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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (24)transporters (2) Show 26 proteins XML

enzymes (24)transporters (2) Show 26 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014821

Secondary Accession Numbers

HMDB14821

Metabolite Identification

Common Name

Midazolam

Description

A short-acting hypnotic-sedative drug with anxiolytic and amnestic properties. It is used in dentistry, cardiac surgery, endoscopic procedures, as preanesthetic medication, and as an adjunct to local anesthesia. The short duration and cardiorespiratory stability makes it useful in poor-risk, elderly, and cardiac patients. It is water-soluble at pH less than 4 and lipid-soluble at physiological pH. [PubChem] Midazolam is a schedule IV drug in the United States.

Structure

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

HMDB0014821
     RDKit          3D
Midazolam
 36 39  0  0  0  0  0  0  0  0999 V2000
   -3.8245   -0.2842    1.6352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1735    0.8319    0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4889    2.1644    1.0198 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6104    2.8968    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7388    2.0368   -0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1341    0.7889    0.1373 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4807   -0.4055   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765   -1.4190   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8364   -2.6315   -0.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4647   -2.7453   -1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2118   -4.2733   -1.7033 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3914   -1.6813   -0.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1242   -0.5067   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093    0.5115   -0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2337    0.1775    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673   -1.0006    0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9936   -1.2768    0.8298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9435   -0.3241    0.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5595    0.9027    0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2341    1.1517   -0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8665    2.3532   -0.6489 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.6408    1.7633   -0.6896 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5827    2.4009   -1.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8353   -0.5413    1.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0130    0.1594    2.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1586   -1.1223    1.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6645    3.9690    0.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4058   -1.2977   -0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5156   -3.4594   -1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4425   -1.7328   -1.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9747   -1.8012    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2960   -2.2429    1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9859   -0.5298    0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3395    1.6379   -0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7817    2.0403   -2.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799    3.4897   -1.1773 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  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
 14 22  2  0
 22 23  1  0
  6  2  1  0
 13  7  1  0
 20 15  1  0
 23  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  8 28  1  0
  9 29  1  0
 12 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 23 35  1  0
 23 36  1  0
M  END

683
  Mrv0541 02231214552D          

 23 26  0  0  0  0            999 V2000
    1.6500   -0.2321    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.8438    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -1.3269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2284    0.4805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7352   -2.2849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0726   -0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5592   -0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890   -0.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7428   -0.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4034    0.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9281   -2.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1244   -1.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4517   -1.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0718    0.1014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0454    1.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3328   -2.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6286   -1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4374   -0.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5102    1.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2227    1.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1523    2.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8648    2.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296    2.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 19  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3 11  1  0  0  0  0
  4  9  1  0  0  0  0
  4 10  2  0  0  0  0
  5 11  2  0  0  0  0
  5 12  1  0  0  0  0
  6  8  2  0  0  0  0
  6 13  1  0  0  0  0
  7  9  1  0  0  0  0
  7 12  2  0  0  0  0
  8 10  1  0  0  0  0
  8 14  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  2  0  0  0  0
 15 19  1  0  0  0  0
 15 20  2  0  0  0  0
 17 18  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014821

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=NC=C2CN=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N12

> <INCHI_IDENTIFIER>
InChI=1S/C18H13ClFN3/c1-11-21-9-13-10-22-18(14-4-2-3-5-16(14)20)15-8-12(19)6-7-17(15)23(11)13/h2-9H,10H2,1H3

> <INCHI_KEY>
DDLIGBOFAVUZHB-UHFFFAOYSA-N

> <FORMULA>
C18H13ClFN3

> <MOLECULAR_WEIGHT>
325.767

> <EXACT_MASS>
325.078203343

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.70084245900745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.89

> <JCHEM_LOGP>
3.3348000000000004

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.571590140482956

> <JCHEM_POLAR_SURFACE_AREA>
30.18

> <JCHEM_REFRACTIVITY>
99.42970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.87e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
midazolam

