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WAY-267464 - Wikipedia

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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	847375-16-0^Y
PubChem CID	9938214
ChemSpider	31047382^N
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)^N Key:HWPGRFRXZNLZEX-UHFFFAOYSA-N^N
^NY (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] 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).^[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

^ 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".

Oxytocin and vasopressin receptor modulators

Oxytocin

Agonists: Peptide: Aspartocin
Carbetocin
Cargutocin
Demoxytocin
Lipo-oxytocin-1
Merotocin
Nacartocin
Oxytocin
PF-06478939
PF-06655075 (PF1)
TGOT
Vasotocin (argiprestocin); Non-peptide: CA7
LIT-001
TC OT 39
WAY-267464
WJ0679

Vasopressin

V_1A	Agonists: Felypressin Lypressin Ornipressin Selepressin Terlipressin Vasopressin (argipressin) Vasotocin (argiprestocin) Antagonists: Atosiban Balovaptan Conivaptan FR-218944 JNJ-17079166 JNJ-17308616 LIT-001 LY-307174 PF-184563 Relcovaptan RG7713 SRX246 SRX251 TC OT 39 WAY-267464 YM-218 YM-471 YM-35471
V_1B	Agonists: Desmopressin Felypressin Lypressin Ornipressin Terlipressin Vasopressin (argipressin) Vasotocin (argiprestocin) Antagonists: ABT-436 ABT-558 Brezivaptan Nelivaptan ORG-52186 (SCH-740935) TASP-0233278 TASP-0390325 Ligands: TASP-699
V₂	Agonists: Desmopressin Felypressin LIT-001 Lypressin Ornipressin TC OT 39 Terlipressin Vasopressin (argipressin) Vasotocin (argiprestocin) Antagonists: Conivaptan JNJ-17079166 Lixivaptan Mozavaptan RWJ-351647 Satavaptan Tolvaptan YM-471 YM-35471
Unsorted	Antagonists: Balovaptan Ribuvaptan RWJ-339489 VMAX-367 VMAX-372 VMAX-382 YM-222546 Other inhibitors: Demeclocycline Lithium (lithium carbonate)

Others

Carrier proteins: Neurophysin (I, II)

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See also

References