WAY-267464

Details

Stereochemistry	ACHIRAL
Molecular Formula	C32H35N7O4
Molecular Weight	581.6648
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1N=CC2=C1NC3=CC=CC=C3N(C2)C(=O)C4=CC(C)=C(CNC(=O)N5CCN(CC6=CC(O)=CC(O)=C6)CC5)C=C4

InChI

InChIKey=HWPGRFRXZNLZEX-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C32H35N7O4
Molecular Weight	581.6648
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19615387
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/22420322 | https://www.ncbi.nlm.nih.gov/pubmed/25761839

WAY 267464 dihydrochloride is a potent and selective agonist at the oxytocin receptor (OTR). WAY 267464 has been shown to cross the blood-brain-barrier to a significantly greater extent than exogenously applied oxytocin. WAY 267464 dose-dependently reduced anxiety on the four-plate test and prevented the deficits in prepulse inhibition induced by MK-801 or amphetamine. The ability of WAY 267464 to function as a V1AR antagonist may limit its potential therapeutic use in humans, as it would conceivably prevent the improvements in social behavior and social cognition that may be assumed to arise from a primary OTR agonist action.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Oxytocin receptor 19 Target ID: CHEMBL2049 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19615387	Agonist 2678		58.4 nM [Ki]
Vasopressin V1a receptor 17 Target ID: CHEMBL1889 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22420322	Antagonist 2778		113.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19615387	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Receptor and behavioral pharmacology of WAY-267464, a non-peptide oxytocin receptor agonist.	2010 Jan	19615387
Non-peptide oxytocin receptor ligands and hamster circadian wheel running rhythms.	2014 Oct 17	25148710
WAY 267,464, a non-peptide oxytocin receptor agonist, impairs social recognition memory in rats through a vasopressin 1A receptor antagonist action.	2015 Aug	25761839
Flexible analogues of WAY-267,464: Synthesis and pharmacology at the human oxytocin and vasopressin 1a receptors.	2016 Jan 27	26741855

Patents

Sample Use Guides

In Vivo Use Guide

Rats: 10 and 100 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

Functional response of the receptors were measured with luciferase reporter assays, based on the downstream activation, following agonist treatment, of the NFAT response element that has been additionally expressed in those cells as a fusion to the luciferase gene. For the OTR, oxytocin had a functional EC50 of 9.0 nM and WAY 267,464 showed weaker activity, with an observed EC50 of 881 nM. Oxytocin generated a functional response at the V1aR with an EC50 of 59.7 nM, whereas WAY 267,464 did not activate the receptor at concentrations as high as 100 uM. The EC50 of a vasopressin control at the V1aR was measured to be 13.5 nM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 18:06:04 UTC 2023` Edited by `admin` on `Sat Dec 16 18:06:04 UTC 2023`
Record UNII	XXL55X3DKM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

WAY-267464

Code

English

WAY-267,464

Code

English

1-PIPERAZINECARBOXAMIDE, N-((4-((4,10-DIHYDRO-1-METHYLPYRAZOLO(3,4-B)(1,5)BENZODIAZEPIN-5(1H)-YL)CARBONYL)-2-METHYLPHENYL)METHYL)-4-((3,5-DIHYDROXYPHENYL)METHYL)-

Systematic Name

English

N-((4-((4,10-DIHYDRO-1-METHYLPYRAZOLO(3,4-B)(1,5)BENZODIAZEPIN-5(1H)-YL)CARBONYL)-2-METHYLPHENYL)METHYL)-4-((3,5-DIHYDROXYPHENYL)METHYL)-1-PIPERAZINECARBOXAMIDE

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

WAY-267464