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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2020-02-26 21:41:27 UTC

HMDB ID

HMDB0015346

Secondary Accession Numbers

HMDB15346

Metabolite Identification

Common Name

Estazolam

Description

Estazolam is only found in individuals that have used or taken this drug. It is a benzodiazepine with anticonvulsant, hypnotic, and muscle relaxant properties. It has been shown in some cases to be more potent than diazepam or nitrazepam. [PubChem]Benzodiazepines bind nonspecifically to benzodiazepine receptors, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABA_A) receptors, this enhances the effects GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.

Structure

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

HMDB0015346
     RDKit          3D
Estazolam
 32 35  0  0  0  0  0  0  0  0999 V2000
    0.4853    4.0144    1.9046 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4460    2.6594    1.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8319    2.7370    1.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5704    1.6596    0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8741    0.5427    0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4899    0.4658    0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386    1.5239    0.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3725   -0.6335    0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6859   -0.3824   -0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2260    0.7931   -0.8733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5429    0.8800   -1.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3638   -0.2213   -1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8397   -1.4257   -0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5462   -1.4976   -0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062   -1.8767    0.2210 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2176   -2.4650    0.7315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4225   -1.8383    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4819   -2.4982   -0.3051 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4046   -1.6114   -0.7651 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9208   -0.3684   -0.5955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365   -0.5281   -0.0462 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3405    3.6390    1.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6294    1.6772    0.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3105    1.4359    1.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6036    1.6992   -0.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9498    1.8583   -1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4065   -0.1322   -1.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4748   -2.3290   -0.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1698   -2.4730   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -3.5349    0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2214   -2.3154    1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4160    0.5457   -0.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  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  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
  7  2  1  0
 14  9  1  0
 21 17  1  0
 21  5  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 20 32  1  0
M  END

3261
  Mrv0541 02231215192D          

 21 24  0  0  0  0            999 V2000
    1.6500   -0.4448    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.8158   -1.5395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2283    0.2678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1244   -1.7758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7351   -2.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0726   -1.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890   -0.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4033    0.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5592   -1.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7427   -0.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0455    1.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4517   -1.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0718   -0.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9280   -2.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6286   -1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4374   -0.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5102    1.6927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2227    1.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1522    2.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8648    1.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3295    2.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  2  6  1  0  0  0  0
  2  9  1  0  0  0  0
  2 14  1  0  0  0  0
  3  8  2  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5 14  2  0  0  0  0
  6  7  2  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  7 13  1  0  0  0  0
  8 11  1  0  0  0  0
  9 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>
HMDB0015346

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC2=C(C=C1)N1C=NN=C1CN=C2C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H11ClN4/c17-12-6-7-14-13(8-12)16(11-4-2-1-3-5-11)18-9-15-20-19-10-21(14)15/h1-8,10H,9H2

> <INCHI_KEY>
CDCHDCWJMGXXRH-UHFFFAOYSA-N

> <FORMULA>
C16H11ClN4

> <MOLECULAR_WEIGHT>
294.738

> <EXACT_MASS>
294.067224079

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.827221942297236

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaene

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
2.0913

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.40070520410853

> <JCHEM_PKA_STRONGEST_BASIC>
4.971016976851028

> <JCHEM_POLAR_SURFACE_AREA>
43.07

> <JCHEM_REFRACTIVITY>
94.43830000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
estazolam

