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Chemical compound
WAY-267464
Routes of administration ?
ATC code
Legal status
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 )
Formula C 32 H 35 N 7 O 4
Molar mass 581.677 g·mol−1 3D model (
JSmol )
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=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
N Y
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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 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]
See also
References
^ 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
^ 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
9780444532015 .
PMID
18655903 .
^ 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 .
^ 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 .
^ European Patent 1512687 Piperazines as oxytocin agonists
^
"Research programme: Oxytocin receptor agonist - Wyeth - AdisInsight" .