5-((6-(2,4-bis(TrifluoroMethyl)phenyl)pyridazin-3-yl)Methyl)-2-(2-fluorophenyl)-5H-iMidazo[4,5-c]pyridine Chemical Properties

Boiling point:

558.0±60.0 °C(Predicted)

Density 

1.46

storage temp. 

Store at -20°C

solubility 

≥24.95 mg/mL in DMSO; insoluble in H2O; ≥100 mg/mL in EtOH

form 

solid

pka

8.28±0.20(Predicted)

color 

White to off-white

InChI

1S/C25H14F7N5/c26-19-4-2-1-3-17(19)23-33-21-9-10-37(13-22(21)34-23)12-15-6-8-20(36-35-15)16-7-5-14(24(27,28)29)11-18(16)25(30,31)32/h1-11,13H,12H2

InChIKey

XBEQSQDCBSKCHJ-UHFFFAOYSA-N

SMILES

FC(F)(F)c1c(ccc(c1)C(F)(F)F)c2nnc(cc2)C[n]3cc4nc(nc4cc3)c5c(cccc5)F

Safety Information

WGK Germany 

WGK 3

Storage Class

11 - Combustible Solids

5-((6-(2,4-bis(TrifluoroMethyl)phenyl)pyridazin-3-yl)Methyl)-2-(2-fluorophenyl)-5H-iMidazo[4,5-c]pyridine Usage And Synthesis

Uses

Tegobuvir is a specific, covalent inhibitor of the HCV NS5B polymerase.

Biological Activity

Tegobuvir (GS-9190; TGV) is an orally active, non-cytotoxic imidazopyridine that, upon CYP-mediated intracellular activation, forms a glutathione conjugate th at acts as a covalent, potent and genotype 1 replicons-selective non-nucleoside inhibitor (NNI) against hepatitis C virus (HCV) NS5B RNA-dependent RNA polymerase (IC50 = 0.8 nM/1b, 13.8 nM/1a, 21.9 μM/2a, >50 μM/1a; IC50 >100 nM against 2b, 3a, 4a, 5a, and 6a). When combined with suboptimal concentrations of other direct acting antivirals (DAAs) in cultures, tegobuvir (6-30 nM) is highly effective in curing cells from HCV replicon and in delaying or preventing the development of resistance against other DAAs.

References

[1]. zeuzem s, andreone p, pol s, lawitz e, diago m, roberts s, focaccia r, younossi z, foster gr, horban a et al: telaprevir for retreatment of hcv infection. n engl j med 2011, 364(25):2417-2428.
[2]. wong ka, xu s, martin r, miller md, mo h: tegobuvir (gs-9190) potency against hcv chimeric replicons derived from consensus ns5b sequences from genotypes 2b, 3a, 4a, 5a, and 6a. virology 2012, 429(1):57-62.
[3]. shih ih, vliegen i, peng b, yang h, hebner c, paeshuyse j, purstinger g, fenaux m, tian y, mabery e et al: mechanistic characterization of gs-9190 (tegobuvir), a novel nonnucleoside inhibitor of hepatitis c virus ns5b polymerase. antimicrob agents chemother 2011, 55(9):4196-4203.
[4]. behrens se, tomei l, de francesco r: identification and properties of the rna-dependent rna polymerase of hepatitis c virus. embo j 1996, 15(1):12-22.
[5]. hebner cm, han b, brendza km, nash m, sulfab m, tian y, hung m, fung w, vivian rw, trenkle j et al: the hcv non-nucleoside inhibitor tegobuvir utilizes a novel mechanism of action to inhibit ns5b polymerase function. plos one 2012, 7(6):e39163.

5-((6-(2,4-bis(TrifluoroMethyl)phenyl)pyridazin-3-yl)Methyl)-2-(2-fluorophenyl)-5H-iMidazo[4,5-c]pyridine(1000787-75-6)Related Product Information

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