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014821
     RDKit          3D
Midazolam
 36 39  0  0  0  0  0  0  0  0999 V2000
   -3.8245   -0.2842    1.6352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1735    0.8319    0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4889    2.1644    1.0198 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6104    2.8968    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7388    2.0368   -0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1341    0.7889    0.1373 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4807   -0.4055   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765   -1.4190   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8364   -2.6315   -0.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4647   -2.7453   -1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2118   -4.2733   -1.7033 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3914   -1.6813   -0.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1242   -0.5067   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093    0.5115   -0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2337    0.1775    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673   -1.0006    0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9936   -1.2768    0.8298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9435   -0.3241    0.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5595    0.9027    0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2341    1.1517   -0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8665    2.3532   -0.6489 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.6408    1.7633   -0.6896 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5827    2.4009   -1.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8353   -0.5413    1.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0130    0.1594    2.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1586   -1.1223    1.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6645    3.9690    0.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4058   -1.2977   -0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5156   -3.4594   -1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4425   -1.7328   -1.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9747   -1.8012    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2960   -2.2429    1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9859   -0.5298    0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3395    1.6379   -0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7817    2.0403   -2.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799    3.4897   -1.1773 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  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
 14 22  2  0
 22 23  1  0
  6  2  1  0
 13  7  1  0
 20 15  1  0
 23  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  8 28  1  0
  9 29  1  0
 12 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 23 35  1  0
 23 36  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 683                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080  -0.433   0.000  0.00  0.00          Cl+0
HETATM    2  F   UNK     0       9.955   3.442   0.000  0.00  0.00           F+0
HETATM    3  N   UNK     0       8.990  -2.477   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       9.760   0.897   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      10.706  -4.265   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.602  -1.809   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.377  -1.809   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.259  -0.307   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.720  -0.307   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.220   0.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.199  -3.993   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.432  -2.918   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.443  -2.918   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.734   0.189   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.551   2.284   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.088  -5.059   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.907  -2.457   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.550  -0.893   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.419   3.557   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.016   2.399   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.751   4.944   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.348   3.787   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.215   5.059   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3    6    7   11                                                  
CONECT    4    9   10                                                       
CONECT    5   11   12                                                       
CONECT    6    3    8   13                                                  
CONECT    7    3    9   12                                                  
CONECT    8    6   10   14                                                  
CONECT    9    4    7                                                       
CONECT   10    4    8   15                                                  
CONECT   11    3    5   16                                                  
CONECT   12    5    7                                                       
CONECT   13    6   17                                                       
CONECT   14    8   18                                                       
CONECT   15   10   19   20                                                  
CONECT   16   11                                                            
CONECT   17   13   18                                                       
CONECT   18    1   14   17                                                  
CONECT   19    2   15   21                                                  
CONECT   20   15   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   23                                                       
CONECT   23   21   22                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0014821
HETATM    1  C1  UNL     1      -3.824  -0.284   1.635  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.174   0.832   0.929  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.489   2.164   1.020  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.610   2.897   0.269  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.739   2.037  -0.299  1.00  0.00           C  
HETATM    6  N2  UNL     1      -2.134   0.789   0.137  1.00  0.00           N  
HETATM    7  C5  UNL     1      -1.481  -0.406  -0.271  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.377  -1.419  -0.429  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.836  -2.631  -0.881  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.465  -2.745  -1.143  1.00  0.00           C  
HETATM   11 CL1  UNL     1       0.212  -4.273  -1.703  1.00  0.00          CL  
HETATM   12  C9  UNL     1       0.391  -1.681  -0.967  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.124  -0.507  -0.524  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.909   0.511  -0.391  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.234   0.178   0.034  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.667  -1.001   0.527  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.994  -1.277   0.830  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.944  -0.324   0.633  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.560   0.903   0.133  1.00  0.00           C  
HETATM   20  C17 UNL     1       3.234   1.152  -0.161  1.00  0.00           C  
HETATM   21  F1  UNL     1       2.866   2.353  -0.649  1.00  0.00           F  
HETATM   22  N3  UNL     1       0.641   1.763  -0.690  1.00  0.00           N  
HETATM   23  C18 UNL     1      -0.583   2.401  -1.158  1.00  0.00           C  
HETATM   24  H1  UNL     1      -4.835  -0.541   1.331  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.013   0.159   2.682  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.159  -1.122   1.932  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.665   3.969   0.190  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.406  -1.298  -0.287  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.516  -3.459  -1.014  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.443  -1.733  -1.233  1.00  0.00           H  
HETATM   31  H8  UNL     1       1.975  -1.801   0.787  1.00  0.00           H  
HETATM   32  H9  UNL     1       4.296  -2.243   1.223  1.00  0.00           H  
HETATM   33  H10 UNL     1       5.986  -0.530   0.866  1.00  0.00           H  
HETATM   34  H11 UNL     1       5.339   1.638  -0.011  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.782   2.040  -2.172  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.480   3.490  -1.177  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    6
CONECT    3    4
CONECT    4    5    5   27
CONECT    5    6   23
CONECT    6    7
CONECT    7    8    8   13
CONECT    8    9   28
CONECT    9   10   10   29
CONECT   10   11   12
CONECT   12   13   13   30
CONECT   13   14
CONECT   14   15   22   22
CONECT   15   16   16   20
CONECT   16   17   31
CONECT   17   18   18   32
CONECT   18   19   33
CONECT   19   20   20   34
CONECT   20   21
CONECT   22   23
CONECT   23   35   36
END

