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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6)transporters (5) Show 11 proteins XML

enzymes (6)transporters (5) Show 11 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015256

Secondary Accession Numbers

HMDB15256

Metabolite Identification

Common Name

Tolbutamide

Description

Tolbutamide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It is structurally similar to acetohexamide, chlorpropamide and tolazamide and belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating cells of the pancreas to release insulin. Sulfonylureas increase both basal insulin secretion and meal-stimulated insulin release. Medications in this class differ in their dose, rate of absorption, duration of action, route of elimination and binding site on their target pancreatic cell receptor. Sulfonylureas also increase peripheral glucose utilization, decrease hepatic gluconeogenesis and may increase the number and sensitivity of insulin receptors. Sulfonylureas are associated with weight gain, though less so than insulin. Due to their mechanism of action, sulfonylureas may cause hypoglycemia and require consistent food intake to decrease this risk. The risk of hypoglycemia is increased in elderly, debilitated and malnourished individuals. Tolbutamide appears to be metabolized in the liver. Tolbutamide and its metabolites are excreted in urine (75-85%) and feces.

Structure

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

HMDB0015256
     RDKit          3D
Tolbutamide
 36 36  0  0  0  0  0  0  0  0999 V2000
   -5.5111    1.4877   -0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0301    0.3772   -1.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0454   -0.5468   -0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7788    0.1055   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9348   -0.9103    0.3729 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6460   -0.6415    0.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1374    0.5069    0.9326 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826   -1.7235    1.4784 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6480   -1.5393    2.1721 S   0  0  0  0  0  6  0  0  0  0  0  0
    2.2202   -2.8739    2.5416 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5148   -0.7573    3.4639 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7413   -0.6716    1.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4414   -1.3926    0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3059   -0.7008   -0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4519    0.6654   -0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3819    1.4185   -1.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7544    1.3899    0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8903    0.6935    1.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5942    1.6425   -0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9364    2.3945   -0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3823    1.2284    0.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6128    0.8569   -2.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8960   -0.2388   -1.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7918   -1.3981   -1.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5346   -0.9615    0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2295    0.6281   -1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9611    0.8599    0.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926   -1.8895    0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294   -2.7031    1.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3534   -2.4600    0.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8953   -1.2060   -1.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9477    2.1017   -0.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0714    0.6755   -1.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8176    1.9587   -2.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8350    2.4436    0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2911    1.1802    2.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END

1124
  Mrv0541 02231215162D          

 18 18  0  0  0  0            999 V2000
    2.4751   -0.6188    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  2  0  0  0  0
  1  6  1  0  0  0  0
  1 10  1  0  0  0  0
  4 12  2  0  0  0  0
  5  8  1  0  0  0  0
  5 12  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 11  1  0  0  0  0
 10 13  2  0  0  0  0
 10 14  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  2  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015256

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H18N2O3S/c1-3-4-9-13-12(15)14-18(16,17)11-7-5-10(2)6-8-11/h5-8H,3-4,9H2,1-2H3,(H2,13,14,15)

> <INCHI_KEY>
JLRGJRBPOGGCBT-UHFFFAOYSA-N

> <FORMULA>
C12H18N2O3S

> <MOLECULAR_WEIGHT>
270.348

> <EXACT_MASS>
270.103813142

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.09953664240288

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-butyl-1-(4-methylbenzenesulfonyl)urea

