGPS
logP	3.55	ALOGPS
logP	3.55	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	8.51	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	84.93 m³·mol⁻¹	ChemAxon
Polarizability	31.53 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]+	164.823	31661259
DarkChem	[M-H]-	165.278	31661259
DeepCCS	[M+H]+	162.848	30932474
DeepCCS	[M-H]-	160.49	30932474
DeepCCS	[M-2H]-	193.376	30932474
DeepCCS	[M+Na]+	168.941	30932474
AllCCS	[M+H]+	163.4	32859911
AllCCS	[M+H-H2O]+	159.6	32859911
AllCCS	[M+NH4]+	167.0	32859911
AllCCS	[M+Na]+	168.0	32859911
AllCCS	[M-H]-	172.3	32859911
AllCCS	[M+Na-2H]-	171.9	32859911
AllCCS	[M+HCOO]-	171.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclizine	CN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1	2689.8	Standard polar	33892256
Cyclizine	CN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1	2063.7	Standard non polar	33892256
Cyclizine	CN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1	2066.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Cyclizine EI-B (Non-derivatized)	splash10-0aos-9620000000-ed8810ea85a4b69f8507	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Cyclizine EI-B (Non-derivatized)	splash10-0aos-9620000000-ed8810ea85a4b69f8507	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclizine GC-MS (Non-derivatized) - 70eV, Positive	splash10-014r-6920000000-1ddcd42966325717db73	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclizine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 45V, Positive-QTOF	splash10-0gb9-0900000000-d6c91a9722832a6aa738	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 75V, Positive-QTOF	splash10-014i-0900000000-4b42cb223e1f1f2e4e90	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 90V, Positive-QTOF	splash10-014i-2900000000-543bd0eeb1ff13d335d4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 50V, Positive-QTOF	splash10-0gb9-0900000000-bec36f8829bd4780e1cb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 60V, Positive-QTOF	splash10-0gb9-0900000000-009d1551a59545ae449f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 40V, Positive-QTOF	splash10-0uxr-0900000000-361d751c7870eb29ba4e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 10V, Positive-QTOF	splash10-014i-0900000000-240a440d2dd63341247d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 80V, Positive-QTOF	splash10-0gb9-0900000000-4afdf8368a89122da2f0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 35V, Positive-QTOF	splash10-0gb9-0900000000-a86e695095f2ce184b7c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 45V, Positive-QTOF	splash10-0gb9-0900000000-bd83a5179314abf6afc5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 15V, Positive-QTOF	splash10-014i-0900000000-07a74edb751eeb230f23	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 20V, Positive-QTOF	splash10-014i-0900000000-0323096b4a21e2a8db23	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 15V, Positive-QTOF	splash10-014i-0900000000-4866511b3bef8af755b2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 30V, Positive-QTOF	splash10-014i-0900000000-748187bceefb902de284	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 25V, Positive-QTOF	splash10-014i-0900000000-0377cce0b27805d479b5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 80V, Positive-QTOF	splash10-0gb9-0900000000-9b7722ff0880ab6ea3f6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 90V, Positive-QTOF	splash10-014i-2900000000-eceae62b15337b573a02	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 45V, Positive-QTOF	splash10-0gb9-0900000000-07d26fc06a38dc6e874d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclizine 40V, Positive-QTOF	splash10-014i-0900000000-3265205697ae7aa25720	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclizine 10V, Positive-QTOF	splash10-014i-0190000000-f7a13fb94d177c5350a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclizine 20V, Positive-QTOF	splash10-014i-1690000000-881d405f0ad451201d6b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclizine 40V, Positive-QTOF	splash10-014i-5910000000-f9a37fa63dc7990a9a89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclizine 10V, Negative-QTOF	splash10-014i-0090000000-6f0c5476da21d301550c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclizine 20V, Negative-QTOF	splash10-014i-1090000000-c691b21d5e972ebf73a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclizine 40V, Negative-QTOF	splash10-0006-9830000000-c56f9fb789eebf207dba	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Cyclizine 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 DB01176	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01176	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01176

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6470

KEGG Compound ID

C06930

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cyclizine

METLIN ID

Not Available

PubChem Compound

6726

PDB ID

Not Available

ChEBI ID

3994

Food Biomarker Ontology

Not Available

VMH ID

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MarkerDB ID

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Good Scents ID

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References

Synthesis Reference

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Material Safety Data Sheet (MSDS)

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General References

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Enzymes

Enzyme Details

1. Estrogen sulfotransferase

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone. May play a role in the regulation of estrogen receptor activity by metabolizing free estradiol. Maximally sulfates beta-estradiol and estrone at concentrations of 20 nM. Also sulfates dehydroepiandrosterone, pregnenolone, ethinylestradiol, equalenin, diethylstilbesterol and 1-naphthol, at significantly higher concentrations; however, cortisol, testosterone and dopamine are not sulfated.
Gene Name:: SULT1E1
Uniprot ID:: P49888
Molecular weight:: 35126.185

References

Bamforth KJ, Dalgliesh K, Coughtrie MW: Inhibition of human liver steroid sulfotransferase activities by drugs: a novel mechanism of drug toxicity? Eur J Pharmacol. 1992 May 1;228(1):15-21. [PubMed:1397064 ]

Enzyme Details

2. 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

3. 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 ]
Leza JC, Lizasoain I, Lorenzo P: H1- and H2-histamine receptor blockers and opiate analgesia in mice. Methods Find Exp Clin Pharmacol. 1990 Dec;12(10):671-8. [PubMed:1983158 ]

Showing metabocard for Cyclizine (HMDB0015307)

MOL for HMDB0015307 (Cyclizine)

3D MOL for HMDB0015307 (Cyclizine)

3D SDF for HMDB0015307 (Cyclizine)

3D-SDF for HMDB0015307 (Cyclizine)

PDB for HMDB0015307 (Cyclizine)

3D PDB for HMDB0015307 (Cyclizine)

SMILES for HMDB0015307 (Cyclizine)

INCHI for HMDB0015307 (Cyclizine)

Structure for HMDB0015307 (Cyclizine)

3D Structure for HMDB0015307 (Cyclizine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References