HMDB0014821
     RDKit          3D
Midazolam
 36 39  0  0  0  0  0  0  0  0999 V2000
   -3.8245   -0.2842    1.6352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1735    0.8319    0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4889    2.1644    1.0198 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6104    2.8968    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7388    2.0368   -0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1341    0.7889    0.1373 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4807   -0.4055   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765   -1.4190   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8364   -2.6315   -0.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4647   -2.7453   -1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2118   -4.2733   -1.7033 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3914   -1.6813   -0.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1242   -0.5067   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093    0.5115   -0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2337    0.1775    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673   -1.0006    0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9936   -1.2768    0.8298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9435   -0.3241    0.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5595    0.9027    0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2341    1.1517   -0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8665    2.3532   -0.6489 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.6408    1.7633   -0.6896 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5827    2.4009   -1.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8353   -0.5413    1.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0130    0.1594    2.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1586   -1.1223    1.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6645    3.9690    0.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4058   -1.2977   -0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5156   -3.4594   -1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4425   -1.7328   -1.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9747   -1.8012    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2960   -2.2429    1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9859   -0.5298    0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3395    1.6379   -0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7817    2.0403   -2.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799    3.4897   -1.1773 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  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
 14 22  2  0
 22 23  1  0
  6  2  1  0
 13  7  1  0
 20 15  1  0
 23  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  8 28  1  0
  9 29  1  0
 12 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 23 35  1  0
 23 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Buccolam	ChEBI
Dormicum	ChEBI
Mezolam	ChEBI
Midazolamum	ChEBI
Nayzilam	Kegg
Dea no. 2884	HMDB
Midazolam base	HMDB
Maleate, midazolam	HMDB
Midazolam maleate	HMDB
Hydrochloride, midazolam	HMDB
Midazolam hydrochloride	HMDB
Versed	HMDB

Chemical Formula

C₁₈H₁₃ClFN₃

Average Molecular Weight

325.767

Monoisotopic Molecular Weight

325.078203343

IUPAC Name

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

Traditional Name

midazolam

CAS Registry Number

59467-70-8

SMILES

CC1=NC=C2CN=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N12

InChI Identifier

InChI=1S/C18H13ClFN3/c1-11-21-9-13-10-22-18(14-4-2-3-5-16(14)20)15-8-12(19)6-7-17(15)23(11)13/h2-9H,10H2,1H3

