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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

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 Code

11 - Combustible Solids

WGK

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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Yakov M Koen et al.
Chemical research in toxicology, 25(5), 1145-1154 (2012-04-03)
Tienilic acid (TA) is a uricosuric diuretic that was withdrawn from the market only months after its introduction because of reports of serious incidents of drug-induced liver injury including some fatalities.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
S Poli-Scaife et al.
Biochemistry, 36(42), 12672-12682 (1997-10-23)
Purified recombinant human liver cytochrome P450 2C9 was produced, from expression of the corresponding cDNA in yeast, in quantities large enough for UV-visible and 1H NMR experiments. Its interaction with several substrates (tienilic acid and two derivatives, lauric acid and
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
M Pilar López-García et al.
Biochemical pharmacology, 70(12), 1870-1882 (2005-11-01)
Drug-induced autoimmune hepatitis is among the most severe hepatic idiosyncratic adverse drug reactions. Considered multifactorial, the disease combines immunological and metabolic aspects, the latter being to date much better known. As for many other model drugs, studies on tienilic acid
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
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