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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

HMDB0015512

Secondary Accession Numbers

HMDB15512

Metabolite Identification

Common Name

Clotiazepam

Description

Clotiazepam, also known as rize, belongs to the class of organic compounds known as thienodiazepines. These are heteropolycyclic containing a thiophene ring fused to a diazepine ring. Thiophene is 5-membered ring consisting of four carbon and one sulfur atoms. Diazepine is a 7-membered ring consisting of five carbon and two nitrogen atoms. Clotiazepam is metabolised to hydroxy-clotiazepam and desmethyl-clotiazepam. Clotiazepam is a drug which is used for the treatment of anxiety disorders. Clotiazepam binds to the benzodiazepine site of the GABAA receptor where it acts as a full agonist; this action results in an enhanced GABA inhibitory effect at the GABAA receptor which results in the pharmacological effects of clotiazepam. Clotiazepam is a moderately basic compound (based on its pKa). Clotiazepam is a potentially toxic compound. It is metabolised via oxidation. The use of drops is suggested for a more marked initial effect and the sublingual route for easier administration, especially in the elderly. There has been a report of hepatitis caused by clotiazepam.

Structure

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

HMDB0015512
     RDKit          3D
Clotiazepam
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.5877   -2.1540    1.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4660   -1.7965   -0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4440   -0.6971   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0920   -0.7902   -0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3771    0.3428   -0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0972    1.5152   -0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006    1.0011   -0.0863 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6158    2.8823   -0.3983 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256    3.8255    0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5469    3.3029   -1.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8433    4.4787   -1.0434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3902    2.4110   -1.9701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7887    1.2267   -1.2303 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017    0.3296   -0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8835   -0.7234    0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4430   -1.6935    0.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2740   -2.7021    1.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5754   -2.7435    0.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0794   -1.7884    0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2225   -0.7957   -0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9060    0.4096   -1.4434 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3363   -1.2886    2.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6252   -2.4497    1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460   -2.9550    1.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3920   -1.5076   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0392   -2.6615   -0.5920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6649   -1.8104   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3151    3.7935    1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5087    3.6431    0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1954    4.8433   -0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3361    2.9148   -2.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7738    2.1005   -2.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4090   -1.6418    1.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8373   -3.4396    2.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2058   -3.5453    1.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1123   -1.8369   -0.2512 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
  7  3  1  0
 20 15  1  0
 14  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  9 28  1  0
  9 29  1  0
  9 30  1  0
 12 31  1  0
 12 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
M  END

1559
  Mrv0541 02231215332D          

 21 23  0  0  0  0            999 V2000
    4.5315    0.6150    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.3908   -1.4629    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.2011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9664   -1.7330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538   -0.0668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6048   -0.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6089   -1.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9572    0.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689   -0.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3842   -0.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6940   -0.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995   -0.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1612   -1.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1368    0.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541   -2.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1100   -1.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9240    1.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292    1.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1035    1.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7088    2.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4959    2.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2  7  1  0  0  0  0
  2  9  1  0  0  0  0
  3 13  2  0  0  0  0
  4  7  1  0  0  0  0
  4 13  1  0  0  0  0
  4 15  1  0  0  0  0
  5  8  2  0  0  0  0
  5 12  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 14 17  1  0  0  0  0
 14 18  2  0  0  0  0
 17 19  2  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015512

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=CC2=C(S1)N(C)C(=O)CN=C2C1=CC=CC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C16H15ClN2OS/c1-3-10-8-12-15(11-6-4-5-7-13(11)17)18-9-14(20)19(2)16(12)21-10/h4-8H,3,9H2,1-2H3

> <INCHI_KEY>
CHBRHODLKOZEPZ-UHFFFAOYSA-N

> <FORMULA>
C16H15ClN2OS

> <MOLECULAR_WEIGHT>
318.821

> <EXACT_MASS>
318.059361509

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
33.01238216949369

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(2-chlorophenyl)-7-ethyl-1-methyl-1H,2H,3H-thieno[2,3-e][1,4]diazepin-2-one

> <ALOGPS_LOGP>
3.58

> <JCHEM_LOGP>
4.1129539663333325

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.388366642131673

> <JCHEM_POLAR_SURFACE_AREA>
32.67

> <JCHEM_REFRACTIVITY>
85.65790000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
Rize

