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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (23) Show 23 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:38 UTC

HMDB ID

HMDB0014493

Secondary Accession Numbers

HMDB14493

Metabolite Identification

Common Name

Clobazam

Description

Clobazam is only found in individuals that have used or taken this drug. It is a drug which is a benzodiazepine derivative. It has been marketed as an anxiolytic since 1975 and an anticonvulsant since 1984. [Wikipedia ]Clobazam binds at a distinct binding site associated with a Cl^- ionopore at the GABA-A receptor, increasing the duration of time for which the Cl^- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is prolonged as a result.

Structure

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

HMDB0014493
     RDKit          3D
Clobazam
 34 36  0  0  0  0  0  0  0  0999 V2000
   -3.9889    0.6919   -0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5806    0.8741    0.0756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0878    2.2110    0.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0212    3.0663    0.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7547    2.8173    0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3014    1.9308   -0.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1938    2.4792   -1.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5434    0.5180   -0.1595 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8881    0.1012   -0.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531   -0.6847   -1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5601   -1.0691   -1.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4975   -0.6687   -0.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1807    0.1232    0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8383    0.4940    0.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4310   -0.4456    0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1095   -1.6811    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7012   -2.7513    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399   -4.3127    0.9984 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0823   -2.6017    0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6431   -1.3605    0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8158   -0.2989    0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3311    1.6793   -0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5995    0.5937    0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2099   -0.0692   -0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8264    3.7027   -0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5375    3.2349    1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5538   -1.0220   -2.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9085   -1.7063   -2.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5570   -0.9618   -0.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9121    0.4460    1.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5552    1.1252    1.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1627   -1.8305    0.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7337   -3.4231    1.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7104   -1.2016    0.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
 14  9  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  5 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 19 33  1  0
 20 34  1  0
M  END

349
  Mrv0541 02231214372D          

 21 23  0  0  0  0            999 V2000
    2.8172   -2.3593    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.1124    1.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6107    2.3593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1245    0.1666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4543    0.9709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3812   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6379    0.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7937    1.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3081    0.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9687    1.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7695   -0.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4586   -1.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205   -0.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7524   -1.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9781   -1.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5375   -0.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6466   -1.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1825   -0.5608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2915   -1.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0595   -1.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  2  9  2  0  0  0  0
  3 10  2  0  0  0  0
  4  6  1  0  0  0  0
  4  9  1  0  0  0  0
  4 11  1  0  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  0  0  0  0
  6  7  2  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 17  2  0  0  0  0
 11 18  1  0  0  0  0
 12 15  2  0  0  0  0
 13 16  2  0  0  0  0
 15 16  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014493

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=C(C=C(Cl)C=C2)N(C2=CC=CC=C2)C(=O)CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H13ClN2O2/c1-18-13-8-7-11(17)9-14(13)19(16(21)10-15(18)20)12-5-3-2-4-6-12/h2-9H,10H2,1H3

> <INCHI_KEY>
CXOXHMZGEKVPMT-UHFFFAOYSA-N

> <FORMULA>
C16H13ClN2O2

> <MOLECULAR_WEIGHT>
300.74

> <EXACT_MASS>
300.066555377

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.066074049985147

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-chloro-1-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-2,4-dione

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
2.554375973333333

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.068303914570974

> <JCHEM_PKA_STRONGEST_BASIC>
-6.723067238972568

> <JCHEM_POLAR_SURFACE_AREA>
40.620000000000005

> <JCHEM_REFRACTIVITY>
80.29860000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
clobazam

