:Prinaberel

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = (4Z)-2-Fluoro-4-(5-hydroxy-7-vinyl-1,3-benzoxazol-2(3H)-ylidene)-2,5-cyclohexadien-1-one

| image = Prinaberel.svg

| width = 250

| CAS_number = 524684-52-4

| CAS_supplemental =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = A9C8MNF7CA

| ATC_prefix = None

| ATC_suffix =

| PubChem = 5326893

| ChemSpiderID = 4484184

| C=15 | H=10 | F=1 | N=1 | O=3

| smiles = O=C3\C=C/C(=C2/Oc1c(cc(O)cc1N2)\C=C)/C=C3/F

| StdInChI = 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/h2-7,17-18H,1H2/b15-9-

| StdInChIKey = FCXYSEXZEGPLGG-DHDCSXOGSA-N

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| pregnancy_category =

| legal_status =

| routes_of_administration =

}}

Prinaberel (INN, USAN) (developmental code names ERB-041, WAY-202041) is a synthetic, nonsteroidal, and highly selective agonist of the ERβ subtype of the estrogen receptor.{{cite journal |vauthors=Harris HA, Albert LM, Leathurby Y, etal | title = Evaluation of an estrogen receptor-beta agonist in animal models of human disease | journal = Endocrinology | volume = 144 | issue = 10 | pages = 4241–9 |date=October 2003 | pmid = 14500559 | doi = 10.1210/en.2003-0550 | url = http://endo.endojournals.org/cgi/pmidlookup?view=long&pmid=14500559| doi-access = free }} It is used in scientific research to elucidate the role of the ERβ receptor.{{cite journal |vauthors=Koehler KF, Helguero LA, Haldosén LA, Warner M, Gustafsson JA | title = Reflections on the discovery and significance of estrogen receptor beta | journal = Endocrine Reviews | volume = 26 | issue = 3 | pages = 465–78 |date=May 2005 | pmid = 15857973 | doi = 10.1210/er.2004-0027 | url = http://edrv.endojournals.org/cgi/pmidlookup?view=long&pmid=15857973| doi-access = free }} 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.{{cite journal | author = Harris HA | title = Preclinical characterization of selective estrogen receptor beta agonists: new insights into their therapeutic potential | journal = Ernst Schering Foundation Symposium Proceedings | volume = 2006/1| issue = 1 | pages = 149–61 | year = 2006 | pmid = 17824176 | doi = 10.1007/2789_2006_021| isbn = 978-3-540-49547-5 }} Accordingly, prinaberel either was or still is under investigation by Wyeth for the treatment of some of these conditions.{{cite web | url = http://business.highbeam.com/436989/article-1G1-146524305/prinaberel-wyeth-phase-change-ii-usa | archive-url = https://web.archive.org/web/20160307162827/https://business.highbeam.com/436989/article-1G1-146524305/prinaberel-wyeth-phase-change-ii-usa | url-status = dead | archive-date = 2016-03-07 | title = Prinaberel - Wyeth phase change II, USA (endometriosis) | date = 2006-06-05 | work = R & D Focus Drug News | access-date = 2012-05-20}}