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015346
     RDKit          3D
Estazolam
 32 35  0  0  0  0  0  0  0  0999 V2000
    0.4853    4.0144    1.9046 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4460    2.6594    1.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8319    2.7370    1.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5704    1.6596    0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8741    0.5427    0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4899    0.4658    0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386    1.5239    0.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3725   -0.6335    0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6859   -0.3824   -0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2260    0.7931   -0.8733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5429    0.8800   -1.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3638   -0.2213   -1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8397   -1.4257   -0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5462   -1.4976   -0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062   -1.8767    0.2210 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2176   -2.4650    0.7315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4225   -1.8383    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4819   -2.4982   -0.3051 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4046   -1.6114   -0.7651 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9208   -0.3684   -0.5955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365   -0.5281   -0.0462 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3405    3.6390    1.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6294    1.6772    0.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3105    1.4359    1.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6036    1.6992   -0.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9498    1.8583   -1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4065   -0.1322   -1.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4748   -2.3290   -0.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1698   -2.4730   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -3.5349    0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2214   -2.3154    1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4160    0.5457   -0.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  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  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
  7  2  1  0
 14  9  1  0
 21 17  1  0
 21  5  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 20 32  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3261                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080  -0.830   0.000  0.00  0.00          Cl+0
HETATM    2  N   UNK     0       8.989  -2.874   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       9.759   0.500   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      11.432  -3.315   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      10.706  -4.662   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.602  -2.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.259  -0.704   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.219   0.500   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.377  -2.206   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.720  -0.704   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.552   1.887   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.443  -3.315   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.734  -0.208   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.199  -4.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.907  -2.854   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.550  -1.290   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.419   3.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.016   2.002   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.751   4.547   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.348   3.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.215   4.662   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2    6    9   14                                                  
CONECT    3    8   10                                                       
CONECT    4    5    9                                                       
CONECT    5    4   14                                                       
CONECT    6    2    7   12                                                  
CONECT    7    6    8   13                                                  
CONECT    8    3    7   11                                                  
CONECT    9    2    4   10                                                  
CONECT   10    3    9                                                       
CONECT   11    8   17   18                                                  
CONECT   12    6   15                                                       
CONECT   13    7   16                                                       
CONECT   14    2    5                                                       
CONECT   15   12   16                                                       
CONECT   16    1   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   48    0
END

COMPND    HMDB0015346
HETATM    1 CL1  UNL     1       0.485   4.014   1.905  1.00  0.00          CL  
HETATM    2  C1  UNL     1      -0.446   2.659   1.292  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.832   2.737   1.162  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.570   1.660   0.671  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.874   0.543   0.329  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.490   0.466   0.453  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.239   1.524   0.942  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.372  -0.634   0.074  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.686  -0.382  -0.480  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.226   0.793  -0.873  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.543   0.880  -1.286  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.364  -0.221  -1.321  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.840  -1.426  -0.930  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.546  -1.498  -0.525  1.00  0.00           C  
HETATM   15  N1  UNL     1       0.006  -1.877   0.221  1.00  0.00           N  
HETATM   16  C14 UNL     1      -1.218  -2.465   0.732  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.423  -1.838   0.153  1.00  0.00           C  
HETATM   18  N2  UNL     1      -3.482  -2.498  -0.305  1.00  0.00           N  
HETATM   19  N3  UNL     1      -4.405  -1.611  -0.765  1.00  0.00           N  
HETATM   20  C16 UNL     1      -3.921  -0.368  -0.596  1.00  0.00           C  
HETATM   21  N4  UNL     1      -2.737  -0.528  -0.046  1.00  0.00           N  
HETATM   22  H1  UNL     1      -2.341   3.639   1.442  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.629   1.677   0.561  1.00  0.00           H  
HETATM   24  H3  UNL     1       1.311   1.436   1.106  1.00  0.00           H  
HETATM   25  H4  UNL     1       1.604   1.699  -0.941  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.950   1.858  -1.598  1.00  0.00           H  
HETATM   27  H6  UNL     1       5.407  -0.132  -1.652  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.475  -2.329  -0.949  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.170  -2.473  -0.224  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.218  -3.535   0.487  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.221  -2.315   1.822  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.416   0.546  -0.859  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3    7
CONECT    3    4   22
CONECT    4    5    5   23
CONECT    5    6   21
CONECT    6    7    7    8
CONECT    7   24
CONECT    8    9   15   15
CONECT    9   10   10   14
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   29
CONECT   15   16
CONECT   16   17   30   31
CONECT   17   18   18   21
CONECT   18   19
CONECT   19   20   20
CONECT   20   21   32
END