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014493
     RDKit          3D
Clobazam
 34 36  0  0  0  0  0  0  0  0999 V2000
   -3.9889    0.6919   -0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5806    0.8741    0.0756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0878    2.2110    0.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0212    3.0663    0.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7547    2.8173    0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3014    1.9308   -0.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1938    2.4792   -1.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5434    0.5180   -0.1595 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8881    0.1012   -0.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531   -0.6847   -1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5601   -1.0691   -1.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4975   -0.6687   -0.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1807    0.1232    0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8383    0.4940    0.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4310   -0.4456    0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1095   -1.6811    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7012   -2.7513    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399   -4.3127    0.9984 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0823   -2.6017    0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6431   -1.3605    0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8158   -0.2989    0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3311    1.6793   -0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5995    0.5937    0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2099   -0.0692   -0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8264    3.7027   -0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5375    3.2349    1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5538   -1.0220   -2.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9085   -1.7063   -2.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5570   -0.9618   -0.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9121    0.4460    1.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5552    1.1252    1.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1627   -1.8305    0.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7337   -3.4231    1.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7104   -1.2016    0.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
 14  9  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  5 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 19 33  1  0
 20 34  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 349                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       5.259  -4.404   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       9.543   2.155   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.873   4.404   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       7.699   0.311   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.581   1.812   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.312  -0.357   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   0.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.082   3.016   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.042   1.812   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.542   3.016   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.903  -0.649   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.456  -1.955   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.585  -0.572   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   2.155   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.138  -2.869   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.692  -2.173   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.337  -0.087   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.674  -2.172   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.541  -1.047   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.877  -3.132   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.311  -2.569   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    6    9   11                                                  
CONECT    5    7   10   14                                                  
CONECT    6    4    7   12                                                  
CONECT    7    5    6   13                                                  
CONECT    8    9   10                                                       
CONECT    9    2    4    8                                                  
CONECT   10    3    5    8                                                  
CONECT   11    4   17   18                                                  
CONECT   12    6   15                                                       
CONECT   13    7   16                                                       
CONECT   14    5                                                            
CONECT   15    1   12   16                                                  
CONECT   16   13   15                                                       
CONECT   17   11   19                                                       
CONECT   18   11   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   21                                                       
CONECT   21   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0014493
HETATM    1  C1  UNL     1      -3.989   0.692  -0.203  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.581   0.874   0.076  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.088   2.211   0.151  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.021   3.066   0.291  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.755   2.817   0.103  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.301   1.931  -0.348  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.194   2.479  -1.041  1.00  0.00           O  
HETATM    8  N2  UNL     1       0.543   0.518  -0.159  1.00  0.00           N  
HETATM    9  C5  UNL     1       1.888   0.101  -0.319  1.00  0.00           C  
HETATM   10  C6  UNL     1       2.253  -0.685  -1.378  1.00  0.00           C  
HETATM   11  C7  UNL     1       3.560  -1.069  -1.503  1.00  0.00           C  
HETATM   12  C8  UNL     1       4.497  -0.669  -0.570  1.00  0.00           C  
HETATM   13  C9  UNL     1       4.181   0.123   0.515  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.838   0.494   0.605  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.431  -0.446   0.165  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.110  -1.681   0.395  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.701  -2.751   0.709  1.00  0.00           C  
HETATM   18 CL1  UNL     1       0.040  -4.313   0.998  1.00  0.00          CL  
HETATM   19  C14 UNL     1      -2.082  -2.602   0.799  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.643  -1.360   0.570  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.816  -0.299   0.256  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.331   1.679  -0.649  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.599   0.594   0.721  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.210  -0.069  -0.979  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.826   3.703  -0.570  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.538   3.235   1.125  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.554  -1.022  -2.132  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.908  -1.706  -2.331  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.557  -0.962  -0.645  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.912   0.446   1.258  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.555   1.125   1.450  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.163  -1.831   0.346  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.734  -3.423   1.038  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.710  -1.202   0.633  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   21
CONECT    3    4    4    5
CONECT    5    6   25   26
CONECT    6    7    7    8
CONECT    8    9   15
CONECT    9   10   10   14
CONECT   10   11   27
CONECT   11   12   12   28
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   31
CONECT   15   16   16   21
CONECT   16   17   32
CONECT   17   18   19   19
CONECT   19   20   33
CONECT   20   21   21   34
END

HMDB0014493
     RDKit          3D
Clobazam
 34 36  0  0  0  0  0  0  0  0999 V2000
   -3.9889    0.6919   -0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5806    0.8741    0.0756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0878    2.2110    0.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0212    3.0663    0.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7547    2.8173    0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3014    1.9308   -0.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1938    2.4792   -1.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5434    0.5180   -0.1595 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8881    0.1012   -0.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531   -0.6847   -1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5601   -1.0691   -1.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4975   -0.6687   -0.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1807    0.1232    0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8383    0.4940    0.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4310   -0.4456    0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1095   -1.6811    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7012   -2.7513    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399   -4.3127    0.9984 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0823   -2.6017    0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6431   -1.3605    0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8158   -0.2989    0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3311    1.6793   -0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5995    0.5937    0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2099   -0.0692   -0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8264    3.7027   -0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5375    3.2349    1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5538   -1.0220   -2.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9085   -1.7063   -2.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5570   -0.9618   -0.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9121    0.4460    1.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5552    1.1252    1.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1627   -1.8305    0.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7337   -3.4231    1.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7104   -1.2016    0.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
 14  9  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  5 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 19 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Phenyl-5-methyl-8-chloro-1,2,4,5-tetrahydro-2,4-dioxo-3H-1,5-benzodiazepine	ChEBI
7-Chloro-1-methyl-5-phenyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione	ChEBI
Clobazamum	ChEBI
Mystan	Kegg
Onfi	Kegg
Urbanyl	HMDB
Frisium	HMDB
1-Phenyl-5-methyl-8-chloro-1,2,4,5- tetrahydro-2,4-diketo-3H-1,5-benzodiazepine	HMDB