InChI Key

DDLIGBOFAVUZHB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as imidazo[1,5-a][1,4]benzodiazepines. Imidazo[1,5-a][1,4]benzodiazepines are compounds containing an imidazole ring and a 1,4-benzodiazepine ring system, both sharing one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

Imidazo[1,5-a][1,4]benzodiazepines

Alternative Parents

Substituents

Imidazo[1,5-a][1,4]benzodiazepine
Para-diazepine
Fluorobenzene
Halobenzene
Aryl chloride
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Benzenoid
N-substituted imidazole
Heteroaromatic compound
Azole
Imidazole
Ketimine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organofluoride
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organochloride
Imine
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

diazepine (CHEBI:6931 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014821)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	159 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0099 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	172.8	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0099 g/L	ALOGPS
logP	3.89	ALOGPS
logP	3.33	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	6.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.18 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	99.43 m³·mol⁻¹	ChemAxon
Polarizability	32.7 Å³	ChemAxon
Number of Rings	4	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-2H]-	207.721	30932474
DeepCCS	[M+Na]+	182.948	30932474
AllCCS	[M+H]+	173.0	32859911
AllCCS	[M+H-H2O]+	169.5	32859911
AllCCS	[M+NH4]+	176.2	32859911
AllCCS	[M+Na]+	177.1	32859911
AllCCS	[M-H]-	174.0	32859911
AllCCS	[M+Na-2H]-	172.9	32859911
AllCCS	[M+HCOO]-	171.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Midazolam	CC1=NC=C2CN=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N12	3687.1	Standard polar	33892256
Midazolam	CC1=NC=C2CN=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N12	2635.7	Standard non polar	33892256
Midazolam	CC1=NC=C2CN=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N12	2579.0	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 - Midazolam GC-MS (Non-derivatized) - 70eV, Positive	splash10-002g-5092000000-4478c9440e5f31cecc49	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Midazolam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Midazolam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-3839000000-42781254e15bcd5b31b6	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam LC-ESI-qTof , Positive-QTOF	splash10-03di-0910000000-98021a5812f1663e9397	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam LC-ESI-QTOF , positive-QTOF	splash10-004i-0009000000-2411220f611ba30ef225	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam LC-ESI-QTOF , positive-QTOF	splash10-004i-0009000000-c724b297ae99edb399d3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam LC-ESI-QTOF , positive-QTOF	splash10-004l-0098000000-b57c162c4eeaad9ef111	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam LC-ESI-QTOF , positive-QTOF	splash10-0006-0090000000-a3133528f5491f4c9a6b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam LC-ESI-QTOF , positive-QTOF	splash10-05fs-0290000000-ee126555f849ecfff795	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam LC-ESI-QFT , positive-QTOF	splash10-004i-0009000000-4ae622c7b53369b0cfb1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam LC-ESI-QFT , positive-QTOF	splash10-004i-0019000000-00c3c9e2813a454acda1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam LC-ESI-QFT , positive-QTOF	splash10-002f-0093000000-a8ca99ef6c84536bff07	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam LC-ESI-QFT , positive-QTOF	splash10-0006-0091000000-3edc4aa6f67d99b789a8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam LC-ESI-QFT , positive-QTOF	splash10-0abd-0290000000-aa5e16437618ad2adb86	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam LC-ESI-QFT , positive-QTOF	splash10-05fs-0490000000-a323090224c5b01e3990	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam , positive-QTOF	splash10-004i-0189000000-6e704a4a2a65211394ab	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam , positive-QTOF	splash10-03di-0910000000-98021a5812f1663e9397	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam 15V, Positive-QTOF	splash10-004i-0009000000-5b177595069a22f7499c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam 30V, Positive-QTOF	splash10-004i-0019000000-d4a03e7fbafc667f26cd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam 50V, Positive-QTOF	splash10-05fs-0290000000-073275db750ee5c73815	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam 40V, Positive-QTOF	splash10-0006-0090000000-1c567d03f4799499290c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Midazolam 45V, Positive-QTOF	splash10-002f-0093000000-77027f57247046e6973c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Midazolam 10V, Positive-QTOF	splash10-004i-0019000000-75a4c3ae620bf5e6503a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Midazolam 20V, Positive-QTOF	splash10-004i-0029000000-6729271ff5dbb7d43009	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Midazolam 40V, Positive-QTOF	splash10-0a7i-1390000000-39f40fc60488c1207b28	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Midazolam 10V, Negative-QTOF	splash10-00di-0009000000-b77187b6c2f47259d8d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Midazolam 20V, Negative-QTOF	splash10-00di-0029000000-91cf028d658129087ce6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Midazolam 40V, Negative-QTOF	splash10-0ufu-5091000000-645cab1e9777fb49b7b2	2016-08-03	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 DB00683	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00683	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

