tienilic acid (CHEBI:9590)

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ChEBI Name	tienilic acid

ChEBI ID	CHEBI:9590

Definition	An 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 A loop diuretic used to treat hypertension, it was withdrawn from the market in 1982 due to links with hepatitis.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C13H8Cl2O4S

Net Charge

Average Mass

331.17100

Monoisotopic Mass

329.95204

InChI

InChI=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)

InChIKey

AGHANLSBXUWXTB-UHFFFAOYSA-N

SMILES

OC(=O)COc1ccc(C(=O)c2cccs2)c(Cl)c1Cl

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	hepatotoxic agent A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.

Application(s):	loop diuretic A diuretic that acts on the ascending loop of Henle in the kidney. antihypertensive agent Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.

ChEBI Ontology
Outgoing	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

Synonyms	Sources
(2,3-Dichloro-4-(2-thenoyl)phenoxy)acetic acid	DrugBank
(2,3-Dichloro-4-(2-thiophenecarbonyl)phenoxy)acetic acid	DrugBank
4-(2-Theonyl)-2,3-dichlorphenoxyessigsäure	ChemIDplus
4-(2-Thienylketo)-2,3-dichlorophenoxyacetic acid	DrugBank
Thienylic acid	DrugBank
Ticrynafen	KEGG COMPOUND

Last Modified

22 February 2017