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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 15:16:52 UTC

Update Date

2022-03-07 02:52:00 UTC

HMDB ID

HMDB0015511

Secondary Accession Numbers

HMDB15511

Metabolite Identification

Common Name

Bromazepam

Description

Bromazepam is only found in individuals that have used or taken this drug. It is one of the benzodiazepines that is used in the treatment of anxiety disorders. [PubChem] It is a Schedule IV drug in the U.S. and Canada and under the Convention on Psychotropic Substances.Bromazepam binds to the GABA receptor GABA_A, causing a conformational change and increasing inhibitory effects of GABA. Other neurotransmitters are not influenced.

Structure

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

HMDB0015511
     RDKit          3D
Bromazepam
 29 31  0  0  0  0  0  0  0  0999 V2000
   -2.4267    3.5822   -0.9265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0907    2.5048   -0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1825    2.6246    0.8470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0290    1.8243    0.6528 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2059    0.5967    0.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5466    0.0689    0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5742    0.9542    0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9069    0.6197    0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2561   -0.6220   -0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267   -1.4889   -0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432   -1.1110   -0.2724 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936   -0.3153   -0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5991   -1.6237    0.3074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4986   -2.6438    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0738   -4.4442    0.5163 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.7293   -2.3059   -0.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0686   -1.0175   -0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1273   -0.0415   -0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6056    1.2769   -0.8895 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8920    3.6634    0.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7713    2.2717    1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3186    1.9448    0.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6473    1.3624    0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2963   -0.8924   -0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4993   -2.4712   -0.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3373   -1.8713    0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4428   -3.0861   -0.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0156   -0.7102   -1.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701    1.3503   -1.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19  2  1  0
 11  6  1  0
 18 12  1  0
  3 20  1  0
  3 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  0
 16 27  1  0
 17 28  1  0
 19 29  1  0
M  END

1558
  Mrv0541 02231215332D          

 19 21  0  0  0  0            999 V2000
    2.5467   -2.3593    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.3403    2.3593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1839    0.9709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0375    0.9709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2670   -0.0464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1107   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3674    0.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8540    0.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1881   -1.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5232    1.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4990   -0.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6982    1.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4818   -1.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7076   -1.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3760   -1.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0210   -1.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9120   -0.5608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7890   -1.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2 13  2  0  0  0  0
  3  7  1  0  0  0  0
  3 13  1  0  0  0  0
  4  8  2  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 18  2  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  7 12  1  0  0  0  0
  8 11  1  0  0  0  0
  9 14  2  0  0  0  0
 10 13  1  0  0  0  0
 11 16  2  0  0  0  0
 12 15  2  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015511

> <DATABASE_NAME>
hmdb

> <SMILES>
BrC1=CC2=C(NC(=O)CN=C2C2=CC=CC=N2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H10BrN3O/c15-9-4-5-11-10(7-9)14(17-8-13(19)18-11)12-3-1-2-6-16-12/h1-7H,8H2,(H,18,19)

> <INCHI_KEY>
VMIYHDSEFNYJSL-UHFFFAOYSA-N

> <FORMULA>
C14H10BrN3O

> <MOLECULAR_WEIGHT>
316.153

> <EXACT_MASS>
315.000724604

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.10544719289046

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-bromo-5-(pyridin-2-yl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
2.5449063463333332

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.238633643745393

> <JCHEM_PKA_STRONGEST_BASIC>
2.675365429288418

> <JCHEM_POLAR_SURFACE_AREA>
54.35

> <JCHEM_REFRACTIVITY>
76.98510000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bromazepam