Chemical Formula

C₁₆H₁₃ClN₂O₂

Average Molecular Weight

300.74

Monoisotopic Molecular Weight

300.066555377

IUPAC Name

7-chloro-1-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-2,4-dione

Traditional Name

clobazam

CAS Registry Number

22316-47-8

SMILES

CN1C2=C(C=C(Cl)C=C2)N(C2=CC=CC=C2)C(=O)CC1=O

InChI Identifier

InChI=1S/C16H13ClN2O2/c1-18-13-8-7-11(17)9-14(13)19(16(21)10-15(18)20)12-5-3-2-4-6-12/h2-9H,10H2,1H3

InChI Key

CXOXHMZGEKVPMT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodiazepines. These are organic compounds containing a benzene ring fused to either isomers of diazepine(unsaturated seven-member heterocycle with two nitrogen atoms replacing two carbon atoms).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

Not Available

Direct Parent

Benzodiazepines

Alternative Parents

Substituents

Benzodiazepine
Para-diazepine
Aryl chloride
Aryl halide
Monocyclic benzene moiety
1,3-dicarbonyl compound
Benzenoid
Tertiary carboxylic acid amide
Lactam
Carboxamide group
Carboxylic acid derivative
Azacycle
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:31413 )
1,4-benzodiazepinone (CHEBI:31413 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014493)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

anticonvulsant (HMDB: HMDB0014493)

Pharmaceutical industry

anxiolytic drug (HMDB: HMDB0014493)

GABA modulator (HMDB: HMDB0014493)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.16 g/L	Not Available
LogP	2.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	165.7	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	2.14	ALOGPS
logP	2.55	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.62 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.3 m³·mol⁻¹	ChemAxon
Polarizability	30.07 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	167.118	30932474
DeepCCS	[M-H]-	164.76	30932474
DeepCCS	[M-2H]-	197.646	30932474
DeepCCS	[M+Na]+	173.211	30932474
AllCCS	[M+H]+	166.8	32859911
AllCCS	[M+H-H2O]+	163.4	32859911
AllCCS	[M+NH4]+	170.0	32859911
AllCCS	[M+Na]+	170.9	32859911
AllCCS	[M-H]-	166.9	32859911
AllCCS	[M+Na-2H]-	166.3	32859911
AllCCS	[M+HCOO]-	165.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Clobazam	CN1C2=C(C=C(Cl)C=C2)N(C2=CC=CC=C2)C(=O)CC1=O	3860.4	Standard polar	33892256
Clobazam	CN1C2=C(C=C(Cl)C=C2)N(C2=CC=CC=C2)C(=O)CC1=O	2551.0	Standard non polar	33892256
Clobazam	CN1C2=C(C=C(Cl)C=C2)N(C2=CC=CC=C2)C(=O)CC1=O	2572.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Clobazam GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-0290000000-85c722aae16a6c4f1e1a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clobazam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0pb9-6392000000-a76f30f353b3407df0c6	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 - Clobazam LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0090000000-3b46d60abcc8dfacf4d8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobazam LC-ESI-QFT , positive-QTOF	splash10-0udi-0019000000-71512d7a18cf60430dd9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobazam LC-ESI-QFT , positive-QTOF	splash10-0a4i-0092000000-e687a1e3760fb870dbc9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobazam LC-ESI-QFT , positive-QTOF	splash10-0a4i-0090000000-d450ded1f22039f00b63	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobazam LC-ESI-QFT , positive-QTOF	splash10-0ab9-0190000000-e4211cbc2957a587e3d3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobazam LC-ESI-QFT , positive-QTOF	splash10-05fr-0590000000-51f4fa0445c2d047ef6b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobazam LC-ESI-QFT , positive-QTOF	splash10-0g4j-1960000000-a89e1c91bfa7b974be48	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobazam LC-ESI-QFT , positive-QTOF	splash10-014j-4920000000-93c0877b3acf519d2b98	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobazam LC-ESI-QFT , positive-QTOF	splash10-016u-7900000000-bc29714be08b6ae4120b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobazam LC-ESI-QFT , positive-QTOF	splash10-0hi6-9600000000-7c6a3974d95a0015757e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobazam -1V, Positive-QTOF	splash10-0a4i-0090000000-f8bfd7fb18f6c2191b61	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobazam 15V, Positive-QTOF	splash10-0udi-0019000000-71512d7a18cf60430dd9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobazam 75V, Positive-QTOF	splash10-05fr-0590000000-d54a49898cc15a62a5e6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobazam 60V, Positive-QTOF	splash10-0ab9-0190000000-55d5faa9832676ff3cbe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobazam 30V, Positive-QTOF	splash10-0a4i-0092000000-ea34c0db78be09efb678	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobazam 45V, Positive-QTOF	splash10-0a4i-0090000000-35ff57d7b80e2c98ae57	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobazam 90V, Positive-QTOF	splash10-0g4j-1960000000-cf4e19e49420cb7d7a8f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobazam 10V, Positive-QTOF	splash10-0udi-0009000000-c177e3ba787d31e6efa9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobazam 20V, Positive-QTOF	splash10-0udi-1019000000-ecf7835c598275ee85fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobazam 40V, Positive-QTOF	splash10-0f6x-9560000000-ac11ec0388fbae849904	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobazam 10V, Negative-QTOF	splash10-0002-0090000000-5aff96d7f16fb8885018	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobazam 20V, Negative-QTOF	splash10-0002-0090000000-38aef9b903ce595b395d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobazam 40V, Negative-QTOF	splash10-0f9f-4490000000-02ff5e375a7cffbef887	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobazam 10V, Positive-QTOF	splash10-0udi-0009000000-d5f71cf6ca39e39e4e90	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobazam 20V, Positive-QTOF	splash10-0udi-0069000000-00f02d6bca08146095d7	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00349	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00349	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