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015512
     RDKit          3D
Clotiazepam
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.5877   -2.1540    1.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4660   -1.7965   -0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4440   -0.6971   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0920   -0.7902   -0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3771    0.3428   -0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0972    1.5152   -0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006    1.0011   -0.0863 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6158    2.8823   -0.3983 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256    3.8255    0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5469    3.3029   -1.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8433    4.4787   -1.0434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3902    2.4110   -1.9701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7887    1.2267   -1.2303 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017    0.3296   -0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8835   -0.7234    0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4430   -1.6935    0.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2740   -2.7021    1.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5754   -2.7435    0.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0794   -1.7884    0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2225   -0.7957   -0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9060    0.4096   -1.4434 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3363   -1.2886    2.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6252   -2.4497    1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460   -2.9550    1.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3920   -1.5076   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0392   -2.6615   -0.5920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6649   -1.8104   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3151    3.7935    1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5087    3.6431    0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1954    4.8433   -0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3361    2.9148   -2.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7738    2.1005   -2.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4090   -1.6418    1.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8373   -3.4396    2.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2058   -3.5453    1.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1123   -1.8369   -0.2512 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
  7  3  1  0
 20 15  1  0
 14  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  9 28  1  0
  9 29  1  0
  9 30  1  0
 12 31  1  0
 12 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1559                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       8.459   1.148   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0       8.196  -2.731   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       3.080  -4.109   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       5.537  -3.235   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.020  -0.125   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.729  -0.729   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.737  -2.269   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.520   0.225   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.089  -1.487   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.184  -0.252   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.629  -1.479   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.359  -1.516   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.034  -2.900   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.855   1.729   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.888  -4.735   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.405  -2.809   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.325   2.190   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.721   2.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.660   3.693   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.056   4.273   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.526   4.735   0.000  0.00  0.00           C+0
CONECT    1   17                                                            
CONECT    2    7    9                                                       
CONECT    3   13                                                            
CONECT    4    7   13   15                                                  
CONECT    5    8   12                                                       
CONECT    6    7    8   10                                                  
CONECT    7    2    4    6                                                  
CONECT    8    5    6   14                                                  
CONECT    9    2   10   11                                                  
CONECT   10    6    9                                                       
CONECT   11    9   16                                                       
CONECT   12    5   13                                                       
CONECT   13    3    4   12                                                  
CONECT   14    8   17   18                                                  
CONECT   15    4                                                            
CONECT   16   11                                                            
CONECT   17    1   14   19                                                  
CONECT   18   14   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    HMDB0015512
HETATM    1  C1  UNL     1       3.588  -2.154   1.398  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.466  -1.797  -0.048  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.444  -0.697  -0.157  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.092  -0.790  -0.334  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.377   0.343  -0.399  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.097   1.515  -0.285  1.00  0.00           C  
HETATM    7  S1  UNL     1       2.701   1.001  -0.086  1.00  0.00           S  
HETATM    8  N1  UNL     1       0.616   2.882  -0.398  1.00  0.00           N  
HETATM    9  C7  UNL     1       1.426   3.825   0.286  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.547   3.303  -1.131  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.843   4.479  -1.043  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.390   2.411  -1.970  1.00  0.00           C  
HETATM   13  N2  UNL     1      -1.789   1.227  -1.230  1.00  0.00           N  
HETATM   14  C10 UNL     1      -1.102   0.330  -0.554  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.884  -0.723   0.054  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.443  -1.693   0.899  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.274  -2.702   1.334  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.575  -2.744   0.918  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.079  -1.788   0.066  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.222  -0.796  -0.350  1.00  0.00           C  
HETATM   21 CL1  UNL     1      -3.906   0.410  -1.443  1.00  0.00          CL  
HETATM   22  H1  UNL     1       3.336  -1.289   2.054  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.625  -2.450   1.662  1.00  0.00           H  
HETATM   24  H3  UNL     1       2.846  -2.955   1.684  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.392  -1.508  -0.541  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.039  -2.661  -0.592  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.665  -1.810  -0.464  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.315   3.794   1.390  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.509   3.643   0.084  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.195   4.843  -0.047  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.336   2.915  -2.257  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.774   2.101  -2.837  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.409  -1.642   1.306  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.837  -3.440   2.009  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.206  -3.545   1.274  1.00  0.00           H  
HETATM   36  H15 UNL     1      -5.112  -1.837  -0.251  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4    4    7
CONECT    4    5   27
CONECT    5    6    6   14
CONECT    6    7    8
CONECT    8    9   10
CONECT    9   28   29   30
CONECT   10   11   11   12
CONECT   12   13   31   32
CONECT   13   14   14
CONECT   14   15
CONECT   15   16   16   20
CONECT   16   17   33
CONECT   17   18   18   34
CONECT   18   19   35
CONECT   19   20   20   36
CONECT   20   21
END

