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SML0505

Sigma-Aldrich

Tienilic Acid

≥98% (HPLC)

Synonym(s):

Ticrynafen, Tienylic acid, [2,3-Dichloro-4-(2-thienylcarbonyl)phenoxy]-acetic acid

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About This Item

Empirical Formula (Hill Notation):
C13H8Cl2O4S
CAS Number:
40180-04-9
Molecular Weight:
331.17
EC Number:
254-826-3
MDL number:
MFCD00867339
UNSPSC Code:
12161501
PubChem Substance ID:
329825452
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL (clear solution)

shipped in

wet ice

storage temp.

−20°C

SMILES string

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

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)

InChI key

AGHANLSBXUWXTB-UHFFFAOYSA-N

Biochem/physiol Actions

Tienilic Acid (Ticrynafen) is a P450 inhibitor, a specific suicide substrate for CYP2C9 and CYP2C10. It was once used as a loop diuretic drug with uric acid-lowering (uricosuric) actvity, but was removed from market because of hepatotoxicity.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Daisuke Satoh et al.
PloS one, 12(10), e0187072-e0187072 (2017-10-25)
The utility of HepG2 cells to assess drug metabolism and toxicity induced by chemical compounds is hampered by their low cytochrome P450 (CYP) activities. To overcome this limitation, we established HepG2 cell lines expressing major CYP enzymes involved in drug
Peter M Rademacher et al.
Chemical research in toxicology, 25(4), 895-903 (2012-02-15)
The uricosuric diuretic agent tienilic acid (TA) is a thiophene-containing compound that is metabolized by P450 2C9 to 5-OH-TA. A reactive metabolite of TA also forms a covalent adduct to P450 2C9 that inactivates the enzyme and initiates immune-mediated hepatic
Use of isotopes and LC-MS-ESI-TOF for mechanistic studies of tienilic acid metabolic activation.
M Belghazi et al.
Advances in experimental medicine and biology, 500, 139-144 (2002-01-05)
Hideo Takakusa et al.
Drug metabolism and disposition: the biological fate of chemicals, 36(5), 816-823 (2008-01-30)
The metabolic activation of a drug to an electrophilic reactive metabolite and its covalent binding to cellular macromolecules is considered to be involved in the occurrence of idiosyncratic drug toxicity (IDT). As a cellular defense system against oxidative and electrophilic
Takayoshi Nishiya et al.
Toxicology and applied pharmacology, 232(2), 280-291 (2008-08-19)
To investigate the hepatotoxic potential of tienilic acid in vivo, we administered a single oral dose of tienilic acid to Sprague-Dawley rats and performed general clinicopathological examinations and hepatic gene expression analysis using Affymetrix microarrays. No change in the serum
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