CHEBI:27999 - tolbutamide

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ChEBI Name tolbutamide
ChEBI ID CHEBI:27999
Definition An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:9616, CHEBI:27019
Supplier Information ChemicalBook:CB4709039, eMolecules:511449, Selleckchem:tolbutamide, ZINC000001530703
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Tolbutamide is a first-generation potassium channel blocker, sulfonylurea oral hypoglycemic medication. This drug may be used in the management of type 2 diabetes if diet alone is not effective. Tolbutamide stimulates the secretion of insulin by the pancreas. It is not routinely used due to a higher incidence of adverse effects compared to newer, second-generation sulfonylureas, such as Glibenclamide. It generally has a short duration of action due to its rapid metabolism, so is safe for use in older people. It was discovered in 1956.
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Formula C12H18N2O3S
Net Charge 0
Average Mass 270.34800
Monoisotopic Mass 270.10381
InChI 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
SMILES CCCCNC(=O)NS(=O)(=O)c1ccc(C)cc1
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
insulin secretagogue
A secretagogue that causes the secretion of insulin.
potassium channel blocker
An agent that inhibits cell membrane glycoproteins that are selectively permeable to potassium ions.
Application(s): hypoglycemic agent
A drug which lowers the blood glucose level.
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ChEBI Ontology
Outgoing tolbutamide (CHEBI:27999) has role human metabolite (CHEBI:77746)
tolbutamide (CHEBI:27999) has role hypoglycemic agent (CHEBI:35526)
tolbutamide (CHEBI:27999) has role insulin secretagogue (CHEBI:90415)
tolbutamide (CHEBI:27999) has role potassium channel blocker (CHEBI:50509)
tolbutamide (CHEBI:27999) is a N-sulfonylurea (CHEBI:76983)
IUPAC Name
N-[(butylamino)carbonyl]-4-methylbenzenesulfonamide
INNs Sources
tolbutamida ChemIDplus
tolbutamide ChemIDplus
tolbutamidum ChemIDplus
Synonyms Sources
1-Butyl-3-(p-methylphenylsulfonyl)urea ChemIDplus
1-Butyl-3-(p-tolylsulfonyl)urea ChemIDplus
1-Butyl-3-tosylurea ChemIDplus
1-p-Toluenesulfonyl-3-butylurea ChemIDplus
3-(p-Tolyl-4-sulfonyl)-1-butylurea ChemIDplus
N-(4-Methylbenzenesulfonyl)-N'-butylurea ChemIDplus
N-(4-Methylphenylsulfonyl)-N'-butylurea ChemIDplus
N-(p-Methylbenzenesulfonyl)-N'-butylurea NIST Chemistry WebBook
N-(Sulfonyl-p-methylbenzene)-N'-N-butylurea NIST Chemistry WebBook
N-Butyl-N'-(4-methylphenylsulfonyl)urea ChemIDplus
N-Butyl-N'-(p-tolylsulfonyl)urea ChemIDplus
N-Butyl-N'-p-toluenesulfonylurea ChemIDplus
N-n-Butyl-N'-tosylurea ChemIDplus
Orinase (TN) KEGG DRUG
Tolbutamide KEGG COMPOUND
Tolylsulfonylbutylurea NIST Chemistry WebBook
Manual Xrefs Databases
2696 DrugCentral
C07148 KEGG COMPOUND
D00380 KEGG DRUG
DB01124 DrugBank
DE1066575 Patent
GB808071 Patent
LSM-3907 LINCS
Tolbutamide Wikipedia
US2968158 Patent
View more database links
Registry Numbers Types Sources
1984428 Reaxys Registry Number Reaxys
64-77-7 CAS Registry Number KEGG COMPOUND
64-77-7 CAS Registry Number NIST Chemistry WebBook
64-77-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
22 February 2017