CHEBI:3213 - bumetanide

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ChEBI Name bumetanide
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
Monoisotopic Mass 364.10929
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)
SMILES CCCCNc1cc(cc(c1Oc1ccccc1)S(N)(=O)=O)C(O)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): EC (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, 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 (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)
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
Manual Xrefs Databases
427 DrugCentral
Bumetanide Wikipedia
DB00887 DrugBank
DE1964503 Patent
DE1964504 Patent
HMDB0015024 HMDB
US3806534 Patent
View more database links
Registry Numbers Types Sources
2185351 Beilstein Registry Number Beilstein
2185351 Reaxys Registry Number Reaxys
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 Europe PMC
28166217 PubMed citation Europe PMC
3989818 PubMed citation ChEMBL
Last Modified
14 June 2017