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
2.295335827333333

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.114800808981375

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.333945172256472

> <JCHEM_POLAR_SURFACE_AREA>
75.27

> <JCHEM_REFRACTIVITY>
70.27

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tolbutamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015256
     RDKit          3D
Tolbutamide
 36 36  0  0  0  0  0  0  0  0999 V2000
   -5.5111    1.4877   -0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0301    0.3772   -1.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0454   -0.5468   -0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7788    0.1055   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9348   -0.9103    0.3729 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6460   -0.6415    0.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1374    0.5069    0.9326 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826   -1.7235    1.4784 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6480   -1.5393    2.1721 S   0  0  0  0  0  6  0  0  0  0  0  0
    2.2202   -2.8739    2.5416 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5148   -0.7573    3.4639 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7413   -0.6716    1.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4414   -1.3926    0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3059   -0.7008   -0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4519    0.6654   -0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3819    1.4185   -1.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7544    1.3899    0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8903    0.6935    1.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5942    1.6425   -0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9364    2.3945   -0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3823    1.2284    0.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6128    0.8569   -2.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8960   -0.2388   -1.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7918   -1.3981   -1.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5346   -0.9615    0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2295    0.6281   -1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9611    0.8599    0.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926   -1.8895    0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294   -2.7031    1.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3534   -2.4600    0.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8953   -1.2060   -1.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9477    2.1017   -0.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0714    0.6755   -1.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8176    1.9587   -2.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8350    2.4436    0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2911    1.1802    2.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1124                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       4.620  -1.155   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       3.080  -1.155   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.160  -1.155   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.288   0.385   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       5.954   2.695   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       4.620   0.385   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.288   5.005   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.288   3.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.621   5.775   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.620  -2.695   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.621   7.315   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.954   1.155   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.286  -3.465   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.954  -3.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.620  -5.775   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.286  -5.005   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.954  -5.005   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.620  -7.315   0.000  0.00  0.00           C+0
CONECT    1    2    3    6   10                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   12                                                            
CONECT    5    8   12                                                       
CONECT    6    1   12                                                       
CONECT    7    8    9                                                       
CONECT    8    5    7                                                       
CONECT    9    7   11                                                       
CONECT   10    1   13   14                                                  
CONECT   11    9                                                            
CONECT   12    4    5    6                                                  
CONECT   13   10   16                                                       
CONECT   14   10   17                                                       
CONECT   15   16   17   18                                                  
CONECT   16   13   15                                                       
CONECT   17   14   15                                                       
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0015256
HETATM    1  C1  UNL     1      -5.511   1.488  -0.449  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.030   0.377  -1.333  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.045  -0.547  -0.689  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.779   0.106  -0.225  1.00  0.00           C  
HETATM    5  N1  UNL     1      -1.935  -0.910   0.373  1.00  0.00           N  
HETATM    6  C5  UNL     1      -0.646  -0.642   0.923  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.137   0.507   0.933  1.00  0.00           O  
HETATM    8  N2  UNL     1       0.083  -1.723   1.478  1.00  0.00           N  
HETATM    9  S1  UNL     1       1.648  -1.539   2.172  1.00  0.00           S  
HETATM   10  O2  UNL     1       2.220  -2.874   2.542  1.00  0.00           O  
HETATM   11  O3  UNL     1       1.515  -0.757   3.464  1.00  0.00           O  
HETATM   12  C6  UNL     1       2.741  -0.672   1.116  1.00  0.00           C  
HETATM   13  C7  UNL     1       3.441  -1.393   0.172  1.00  0.00           C  
HETATM   14  C8  UNL     1       4.306  -0.701  -0.648  1.00  0.00           C  
HETATM   15  C9  UNL     1       4.452   0.665  -0.513  1.00  0.00           C  
HETATM   16  C10 UNL     1       5.382   1.418  -1.395  1.00  0.00           C  
HETATM   17  C11 UNL     1       3.754   1.390   0.429  1.00  0.00           C  
HETATM   18  C12 UNL     1       2.890   0.693   1.248  1.00  0.00           C  
HETATM   19  H1  UNL     1      -6.594   1.643  -0.711  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.936   2.395  -0.663  1.00  0.00           H  
HETATM   21  H3  UNL     1      -5.382   1.228   0.626  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.613   0.857  -2.266  1.00  0.00           H  
HETATM   23  H5  UNL     1      -5.896  -0.239  -1.713  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.792  -1.398  -1.341  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.535  -0.961   0.240  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.230   0.628  -1.037  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.961   0.860   0.582  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.293  -1.889   0.400  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.329  -2.703   1.481  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.353  -2.460   0.037  1.00  0.00           H  
HETATM   31  H13 UNL     1       4.895  -1.206  -1.419  1.00  0.00           H  
HETATM   32  H14 UNL     1       5.948   2.102  -0.734  1.00  0.00           H  
HETATM   33  H15 UNL     1       6.071   0.675  -1.862  1.00  0.00           H  
HETATM   34  H16 UNL     1       4.818   1.959  -2.175  1.00  0.00           H  
HETATM   35  H17 UNL     1       3.835   2.444   0.567  1.00  0.00           H  
HETATM   36  H18 UNL     1       2.291   1.180   2.029  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   28
CONECT    6    7    7    8
CONECT    8    9   29
CONECT    9   10   10   11   11
CONECT    9   12
CONECT   12   13   13   18
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   15   16   17
CONECT   16   32   33   34
CONECT   17   18   18   35
CONECT   18   36
END

