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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:42 UTC

HMDB ID

HMDB0014704

Secondary Accession Numbers

HMDB14704

Metabolite Identification

Common Name

Carbamazepine

Description

Carbamazepine, also known as tegretol or carnexiv, belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom. Carbamazepine is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, carbamazepine participates in a number of enzymatic reactions. In particular, carbamazepine can be converted into 3-hydroxycarbamazepine through its interaction with the enzymes cytochrome P450 3A4, cytochrome P450 2B6, and cytochrome P450 3A7. In addition, carbamazepine can be converted into carbamazepine-10,11-epoxide; which is catalyzed by the enzymes cytochrome P450 2C8, cytochrome P450 3A4, cytochrome P450 3A5, cytochrome P450 3A7, and cytochrome P450 2C19. In humans, carbamazepine is involved in carbamazepine metabolism pathway. Carbamazepine is a potentially toxic compound. A dibenzoazepine that is 5H-dibenzoazepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant.

Structure

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

HMDB0014704
     RDKit          3D
Carbamazepine
 30 32  0  0  0  0  0  0  0  0999 V2000
    0.2988   -3.2125   -0.2893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958   -2.1040   -0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8157   -2.4587   -0.3372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2782   -0.7724   -0.0065 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924   -0.3944    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7836   -1.3395    0.8317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1565   -1.1680    1.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7592   -0.0431    0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0439    0.8923   -0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    0.7352   -0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0610    1.8151   -1.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425    2.1202   -1.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3725    1.4522   -0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5057    2.2222   -0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6098    1.7142    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6080    0.4546    0.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4653   -0.3205    0.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3506    0.1663    0.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2272   -4.0917    0.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792   -3.0975   -0.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2549   -2.1710    1.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6901   -1.9284    1.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.0816    0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5002    1.7721   -0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7355    2.4127   -1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5348    2.9494   -1.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4672    3.2154   -0.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5035    2.3557    0.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4591    0.0436    1.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3849   -1.3013    1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  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
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18  4  1  0
 10  5  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

564
  Mrv1652305271900052D          

 18 20  0  0  0  0            999 V2000
    4.5536   -1.2161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8677   -0.0280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1818   -1.2161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5814    0.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1540    0.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7576    1.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9778    1.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637    1.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4717    1.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1774   -0.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5580   -0.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5421    1.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1933    1.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8677   -0.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9676   -0.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7678   -0.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1512    0.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    0.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  2  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2 14  1  0  0  0  0
  3 14  1  0  0  0  0
  4  6  1  0  0  0  0
  4 10  2  0  0  0  0
  5  7  1  0  0  0  0
  5 11  2  0  0  0  0
  6  8  1  0  0  0  0
  6 12  2  0  0  0  0
  7  9  1  0  0  0  0
  7 13  2  0  0  0  0
  8  9  2  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014704

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H12N2O/c16-15(18)17-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)17/h1-10H,(H2,16,18)

> <INCHI_KEY>
FFGPTBGBLSHEPO-UHFFFAOYSA-N

> <FORMULA>
C15H12N2O

> <MOLECULAR_WEIGHT>
236.2686

> <EXACT_MASS>
236.094963016

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
25.002490841556707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
2.7660303863333335

