CHEBI:3213 - bumetanide

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ChEBI Name bumetanide
ChEBI ID CHEBI:3213
Definition A member of the class of benzoic acids that is 4-phenoxybenzoic acid in which the hydrogens ortho to the phenoxy group are substituted by butylamino and sulfamoyl groups. Bumetanide is a diuretic, and is used for treatment of oedema associated with congestive heart failure, hepatic and renal disease.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:239281
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Formula C17H20N2O5S
Net Charge 0
Average Mass 364.41600
InChI InChI=1S/C17H20N2O5S/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23)
InChIKey MAEIEVLCKWDQJH-UHFFFAOYSA-N
SMILES CCCCNc1cc(cc(c1Oc1ccccc1)S(N)(=O)=O)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor
A EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of channel-conductance-controlling ATPase (EC 3.6.3.49, also known as cystic fibrosis conductance regulator, CFCR).
Application(s): diuretic
An agent that promotes the excretion of urine through its effects on kidney function.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing bumetanide (CHEBI:3213) has role diuretic (CHEBI:35498)
bumetanide (CHEBI:3213) has role EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor (CHEBI:131770)
bumetanide (CHEBI:3213) is a amino acid (CHEBI:33709)
bumetanide (CHEBI:3213) is a benzoic acids (CHEBI:22723)
bumetanide (CHEBI:3213) is a sulfonamide (CHEBI:35358)
IUPAC Name
3-(butylamino)-4-phenoxy-5-sulfamoylbenzoic acid
INNs Sources
bumetanida ChemIDplus
bumetanide ChemIDplus
bumetanidum ChemIDplus
Synonyms Sources
3-(aminosulfonyl)-5-(butylamino)-4-phenoxybenzoic acid ChemIDplus
3-butylamino-4-(phenoxy)-5-sulfamoylbenzoic acid DrugBank
3-butylamino-4-phenoxy-5-sulfamoyl-benzoic acid ChEMBL
3-butylamino-4-phenoxy-5-sulfamoylbenzoic acid ChEMBL
Database Links Databases
Bumetanide Wikipedia
D00247 KEGG DRUG
DB00887 DrugBank
DE1964503 Patent
DE1964504 Patent
HMDB15024 HMDB
LSM-2848 LINCS
US3806534 Patent
View more database links
Registry Numbers Types Sources
2185351 Reaxys Registry Number Reaxys
2185351 Beilstein Registry Number Beilstein
28395-03-1 CAS Registry Number KEGG DRUG
28395-03-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
18374572 PubMed citation ChEMBL
19454284 PubMed citation CiteXplore
3989818 PubMed citation ChEMBL
Last Modified
19 April 2016