Tienilic acid
Trade name: ticrynafen
Approved
Jun 1, 1979
Ticrynafen, or tienilic acid, is a diuretic drug with uric acid-lowering action, formerly marketed for the treatment of hypertension. It was withdrawn from the market only months after its introduction because of reports of serious incidents of drug-induced liver injury including some fatalities. Its hepatotoxicity is considered to be primarily immunoallergic in nature. Tienilic acid is a thiophene-containing mechanism-based inactivator of P450 2C9, resulting from covalent modification of the P450 2C9 protein. The bioactivation mechanism involves oxidation of the thiophene ring system. — NCATS
Clinical trial activity
0 trials · 0 clinical orgs · 1 marketing orgs
Timeline
1970s
- Jun 1, 1979
Earliest FDA Approval
Indications
Approved for
Mechanism of action
- Unspecified targetOTHER
Unknown
Uricosuric diuretic action
Approval history
- withdrawnJun 1, 1979
Chemistry & pharmacology
SMILES
OC(=O)COC1=CC=C(C(=O)C2=CC=CS2)C(Cl)=C1Cl- Mol. weight
- 331.171 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
Oral
No
Parenteral
No
Topical
No
Sources
- WikipediaTienilic acid ↗
- NCATSHC95205SY4 ↗
- ChEMBLCHEMBL267744 ↗
Also known as
- (2,3-dichloro-4-(2-thenoyl)phenoxy)acetic acid
- (2,3-dichloro-4-(2-thenoyl)phenoxy)acetic acid
- (2,3-dichloro-4-(2-thienylcarbonyl)phenoxy)acetic acid
- (2,3-dichloro-4-(2-thienylcarbonyl)phenoxy)acetic acid
- (2,3-dichloro-4-(2-thiophenecarbonyl)phenoxy)acetic acid
- (2,3-dichloro-4-(2-thiophenecarbonyl)phenoxy)acetic acid
- 4-(2-theonyl)-2,3-dichlorphenoxyessigsaeure
- 4-(2-theonyl)-2,3-dichlorphenoxyessigsaeure
- 4-(2-thienylketo)-2,3-dichlorophenoxyacetic acid
- 4-(2-thienylketo)-2,3-dichlorophenoxyacetic acid
- acide tienilique
- acide tienilique
- acido tienilico
- acido tienilico
- acidum tienilicum
- acidum tienilicum
- selacryn
- selacryn
- selacryn
- selacryn
- sk&f-62698
- sk&f-62698
- thienylic acid
- thienylic acid
- thienylic acid
- ticrynafen
- ticrynafen
- ticrynafen
- ticrynafen
- ticrynafen
- ticrynafen
- ticrynafen
- ticrynafen
- tienilic acid
- tienilic acid
- tienilic acid
- tienilic acid
- tienilic acid
- tienilico acido
- tienilico acido
- tienylic acid
Organizations
Marketing (1)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Smith, Kline & French | For profit | NDA | — |