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.958359453242029

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7540181335527305

> <JCHEM_POLAR_SURFACE_AREA>
46.33

> <JCHEM_REFRACTIVITY>
71.88800000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014704
     RDKit          3D
Carbamazepine
 30 32  0  0  0  0  0  0  0  0999 V2000
    0.2988   -3.2125   -0.2893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958   -2.1040   -0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8157   -2.4587   -0.3372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2782   -0.7724   -0.0065 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924   -0.3944    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7836   -1.3395    0.8317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1565   -1.1680    1.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7592   -0.0431    0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0439    0.8923   -0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    0.7352   -0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0610    1.8151   -1.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425    2.1202   -1.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3725    1.4522   -0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5057    2.2222   -0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6098    1.7142    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6080    0.4546    0.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4653   -0.3205    0.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3506    0.1663    0.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2272   -4.0917    0.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792   -3.0975   -0.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2549   -2.1710    1.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6901   -1.9284    1.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.0816    0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5002    1.7721   -0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7355    2.4127   -1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5348    2.9494   -1.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4672    3.2154   -0.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5035    2.3557    0.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4591    0.0436    1.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3849   -1.3013    1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  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
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18  4  1  0
 10  5  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 564                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       8.500  -2.270   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       7.220  -0.052   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       5.939  -2.270   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.552   0.589   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.887   0.589   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.881   2.031   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.559   2.031   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.959   3.187   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.481   3.187   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.664  -0.475   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.775  -0.475   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.345   2.507   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.094   2.507   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.220  -1.531   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.140  -0.033   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.300  -0.033   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.482   1.469   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.957   1.469   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2    4    5   14                                                  
CONECT    3   14                                                            
CONECT    4    2    6   10                                                  
CONECT    5    2    7   11                                                  
CONECT    6    4    8   12                                                  
CONECT    7    5    9   13                                                  
CONECT    8    6    9                                                       
CONECT    9    7    8                                                       
CONECT   10    4   15                                                       
CONECT   11    5   16                                                       
CONECT   12    6   17                                                       
CONECT   13    7   18                                                       
CONECT   14    1    2    3                                                  
CONECT   15   10   17                                                       
CONECT   16   11   18                                                       
CONECT   17   12   15                                                       
CONECT   18   13   16                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0014704
HETATM    1  N1  UNL     1       0.299  -3.213  -0.289  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.596  -2.104  -0.203  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.816  -2.459  -0.337  1.00  0.00           O  
HETATM    4  N2  UNL     1      -0.278  -0.772  -0.007  1.00  0.00           N  
HETATM    5  C2  UNL     1       1.092  -0.394   0.119  1.00  0.00           C  
HETATM    6  C3  UNL     1       1.784  -1.340   0.832  1.00  0.00           C  
HETATM    7  C4  UNL     1       3.157  -1.168   1.046  1.00  0.00           C  
HETATM    8  C5  UNL     1       3.759  -0.043   0.527  1.00  0.00           C  
HETATM    9  C6  UNL     1       3.044   0.892  -0.183  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.672   0.735  -0.406  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.061   1.815  -1.156  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.242   2.120  -1.203  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.372   1.452  -0.519  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.506   2.222  -0.418  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.610   1.714   0.223  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.608   0.455   0.767  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.465  -0.321   0.665  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.351   0.166   0.026  1.00  0.00           C  
HETATM   19  H1  UNL     1       0.227  -4.092   0.247  1.00  0.00           H  
HETATM   20  H2  UNL     1       1.079  -3.097  -0.959  1.00  0.00           H  
HETATM   21  H3  UNL     1       1.255  -2.171   1.231  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.690  -1.928   1.612  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.840   0.082   0.701  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.500   1.772  -0.592  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.736   2.413  -1.717  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.535   2.949  -1.804  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.467   3.215  -0.860  1.00  0.00           H  
HETATM   28  H10 UNL     1      -4.504   2.356   0.288  1.00  0.00           H  
HETATM   29  H11 UNL     1      -4.459   0.044   1.269  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.385  -1.301   1.102  1.00  0.00           H  
CONECT    1    2   19   20
CONECT    2    3    3    4
CONECT    4    5   18
CONECT    5    6    6   10
CONECT    6    7   21
CONECT    7    8    8   22
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   11
CONECT   11   12   12   25
CONECT   12   13   26
CONECT   13   14   14   18
CONECT   14   15   27
CONECT   15   16   16   28
CONECT   16   17   29
CONECT   17   18   18   30
END