DB00349

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2687

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Clobazam

METLIN ID

Not Available

PubChem Compound

2789

PDB ID

Not Available

ChEBI ID

31413

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Freche C: [Study of an anxiolytic, clobazam, in otorhinolaryngology in psychosomatic pharyngeal manifestations]. Sem Hop Ther. 1975 Apr;51(4):261-3. [PubMed:5777 ]
Authors unspecified: Clobazam in treatment of refractory epilepsy: the Canadian experience. A retrospective study. Canadian Clobazam Cooperative Group. Epilepsia. 1991 May-Jun;32(3):407-16. [PubMed:2044502 ]
Wildin JD, Pleuvry BJ, Mawer GE, Onon T, Millington L: Respiratory and sedative effects of clobazam and clonazepam in volunteers. Br J Clin Pharmacol. 1990 Feb;29(2):169-77. [PubMed:2106335 ]
Kilpatrick C, Bury R, Fullinfaw R, Moulds R: Clobazam in the treatment of epilepsy. Clin Exp Neurol. 1987;23:139-44. [PubMed:3117456 ]
Giarratano M, Standley K, Benbadis SR: Clobazam for treatment of epilepsy. Expert Opin Pharmacother. 2012 Feb;13(2):227-33. doi: 10.1517/14656566.2012.647686. Epub 2012 Jan 13. [PubMed:22242724 ]
Walzer M, Bekersky I, Blum RA, Tolbert D: Pharmacokinetic drug interactions between clobazam and drugs metabolized by cytochrome P450 isoenzymes. Pharmacotherapy. 2012 Apr;32(4):340-53. doi: 10.1002/j.1875-9114.2012.01028.x. Epub 2012 Mar 15. [PubMed:22422635 ]
Yang LP, Scott LJ: Clobazam : in patients with Lennox-Gastaut syndrome. CNS Drugs. 2012 Nov;26(11):983-91. doi: 10.1007/s40263-012-0007-0. [PubMed:23034582 ]

Only showing the first 10 proteins. There are 23 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 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

Enzyme Details

2. Cytochrome P450 2C19

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

References

Enzyme Details

3. Cytochrome P450 2C18

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

References

Enzyme Details

4. 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

Enzyme Details

5. Gamma-aminobutyric acid receptor subunit gamma-2

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRG2
Uniprot ID:: P18507
Molecular weight:: 54161.8

References

Enzyme Details

6. Gamma-aminobutyric acid receptor subunit alpha-1

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA1
Uniprot ID:: P14867
Molecular weight:: 51801.4

References

Enzyme Details

7. Gamma-aminobutyric acid receptor subunit alpha-2

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA2
Uniprot ID:: P47869
Molecular weight:: 51325.9

References

Enzyme Details

8. Gamma-aminobutyric acid receptor subunit alpha-3

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA3
Uniprot ID:: P34903
Molecular weight:: 55164.1

References

Enzyme Details

9. Gamma-aminobutyric acid receptor subunit alpha-4

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA4
Uniprot ID:: P48169
Molecular weight:: 61622.6

References

Enzyme Details

10. Gamma-aminobutyric acid receptor subunit alpha-5

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA5
Uniprot ID:: P31644
Molecular weight:: 52145.6

References

Only showing the first 10 proteins. There are 23 proteins in total.

Show all enzymes and transporters

Showing metabocard for Clobazam (HMDB0014493)

MOL for HMDB0014493 (Clobazam)

3D MOL for HMDB0014493 (Clobazam)

3D SDF for HMDB0014493 (Clobazam)

3D-SDF for HMDB0014493 (Clobazam)

PDB for HMDB0014493 (Clobazam)

3D PDB for HMDB0014493 (Clobazam)

SMILES for HMDB0014493 (Clobazam)

INCHI for HMDB0014493 (Clobazam)

Structure for HMDB0014493 (Clobazam)

3D Structure for HMDB0014493 (Clobazam)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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