WAY-267464

WAY-267464
Clinical data
Other names	WAY267464; WAY-267,464
Drug class	Oxytocin receptor agonist; Vasopressin V1A receptor antagonist
ATC code	None;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	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;
CAS Number	847375-16-0 ;
PubChem CID	9938214;
ChemSpider	31047382 ;
UNII	XXL55X3DKM;
CompTox Dashboard (EPA)	DTXSID30433044 ;
Chemical and physical data
Formula	C32H35N7O4
Molar mass	581.677 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	InChI InChI=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) ; Key:HWPGRFRXZNLZEX-UHFFFAOYSA-N ;
	(what is this?) (verify)

WAY-267464 is a potent, selective, non-peptide agonist for the oxytocin receptor, with negligible affinity for the vasopressin receptors.^[1]^[2] 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).^[3] 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.^[4] It was developed by a team at Ferring Pharmaceuticals.^[5] 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.^[6]

References

↑ US application 2007/0117794, Rahman Z, Resnick L, Rosenzweig-Lipson SJ, Ring RH, "Methods of treatment using oxytocin receptor agonists", published 2007-05-24, issued 1841-03-16, assigned to Wyeth Corp
↑ Manning M, Stoev S, Chini B, Durroux T, Mouillac B, Guillon G (2008). "Peptide and non-peptide agonists and antagonists for the vasopressin and oxytocin V1a, V1b, V2 and OT receptors: Research tools and potential therapeutic agents☆". Advances in Vasopressin and Oxytocin — from Genes to Behaviour to Disease. Progress in Brain Research. Vol. 170. pp. 473–512. doi:10.1016/S0079-6123(08)00437-8. ISBN 978-0-444-53201-5. PMID 18655903.
↑ Hicks C, Ramos L, Reekie T, Misagh GH, Narlawar R, Kassiou M, et al. (June 2014). "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". British Journal of Pharmacology. 171 (11): 2868–2887. doi:10.1111/bph.12613. PMC 4243861. PMID 24641248.
↑ Ring RH, Schechter LE, Leonard SK, Dwyer JM, Platt BJ, Graf R, et al. (July 2009). "Receptor and behavioral pharmacology of WAY-267464, a non-peptide oxytocin receptor agonist". Neuropharmacology. 58 (1): 69–77. doi:10.1016/j.neuropharm.2009.07.016. PMID 19615387. S2CID 8592340.
↑ EP 1512687, Hudson P, Pitt GR, Batt AR, Roe MB, "Piperazines as oxytocin agonists", published 2005-03-09, assigned to Ferring BV
↑ "Research programme: Oxytocin receptor agonist - Wyeth". AdisInsight.

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[WO_2007050353-1] US application 2007/0117794, Rahman Z, Resnick L, Rosenzweig-Lipson SJ, Ring RH, "Methods of treatment using oxytocin receptor agonists", published 2007-05-24, issued 1841-03-16, assigned to Wyeth Corp

[Manning_2008-2] Manning M, Stoev S, Chini B, Durroux T, Mouillac B, Guillon G (2008). "Peptide and non-peptide agonists and antagonists for the vasopressin and oxytocin V1a, V1b, V2 and OT receptors: Research tools and potential therapeutic agents☆". Advances in Vasopressin and Oxytocin — from Genes to Behaviour to Disease. Progress in Brain Research. Vol. 170. pp. 473–512. doi:10.1016/S0079-6123(08)00437-8. ISBN 978-0-444-53201-5. PMID 18655903.

[Hicks_2014-3] Hicks C, Ramos L, Reekie T, Misagh GH, Narlawar R, Kassiou M, et al. (June 2014). "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". British Journal of Pharmacology. 171 (11): 2868–2887. doi:10.1111/bph.12613. PMC 4243861. PMID 24641248.

[Ring_2009-4] Ring RH, Schechter LE, Leonard SK, Dwyer JM, Platt BJ, Graf R, et al. (July 2009). "Receptor and behavioral pharmacology of WAY-267464, a non-peptide oxytocin receptor agonist". Neuropharmacology. 58 (1): 69–77. doi:10.1016/j.neuropharm.2009.07.016. PMID 19615387. S2CID 8592340.

[5] EP 1512687, Hudson P, Pitt GR, Batt AR, Roe MB, "Piperazines as oxytocin agonists", published 2005-03-09, assigned to Ferring BV

[AdisInsight-6] "Research programme: Oxytocin receptor agonist - Wyeth". AdisInsight.

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See also

References