HMDB0014704
     RDKit          3D
Carbamazepine
 30 32  0  0  0  0  0  0  0  0999 V2000
    0.2988   -3.2125   -0.2893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958   -2.1040   -0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8157   -2.4587   -0.3372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2782   -0.7724   -0.0065 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924   -0.3944    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7836   -1.3395    0.8317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1565   -1.1680    1.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7592   -0.0431    0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0439    0.8923   -0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    0.7352   -0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0610    1.8151   -1.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425    2.1202   -1.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3725    1.4522   -0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5057    2.2222   -0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6098    1.7142    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6080    0.4546    0.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4653   -0.3205    0.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3506    0.1663    0.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2272   -4.0917    0.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792   -3.0975   -0.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2549   -2.1710    1.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6901   -1.9284    1.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.0816    0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5002    1.7721   -0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7355    2.4127   -1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5348    2.9494   -1.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4672    3.2154   -0.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5035    2.3557    0.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4591    0.0436    1.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3849   -1.3013    1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  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
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18  4  1  0
 10  5  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Carbamoyl-5H-dibenz(b,F)azepine	ChEBI
5-Carbamoyl-5H-dibenz[b,F]azepine	ChEBI
5-Carbamoyl-5H-dibenzo(b,F)azepine	ChEBI
5-Carbamyl-5H-dibenzo(b,F)azepine	ChEBI
5H-Dibenz(b,F)azepine-5-carboxamide	ChEBI
Carbamazepen	ChEBI
Carbamazepina	ChEBI
Carbamazepinum	ChEBI
Carnexiv	ChEBI
Equetro	Kegg
Tegretol	Kegg
Carbamezepine	HMDB
Neurotol	HMDB
Amizepine	HMDB
Carbamazepine acetate	HMDB
Carbamazepine anhydrous	HMDB
Carbamazepine dihydrate	HMDB
Carbamazepine hydrochloride	HMDB
Carbamazepine phosphate	HMDB
Epitol	HMDB
Finlepsin	HMDB
Carbamazepine L-tartrate (4:1)	HMDB
Carbamazepine sulfate (2:1)	HMDB
Carbazepin	HMDB

Chemical Formula

C₁₅H₁₂N₂O

Average Molecular Weight

236.2686

Monoisotopic Molecular Weight

236.094963016

IUPAC Name

2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide

Traditional Name

2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide

CAS Registry Number

298-46-4

SMILES

NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C12

InChI Identifier

InChI=1S/C15H12N2O/c16-15(18)17-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)17/h1-10H,(H2,16,18)

InChI Key

FFGPTBGBLSHEPO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzazepines

Sub Class

Dibenzazepines

Direct Parent

Dibenzazepines

Alternative Parents

Substituents

Dibenzazepine
Azepine
Benzenoid
Urea
Carbonic acid derivative
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

ureas (CHEBI:3387 )
dibenzoazepine (CHEBI:3387 )

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: HMDB0014704)

Source

Exogenous

Exogenous (HMDB: HMDB0014704)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Carbamazepine Metabolism Pathway (PathBank: SMP0000634)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	190.2 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.15 g/L	Not Available
LogP	2.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	150.3	30932474
[M+H]+	Not Available	149.012	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000958

