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CHEBI:9590 - tienilic acid

ChEBI IDCHEBI:9590
ChEBI Nametienilic acid
Stars
DefinitionAn aromatic ketone that is 2,3-dichlorophenoxyacetic acid in which the hydrogen at position 4 on the benzene ring is replaced by a thiophenecarbonyl group. A loop diuretic used to treat hypertension, it was withdrawn from the market in 1982 due to links with hepatitis.
Last Modified22 February 2017
DownloadsMolfile
FormulaC13H8Cl2O4S
Net Charge0
Average Mass331.176
Monoisotopic Mass329.95204
SMILESO=C(O)COc1ccc(C(=O)c2cccs2)c(Cl)c1Cl
InChIInChI=1S/C13H8Cl2O4S/c14-11-7(13(18)9-2-1-5-20-9)3-4-8(12(11)15)19-6-10(16)17/h1-5H,6H2,(H,16,17)
InChIKeyAGHANLSBXUWXTB-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
hepatotoxic agent  A role played by a chemical compound exhibiting itself through the ability to induce damage to the liver in animals.
Applications:
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
loop diuretic  A diuretic that acts on the ascending loop of Henle in the kidney.
ChEBI Ontology
Outgoing Relation(s)
tienilic acid (CHEBI:9590) has role antihypertensive agent (CHEBI:35674)
tienilic acid (CHEBI:9590) has role hepatotoxic agent (CHEBI:50908)
tienilic acid (CHEBI:9590) has role loop diuretic (CHEBI:77608)
tienilic acid (CHEBI:9590) is a aromatic ether (CHEBI:35618)
tienilic acid (CHEBI:9590) is a aromatic ketone (CHEBI:76224)
tienilic acid (CHEBI:9590) is a dichlorobenzene (CHEBI:23697)
tienilic acid (CHEBI:9590) is a monocarboxylic acid (CHEBI:25384)
tienilic acid (CHEBI:9590) is a thiophenes (CHEBI:26961)
IUPAC Name 
[2,3-dichloro-4-(2-thienylcarbonyl)phenoxy]acetic acid
INNs  Source
tienilic acidKEGG DRUG
acide tiéniliqueWHO MedNet
acidum tienilicumDrugBank
ácido tienilicoWHO MedNet
Synonyms  Source
TicrynafenKEGG COMPOUND
Thienylic acidDrugBank
4-(2-Thienylketo)-2,3-dichlorophenoxyacetic acidDrugBank
(2,3-Dichloro-4-(2-thiophenecarbonyl)phenoxy)acetic acidDrugBank
(2,3-Dichloro-4-(2-thenoyl)phenoxy)acetic acidDrugBank
4-(2-Theonyl)-2,3-dichlorphenoxyessigsäureChemIDplus
Manual XrefsDatabases
C11702KEGG COMPOUND
D02386KEGG DRUG
DB04831DrugBank
Tienilic_acidWikipedia
LSM-5478LINCS
2658DrugCentral
Registry NumbersSources
Reaxys:1260086Reaxys
CAS:40180-04-9KEGG COMPOUND
CAS:40180-04-9ChemIDplus
Citations