Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1612)
Drug Name
Tolbutamide
Synonyms
Tolbusal; Tolbutamid; Tolbutamida; Tolbutamidum; Toluina; Tolumid; Toluvan; Tolylsulfonylbutylurea; Willbutamide; Aglicid; Arkozal; Artosin; Artozin; Butamid; Butamide; Diaben; Diabetamid; Diabetol; Diabuton; Diasulfon; Dirastan; Dolipol; Drabet; Glyconon; Ipoglicone; Mobenol; N-Butyl-N'-(p-tolylsulfonyl)urea; N-n-Butyl-N'-tosylurea; Orabet; Oralin; Orezan; Orinase; Orinaz; Oterben; Pramidex; Rastinon; Sk-tolbutamide; tolbutamide; 1-Butyl-3-(p-methylphenylsulfonyl)urea; 1-Butyl-3-(p-tolylsulfonyl)urea; 1-Butyl-3-tosylurea; 64-77-7
Indication Diabetes mellitus [ICD11: 5A10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 270.35 Topological Polar Surface Area 83.6
Heavy Atom Count 18 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
5505
PubChem SID
9357 ; 85591 ; 640044 ; 855782 ; 5658513 ; 7847446 ; 7980810 ; 8144417 ; 8149557 ; 8153385 ; 10321470 ; 10531694 ; 11111857 ; 11111858 ; 11120087 ; 11120575 ; 11121063 ; 11121572 ; 11122052 ; 11147170 ; 11335516 ; 11360755 ; 11362641 ; 11363341 ; 11364689 ; 11365203 ; 11365903 ; 11367251 ; 11367765 ; 11368465 ; 11369813 ; 11370553 ; 11370554 ; 11371678 ; 11372854 ; 11373366 ; 11373934 ; 11375413 ; 11375927 ; 11376627 ; 11377976 ; 11457019 ; 11461727 ; 11466218 ; 11467338 ; 11484736 ; 11485776 ; 11489026 ; 11490415 ; 11492173
ChEBI ID
ChEBI:27999
CAS Number
64-77-7
TTD Drug ID
D06OIV
Formula
C12H18N2O3S
Canonical SMILES
CCCCNC(=O)NS(=O)(=O)C1=CC=C(C=C1)C
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)
InChIKey
JLRGJRBPOGGCBT-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
4-Hydroxy tolbutamide DM006308
3656
Oxidation - Hydrolyzationn 1 [6]
p-Toluenesulfonylurea DM006311
74327
Unclear 1 [7]
1-butyl-3-(p-formylphenyl)sulphonylurea DM006309
192221
Unclear 2 [8]
4-Carboxytolbutamide DM006310
13067200
Unclear 2 [7]
1-butyl-3-(p-carboxyphenyl)sulphonylurea DM014797 N. A. Oxidation - Oxidationn 3 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006775 Tolbutamide 4-Hydroxy tolbutamide Oxidation - Hydrolyzationn CYP2C19 ... [6]
MR006779 Tolbutamide p-Toluenesulfonylurea Unclear Unclear [7]
MR006776 4-Hydroxy tolbutamide 1-butyl-3-(p-formylphenyl)sulphonylurea Unclear Unclear [8]
MR006778 4-Hydroxy tolbutamide 4-Carboxytolbutamide Unclear ADH ... [7]
MR006777 1-butyl-3-(p-formylphenyl)sulphonylurea 1-butyl-3-(p-carboxyphenyl)sulphonylurea Oxidation - Oxidationn Unclear [8]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[5]
References
1 Tolbutamide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
3 Prediction of in vivo drug-drug interactions between tolbutamide and various sulfonamides in humans based on in vitro experiments. Drug Metab Dispos. 2000 Apr;28(4):475-81.
4 Effects of organic solvents on the activities of cytochrome P450 isoforms, UDP-dependent glucuronyl transferase, and phenol sulfotransferase in human hepatocytes. Drug Metab Dispos. 2001 Feb;29(2):141-4.
5 CYP2C19 participates in tolbutamide hydroxylation by human liver microsomes. Drug Metab Dispos. 2000 Mar;28(3):354-9.
6 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.
7 Methyl-hydroxylation and subsequent oxidation to produce carboxylic acid is the major metabolic pathway of tolbutamide in chimeric TK-NOG mice transplanted with human hepatocytes
8 A new aspect of tolbutamide metabolism in the rabbit: the role of 1-butyl-3-(p-formylphenyl)sulphonylurea

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