way-204688 way-204688 way-204688, also known as sim-688, is a synthetic nonsteroidal estrogen and nuclear factor κb (nf-κb) inhibitor which was originated by arqule and wyeth and was under development by wyeth for the treatment of rheumatoid arthritis, non-specific inflammation, and sepsis but was never marketed. it is a "pathway-selective" estrogen receptor (er) ligand which inhibits nf-κb with an ic50 of 122 nm and with maximal inhibition relative to estradiol of 94%. inhibition of nf-κb by way-204688 appears to be dependent on agonism of the erα, as it is reversed by the erα antagonist fulvestrant, but is not dependent on the erβ. in contrast to the case of nf-κb inhibition, way-204688 produces only slight elevation of creatine kinase in vitro, a measure of classical estradiol effects. it reached phase i clinical trials prior to the discontinuation of its development. way-204688clinical datadrug classnonsteroidal estrogen; nuclear factor κb inhibitoridentifiers iupac name (2s)-2--2-methyl-3-oxo-3-piperidin-1-yl]propanenitrile cas number796854-35-8 ypubchem cid9829162chemspider28655006uniiqt9vf4mw6uchemblchembl238890chemical and physical dataformulac34h31f3n2o2molar mass556.629 g·mol−13d model (jsmol)interactive image smiles c(c#n)((c1=cc=cc=c1oc)c2=cc=cc3=cc=cc=c32)c(=o)n4ccc(cc4)c5=cc(=cc=c5)c(f)(f)f inchi inchi=1s/c34h31f3n2o2/c1-33(22-38,32(40)39-19-17-23(18-20-39)25-11-7-12-26(21-25)34(35,36)37)31(29-14-5-6-16-30(29)41-2)28-15-8-10-24-9-3-4-13-27(24)28/h3-16,21,23,31h,17-20h2,1-2h3/t31-,33+/m0/s1key:jzponcmnbseyqw-cqtotrcisa-n