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CHEBI:3213 - bumetanide

ChEBI IDCHEBI:3213
ChEBI Namebumetanide
Stars
DefinitionA 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.
Secondary ChEBI IDCHEBI:239281
Last Modified14 June 2017
DownloadsMolfile
FormulaC17H20N2O5S
Net Charge0
Average Mass364.423
Monoisotopic Mass364.10929
SMILESCCCCNc1cc(C(=O)O)cc(S(N)(=O)=O)c1Oc1ccccc1
InChIInChI=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)
InChIKeyMAEIEVLCKWDQJH-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
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:
diuretic  An agent that promotes the excretion of urine through its effects on kidney function.
ChEBI Ontology
Outgoing Relation(s)
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  Source
bumetanideChemIDplus
bumetanidaChemIDplus
bumetanidumChemIDplus
Synonyms  Source
3-butylamino-4-phenoxy-5-sulfamoylbenzoic acidChEMBL
3-butylamino-4-phenoxy-5-sulfamoyl-benzoic acidChEMBL
3-(aminosulfonyl)-5-(butylamino)-4-phenoxybenzoic acidChemIDplus
3-butylamino-4-(phenoxy)-5-sulfamoylbenzoic acidDrugBank
Manual XrefsDatabases
D00247KEGG DRUG
DB00887DrugBank
DE1964503Patent
DE1964504Patent
US3806534Patent
BumetanideWikipedia
HMDB0015024HMDB
LSM-2848LINCS
427DrugCentral
Registry NumbersSources
Reaxys:2185351Reaxys
CAS:28395-03-1KEGG DRUG
CAS:28395-03-1ChemIDplus
Citations