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015511
     RDKit          3D
Bromazepam
 29 31  0  0  0  0  0  0  0  0999 V2000
   -2.4267    3.5822   -0.9265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0907    2.5048   -0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1825    2.6246    0.8470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0290    1.8243    0.6528 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2059    0.5967    0.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5466    0.0689    0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5742    0.9542    0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9069    0.6197    0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2561   -0.6220   -0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267   -1.4889   -0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432   -1.1110   -0.2724 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936   -0.3153   -0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5991   -1.6237    0.3074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4986   -2.6438    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0738   -4.4442    0.5163 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.7293   -2.3059   -0.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0686   -1.0175   -0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1273   -0.0415   -0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6056    1.2769   -0.8895 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8920    3.6634    0.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7713    2.2717    1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3186    1.9448    0.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6473    1.3624    0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2963   -0.8924   -0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4993   -2.4712   -0.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3373   -1.8713    0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4428   -3.0861   -0.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0156   -0.7102   -1.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701    1.3503   -1.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19  2  1  0
 11  6  1  0
 18 12  1  0
  3 20  1  0
  3 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  0
 16 27  1  0
 17 28  1  0
 19 29  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1558                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Br   UNK     0       4.754  -4.404   0.000  0.00  0.00          Br+0
HETATM    2  O   UNK     0       4.369   4.404   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       4.077   1.812   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       7.537   1.812   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       9.832  -0.087   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.807  -0.357   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.419   0.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.194   0.311   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.951  -1.955   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.577   3.016   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.398  -0.649   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -0.572   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.037   3.016   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.633  -2.869   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.188  -2.173   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.169  -2.172   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.373  -3.132   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.036  -1.047   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.806  -2.569   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2   13                                                            
CONECT    3    7   13                                                       
CONECT    4    8   10                                                       
CONECT    5   11   18                                                       
CONECT    6    7    8    9                                                  
CONECT    7    3    6   12                                                  
CONECT    8    4    6   11                                                  
CONECT    9    6   14                                                       
CONECT   10    4   13                                                       
CONECT   11    5    8   16                                                  
CONECT   12    7   15                                                       
CONECT   13    2    3   10                                                  
CONECT   14    1    9   15                                                  
CONECT   15   12   14                                                       
CONECT   16   11   17                                                       
CONECT   17   16   19                                                       
CONECT   18    5   19                                                       
CONECT   19   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0015511
HETATM    1  O1  UNL     1      -2.427   3.582  -0.927  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.091   2.505  -0.350  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.182   2.625   0.847  1.00  0.00           C  
HETATM    4  N1  UNL     1       0.029   1.824   0.653  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.206   0.597   0.286  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.547   0.069   0.177  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.574   0.954   0.545  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.907   0.620   0.446  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.256  -0.622  -0.028  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.227  -1.489  -0.389  1.00  0.00           C  
HETATM   11  N2  UNL     1       1.943  -1.111  -0.272  1.00  0.00           N  
HETATM   12  C9  UNL     1      -0.894  -0.315  -0.006  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.599  -1.624   0.307  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.499  -2.644   0.083  1.00  0.00           C  
HETATM   15 BR1  UNL     1      -1.074  -4.444   0.516  1.00  0.00          BR  
HETATM   16  C12 UNL     1      -2.729  -2.306  -0.475  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.069  -1.018  -0.801  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.127  -0.041  -0.553  1.00  0.00           C  
HETATM   19  N3  UNL     1      -2.606   1.277  -0.890  1.00  0.00           N  
HETATM   20  H1  UNL     1      -0.892   3.663   0.993  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.771   2.272   1.719  1.00  0.00           H  
HETATM   22  H3  UNL     1       2.319   1.945   0.924  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.647   1.362   0.752  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.296  -0.892  -0.109  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.499  -2.471  -0.765  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.337  -1.871   0.767  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.443  -3.086  -0.657  1.00  0.00           H  
HETATM   28  H9  UNL     1      -4.016  -0.710  -1.237  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.370   1.350  -1.557  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   19
CONECT    3    4   20   21
CONECT    4    5    5
CONECT    5    6   12
CONECT    6    7    7   11
CONECT    7    8   22
CONECT    8    9    9   23
CONECT    9   10   24
CONECT   10   11   11   25
CONECT   12   13   13   18
CONECT   13   14   26
CONECT   14   15   16   16
CONECT   16   17   27
CONECT   17   18   18   28
CONECT   18   19
CONECT   19   29
END

