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SML0505

Sigma-Aldrich

Tienilic Acid

≥98% (HPLC)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C13H8Cl2O4S
CAS-Nummer:
40180-04-9
Molekulargewicht:
331.17
EG-Nummer:
254-826-3
MDL-Nummer:
MFCD00867339
UNSPSC-Code:
12161501
PubChem Substanz-ID:
329825452
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Farbe

white to beige

Löslichkeit

DMSO: 5 mg/mL (clear solution)

Versandbedingung

wet ice

Lagertemp.

−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)

InChIKey

AGHANLSBXUWXTB-UHFFFAOYSA-N

Biochem./physiol. Wirkung

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

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Analysenzertifikate (COA)

Lot/Batch Number
0000400341
0000400343
0000400343
0000400341
0000227013

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Takayoshi Nishiya et al.
Toxicology letters, 183(1-3), 81-89 (2008-11-11)
Tienilic acid is reported to be converted into electrophilic metabolites by cytochrome P450 (CYP) in vitro. In vivo, however, the metabolites have not been detected and their effect on liver function is unknown. We previously demonstrated that tienilic acid decreased
Mahendra Ramesh Shiradkar et al.
Bioorganic & medicinal chemistry, 15(19), 6397-6406 (2007-07-24)
Based on the earlier results of our in-house database and compound library, a series of novel clubbed thienyl triazoles was designed which may emerge as potential cdk5/p25 inhibitors, for the treatment of Alzheimer's disease. A benign synthesis was planned so
E Bonierbale et al.
Chemical research in toxicology, 12(3), 286-296 (1999-03-17)
Tienilic acid (TA) is responsible for an immune-mediated drug-induced hepatitis in humans, while its isomer (TAI) triggers a direct hepatitis in rats. In this study, we describe an immunological approach developed for studying the specificity of the covalent binding of
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
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