HMDB0015256
     RDKit          3D
Tolbutamide
 36 36  0  0  0  0  0  0  0  0999 V2000
   -5.5111    1.4877   -0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0301    0.3772   -1.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0454   -0.5468   -0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7788    0.1055   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9348   -0.9103    0.3729 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6460   -0.6415    0.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1374    0.5069    0.9326 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826   -1.7235    1.4784 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6480   -1.5393    2.1721 S   0  0  0  0  0  6  0  0  0  0  0  0
    2.2202   -2.8739    2.5416 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5148   -0.7573    3.4639 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7413   -0.6716    1.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4414   -1.3926    0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3059   -0.7008   -0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4519    0.6654   -0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3819    1.4185   -1.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7544    1.3899    0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8903    0.6935    1.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5942    1.6425   -0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9364    2.3945   -0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3823    1.2284    0.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6128    0.8569   -2.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8960   -0.2388   -1.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7918   -1.3981   -1.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5346   -0.9615    0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2295    0.6281   -1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9611    0.8599    0.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926   -1.8895    0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294   -2.7031    1.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3534   -2.4600    0.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8953   -1.2060   -1.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9477    2.1017   -0.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0714    0.6755   -1.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8176    1.9587   -2.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8350    2.4436    0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2911    1.1802    2.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Butyl-3-(p-methylphenylsulfonyl)urea	ChEBI
1-Butyl-3-(p-tolylsulfonyl)urea	ChEBI
1-Butyl-3-tosylurea	ChEBI
1-p-Toluenesulfonyl-3-butylurea	ChEBI
3-(p-Tolyl-4-sulfonyl)-1-butylurea	ChEBI
N-(4-Methylbenzenesulfonyl)-n'-butylurea	ChEBI
N-(4-Methylphenylsulfonyl)-n'-butylurea	ChEBI
N-(p-Methylbenzenesulfonyl)-n'-butylurea	ChEBI
N-(Sulfonyl-p-methylbenzene)-n'-N-butylurea	ChEBI
N-Butyl-n'-(4-methylphenylsulfonyl)urea	ChEBI
N-Butyl-n'-(p-tolylsulfonyl)urea	ChEBI
N-Butyl-n'-p-toluenesulfonylurea	ChEBI
N-N-Butyl-n'-tosylurea	ChEBI
Orinase	ChEBI
Tolbutamida	ChEBI
Tolbutamidum	ChEBI
Tolylsulfonylbutylurea	ChEBI
1-Butyl-3-(p-methylphenylsulphonyl)urea	Generator
1-Butyl-3-(p-tolylsulphonyl)urea	Generator
1-p-Toluenesulphonyl-3-butylurea	Generator
3-(p-Tolyl-4-sulphonyl)-1-butylurea	Generator
N-(4-Methylbenzenesulphonyl)-n'-butylurea	Generator
N-(4-Methylphenylsulphonyl)-n'-butylurea	Generator
N-(p-Methylbenzenesulphonyl)-n'-butylurea	Generator
N-(Sulphonyl-p-methylbenzene)-n'-N-butylurea	Generator
N-Butyl-n'-(4-methylphenylsulphonyl)urea	Generator
N-Butyl-n'-(p-tolylsulphonyl)urea	Generator
N-Butyl-n'-p-toluenesulphonylurea	Generator
Tolylsulphonylbutylurea	Generator
Berlin chemie brand OF tolbutamide	HMDB
Berlin-chemie brand OF tolbutamide	HMDB
Diaval	HMDB
Rastinon	HMDB
Tolbutamid r.a.n.	HMDB
Yamanouchi brand OF tolbutamide	HMDB
Artosin	HMDB
Hoechst brand OF tolbutamide	HMDB
Orabet	HMDB
Tolbutamide butamide brand	HMDB
Tolbutamide hoechst brand	HMDB
Apo-tolbutamide	HMDB
Butamide brand OF tolbutamide	HMDB
Dolipol	HMDB
Pfizer brand OF tolbutamide	HMDB
Tolbutamide aventis brand	HMDB
Valdecasas brand OF tolbutamide	HMDB
Apotex brand OF tolbutamide	HMDB
Aventis brand OF tolbutamide	HMDB
Diabetol	HMDB
R.A.N. brand OF tolbutamide	HMDB
Tolbutamide pfizer brand	HMDB