HMDB0015511
     RDKit          3D
Bromazepam
 29 31  0  0  0  0  0  0  0  0999 V2000
   -2.4267    3.5822   -0.9265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0907    2.5048   -0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1825    2.6246    0.8470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0290    1.8243    0.6528 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2059    0.5967    0.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5466    0.0689    0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5742    0.9542    0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9069    0.6197    0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2561   -0.6220   -0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267   -1.4889   -0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432   -1.1110   -0.2724 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936   -0.3153   -0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5991   -1.6237    0.3074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4986   -2.6438    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0738   -4.4442    0.5163 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.7293   -2.3059   -0.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0686   -1.0175   -0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1273   -0.0415   -0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6056    1.2769   -0.8895 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8920    3.6634    0.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7713    2.2717    1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3186    1.9448    0.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6473    1.3624    0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2963   -0.8924   -0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4993   -2.4712   -0.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3373   -1.8713    0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4428   -3.0861   -0.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0156   -0.7102   -1.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701    1.3503   -1.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19  2  1  0
 11  6  1  0
 18 12  1  0
  3 20  1  0
  3 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  0
 16 27  1  0
 17 28  1  0
 19 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Lectopam	Kegg
7-Bromo-5-(2-pyridyl)-3H-1,4-benzodiaxepin-2(1H)-one	HMDB
7-Bromo-5-(2-pyridyl)-3H-1,4-benzodiazepin-2(1H)-one	HMDB
1a Brand OF bromazepam	HMDB
Bromazepam lichtenstein brand	HMDB
Bromazepam beta	HMDB
Heumann brand OF bromazepam	HMDB
Lexatin	HMDB
Betapharm brand OF bromazepam	HMDB
Apo-bromazepam	HMDB
Apotex brand OF bromazepam	HMDB
Bromaz 1a pharma	HMDB
Hexal brand OF bromazepam	HMDB
CT-Arzneimittel brand OF bromazepam	HMDB
Durazanil	HMDB
Aliud brand OF bromazepam	HMDB
Apo bromazepam	HMDB
Bromazepam heumann	HMDB
Bromazepam ratiopharm	HMDB
Bromazepam-neuraxpharm	HMDB
Bromazepam-ratiopharm	HMDB
Gen-bromazepam	HMDB
Lexomil	HMDB
Lexotan	HMDB
Roche brand OF bromazepam	HMDB
Neuraxpharm brand OF bromazepam	HMDB
Ratiopharm brand OF bromazepam	HMDB
Anxyrex	HMDB
BromaLich	HMDB
Bromazanil	HMDB
Bromazepam al	HMDB
Bromazepam roche brand	HMDB
Gen bromazepam	HMDB
Genpharm brand OF bromazepam	HMDB
Irex brand OF bromazepam	HMDB
Lexotanil	HMDB
Lichtenstein brand OF bromazepam	HMDB
Merck dura brand OF bromazepam	HMDB
Bromazep von CT	HMDB
CT Arzneimittel brand OF bromazepam	HMDB
Beta, Bromazepam	HMDB
Bromazepam neuraxpharm	HMDB
Von CT, bromazep	HMDB

Chemical Formula

C₁₄H₁₀BrN₃O

Average Molecular Weight

316.153

Monoisotopic Molecular Weight

315.000724604

IUPAC Name

7-bromo-5-(pyridin-2-yl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Traditional Name

bromazepam

CAS Registry Number

1812-30-2

SMILES

BrC1=CC2=C(NC(=O)CN=C2C2=CC=CC=N2)C=C1

InChI Identifier

InChI=1S/C14H10BrN3O/c15-9-4-5-11-10(7-9)14(17-8-13(19)18-11)12-3-1-2-6-16-12/h1-7H,8H2,(H,18,19)

InChI Key

VMIYHDSEFNYJSL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Substituents

1,4-benzodiazepine
Alpha-amino acid or derivatives
Aryl bromide
Aryl halide
Pyridine
Benzenoid
Heteroaromatic compound
Carboxamide group
Ketimine
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organobromide
Organohalogen compound
Hydrocarbon derivative
Imine
Organic nitrogen compound
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015511)

Source

Exogenous

Exogenous (HMDB: HMDB0015511)

