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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:
ion transport inhibitor  A compound which inhibits the movement of an ion across an energy-transducing cell membrane.
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).
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
cardiovascular drug  A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume.
renoprotective agent  Any compound that is able to prevent damage to the kidneys.
antifibrotic agent  Any agent which acts to reduce fibrosis.
antiglaucoma drug  Any drug which can be used to prevent or alleviate glaucoma, a disease in which the optic nerve is damaged, resulting in progressive, irreversible loss of vision. It is often, though not always, associated with increased pressure of the fluid in the eye.
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 antifibrotic agent (CHEBI:233423)
etacrynic acid (CHEBI:4876) has role antiglaucoma drug (CHEBI:39456)
etacrynic acid (CHEBI:4876) has role antineoplastic agent (CHEBI:35610)
etacrynic acid (CHEBI:4876) has role cardiovascular drug (CHEBI:35554)
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) has role renoprotective agent (CHEBI:231911)
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)
etacrynic acid (CHEBI:4876) is a organic molecular entity (CHEBI:50860)
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 acidChEMBL
ethacrynic acidChemIDplus
Methylenebutyrylphenoxyacetic acidDrugBank
Brand Names  Source
CrinurylDrugBank
EdecrilDrugBank
EdecrinChEMBL
EdecrinaDrugBank
EndecrilDrugBank
HidromedinDrugBank
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