WAY-267464

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 451221682

| IUPAC_name = 4-(3,5-Dihydroxybenzyl)-N-(2-methyl-4-[(1-methyl-4,10-dihydropyrazolo[3,4-b][1,5]benzodiazepin-5(1H)-yl)carbonyl]benzyl)piperazine-1-carboxamide

| image = WAY-267464.svg

| tradename =

| pregnancy_category =

| legal_status = Uncontrolled

| routes_of_administration = ?

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 847375-16-0

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

| UNII = XXL55X3DKM

| ATC_prefix = none

| ATC_suffix =

| PubChem = 9938214

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 31047382

| C = 32 | H = 35 | N = 7 | O = 4

| smiles = OC1=CC(O)=CC(CN2CCN(C(NCC3=C(C)C=C(C(N4C5=CC=CC=C5NC6=C(C=NN6C)C4)=O)C=C3)=O)CC2)=C1

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C32H35N7O4/c1-21-13-23(31(42)39-20-25-18-34-36(2)30(25)35-28-5-3-4-6-29(28)39)7-8-24(21)17-33-32(43)38-11-9-37(10-12-38)19-22-14-26(40)16-27(41)15-22/h3-8,13-16,18,35,40-41H,9-12,17,19-20H2,1-2H3,(H,33,43)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = HWPGRFRXZNLZEX-UHFFFAOYSA-N

}}

WAY-267464 is a potent, selective, non-peptide agonist for the oxytocin receptor, with negligible affinity for the vasopressin receptors.{{Ref patent3 | country = US | number = 2007/0117794 | status = application | title = Methods of treatment using oxytocin receptor agonists | pubdate = 2007-05-24 | fdate = | pridate= 2005-10-24 | inventor = Rahman Z, Resnick L, Rosenzweig-Lipson SJ, Ring RH | assign1 =Wyeth Corp | google_patent_id = 3G2iAAAAEBAJ }}{{cite book |vauthors=Manning M, Stoev S, Chini B, Durroux T, Mouillac B, Guillon G |chapter=Peptide and non-peptide agonists and antagonists for the vasopressin and oxytocin V1a, V1b, V2 and OT receptors: Research tools and potential therapeutic agents☆ |title=Advances in Vasopressin and Oxytocin — from Genes to Behaviour to Disease |series=Progress in Brain Research |volume=170 |pages=473–512 |year=2008 |pmid=18655903 |doi=10.1016/S0079-6123(08)00437-8 |isbn=9780444532015 }} Contradictorily however, though originally described as selective for the oxytocin receptor and lacking affinity for the vasopressin receptors, it has since been reported to also act as a potent vasopressin V_1A receptor antagonist (in contrast to oxytocin, which is a weak agonist of the V_1A receptor).{{cite journal |vauthors=Hicks C, Ramos L, Reekie T, etal | title = Body temperature and cardiac changes induced by peripherally administered oxytocin, vasopressin and the non-peptide oxytocin receptor agonist WAY 267,464: a biotelemetry study in rats | journal = Br. J. Pharmacol. | volume = 171 | issue = 11 | pages = 2868–87 |date=June 2014 | pmid = 24641248 | doi = 10.1111/bph.12613 | pmc=4243861}} WAY-267464 has been shown to cross the blood–brain barrier to a significantly greater extent than exogenously applied oxytocin, and in animal tests produces centrally-mediated oxytocinergic actions such as anxiolytic effects, but with no antidepressant effect evident.{{cite journal |vauthors=Ring RH, Schechter LE, Leonard SK, Dwyer JM, Platt BJ, Graf R, Grauer S, Pulicicchio C, Resnick L, Rahman Z, Sukoff Rizzo SJ, Luo B, Beyer CE, Logue SF, Marquis KL, Hughes ZA, Rosenzweig-Lipson S | author-link4=John Dwyer (medicine) |title=Receptor and behavioral pharmacology of WAY-267464, a non-peptide oxytocin receptor agonist |journal=Neuropharmacology |volume= 58|issue= 1|pages= 69–77|date=July 2009 |pmid=19615387 |doi=10.1016/j.neuropharm.2009.07.016 | s2cid=8592340 }} It was developed by a team at Ferring Pharmaceuticals.European Patent 1512687 Piperazines as oxytocin agonists WAY-267464 was under investigation for the potential clinical treatment of anxiety disorders by Wyeth, and reached the preclinical stage of development, but no development has been reported as of 2011.{{cite web | url=https://adisinsight.springer.com/drugs/800029344 | title=Research programme: Oxytocin receptor agonist - Wyeth - AdisInsight }}