| 词条 | WAY-204688 |
| 释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = (2S)-2-[(S)-(2-methoxyphenyl)naphthalen-1-ylmethyl]-2-methyl-3-oxo-3-[4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]propanenitrile | image = WAY-204688.svg | width = | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | class = Nonsteroidal estrogen; Nuclear factor κB inhibitor | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 796854-35-8 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 9829162 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 28655006 | UNII = | KEGG = | ChEBI = | ChEMBL = 238890 | synonyms = | C=34 | H=31 | F=3 | N=2 | O=2 | molecular_weight = 556.629 g/mol | SMILES = C[C@@](C#N)([C@H](C1=CC=CC=C1OC)C2=CC=CC3=CC=CC=C32)C(=O)N4CCC(CC4)C5=CC(=CC=C5)C(F)(F)F | StdInChI_Ref = | StdInChI = 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/s1 | StdInChIKey_Ref = | StdInChIKey = JZPONCMNBSEYQW-CQTOTRCISA-N }}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.[1][2][3] It is a "pathway-selective" estrogen receptor (ER) ligand which inhibits NF-κB with an {{abbrlink|IC50|half-maximal inhibitory concentration}} of 122 nM and with maximal inhibition relative to estradiol of 94%.[3][4] 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.[3][4] 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.[3][4] It reached phase I clinical trials prior to the discontinuation of its development.[1] References1. ^1 https://adisinsight.springer.com/drugs/800022078 2. ^{{cite journal | vauthors = Ivanenkov YA, Balakin KV, Lavrovsky Y | title = Small molecule inhibitors of NF-kB and JAK/STAT signal transduction pathways as promising anti-inflammatory therapeutics | journal = Mini Rev Med Chem | volume = 11 | issue = 1 | pages = 55–78 | date = January 2011 | pmid = 21034406 | doi = 10.2174/138955711793564079 | url = }} 3. ^1 2 3 {{cite journal|last1=Dodge|first1=Jeffrey A.|last2=Richardson|first2=Timothy I.|title=Chapter 10 Novel Selective Estrogen Receptor Modulators (SERMs)|volume=42|year=2007|pages=147–160|issn=00657743|doi=10.1016/S0065-7743(07)42010-3}} 4. ^1 2 {{cite journal | vauthors = Opal SM, Palardy JE, Cristofaro P, Parejo N, Jhung JW, Keith JC, Chippari S, Caggiano TJ, Steffan RJ, Chadwick CC, Harnish DC | title = The activity of pathway-selective estrogen receptor ligands in experimental septic shock | journal = Shock | volume = 24 | issue = 6 | pages = 535–40 | date = December 2005 | pmid = 16317384 | doi = 10.1097/01.shk.0000183388.90895.cb | url = }} External links
9 : Abandoned drugs|Biased ligands|Ethers|Ketones|Naphthalenes|Nitriles|Piperidines|Synthetic estrogens|Trifluoromethyl compounds |
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