Chemical Formula

C₁₂H₁₈N₂O₃S

Average Molecular Weight

270.348

Monoisotopic Molecular Weight

270.103813142

IUPAC Name

3-butyl-1-(4-methylbenzenesulfonyl)urea

Traditional Name

tolbutamide

CAS Registry Number

64-77-7

SMILES

CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1

InChI Identifier

InChI=1S/C12H18N2O3S/c1-3-4-9-13-12(15)14-18(16,17)11-7-5-10(2)6-8-11/h5-8H,3-4,9H2,1-2H3,(H2,13,14,15)

InChI Key

JLRGJRBPOGGCBT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Benzenesulfonamides

Alternative Parents

Substituents

Benzenesulfonamide
Tosyl compound
Benzenesulfonyl group
Toluene
Sulfonylurea
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Carboximidic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-sulfonylurea (CHEBI:27999 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015256)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	128.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.2 g/L	Not Available
LogP	2.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	163.0	30932474
[M+H]+	Not Available	161.869	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000831

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.2 g/L	ALOGPS
logP	2.04	ALOGPS
logP	2.3	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	4.33	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.27 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.27 m³·mol⁻¹	ChemAxon
Polarizability	29.1 Å³	ChemAxon
Number of Rings	1	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]+	163.996	31661259
DarkChem	[M-H]-	162.561	31661259
DeepCCS	[M+H]+	167.048	30932474
DeepCCS	[M-H]-	164.69	30932474
DeepCCS	[M-2H]-	197.575	30932474
DeepCCS	[M+Na]+	173.141	30932474
AllCCS	[M+H]+	162.5	32859911
AllCCS	[M+H-H2O]+	159.2	32859911
AllCCS	[M+NH4]+	165.6	32859911
AllCCS	[M+Na]+	166.5	32859911
AllCCS	[M-H]-	161.9	32859911
AllCCS	[M+Na-2H]-	162.4	32859911
AllCCS	[M+HCOO]-	163.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tolbutamide	CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1	3550.1	Standard polar	33892256
Tolbutamide	CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1	1669.9	Standard non polar	33892256
Tolbutamide	CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1	2257.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tolbutamide,1TMS,isomer #1	CCCCN(C(=O)NS(=O)(=O)C1=CC=C(C)C=C1)[Si](C)(C)C	2314.6	Semi standard non polar	33892256
Tolbutamide,1TMS,isomer #1	CCCCN(C(=O)NS(=O)(=O)C1=CC=C(C)C=C1)[Si](C)(C)C	2304.2	Standard non polar	33892256
Tolbutamide,1TMS,isomer #1	CCCCN(C(=O)NS(=O)(=O)C1=CC=C(C)C=C1)[Si](C)(C)C	3050.5	Standard polar	33892256
Tolbutamide,1TMS,isomer #2	CCCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(C)C=C1	2294.8	Semi standard non polar	33892256
Tolbutamide,1TMS,isomer #2	CCCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(C)C=C1	2200.2	Standard non polar	33892256
Tolbutamide,1TMS,isomer #2	CCCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(C)C=C1	3085.4	Standard polar	33892256
Tolbutamide,2TMS,isomer #1	CCCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(C)C=C1)[Si](C)(C)C	2231.2	Semi standard non polar	33892256
Tolbutamide,2TMS,isomer #1	CCCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(C)C=C1)[Si](C)(C)C	2441.6	Standard non polar	33892256
Tolbutamide,2TMS,isomer #1	CCCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(C)C=C1)[Si](C)(C)C	2828.3	Standard polar	33892256
Tolbutamide,1TBDMS,isomer #1	CCCCN(C(=O)NS(=O)(=O)C1=CC=C(C)C=C1)[Si](C)(C)C(C)(C)C	2537.9	Semi standard non polar	33892256
Tolbutamide,1TBDMS,isomer #1	CCCCN(C(=O)NS(=O)(=O)C1=CC=C(C)C=C1)[Si](C)(C)C(C)(C)C	2531.4	Standard non polar	33892256
Tolbutamide,1TBDMS,isomer #1	CCCCN(C(=O)NS(=O)(=O)C1=CC=C(C)C=C1)[Si](C)(C)C(C)(C)C	3077.1	Standard polar	33892256
Tolbutamide,1TBDMS,isomer #2	CCCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(C)C=C1	2548.9	Semi standard non polar	33892256
Tolbutamide,1TBDMS,isomer #2	CCCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(C)C=C1	2430.5	Standard non polar	33892256