HMDB0015512
     RDKit          3D
Clotiazepam
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.5877   -2.1540    1.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4660   -1.7965   -0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4440   -0.6971   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0920   -0.7902   -0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3771    0.3428   -0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0972    1.5152   -0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006    1.0011   -0.0863 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6158    2.8823   -0.3983 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256    3.8255    0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5469    3.3029   -1.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8433    4.4787   -1.0434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3902    2.4110   -1.9701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7887    1.2267   -1.2303 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017    0.3296   -0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8835   -0.7234    0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4430   -1.6935    0.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2740   -2.7021    1.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5754   -2.7435    0.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0794   -1.7884    0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2225   -0.7957   -0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9060    0.4096   -1.4434 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3363   -1.2886    2.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6252   -2.4497    1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460   -2.9550    1.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3920   -1.5076   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0392   -2.6615   -0.5920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6649   -1.8104   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3151    3.7935    1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5087    3.6431    0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1954    4.8433   -0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3361    2.9148   -2.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7738    2.1005   -2.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4090   -1.6418    1.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8373   -3.4396    2.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2058   -3.5453    1.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1123   -1.8369   -0.2512 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
  7  3  1  0
 20 15  1  0
 14  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  9 28  1  0
  9 29  1  0
  9 30  1  0
 12 31  1  0
 12 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Rize	Kegg

Chemical Formula

C₁₆H₁₅ClN₂OS

Average Molecular Weight

318.821

Monoisotopic Molecular Weight

318.059361509

IUPAC Name

5-(2-chlorophenyl)-7-ethyl-1-methyl-1H,2H,3H-thieno[2,3-e][1,4]diazepin-2-one

Traditional Name

Rize

CAS Registry Number

33671-46-4

SMILES

CCC1=CC2=C(S1)N(C)C(=O)CN=C2C1=CC=CC=C1Cl

InChI Identifier

InChI=1S/C16H15ClN2OS/c1-3-10-8-12-15(11-6-4-5-7-13(11)17)18-9-14(20)19(2)16(12)21-10/h4-8H,3,9H2,1-2H3

InChI Key

CHBRHODLKOZEPZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thienodiazepines. These are heteropolycyclic containing a thiophene ring fused to a diazepine ring. Thiophene is 5-membered ring consisting of four carbon and one sulfur atoms. Diazepine is a 7-membered ring consisting of five carbon and two nitrogen atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thienodiazepines

Sub Class

Not Available

Direct Parent

Thienodiazepines

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Thieno-para-diazepine
2,3,5-trisubstituted thiophene
Para-diazepine
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Thiophene
Tertiary carboxylic acid amide
Carboxamide group
Ketimine
Lactam
Azacycle
Carboxylic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Imine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organohalogen compound
Organochloride
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: HMDB0015512)

Source

Exogenous

Exogenous (HMDB: HMDB0015512)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	118 - 120 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0054 g/L	Not Available
LogP	3.18	MARUYAMA,T ET AL. (1992)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0054 g/L	ALOGPS
logP	3.58	ALOGPS
logP	4.11	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	2.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	32.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.66 m³·mol⁻¹	ChemAxon
Polarizability	33.01 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	163.57	30932474
DeepCCS	[M-H]-	161.212	30932474
DeepCCS	[M-2H]-	194.45	30932474
DeepCCS	[M+Na]+	169.677	30932474
AllCCS	[M+H]+	170.3	32859911
AllCCS	[M+H-H2O]+	166.8	32859911
AllCCS	[M+NH4]+	173.5	32859911
AllCCS	[M+Na]+	174.4	32859911
AllCCS	[M-H]-	175.9	32859911
AllCCS	[M+Na-2H]-	175.7	32859911
AllCCS	[M+HCOO]-	175.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Clotiazepam	CCC1=CC2=C(S1)N(C)C(=O)CN=C2C1=CC=CC=C1Cl	3783.5	Standard polar	33892256
Clotiazepam	CCC1=CC2=C(S1)N(C)C(=O)CN=C2C1=CC=CC=C1Cl	2516.4	Standard non polar	33892256
Clotiazepam	CCC1=CC2=C(S1)N(C)C(=O)CN=C2C1=CC=CC=C1Cl	2470.9	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 - Clotiazepam GC-MS (Non-derivatized) - 70eV, Positive	splash10-0iki-0492000000-857499d04130284e4e31	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clotiazepam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clotiazepam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014u-3494000000-432038f1e527960b02fc	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 - Clotiazepam 10V, Positive-QTOF	splash10-014i-0049000000-45282a7515b9494775c7	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clotiazepam 20V, Positive-QTOF	splash10-014i-1159000000-1ff3be2c8d5ba546d7e8	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clotiazepam 40V, Positive-QTOF	splash10-0a4i-9300000000-d8aa0cda66e62a6b96f7	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clotiazepam 10V, Negative-QTOF	splash10-014i-0029000000-e488e2ee1deb04a7e337	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clotiazepam 20V, Negative-QTOF	splash10-014i-2797000000-62a84846bdd05fc7140f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clotiazepam 40V, Negative-QTOF	splash10-0a6r-9660000000-74eeddd7f53b2ae0bde1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clotiazepam 10V, Positive-QTOF	splash10-014i-0009000000-8f50d8b62b53d25c58b2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clotiazepam 20V, Positive-QTOF	splash10-014i-0029000000-1fe711e000cbbd0f052a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clotiazepam 40V, Positive-QTOF	splash10-003i-0981000000-3c7f1bd750ea8ca9f79b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clotiazepam 10V, Negative-QTOF	splash10-014i-0009000000-e086905fb0819f34744f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clotiazepam 20V, Negative-QTOF	splash10-00lr-9066000000-d3f402d10fb32f4ff8c2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clotiazepam 40V, Negative-QTOF	splash10-001i-5190000000-2dc5059b047387d48b89	2021-10-11	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 DB01559	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01559	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

