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CHEBI:4876 - etacrynic acid

Default Structure
ChEBI IDCHEBI:4876
ChEBI Nameetacrynic acid
Stars
DefinitionAn aromatic ether that is phenoxyacetic acid in which the phenyl ring is substituted by chlorines at positions 2 and 3, and by a 2-methylidenebutanoyl group at position 4. It is a loop diuretic used to treat high blood pressure resulting from diseases such as congestive heart failure, liver failure, and kidney failure. It is also a glutathione S-transferase (EC 2.5.1.18) inhibitor.
Last Modified22 February 2017
DownloadsMolfile
FormulaC13H12Cl2O4
Net Charge0
Average Mass303.141
Monoisotopic Mass302.01126
SMILESC=C(CC)C(=O)c1ccc(OCC(=O)O)c(Cl)c1Cl
InChIInChI=1S/C13H12Cl2O4/c1-3-7(2)13(18)8-4-5-9(12(15)11(8)14)19-6-10(16)17/h4-5H,2-3,6H2,1H3,(H,16,17)
InChIKeyAVOLMBLBETYQHX-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
EC 2.5.1.18 (glutathione transferase) inhibitor  An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of a glutathione transferase (EC 2.5.1.18).
ion transport inhibitor  A compound which inhibits the movement of an ion across an energy-transducing cell membrane.
Application:
loop diuretic  A diuretic that acts on the ascending loop of Henle in the kidney.
ChEBI Ontology
Outgoing Relation(s)
etacrynic acid (CHEBI:4876) has functional parent acetic acid (CHEBI:15366)
etacrynic acid (CHEBI:4876) has role EC 2.5.1.18 (glutathione transferase) inhibitor (CHEBI:76797)
etacrynic acid (CHEBI:4876) has role ion transport inhibitor (CHEBI:50184)
etacrynic acid (CHEBI:4876) has role loop diuretic (CHEBI:77608)
etacrynic acid (CHEBI:4876) is a aromatic ether (CHEBI:35618)
etacrynic acid (CHEBI:4876) is a aromatic ketone (CHEBI:76224)
etacrynic acid (CHEBI:4876) is a dichlorobenzene (CHEBI:23697)
etacrynic acid (CHEBI:4876) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name 
[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
INNs  Source
acide étacryniqueWHO MedNet
ácido etacrínicoWHO MedNet
acidum etacrynicumWHO MedNet
etacrynic acidKEGG DRUG
Synonyms  Source
(2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetic acidChemIDplus
Etacrinic acidDrugBank
EthacrynateDrugBank
ethacrynic acidChemIDplus
Methylenebutyrylphenoxyacetic acidDrugBank
Brand Names  Source
CrinurylDrugBank
EdecrilDrugBank
EdecrinaDrugBank
EndecrilDrugBank
HidromedinDrugBank
HydromedinDrugBank
Manual XrefsDatabases
1071DrugCentral
D00313KEGG DRUG
DB00903DrugBank
EAAPDBeChem
Etacrynic_acidWikipedia
HMDB0015039HMDB
LSM-3420LINCS
Registry NumbersSources
Reaxys:1915060Reaxys
CAS:58-54-8KEGG DRUG
CAS:58-54-8ChemIDplus
Citations