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	2.1	ALOGPS
logP	2.77	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	15.96	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.33 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.89 m³·mol⁻¹	ChemAxon
Polarizability	25 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	154.431	31661259
DarkChem	[M-H]-	151.726	31661259
DeepCCS	[M-2H]-	179.615	30932474
DeepCCS	[M+Na]+	154.806	30932474
AllCCS	[M+H]+	153.1	32859911
AllCCS	[M+H-H2O]+	149.0	32859911
AllCCS	[M+NH4]+	157.0	32859911
AllCCS	[M+Na]+	158.1	32859911
AllCCS	[M-H]-	155.0	32859911
AllCCS	[M+Na-2H]-	154.2	32859911
AllCCS	[M+HCOO]-	153.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Carbamazepine	NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C12	3809.0	Standard polar	33892256
Carbamazepine	NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C12	2170.2	Standard non polar	33892256
Carbamazepine	NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C12	2327.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Carbamazepine,1TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21	2243.7	Semi standard non polar	33892256
Carbamazepine,1TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21	2248.4	Standard non polar	33892256
Carbamazepine,1TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21	3415.9	Standard polar	33892256
Carbamazepine,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C	2331.5	Semi standard non polar	33892256
Carbamazepine,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C	2520.5	Standard non polar	33892256
Carbamazepine,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C	3350.4	Standard polar	33892256
Carbamazepine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21	2447.9	Semi standard non polar	33892256
Carbamazepine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21	2444.3	Standard non polar	33892256
Carbamazepine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21	3511.7	Standard polar	33892256
Carbamazepine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C(C)(C)C	2714.8	Semi standard non polar	33892256
Carbamazepine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C(C)(C)C	2849.9	Standard non polar	33892256
Carbamazepine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C21)[Si](C)(C)C(C)(C)C	3411.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Carbamazepine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-3970000000-8f03b4d1ea6cec6641ec	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carbamazepine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-1910000000-4b2dc85e8da73b101ed2	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 - Carbamazepine LC-ESI-qTof , Positive-QTOF	splash10-000f-1940000000-9677ddf985ba43e76817	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-qTof , Positive-QTOF	splash10-000f-0930000000-b2a70bea75cef0c24556	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-qTof , Positive-QTOF	splash10-0006-2900000000-86f35079f274f4014c3d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-QTOF , positive-QTOF	splash10-000i-0090000000-be63f70e101a786a369b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-QTOF , positive-QTOF	splash10-0006-0910000000-f171a56d3bbeaef24ff4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-QTOF , positive-QTOF	splash10-0006-0900000000-a82def037961e9b94a9a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-QTOF , positive-QTOF	splash10-0006-0900000000-484ce005b4ae5d01fc2a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-QTOF , positive-QTOF	splash10-0006-0900000000-a6992953eac16c120e74	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOF	splash10-0006-0900000000-7a1010be5231131649eb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOF	splash10-000i-0090000000-51ef94c86cca9b541780	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOF	splash10-000i-0490000000-4484ac1671912bc60ba9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOF	splash10-0006-0910000000-e5ca06888593ada95f15	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOF	splash10-0006-0900000000-5742023f1e263fb40066	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOF	splash10-0006-0900000000-f27fb9d17b228cc328b8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOF	splash10-0006-0900000000-63c554c485fd1d117082	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOF	splash10-000i-0090000000-c6c89d3e663885fcc080	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOF	splash10-000i-0490000000-8a1d8d7b932f1b0ad45e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOF	splash10-0006-0910000000-843efaf5294cb110e0b9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine LC-ESI-ITFT , positive-QTOF	splash10-0006-0900000000-7eb2855f73a1ed729181	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine 10V, Positive-QTOF	splash10-000i-0290000000-926be8d54e58a26d40d3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine 20V, Positive-QTOF	splash10-000f-0950000000-68b3fa7ce7380dc8311e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine 40V, Positive-QTOF	splash10-0006-1900000000-60a9fc188e8c79505dee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine 10V, Negative-QTOF	splash10-0006-8960000000-8aa13e4d27b1afb8662d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine 20V, Negative-QTOF	splash10-0006-2900000000-6d502f01257a774384bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine 40V, Negative-QTOF	splash10-0006-9500000000-3d22d3677d67ba94c4ac	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Carbamazepine Metabolism Pathway		Not Available

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 DB00564	21059682	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00564	21059682	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

DB00564

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2457

KEGG Compound ID

C06868

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Carbamazepine

METLIN ID

Not Available

PubChem Compound

2554

PDB ID

Not Available

ChEBI ID

3387

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)

Download (PDF)

General References

Staines AG, Coughtrie MW, Burchell B: N-glucuronidation of carbamazepine in human tissues is mediated by UGT2B7. J Pharmacol Exp Ther. 2004 Dec;311(3):1131-7. Epub 2004 Aug 3. [PubMed:15292462 ]
Sisodiya SM, Goldstein DB: Drug resistance in epilepsy: more twists in the tale. Epilepsia. 2007 Dec;48(12):2369-70. [PubMed:18088268 ]