Tolbutamide,1TBDMS,isomer #2	CCCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(C)C=C1	3115.2	Standard polar	33892256
Tolbutamide,2TBDMS,isomer #1	CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(C)C=C1)[Si](C)(C)C(C)(C)C	2742.7	Semi standard non polar	33892256
Tolbutamide,2TBDMS,isomer #1	CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(C)C=C1)[Si](C)(C)C(C)(C)C	2903.9	Standard non polar	33892256
Tolbutamide,2TBDMS,isomer #1	CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(C)C=C1)[Si](C)(C)C(C)(C)C	2951.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tolbutamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4m-9620000000-80b8e46fa29dc771af14	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tolbutamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tolbutamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide LC-ESI-qTof , Positive-QTOF	splash10-0006-0190000000-7ff8ebe7a2c8d9b989ec	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide LC-ESI-qTof , Positive-QTOF	splash10-05fr-1920000000-defac8a82087405b74df	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide , positive-QTOF	splash10-0006-0190000000-7ff8ebe7a2c8d9b989ec	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide , positive-QTOF	splash10-05fr-1920000000-defac8a82087405b74df	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide 60V, Positive-QTOF	splash10-0aou-9700000000-4ddde0b1cb5c52cde5e9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide 45V, Positive-QTOF	splash10-0avi-6900000000-7a66f373c605dedbdaca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide 15V, Positive-QTOF	splash10-00di-9630000000-2017f03bf9e28638cee8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide 30V, Positive-QTOF	splash10-05fr-8900000000-2a951aa06eb51e26b18d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide 90V, Positive-QTOF	splash10-0006-9000000000-c10cd87bcaddb53a298d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide 75V, Positive-QTOF	splash10-0006-9200000000-9e34241200e278e9e064	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide 10V, Positive-QTOF	splash10-00di-9610000000-75888e656e58b74cf3ee	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide 20V, Positive-QTOF	splash10-0596-9200000000-f75d5d5d54176257be85	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide 10V, Negative-QTOF	splash10-00di-0930000000-8d71b509124429eea629	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide 40V, Negative-QTOF	splash10-0a6r-6900000000-96b6cdfc78c2cfa0a77b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide 20V, Negative-QTOF	splash10-00di-0900000000-a8b79ea32dfd9e27bdda	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide 15V, Negative-QTOF	splash10-00di-0930000000-9f5b4960f823b6c7b58a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide 60V, Negative-QTOF	splash10-0ab9-1900000000-d6a5548288198dd86802	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide 75V, Negative-QTOF	splash10-0a6r-5900000000-93ef59adf84191071087	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolbutamide 90V, Negative-QTOF	splash10-06vi-9500000000-9a73e07e1dc0aa3f9d1d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolbutamide 10V, Positive-QTOF	splash10-00di-9780000000-b9e42f04441a4750b9a9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolbutamide 20V, Positive-QTOF	splash10-05fr-9400000000-731942a1402d4374a5db	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolbutamide 40V, Positive-QTOF	splash10-0a4l-9000000000-11ce33c22d2669eeac48	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolbutamide 10V, Negative-QTOF	splash10-01b9-2590000000-33755b9fecfcb717c051	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolbutamide 20V, Negative-QTOF	splash10-00di-2910000000-c5e9ee1500acc1154c87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolbutamide 40V, Negative-QTOF	splash10-00fu-9700000000-97a794e19f654b96f09b	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 DB01124	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01124	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01124