DB01559

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2709

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Clotiazepam

METLIN ID

Not Available

PubChem Compound

2811

PDB ID

Not Available

ChEBI ID

1178501

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

Nakazawa Y, Kotorii M, Oshima M, Horikawa S, Tachibana H: Effects of thienodiazepine derivatives on human sleep as compared to those of benzodiazepine derivatives. Psychopharmacologia. 1975 Oct 31;44(2):165-71. [PubMed:709 ]

Only showing the first 10 proteins. There are 20 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

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

Enzyme Details

2. Cytochrome P450 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

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

Enzyme Details

3. 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

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

Enzyme Details

4. Cytochrome P450 2B6

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

References

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

Enzyme Details

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

Baburin I, Khom S, Timin E, Hohaus A, Sieghart W, Hering S: Estimating the efficiency of benzodiazepines on GABA(A) receptors comprising gamma1 or gamma2 subunits. Br J Pharmacol. 2008 Oct;155(3):424-33. doi: 10.1038/bjp.2008.271. Epub 2008 Jul 7. [PubMed:18604239 ]
Mandrioli R, Mercolini L, Raggi MA: Benzodiazepine metabolism: an analytical perspective. Curr Drug Metab. 2008 Oct;9(8):827-44. [PubMed:18855614 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

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

Baburin I, Khom S, Timin E, Hohaus A, Sieghart W, Hering S: Estimating the efficiency of benzodiazepines on GABA(A) receptors comprising gamma1 or gamma2 subunits. Br J Pharmacol. 2008 Oct;155(3):424-33. doi: 10.1038/bjp.2008.271. Epub 2008 Jul 7. [PubMed:18604239 ]
Mandrioli R, Mercolini L, Raggi MA: Benzodiazepine metabolism: an analytical perspective. Curr Drug Metab. 2008 Oct;9(8):827-44. [PubMed:18855614 ]

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

Mandrioli R, Mercolini L, Raggi MA: Benzodiazepine metabolism: an analytical perspective. Curr Drug Metab. 2008 Oct;9(8):827-44. [PubMed:18855614 ]

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

Mandrioli R, Mercolini L, Raggi MA: Benzodiazepine metabolism: an analytical perspective. Curr Drug Metab. 2008 Oct;9(8):827-44. [PubMed:18855614 ]

Enzyme Details

9. 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

Mandrioli R, Mercolini L, Raggi MA: Benzodiazepine metabolism: an analytical perspective. Curr Drug Metab. 2008 Oct;9(8):827-44. [PubMed:18855614 ]

Enzyme Details

10. 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

Mandrioli R, Mercolini L, Raggi MA: Benzodiazepine metabolism: an analytical perspective. Curr Drug Metab. 2008 Oct;9(8):827-44. [PubMed:18855614 ]

Only showing the first 10 proteins. There are 20 proteins in total.

Show all enzymes and transporters

Showing metabocard for Clotiazepam (HMDB0015512)

MOL for HMDB0015512 (Clotiazepam)

3D MOL for HMDB0015512 (Clotiazepam)

3D SDF for HMDB0015512 (Clotiazepam)

3D-SDF for HMDB0015512 (Clotiazepam)

PDB for HMDB0015512 (Clotiazepam)

3D PDB for HMDB0015512 (Clotiazepam)

SMILES for HMDB0015512 (Clotiazepam)

INCHI for HMDB0015512 (Clotiazepam)

Structure for HMDB0015512 (Clotiazepam)

3D Structure for HMDB0015512 (Clotiazepam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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