WAY-267464

WAY-267464 is a potent, selective, non-peptide agonist for the oxytocin receptor, with negligible affinity for the vasopressin receptors.[1][2] 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 antagonist (in contrast to oxytocin, which is a weak agonist of the V1A 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
Clinical data
Routes of
administration		?
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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC32H35N7O4
Molar mass581.677 g·mol−1
3D model (JSmol)
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) N
  • Key:HWPGRFRXZNLZEX-UHFFFAOYSA-N N
 NY (what is this?)  (verify)

WAY-267464 is or was under investigation for the potential clinical treatment of anxiety disorders by Wyeth.

See also

References
  1. Rahman Z, Resnick L, Rosenzweig-Lipson SJ, Ring RH,"Methods of treatment using oxytocin receptor agonists", US patent application 2007/0117794, published 2007-05-24 , assigned to Wyeth Corp
  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. Progress in Brain Research. Vol. 170. pp. 473–512. doi:10.1016/S0079-6123(08)00437-8. PMID 18655903.
  3. Hicks C, Ramos L, Reekie T, 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". Br. J. Pharmacol. 171 (11): 2868–87. doi:10.1111/bph.12613. PMC 4243861. PMID 24641248.
  4. 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 (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. European Patent 1512687 Piperazines as oxytocin agonists


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