Process

Not Available

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	0.04 g/L	Not Available
LogP	2.05	SANGSTER (1994)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	159.8	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	2.09	ALOGPS
logP	2.54	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	12.24	ChemAxon
pKa (Strongest Basic)	2.68	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.35 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.99 m³·mol⁻¹	ChemAxon
Polarizability	28.11 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]+	159.804	30932474
DeepCCS	[M-H]-	157.409	30932474
DeepCCS	[M-2H]-	190.427	30932474
DeepCCS	[M+Na]+	165.811	30932474
AllCCS	[M+H]+	167.5	32859911
AllCCS	[M+H-H2O]+	163.7	32859911
AllCCS	[M+NH4]+	170.9	32859911
AllCCS	[M+Na]+	171.9	32859911
AllCCS	[M-H]-	162.9	32859911
AllCCS	[M+Na-2H]-	162.6	32859911
AllCCS	[M+HCOO]-	162.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.77 minutes	32390414
Predicted by Siyang on May 30, 2022	11.3075 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.28 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	30.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1856.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	317.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	139.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	195.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	153.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	386.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	529.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	64.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	939.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	268.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1151.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	323.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	274.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	293.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	62.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	37.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bromazepam	BrC1=CC2=C(NC(=O)CN=C2C2=CC=CC=N2)C=C1	3397.9	Standard polar	33892256
Bromazepam	BrC1=CC2=C(NC(=O)CN=C2C2=CC=CC=N2)C=C1	2642.5	Standard non polar	33892256
Bromazepam	BrC1=CC2=C(NC(=O)CN=C2C2=CC=CC=N2)C=C1	2649.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bromazepam,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=N2)C2=CC(Br)=CC=C21	2375.1	Semi standard non polar	33892256
Bromazepam,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=N2)C2=CC(Br)=CC=C21	2481.4	Standard non polar	33892256
Bromazepam,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=N2)C2=CC(Br)=CC=C21	3788.8	Standard polar	33892256
Bromazepam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=N2)C2=CC(Br)=CC=C21	2603.8	Semi standard non polar	33892256
Bromazepam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=N2)C2=CC(Br)=CC=C21	2700.3	Standard non polar	33892256
Bromazepam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=N2)C2=CC(Br)=CC=C21	3875.7	Standard polar	33892256

Spectra

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 DB01558	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01558	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

DB01558

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2347

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bromazepam

METLIN ID

Not Available

PubChem Compound

2441

PDB ID

Not Available

ChEBI ID

116960

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

Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines]. Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [PubMed:2570451 ]
Ochs HR, Greenblatt DJ, Friedman H, Burstein ES, Locniskar A, Harmatz JS, Shader RI: Bromazepam pharmacokinetics: influence of age, gender, oral contraceptives, cimetidine, and propranolol. Clin Pharmacol Ther. 1987 May;41(5):562-70. [PubMed:2882883 ]
van Harten J: Overview of the pharmacokinetics of fluvoxamine. Clin Pharmacokinet. 1995;29 Suppl 1:1-9. [PubMed:8846617 ]
Oda M, Kotegawa T, Tsutsumi K, Ohtani Y, Kuwatani K, Nakano S: The effect of itraconazole on the pharmacokinetics and pharmacodynamics of bromazepam in healthy volunteers. Eur J Clin Pharmacol. 2003 Nov;59(8-9):615-9. Epub 2003 Sep 27. [PubMed:14517708 ]

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 2E1

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

References

Enzyme Details

4. Cytochrome P450 1A2

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

References

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 Bromazepam (HMDB0015511)

MOL for HMDB0015511 (Bromazepam)

3D MOL for HMDB0015511 (Bromazepam)

3D SDF for HMDB0015511 (Bromazepam)

3D-SDF for HMDB0015511 (Bromazepam)

PDB for HMDB0015511 (Bromazepam)

3D PDB for HMDB0015511 (Bromazepam)

SMILES for HMDB0015511 (Bromazepam)

INCHI for HMDB0015511 (Bromazepam)

Structure for HMDB0015511 (Bromazepam)

3D Structure for HMDB0015511 (Bromazepam)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

References

References

References

References

References

References

References

References

References