CHEBI:27999 - tolbutamide

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C12H18N2O3S
Net Charge 0
Average Mass 270.34800
Monoisotopic Mass 270.104
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.
View more via ChEBI Ontology
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 Types Sources
11835228 PubMed citation Europe PMC
11840346 PubMed citation Europe PMC
11911494 PubMed citation Europe PMC
12042355 PubMed citation Europe PMC
12355256 PubMed citation Europe PMC
15207658 PubMed citation Europe PMC
15317941 PubMed citation Europe PMC
15620874 PubMed citation Europe PMC
15655519 PubMed citation Europe PMC
16290322 PubMed citation Europe PMC
16426753 PubMed citation Europe PMC
19059420 PubMed citation Europe PMC
20880646 PubMed citation Europe PMC
21178111 PubMed citation Europe PMC
21193530 PubMed citation Europe PMC
21471135 PubMed citation Europe PMC
21535124 PubMed citation Europe PMC
21712613 PubMed citation Europe PMC
21757329 PubMed citation Europe PMC
21827497 PubMed citation Europe PMC
21831467 PubMed citation Europe PMC
22028182 PubMed citation Europe PMC
22079696 PubMed citation Europe PMC
Last Modified
22 February 2017