WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H563480
CAS#: 669764-18-5
Description: WAY-169916 is a pathway-selective estrogen receptor (ER) inhibitor. It acts by inhibiting NF-kB transcriptional activity but being devoid of conventional estrogenic activity.
Hodoodo Cat#: H563480
Name: WAY-169916
CAS#: 669764-18-5
Chemical Formula: C17H13F3N2O2
Exact Mass: 334.09
Molecular Weight: 334.290
Elemental Analysis: C, 61.08; H, 3.92; F, 17.05; N, 8.38; O, 9.57
Synonym: WAY-169916; WAY 169916; WAY169916;
IUPAC/Chemical Name: 4-(1-allyl-7-(trifluoromethyl)-1H-indazol-3-yl)benzene-1,3-diol
InChi Key: ZDUDMCQPFKPISO-UHFFFAOYSA-N
InChi Code: InChI=1S/C17H13F3N2O2/c1-2-8-22-16-12(4-3-5-13(16)17(18,19)20)15(21-22)11-7-6-10(23)9-14(11)24/h2-7,9,23-24H,1,8H2
SMILES Code: OC1=CC=C(C2=NN(CC=C)C3=C2C=CC=C3C(F)(F)F)C(O)=C1
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.03.00
More Info:
Biological target: | |
In vitro activity: | |
In vivo activity: |
The following data is based on the product molecular weight 334.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
---|---|---|---|
1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
Formulation protocol: | |
In vitro protocol: | |
In vivo protocol: |
1: Liu Z, Wang L, Tan H, Zhou S, Fu T, Xia Y, Zhang Y, Wang J. Synthesis of 1H-indazoles from N-tosylhydrazones and nitroaromatic compounds. Chem Commun (Camb). 2014 May 21;50(39):5061-3. doi: 10.1039/c4cc00962b. Epub 2014 Apr 9. PubMed PMID: 24714999.
2: Gao L, Tu Y, Ågren H, Eriksson LA. Characterization of agonist binding to His524 in the estrogen receptor α ligand binding domain. J Phys Chem B. 2012 Apr 26;116(16):4823-30. doi: 10.1021/jp300895g. Epub 2012 Apr 17. PubMed PMID: 22482773.
3: Bruning JB, Parent AA, Gil G, Zhao M, Nowak J, Pace MC, Smith CL, Afonine PV, Adams PD, Katzenellenbogen JA, Nettles KW. Coupling of receptor conformation and ligand orientation determine graded activity. Nat Chem Biol. 2010 Nov;6(11):837-43. doi: 10.1038/nchembio.451. Epub 2010 Oct 10. PubMed PMID: 20924370; PubMed Central PMCID: PMC2974172.
4: Murray IA, Krishnegowda G, DiNatale BC, Flaveny C, Chiaro C, Lin JM, Sharma AK, Amin S, Perdew GH. Development of a selective modulator of aryl hydrocarbon (Ah) receptor activity that exhibits anti-inflammatory properties. Chem Res Toxicol. 2010 May 17;23(5):955-66. doi: 10.1021/tx100045h. PubMed PMID: 20423157; PubMed Central PMCID: PMC2871980.
5: Murray IA, Morales JL, Flaveny CA, Dinatale BC, Chiaro C, Gowdahalli K, Amin S, Perdew GH. Evidence for ligand-mediated selective modulation of aryl hydrocarbon receptor activity. Mol Pharmacol. 2010 Feb;77(2):247-54. doi: 10.1124/mol.109.061788. Epub 2009 Nov 10. PubMed PMID: 19903824; PubMed Central PMCID: PMC2812074.
6: Booth EA, Marchesi M, Knittel AK, Kilbourne EJ, Lucchesi BR. The pathway-selective estrogen receptor ligand WAY-169916 reduces infarct size after myocardial ischemia and reperfusion by an estrogen receptor dependent mechanism. J Cardiovasc Pharmacol. 2007 Jun;49(6):401-7. PubMed PMID: 17577105.
7: Harnish DC, Liu X, Kenney T, Winneker RC, Chadwick C, Friedrichs GS, Kilbourne EJ. The pathway-selective estrogen receptor ligand WAY-169916 displays differential activity in ischemia-reperfusion injury models. J Cardiovasc Pharmacol. 2006 Jun;47(6):788-95. PubMed PMID: 16810080.
8: Steffan RJ, Matelan E, Ashwell MA, Moore WJ, Solvibile WR, Trybulski E, Chadwick CC, Chippari S, Kenney T, Winneker RC, Eckert A, Borges-Marcucci L, Adelman SJ, Xu Z, Mosyak L, Harnish DC. Control of chronic inflammation with pathway selective estrogen receptor ligands. Curr Top Med Chem. 2006;6(2):103-11. Review. PubMed PMID: 16454762.
9: Opal SM, Palardy JE, Cristofaro P, Parejo N, Jhung JW, Keith JC Jr, Chippari S, Caggiano TJ, Steffan RJ, Chadwick CC, Harnish DC. The activity of pathway-selective estrogen receptor ligands in experimental septic shock. Shock. 2005 Dec;24(6):535-40. PubMed PMID: 16317384.
10: Biswas DK, Singh S, Shi Q, Pardee AB, Iglehart JD. Crossroads of estrogen receptor and NF-kappaB signaling. Sci STKE. 2005 Jun 14;2005(288):pe27. Review. PubMed PMID: 15956359.
11: Keith JC Jr, Albert LM, Leathurby Y, Follettie M, Wang L, Borges-Marcucci L, Chadwick CC, Steffan RJ, Harnish DC. The utility of pathway selective estrogen receptor ligands that inhibit nuclear factor-kappa B transcriptional activity in models of rheumatoid arthritis. Arthritis Res Ther. 2005;7(3):R427-38. Epub 2005 Feb 21. PubMed PMID: 15899029; PubMed Central PMCID: PMC1174937.
12: Chadwick CC, Chippari S, Matelan E, Borges-Marcucci L, Eckert AM, Keith JC Jr, Albert LM, Leathurby Y, Harris HA, Bhat RA, Ashwell M, Trybulski E, Winneker RC, Adelman SJ, Steffan RJ, Harnish DC. Identification of pathway-selective estrogen receptor ligands that inhibit NF-kappaB transcriptional activity. Proc Natl Acad Sci U S A. 2005 Feb 15;102(7):2543-8. Epub 2005 Feb 7. PubMed PMID: 15699342; PubMed Central PMCID: PMC548967.
13: Steffan RJ, Matelan E, Ashwell MA, Moore WJ, Solvibile WR, Trybulski E, Chadwick CC, Chippari S, Kenney T, Eckert A, Borges-Marcucci L, Keith JC, Xu Z, Mosyak L, Harnish DC. Synthesis and activity of substituted 4-(indazol-3-yl)phenols as pathway-selective estrogen receptor ligands useful in the treatment of rheumatoid arthritis. J Med Chem. 2004 Dec 16;47(26):6435-8. PubMed PMID: 15588074.