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5304

KEGG Compound ID

C07148

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tolbutamide

METLIN ID

Not Available

PubChem Compound

5505

PDB ID

Not Available

ChEBI ID

27999

Food Biomarker Ontology

Not Available

VMH ID

TOLBUTAMIDE

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 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

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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 ]
Lasker JM, Wester MR, Aramsombatdee E, Raucy JL: Characterization of CYP2C19 and CYP2C9 from human liver: respective roles in microsomal tolbutamide, S-mephenytoin, and omeprazole hydroxylations. Arch Biochem Biophys. 1998 May 1;353(1):16-28. [PubMed:9578596 ]

Enzyme Details

2. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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 ]
Lasker JM, Wester MR, Aramsombatdee E, Raucy JL: Characterization of CYP2C19 and CYP2C9 from human liver: respective roles in microsomal tolbutamide, S-mephenytoin, and omeprazole hydroxylations. Arch Biochem Biophys. 1998 May 1;353(1):16-28. [PubMed:9578596 ]

Enzyme Details

3. Cytochrome P450 2C18

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP2C18
Uniprot ID:: P33260
Molecular weight:: 55710.075

References

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

Enzyme Details

4. Cytochrome P450 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

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. ATP-sensitive inward rectifier potassium channel 1

General function:: Involved in inward rectifier potassium channel activity
Specific function:: In the kidney, probably plays a major role in potassium homeostasis. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. This channel is activated by internal ATP and can be blocked by external barium
Gene Name:: KCNJ1
Uniprot ID:: P48048
Molecular weight:: 44794.6

References

Proks P, Jones P, Ashcroft FM: Interaction of stilbene disulphonates with cloned K(ATP) channels. Br J Pharmacol. 2001 Mar;132(5):973-82. [PubMed:11226127 ]
Smith PA, Proks P: Inhibition of the ATP-sensitive potassium channel from mouse pancreatic beta-cells by surfactants. Br J Pharmacol. 1998 Jun;124(3):529-39. [PubMed:9647478 ]
Liu X, Singh BB, Ambudkar IS: ATP-dependent activation of K(Ca) and ROMK-type K(ATP) channels in human submandibular gland ductal cells. J Biol Chem. 1999 Aug 27;274(35):25121-9. [PubMed:10455193 ]

Enzyme Details

6. ATP-binding cassette sub-family C member 8

General function:: Involved in ATP binding
Specific function:: Putative subunit of the beta-cell ATP-sensitive potassium channel (KATP). Regulator of ATP-sensitive K(+) channels and insulin release
Gene Name:: ABCC8
Uniprot ID:: Q09428
Molecular weight:: 177006.4

References

Mizuno CS, Chittiboyina AG, Kurtz TW, Pershadsingh HA, Avery MA: Type 2 diabetes and oral antihyperglycemic drugs. Curr Med Chem. 2008;15(1):61-74. [PubMed:18220763 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 2B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost
Gene Name:: SLCO2B1
Uniprot ID:: O94956
Molecular weight:: 76697.9

References

Satoh H, Yamashita F, Tsujimoto M, Murakami H, Koyabu N, Ohtani H, Sawada Y: Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B. Drug Metab Dispos. 2005 Apr;33(4):518-23. Epub 2005 Jan 7. [PubMed:15640378 ]

Enzyme Details

2. Solute carrier organic anion transporter family member 1A2

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular weight:: 74144.1

References

Shitara Y, Sugiyama D, Kusuhara H, Kato Y, Abe T, Meier PJ, Itoh T, Sugiyama Y: Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport. Pharm Res. 2002 Feb;19(2):147-53. [PubMed:11883641 ]

Enzyme Details

3. Solute carrier family 15 member 1

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:: SLC15A1
Uniprot ID:: P46059
Molecular weight:: 78805.3

References

Terada T, Sawada K, Saito H, Hashimoto Y, Inui K: Inhibitory effect of novel oral hypoglycemic agent nateglinide (AY4166) on peptide transporters PEPT1 and PEPT2. Eur J Pharmacol. 2000 Mar 24;392(1-2):11-7. [PubMed:10748266 ]

Enzyme Details

4. Solute carrier family 15 member 2

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:: SLC15A2
Uniprot ID:: Q16348
Molecular weight:: 81782.8

References

Terada T, Sawada K, Saito H, Hashimoto Y, Inui K: Inhibitory effect of novel oral hypoglycemic agent nateglinide (AY4166) on peptide transporters PEPT1 and PEPT2. Eur J Pharmacol. 2000 Mar 24;392(1-2):11-7. [PubMed:10748266 ]

Enzyme Details

5. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Uwai Y, Saito H, Hashimoto Y, Inui K: Inhibitory effect of anti-diabetic agents on rat organic anion transporter rOAT1. Eur J Pharmacol. 2000 Jun 16;398(2):193-7. [PubMed:10854830 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Showing metabocard for Tolbutamide (HMDB0015256)

MOL for HMDB0015256 (Tolbutamide)

3D MOL for HMDB0015256 (Tolbutamide)

3D SDF for HMDB0015256 (Tolbutamide)

3D-SDF for HMDB0015256 (Tolbutamide)

PDB for HMDB0015256 (Tolbutamide)

3D PDB for HMDB0015256 (Tolbutamide)

SMILES for HMDB0015256 (Tolbutamide)

INCHI for HMDB0015256 (Tolbutamide)

Structure for HMDB0015256 (Tolbutamide)

3D Structure for HMDB0015256 (Tolbutamide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

Transporters

References

References

References

References

References