HMDB0015346
     RDKit          3D
Estazolam
 32 35  0  0  0  0  0  0  0  0999 V2000
    0.4853    4.0144    1.9046 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4460    2.6594    1.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8319    2.7370    1.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5704    1.6596    0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8741    0.5427    0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4899    0.4658    0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386    1.5239    0.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3725   -0.6335    0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6859   -0.3824   -0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2260    0.7931   -0.8733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5429    0.8800   -1.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3638   -0.2213   -1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8397   -1.4257   -0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5462   -1.4976   -0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062   -1.8767    0.2210 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2176   -2.4650    0.7315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4225   -1.8383    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4819   -2.4982   -0.3051 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4046   -1.6114   -0.7651 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9208   -0.3684   -0.5955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365   -0.5281   -0.0462 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3405    3.6390    1.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6294    1.6772    0.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3105    1.4359    1.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6036    1.6992   -0.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9498    1.8583   -1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4065   -0.1322   -1.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4748   -2.3290   -0.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1698   -2.4730   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -3.5349    0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2214   -2.3154    1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4160    0.5457   -0.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  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  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
  7  2  1  0
 14  9  1  0
 21 17  1  0
 21  5  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 20 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-Chloro-6-phenyl-4H-S-triazolo(4,3-a)(1,4)benzodiazepine	ChEBI
Estazolamum	ChEBI
ProSom	Kegg
D40TA	HMDB
Hormona brand OF estazolam	HMDB
Abbott brand OF estazolam	HMDB
Nuctalon	HMDB
D-40TA	HMDB
Takeda brand OF estazolam	HMDB
Tasedan	HMDB

Chemical Formula

C₁₆H₁₁ClN₄

Average Molecular Weight

294.738

Monoisotopic Molecular Weight

294.067224079

IUPAC Name

12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaene

Traditional Name

estazolam

CAS Registry Number

29975-16-4

SMILES

ClC1=CC2=C(C=C1)N1C=NN=C1CN=C2C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H11ClN4/c17-12-6-7-14-13(8-12)16(11-4-2-1-3-5-11)18-9-15-20-19-10-21(14)15/h1-8,10H,9H2

InChI Key

CDCHDCWJMGXXRH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2,4-triazolo[4,3-a][1,4]benzodiazepines. These are aromatic compounds containing a 1,4-benzodiazepine fused to and sharing a nitrogen atom with a 1,2,4-triazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,2,4-triazolo[4,3-a][1,4]benzodiazepines

Alternative Parents

Substituents

1,2,4-triazolo[4,3-a][1,4]benzodiazepine
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Azole
1,2,4-triazole
Heteroaromatic compound
Ketimine
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Imine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

triazoles (CHEBI:4858 )
triazolobenzodiazepine (CHEBI:4858 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0015346)
Kidney (HMDB: HMDB0015346)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015346)

Source

Exogenous

Exogenous (HMDB: HMDB0015346)

Endogenous

Endogenous (HMDB: HMDB0015346)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Anticonvulsant (HMDB: HMDB0015346)

Pharmaceutical industry

Anxiolytic drug (HMDB: HMDB0015346)