DB00683

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4047

KEGG Compound ID

C07524

BioCyc ID

CPD-20500

BiGG ID

Not Available

Wikipedia Link

Midazolam

METLIN ID

Not Available

PubChem Compound

4192

PDB ID

Not Available

ChEBI ID

6931

Food Biomarker Ontology

Not Available

VMH ID

MDZ

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. [PubMed:6135616 ]
Tokunaga S, Takeda Y, Shinomiya K, Hirase M, Kamei C: Effects of some H1-antagonists on the sleep-wake cycle in sleep-disturbed rats. J Pharmacol Sci. 2007 Feb;103(2):201-6. Epub 2007 Feb 8. [PubMed:17287588 ]
Garratt JC, Gent JP, Feely M, Haigh JR: Can benzodiazepines be classified by characterising their anticonvulsant tolerance-inducing potential? Eur J Pharmacol. 1988 Jan 5;145(1):75-80. [PubMed:2894998 ]
Isojarvi JI, Tokola RA: Benzodiazepines in the treatment of epilepsy in people with intellectual disability. J Intellect Disabil Res. 1998 Dec;42 Suppl 1:80-92. [PubMed:10030438 ]
Vermeeren A: Residual effects of hypnotics: epidemiology and clinical implications. CNS Drugs. 2004;18(5):297-328. [PubMed:15089115 ]
(). FDA label . .

Only showing the first 10 proteins. There are 26 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

Foti RS, Rock DA, Wienkers LC, Wahlstrom JL: Selection of alternative CYP3A4 probe substrates for clinical drug interaction studies using in vitro data and in vivo simulation. Drug Metab Dispos. 2010 Jun;38(6):981-7. doi: 10.1124/dmd.110.032094. Epub 2010 Mar 4. [PubMed:20203109 ]
Pelkonen O, Maenpaa J, Taavitsainen P, Rautio A, Raunio H: Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica. 1998 Dec;28(12):1203-53. [PubMed:9890159 ]
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 ]
Zhou S, Chan E, Lim LY, Boelsterli UA, Li SC, Wang J, Zhang Q, Huang M, Xu A: Therapeutic drugs that behave as mechanism-based inhibitors of cytochrome P450 3A4. Curr Drug Metab. 2004 Oct;5(5):415-42. [PubMed:15544435 ]
Williams JA, Ring BJ, Cantrell VE, Jones DR, Eckstein J, Ruterbories K, Hamman MA, Hall SD, Wrighton SA: Comparative metabolic capabilities of CYP3A4, CYP3A5, and CYP3A7. Drug Metab Dispos. 2002 Aug;30(8):883-91. [PubMed:12124305 ]
Galetin A, Clarke SE, Houston JB: Quinidine and haloperidol as modifiers of CYP3A4 activity: multisite kinetic model approach. Drug Metab Dispos. 2002 Dec;30(12):1512-22. [PubMed:12433827 ]
Obach RS, Reed-Hagen AE: Measurement of Michaelis constants for cytochrome P450-mediated biotransformation reactions using a substrate depletion approach. Drug Metab Dispos. 2002 Jul;30(7):831-7. [PubMed:12065442 ]

