Prinaberel, also known as ERB-041, is a drug which acts as a highly selective agonist of the ERβ subtype of the estrogen receptor. It is used in scientific research to elucidate the role of the ERβ receptor. Studies have indicated that selective ERβ agonists like prinaberel could be useful in the clinical treatment of a variety of medical conditions including inflammatory bowel disease, rheumatoid arthritis, endometriosis, and sepsis. Accordingly, prinaberel either was or still is under investigation by Wyeth for the treatment of some of these conditions. MedKoo Cat#: 206188 Name: Prinaberel CAS#: 524684-52-4 Chemical Formula: C15H10FNO3 Exact Mass: 271.06447 Molecular Weight: 271.24 Elemental Analysis: C, 66.42; H, 3.72; F, 7.00; N, 5.16; O, 17.70 Synonym: ERB041; ERB 041; ERB041; Prinaberel; WAY-202041; WAY202041; WAY 202041 IUPAC/Chemical Name: 2-(3-fluoro-4-hydroxyphenyl)-7-vinylbenzo[d]oxazol-5-ol InChi Key: MQIMZDXIAHJKQP-UHFFFAOYSA-N InChi Code: InChI=1S/C15H10FNO3/c1-2-8-5-10(18)7-12-14(8)20-15(17-12)9-3-4-13(19)11(16)6-9/h2-7,18-19H,1H2 SMILES Code: OC1=CC(C=C)=C(OC(C2=CC=C(O)C(F)=C2)=N3)C3=C1 Technical Data 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, not in water Shelf Life: >2 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). Harmonized System Code: 293490 Additional Information          References 1: Hinsche O, Girgert R, Emons G, Gründker C. Estrogen receptor β selective agonists reduce invasiveness of triple-negative breast cancer cells. Int J Oncol. 2015 Feb;46(2):878-84. doi: 10.3892/ijo.2014.2778. Epub 2014 Nov 25. PubMed PMID: 25420519. 2: Evers NM, van den Berg JH, Wang S, Melchers D, Houtman R, de Haan LH, Ederveen AG, Groten JP, Rietjens IM. Cell proliferation and modulation of interaction of estrogen receptors with coregulators induced by ERα and ERβ agonists. J Steroid Biochem Mol Biol. 2014 Sep;143:376-85. doi: 10.1016/j.jsbmb.2014.06.002. Epub 2014 Jun 9. PubMed PMID: 24923734. 3: Yao PL, Gonzalez FJ, Peters JM. Targeting estrogen receptor-β for the prevention of nonmelanoma skin cancer. Cancer Prev Res (Phila). 2014 Feb;7(2):182-5. doi: 10.1158/1940-6207.CAPR-13-0409. Epub 2014 Jan 24. PubMed PMID: 24464730; PubMed Central PMCID: PMC4114311. 4: Chaudhary SC, Singh T, Talwelkar SS, Srivastava RK, Arumugam A, Weng Z, Elmets CA, Afaq F, Kopelovich L, Athar M. Erb-041, an estrogen receptor-β agonist, inhibits skin photocarcinogenesis in SKH-1 hairless mice by downregulating the WNT signaling pathway. Cancer Prev Res (Phila). 2014 Feb;7(2):186-98. doi: 10.1158/1940-6207.CAPR-13-0276. Epub 2013 Nov 11. PubMed PMID: 24217507; PubMed Central PMCID: PMC3946228. 5: Lattrich C, Schüler S, Häring J, Skrzypczak M, Ortmann O, Treeck O. Effects of a combined treatment with tamoxifen and estrogen receptor β agonists on human breast cancer cell lines. Arch Gynecol Obstet. 2014 Jan;289(1):163-71. doi: 10.1007/s00404-013-2977-7. Epub 2013 Aug 2. PubMed PMID: 23907354. 6: Lee JH, Peters O, Lehmann L, Dence CS, Sharp TL, Carlson KE, Zhou D, Jeyakumar M, Welch MJ, Katzenellenbogen JA. Synthesis and biological evaluation of two agents for imaging estrogen receptor β by positron emission tomography: challenges in PET imaging of a low abundance target. Nucl Med Biol. 2012 Nov;39(8):1105-16. doi: 10.1016/j.nucmedbio.2012.05.011. Epub 2012 Jun 30. PubMed PMID: 22749433; PubMed Central PMCID: PMC3465515. 7: Cutolo M. Selective estrogen receptor agonism lacks clinical benefit in rheumatoid arthritis: comment on the article by van Vollenhoven et al. Arthritis Rheum. 2010 Dec;62(12):3832-3. doi: 10.1002/art.27722. PubMed PMID: 21120998. 8: Zhang L, Blackman BE, Schonemann MD, Zogovic-Kapsalis T, Pan X, Tagliaferri M, Harris HA, Cohen I, Pera RA, Mellon SH, Weiner RI, Leitman DC. Estrogen receptor beta-selective agonists stimulate calcium oscillations in human and mouse embryonic stem cell-derived neurons. PLoS One. 2010 Jul 27;5(7):e11791. doi: 10.1371/journal.pone.0011791. PubMed PMID: 20668547; PubMed Central PMCID: PMC2910705. 