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

Urichuk L, Prior TI, Dursun S, Baker G: Metabolism of atypical antipsychotics: involvement of cytochrome p450 enzymes and relevance for drug-drug interactions. Curr Drug Metab. 2008 Jun;9(5):410-8. [PubMed:18537577 ]
Levy RH: Cytochrome P450 isozymes and antiepileptic drug interactions. Epilepsia. 1995;36 Suppl 5:S8-13. [PubMed:8806399 ]
Cazali N, Tran A, Treluyer JM, Rey E, d'Athis P, Vincent J, Pons G: Inhibitory effect of stiripentol on carbamazepine and saquinavir metabolism in human. Br J Clin Pharmacol. 2003 Nov;56(5):526-36. [PubMed:14651727 ]
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 2C9

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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

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 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

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. 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 ]

Enzyme Details

6. 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 ]

Enzyme Details

7. Cytochrome P450 1A2

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

References

Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423 ]
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

8. Cytochrome P450 2C8

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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Cazali N, Tran A, Treluyer JM, Rey E, d'Athis P, Vincent J, Pons G: Inhibitory effect of stiripentol on carbamazepine and saquinavir metabolism in human. Br J Clin Pharmacol. 2003 Nov;56(5):526-36. [PubMed:14651727 ]
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

9. Sodium channel protein type 5 subunit alpha

General function:: Involved in ion channel activity
Specific function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:: SCN5A
Uniprot ID:: Q14524
Molecular weight:: 226937.5

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Yang YC, Huang CS, Kuo CC: Lidocaine, carbamazepine, and imipramine have partially overlapping binding sites and additive inhibitory effect on neuronal Na+ channels. Anesthesiology. 2010 Jul;113(1):160-74. doi: 10.1097/ALN.0b013e3181dc1dd6. [PubMed:20526191 ]
Yang YC, Kuo CC: Inhibition of Na(+) current by imipramine and related compounds: different binding kinetics as an inactivation stabilizer and as an open channel blocker. Mol Pharmacol. 2002 Nov;62(5):1228-37. [PubMed:12391287 ]
Lipkind GM, Fozzard HA: Molecular model of anticonvulsant drug binding to the voltage-gated sodium channel inner pore. Mol Pharmacol. 2010 Oct;78(4):631-8. doi: 10.1124/mol.110.064683. Epub 2010 Jul 19. [PubMed:20643904 ]

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

Geick A, Eichelbaum M, Burk O: Nuclear receptor response elements mediate induction of intestinal MDR1 by rifampin. J Biol Chem. 2001 May 4;276(18):14581-7. Epub 2001 Jan 31. [PubMed:11297522 ]
Owen A, Pirmohamed M, Tettey JN, Morgan P, Chadwick D, Park BK: Carbamazepine is not a substrate for P-glycoprotein. Br J Clin Pharmacol. 2001 Apr;51(4):345-9. [PubMed:11318771 ]
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 ]
Baltes S, Gastens AM, Fedrowitz M, Potschka H, Kaever V, Loscher W: Differences in the transport of the antiepileptic drugs phenytoin, levetiracetam and carbamazepine by human and mouse P-glycoprotein. Neuropharmacology. 2007 Feb;52(2):333-46. Epub 2006 Oct 10. [PubMed:17045309 ]
Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. [PubMed:12954186 ]

Showing metabocard for Carbamazepine (HMDB0014704)

MOL for HMDB0014704 (Carbamazepine)

3D MOL for HMDB0014704 (Carbamazepine)

3D SDF for HMDB0014704 (Carbamazepine)

3D-SDF for HMDB0014704 (Carbamazepine)

PDB for HMDB0014704 (Carbamazepine)

3D PDB for HMDB0014704 (Carbamazepine)

SMILES for HMDB0014704 (Carbamazepine)

INCHI for HMDB0014704 (Carbamazepine)

Structure for HMDB0014704 (Carbamazepine)

3D Structure for HMDB0014704 (Carbamazepine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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Transporters

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