Enzyme Details

2. 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

Ekins S, Vandenbranden M, Ring BJ, Gillespie JS, Yang TJ, Gelboin HV, Wrighton SA: Further characterization of the expression in liver and catalytic activity of CYP2B6. J Pharmacol Exp Ther. 1998 Sep;286(3):1253-9. [PubMed:9732386 ]
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 ]
Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015 ]

Enzyme Details

3. Cytochrome P450 3A5

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:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

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 ]
Patki KC, Von Moltke LL, Greenblatt DJ: In vitro metabolism of midazolam, triazolam, nifedipine, and testosterone by human liver microsomes and recombinant cytochromes p450: role of cyp3a4 and cyp3a5. Drug Metab Dispos. 2003 Jul;31(7):938-44. [PubMed:12814972 ]
Wandel C, Bocker R, Bohrer H, Browne A, Rugheimer E, Martin E: Midazolam is metabolized by at least three different cytochrome P450 enzymes. Br J Anaesth. 1994 Nov;73(5):658-61. [PubMed:7826796 ]
Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015 ]

Enzyme Details

4. Cytochrome P450 3A7

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:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

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 ]
Gorski JC, Hall SD, Jones DR, VandenBranden M, Wrighton SA: Regioselective biotransformation of midazolam by members of the human cytochrome P450 3A (CYP3A) subfamily. Biochem Pharmacol. 1994 Apr 29;47(9):1643-53. [PubMed:8185679 ]
Ghosal A, Satoh H, Thomas PE, Bush E, Moore D: Inhibition and kinetics of cytochrome P4503A activity in microsomes from rat, human, and cdna-expressed human cytochrome P450. Drug Metab Dispos. 1996 Sep;24(9):940-7. [PubMed:8886602 ]
Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015 ]

Enzyme Details

5. Cytochrome P450 4B1

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:: CYP4B1
Uniprot ID:: P13584
Molecular weight:: 58990.64

References

Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015 ]

Enzyme Details

6. 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

Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]

Enzyme Details

7. 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

Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]

Enzyme Details

8. 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

Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]

Enzyme Details

9. 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

Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]

Enzyme Details

10. 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

Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Schuetz EG, Beck WT, Schuetz JD: Modulators and substrates of P-glycoprotein and cytochrome P4503A coordinately up-regulate these proteins in human colon carcinoma cells. Mol Pharmacol. 1996 Feb;49(2):311-8. [PubMed:8632764 ]
Katoh M, Nakajima M, Yamazaki H, Yokoi T: Inhibitory effects of CYP3A4 substrates and their metabolites on P-glycoprotein-mediated transport. Eur J Pharm Sci. 2001 Feb;12(4):505-13. [PubMed:11231118 ]
Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [PubMed:12699389 ]
Takano M, Hasegawa R, Fukuda T, Yumoto R, Nagai J, Murakami T: Interaction with P-glycoprotein and transport of erythromycin, midazolam and ketoconazole in Caco-2 cells. Eur J Pharmacol. 1998 Oct 9;358(3):289-94. [PubMed:9822896 ]
Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Dempsey PJ, Roden MM, Belas F, Chaudhary AK, Roden DM, Wood AJ, Wilkinson GR: Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein. Pharm Res. 1999 Mar;16(3):408-14. [PubMed:10213372 ]
Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]
Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524 ]

Enzyme Details

2. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880 ]

Only showing the first 10 proteins. There are 26 proteins in total.

Show all enzymes and transporters

Showing metabocard for Midazolam (HMDB0014821)

MOL for HMDB0014821 (Midazolam)

3D MOL for HMDB0014821 (Midazolam)

3D SDF for HMDB0014821 (Midazolam)

3D-SDF for HMDB0014821 (Midazolam)

PDB for HMDB0014821 (Midazolam)

3D PDB for HMDB0014821 (Midazolam)

SMILES for HMDB0014821 (Midazolam)

INCHI for HMDB0014821 (Midazolam)

Structure for HMDB0014821 (Midazolam)

3D Structure for HMDB0014821 (Midazolam)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Transporters

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