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SML0505

Sigma-Aldrich

Tienilic Acid

≥98% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C13H8Cl2O4S
Número de CAS:
40180-04-9
Peso molecular:
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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
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
L L Koenigs et al.
Biochemistry, 38(8), 2312-2319 (1999-02-25)
A general scheme for the purification of baculovirus-expressed cytochrome P450s (P450s) from the crude insect cell pastes has been designed which renders the P450s suitable for analysis by high-performance liquid chromatography (HPLC) electrospray ionization mass spectrometry (ESI-MS). An HPLC/ESI-MS procedure
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
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
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