Biological role

Modulator

GABA modulator (HMDB: HMDB0015346)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	228.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.042 g/L	Not Available
LogP	4.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.042 g/L	ALOGPS
logP	1.72	ALOGPS
logP	2.09	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	18.4	ChemAxon
pKa (Strongest Basic)	4.97	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.44 m³·mol⁻¹	ChemAxon
Polarizability	29.83 Å³	ChemAxon
Number of Rings	4	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]+	164.049	30932474
DeepCCS	[M-H]-	161.691	30932474
DeepCCS	[M-2H]-	194.844	30932474
DeepCCS	[M+Na]+	170.142	30932474
AllCCS	[M+H]+	166.5	32859911
AllCCS	[M+H-H2O]+	162.8	32859911
AllCCS	[M+NH4]+	170.0	32859911
AllCCS	[M+Na]+	171.0	32859911
AllCCS	[M-H]-	168.2	32859911
AllCCS	[M+Na-2H]-	167.2	32859911
AllCCS	[M+HCOO]-	166.2	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.	5.91 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9812 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.39 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	32.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1725.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	340.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	156.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	204.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	166.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	435.7 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	451.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	92.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1034.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	412.8 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	1150.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	315.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	346.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	302.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	149.4 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	12.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Estazolam	ClC1=CC2=C(C=C1)N1C=NN=C1CN=C2C1=CC=CC=C1	3928.0	Standard polar	33892256
Estazolam	ClC1=CC2=C(C=C1)N1C=NN=C1CN=C2C1=CC=CC=C1	2808.4	Standard non polar	33892256
Estazolam	ClC1=CC2=C(C=C1)N1C=NN=C1CN=C2C1=CC=CC=C1	2898.1	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 - Estazolam GC-MS (Non-derivatized) - 70eV, Positive	splash10-016r-2190000000-7bceaaf0dfe0270e210a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estazolam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estazolam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4u-4590000000-dbd088d66293b3b539c3	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estazolam 10V, Positive-QTOF	splash10-0002-0090000000-8b0f7d04b982deb5a038	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estazolam 20V, Positive-QTOF	splash10-0002-0090000000-6608de192721b2ce8c75	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estazolam 40V, Positive-QTOF	splash10-03xu-8690000000-2b0a33869a0469e8d7b5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estazolam 10V, Negative-QTOF	splash10-0006-0090000000-3bf04c7178bea5e8dea2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estazolam 20V, Negative-QTOF	splash10-0006-0090000000-4b4a11f4e7a928221cff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estazolam 40V, Negative-QTOF	splash10-0a5c-1090000000-7609bb7b371102913ae0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estazolam 10V, Positive-QTOF	splash10-0002-0090000000-7f5d232a357b1b41cae8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estazolam 20V, Positive-QTOF	splash10-0002-0090000000-7f5d232a357b1b41cae8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estazolam 40V, Positive-QTOF	splash10-014j-0090000000-b88d0c4f35949ad6a7ab	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estazolam 10V, Negative-QTOF	splash10-0006-0090000000-1901824a83af80ea7083	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estazolam 20V, Negative-QTOF	splash10-0006-0090000000-1901824a83af80ea7083	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estazolam 40V, Negative-QTOF	splash10-0006-0090000000-f5fb876690ac80360a52	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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 DB01215	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01215	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

DB01215

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3146

KEGG Compound ID

C06981

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Estazolam

METLIN ID

Not Available

PubChem Compound

3261

PDB ID

Not Available

ChEBI ID

4858

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

Oishi R, Nishibori M, Itoh Y, Saeki K: Diazepam-induced decrease in histamine turnover in mouse brain. Eur J Pharmacol. 1986 May 27;124(3):337-42. [PubMed:3089825 ]
Usami N, Yamamoto T, Shintani S, Ishikura S, Higaki Y, Katagiri Y, Hara A: Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines. Biol Pharm Bull. 2002 Apr;25(4):441-5. [PubMed:11995921 ]
Watanabe S, Ohta H, Sakurai Y, Takao K, Ueki S: [Electroencephalographic effects of 450191-S and its metabolites in rabbits with chronic electrode implants]. Nihon Yakurigaku Zasshi. 1986 Jul;88(1):19-32. [PubMed:3758874 ]

Only showing the first 10 proteins. There are 17 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. 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

3. 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

4. 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

5. 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

6. 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

Enzyme Details

7. Gamma-aminobutyric acid receptor subunit beta-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:: GABRB1
Uniprot ID:: P18505
Molecular weight:: 54234.1

References

Enzyme Details

8. Gamma-aminobutyric acid receptor subunit beta-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:: GABRB2
Uniprot ID:: P47870
Molecular weight:: 59149.9

References

Enzyme Details

9. Gamma-aminobutyric acid receptor subunit beta-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:: GABRB3
Uniprot ID:: P28472
Molecular weight:: 54115.0

References

Enzyme Details

10. Gamma-aminobutyric acid receptor subunit delta

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:: GABRD
Uniprot ID:: O14764
Molecular weight:: 50707.8

References

Only showing the first 10 proteins. There are 17 proteins in total.

Show all enzymes and transporters

Showing metabocard for Estazolam (HMDB0015346)

MOL for HMDB0015346 (Estazolam)

3D MOL for HMDB0015346 (Estazolam)

3D SDF for HMDB0015346 (Estazolam)

3D-SDF for HMDB0015346 (Estazolam)

PDB for HMDB0015346 (Estazolam)

3D PDB for HMDB0015346 (Estazolam)

SMILES for HMDB0015346 (Estazolam)

INCHI for HMDB0015346 (Estazolam)

Structure for HMDB0015346 (Estazolam)

3D Structure for HMDB0015346 (Estazolam)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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