9: Roman-Blas JA, Castañeda S, Cutolo M, Herrero-Beaumont G. Efficacy and safety of a selective estrogen receptor β agonist, ERB-041, in patients with rheumatoid arthritis: a 12-week, randomized, placebo-controlled, phase II study. Arthritis Care Res (Hoboken). 2010 Nov;62(11):1588-93. doi: 10.1002/acr.20275. Epub 2010 Jun 15. PubMed PMID: 20556817. 10: Christaki E, Opal SM, Keith JC Jr, Kessinian N, Palardy JE, Parejo NA, Lavallie E, Racie L, Mounts W, Malamas MS, Mewshaw RE, Harris HA, Vlasuk GP. Estrogen receptor beta agonism increases survival in experimentally induced sepsis and ameliorates the genomic sepsis signature: a pharmacogenomic study. J Infect Dis. 2010 Apr 15;201(8):1250-7. doi: 10.1086/651276. PubMed PMID: 20205571. 11: Charn TH, Liu ET, Chang EC, Lee YK, Katzenellenbogen JA, Katzenellenbogen BS. Genome-wide dynamics of chromatin binding of estrogen receptors alpha and beta: mutual restriction and competitive site selection. Mol Endocrinol. 2010 Jan;24(1):47-59. doi: 10.1210/me.2009-0252. Epub 2009 Nov 6. PubMed PMID: 19897598; PubMed Central PMCID: PMC2802902. 12: Glace L, Grygielko ET, Boyle R, Wang Q, Laping NJ, Sulpizio AC, Bray JD. Estrogen-induced stromal cell-derived factor-1 (SDF-1/Cxcl12) expression is repressed by progesterone and by Selective Estrogen Receptor Modulators via estrogen receptor alpha in rat uterine cells and tissues. Steroids. 2009 Nov-Dec;74(13-14):1015-24. doi: 10.1016/j.steroids.2009.07.011. Epub 2009 Aug 7. PubMed PMID: 19665469. 13: Paruthiyil S, Cvoro A, Zhao X, Wu Z, Sui Y, Staub RE, Baggett S, Herber CB, Griffin C, Tagliaferri M, Harris HA, Cohen I, Bjeldanes LF, Speed TP, Schaufele F, Leitman DC. Drug and cell type-specific regulation of genes with different classes of estrogen receptor beta-selective agonists. PLoS One. 2009 Jul 17;4(7):e6271. doi: 10.1371/journal.pone.0006271. PubMed PMID: 19609440; PubMed Central PMCID: PMC2707612. 14: Xiu-li W, Wen-jun C, Hui-hua D, Su-ping H, Shi-long F. ERB-041, a selective ER beta agonist, inhibits iNOS production in LPS-activated peritoneal macrophages of endometriosis via suppression of NF-kappaB activation. Mol Immunol. 2009 Jul;46(11-12):2413-8. doi: 10.1016/j.molimm.2009.04.014. Epub 2009 May 17. PubMed PMID: 19447495. 15: Catley MC, Birrell MA, Hardaker EL, de Alba J, Farrow S, Haj-Yahia S, Belvisi MG. Estrogen receptor beta: expression profile and possible anti-inflammatory role in disease. J Pharmacol Exp Ther. 2008 Jul;326(1):83-8. doi: 10.1124/jpet.108.136275. Epub 2008 Mar 28. PubMed PMID: 18375789. 16: Cvoro A, Tatomer D, Tee MK, Zogovic T, Harris HA, Leitman DC. Selective estrogen receptor-beta agonists repress transcription of proinflammatory genes. J Immunol. 2008 Jan 1;180(1):630-6. PubMed PMID: 18097065. 17: Harris HA. Preclinical characterization of selective estrogen receptor beta agonists: new insights into their therapeutic potential. Ernst Schering Found Symp Proc. 2006;(1):149-61. Review. PubMed PMID: 17824176. 18: Rotella D. COMP-structure-based design and development of estrogen receptor modulators. IDrugs. 2006 Nov;9(11):748-50. PubMed PMID: 17096289. 19: Leventhal L, Brandt MR, Cummons TA, Piesla MJ, Rogers KE, Harris HA. An estrogen receptor-beta agonist is active in models of inflammatory and chemical-induced pain. Eur J Pharmacol. 2006 Dec 28;553(1-3):146-8. Epub 2006 Sep 26. PubMed PMID: 17056036. 20: Crabtree JS, Zhang X, Peano BJ, Zhang Z, Winneker RC, Harris HA. Development of a mouse model of mammary gland versus uterus tissue selectivity using estrogen- and progesterone-regulated gene markers. J Steroid Biochem Mol Biol. 2006 Sep;101(1):11-21. Epub 2006 Aug 22. PubMed PMID: 16920353.