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- Tienilic_acid abstract "Tienilic acid (INN and BAN) or ticrynafen (USAN) is a loop diuretic drug with uric acid-lowering (uricosuric) action, formerly marketed for the treatment of hypertension. It was approved by FDA on May 2, 1979, and withdrawn in 1982, after case reports in the United States indicated a link between the use of ticrynafen and hepatitis.Criminal charges were brought against SmithKline executives with regard to hiding data related to toxicity while gaining FDA approval. The company pleaded guilty to 14 counts of failure to report adverse reactions and 20 counts of selling a misbranded drug.Tienilic acid was found to act as a suicide substrate at the cytochrome P450 enzymes involved in drug metabolism. Unfortunately, the metabolic reaction carried out by these enzymes converted tienilic acid to a thiophene sulfoxide which proved highly electrophilic. This encouraged a Michael reaction leading to alkylation of a thiol group in the enzyme's active site. Loss of water from the thiophene sulfoxide restored the thiophene ring and resulted in tienilic acid being covalently linked to the enzyme, thus inhibiting the enzyme irreversibly.The above explanation is a hypothesis. It is still not known (after 15 years) if the reactive intermediate which inactivates the CYP2C9 is the thiophene sulfoxide or the thiophene epoxide. The target on the protein is also not known (could be multiple). However tienilic acid is a good mechanism based inhibitor of CYP2C9 and seems to inactivate it stoichiometrically. Progress in proteomics may one day give the answer.Recent studies indicate that in fact the primary metabolite of tienilic acid (5-OH tienilic acid) cannot be derived from a thiophene-S-oxide intermediate as was previously hypothesized. It was determined to be derived from a thiophene epoxide intermediate and this reactive intermediate is then likely a cause for the covalent binding to as well as mechanism-based inactivation of CYP2C9.".
- Tienilic_acid atcPrefix "C03".
- Tienilic_acid atcSuffix "CC02".
- Tienilic_acid casNumber "40180-04-9".
- Tienilic_acid chEBI "9590".
- Tienilic_acid fdaUniiCode "HC95205SY4".
- Tienilic_acid iupacName "[2,3-dichloro-4-(2-thienylcarbonyl)phenoxy]acetic acid".
- Tienilic_acid pubchem "38409".
- Tienilic_acid thumbnail Tienilic_acid.svg?width=300.
- Tienilic_acid wikiPageID "1908660".
- Tienilic_acid wikiPageRevisionID "604147357".
- Tienilic_acid atcPrefix "3.0".
- Tienilic_acid atcSuffix "CC02".
- Tienilic_acid c "13".
- Tienilic_acid casNumber "40180".
- Tienilic_acid chebi "9590".
- Tienilic_acid chembl "267744".
- Tienilic_acid chemspiderid "35204".
- Tienilic_acid cl "2".
- Tienilic_acid eliminationHalfLife "21600.0".
- Tienilic_acid excretion "Renal and biliary".
- Tienilic_acid h "8".
- Tienilic_acid hasPhotoCollection Tienilic_acid.
- Tienilic_acid inchi "1".
- Tienilic_acid inchikey "AGHANLSBXUWXTB-UHFFFAOYAF".
- Tienilic_acid iupacName "[2,3-dichloro-4-phenoxy]acetic acid".
- Tienilic_acid kegg "D02386".
- Tienilic_acid legalStatus "Withdrawn".
- Tienilic_acid metabolism Liver.
- Tienilic_acid molecularWeight "331.17".
- Tienilic_acid o "4".
- Tienilic_acid proteinBound "95.0".
- Tienilic_acid pubchem "38409".
- Tienilic_acid routesOfAdministration "Oral".
- Tienilic_acid s "1".
- Tienilic_acid smiles "C1=CSCCC2=CCl".
- Tienilic_acid stdinchi "1".
- Tienilic_acid stdinchikey "AGHANLSBXUWXTB-UHFFFAOYSA-N".
- Tienilic_acid unii "HC95205SY4".
- Tienilic_acid subject Category:Acetic_acids.
- Tienilic_acid subject Category:Diuretics.
- Tienilic_acid subject Category:Organochlorides.
- Tienilic_acid subject Category:Phenol_ethers.
- Tienilic_acid subject Category:Thiophenes.
- Tienilic_acid subject Category:Withdrawn_drugs.
- Tienilic_acid type Abstraction100002137.
- Tienilic_acid type AceticAcid114599168.
- Tienilic_acid type AceticAcids.
- Tienilic_acid type Acid114607521.
- Tienilic_acid type CarboxylicAcid114739360.
- Tienilic_acid type Chemical114806838.
- Tienilic_acid type Compound114818238.
- Tienilic_acid type Element114840755.
- Tienilic_acid type Material114580897.
- Tienilic_acid type Matter100020827.
- Tienilic_acid type Part113809207.
- Tienilic_acid type PhenolEthers.
- Tienilic_acid type PhysicalEntity100001930.
- Tienilic_acid type Quintessence114847103.
- Tienilic_acid type Relation100031921.
- Tienilic_acid type Substance100019613.
- Tienilic_acid type Drug.
- Tienilic_acid type DrugProduct.
- Tienilic_acid type FunctionalSubstance.
- Tienilic_acid comment "Tienilic acid (INN and BAN) or ticrynafen (USAN) is a loop diuretic drug with uric acid-lowering (uricosuric) action, formerly marketed for the treatment of hypertension. It was approved by FDA on May 2, 1979, and withdrawn in 1982, after case reports in the United States indicated a link between the use of ticrynafen and hepatitis.Criminal charges were brought against SmithKline executives with regard to hiding data related to toxicity while gaining FDA approval.".
- Tienilic_acid label "Tienilic acid".
- Tienilic_acid sameAs m.065f0j.
- Tienilic_acid sameAs Q7801054.
- Tienilic_acid sameAs Q7801054.
- Tienilic_acid sameAs DB04831.
- Tienilic_acid sameAs Tienilic_acid.
- Tienilic_acid wasDerivedFrom Tienilic_acid?oldid=604147357.
- Tienilic_acid depiction Tienilic_acid.svg.
- Tienilic_acid isPrimaryTopicOf Tienilic_acid.
