WAY-267464: Difference between revisions

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{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
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| verifiedrevid = 408055181
| Watchedfields = changed
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| IUPAC_name = 4-(3,5-dihydroxybenzyl)-''N''-(2-methyl-4-[(1-methyl-4,10-dihydropyrazolo[3,4-b][1,5]benzodiazepin-5(1''H'')-yl)carbonyl]benzyl)piperazine-1-carboxamide
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| verifiedrevid = 451221682
| image = WAY-267464_structure.png
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| IUPAC_name = 4-(3,5-Dihydroxybenzyl)-''N''-(2-methyl-4-[(1-methyl-4,10-dihydropyrazolo[3,4-b][1,5]benzodiazepin-5(1''H'')-yl)carbonyl]benzyl)piperazine-1-carboxamide
| width = 240
| image = WAY-267464.svg


<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
| pregnancy_category =
| pregnancy_category =
| legal_status = Uncontrolled
| legal_status = Uncontrolled
| routes_of_administration = ?
| routes_of_administration = ?


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability =
| bioavailability =
| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 847375-16-0
| CAS_number = 847375-16-0
| UNII_Ref = {{fdacite|correct|FDA}}
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| ATC_prefix = none
| UNII = XXL55X3DKM
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| ATC_suffix =
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| ATC_prefix = none
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| PubChem = 9938214
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| ATC_suffix =
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| PubChem = 9938214
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 31047382


<!--Chemical data-->
<!--Chemical data-->
| C=32 | H=35 | N=7 | O=4
| 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
| molecular_weight = 581.663 g/mol
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| smiles = Oc4cc(O)cc(c4)CN5CCN(CC5)C(=O)NCc2ccc(cc2C)C(=O)N6c1ccccc1Nc3c(C6)cnn3C
| 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-267,464''' is a [[drug]] which acts as a high [[affinity (pharmacology)|affinity]], [[potency (pharmacology)|potent]], [[functional selectivity|selective]], and non-[[peptide]] [[agonist]] for the [[oxytocin receptor]], with negligible affinity for the [[vasopressin receptor]]s.<ref name="WO 2007050353">{{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 }}</ref><ref name="pmid18655903">{{cite journal |author=Manning M, Stoev S, Chini B, Durroux T, Mouillac B, Guillon G |title=Peptide and non-peptide agonists and antagonists for the vasopressin and oxytocin V1a, V1b, V2 and OT receptors: research tools and potential therapeutic agents |journal=Progress in Brain Research |volume=170 |issue= |pages=473–512 |year=2008 |pmid=18655903 |doi=10.1016/S0079-6123(08)00437-8 |url=}}</ref> It 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.<ref name="pmid19615387">{{cite journal |author=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 |title=Receptor and behavioral pharmacology of WAY-267464, a non-peptide oxytocin receptor agonist |journal=Neuropharmacology |volume= 58|issue= 1|pages= 69–77|year=2009 |month=July |pmid=19615387 |doi=10.1016/j.neuropharm.2009.07.016 |url=}}</ref>
'''WAY-267464''' is a potent, selective, [[non-peptide]] [[agonist]] for the [[oxytocin receptor]], with negligible [[affinity (pharmacology)|affinity]] for the [[vasopressin receptor]]s.<ref name="WO 2007050353">{{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 }}</ref><ref name="pmid18655903">{{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 }}</ref> 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 V1A receptor|vasopressin V<sub>1A</sub> receptor]] [[receptor antagonist|antagonist]] (in contrast to oxytocin, which is a weak agonist of the V<sub>1A</sub> receptor).<ref name="pmid24641248">{{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}}</ref> 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.<ref name="pmid19615387">{{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 }}</ref> It was developed by a team at [[Ferring Pharmaceuticals]].<ref>European Patent 1512687 Piperazines as oxytocin agonists</ref> WAY-267464 was under investigation for the potential clinical treatment of [[anxiety disorder]]s by [[Wyeth]], and reached the [[preclinical development|preclinical stage of development]], but no development has been reported as of 2011.<ref name="AdisInsight">{{cite web | url=http://adisinsight.springer.com/drugs/800029344 | title=Research programme: Oxytocin receptor agonist - Wyeth - AdisInsight }}</ref>


== See also ==
==See also==
* [[Carbetocin]]
* [[TC OT 39]]
* [[Demoxytocin]]
* [[LIT-001]]
* [[Oxytocin]]


== References ==
==References==
{{Reflist}}
{{Reflist}}


{{Oxytocin and vasopressin receptor modulators}}


{{Anxiolytics}}
[[Category:Anxiolytics]]
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[[Category:Benzamides]]
{{Oxytocics}}
[[Category:Oxytocin receptor agonists]]
{{Neuropeptidergics}}

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[[Category:Phenols]]
[[Category:Piperazines]]
[[Category:Piperazines]]
[[Category:Amides]]
[[Category:Resorcinols]]
[[Category:Benzodiazepines]]
[[Category:Vasopressin receptor antagonists]]



{{genito-urinary-drug-stub}}
[[sr:WAY-267,464]]
{{nervous-system-drug-stub}}
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