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SML2223

Sigma-Aldrich

WAY-267464 dihydrochloride

≥98% (HPLC)

Synonyme(s) :

4-(3,5-Dihydroxy-benzyl)-piperazine-1-carboxylic acid 2-methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-benzylamide dihydrochloride, 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 dihydrochloride, WAY 267,464 dihydrochloride, WAY 267464 dihydrochloride, WAY-267,464 dihydrochloride, WAY267464 dihydrochloride

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About This Item

Formule empirique (notation de Hill):
C32H35N7O4 · 2HCl
Numéro CAS:
Poids moléculaire :
654.59
Numéro MDL:
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to beige

Solubilité

H2O: 2 mg/mL, clear

Température de stockage

2-8°C

Chaîne SMILES 

O=C(NCC1=CC=C(C=C1C)C(N2CC3=C(NC4=CC=CC=C24)N(N=C3)C)=O)N5CCN(CC5)CC6=CC(O)=CC(O)=C6

InChI

1S/C32H35N7O4.2ClH/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);2*1H

Clé InChI

OTFWXMFLPMUDFP-UHFFFAOYSA-N

Actions biochimiques/physiologiques

WAY-267464 is a non-peptide drug with a novel mechanism of action (MOA) to treat psychosis and schizophrenia.
WAY-267464 is a non-peptide oxytocin receptor (OTR) agonist (EC50 = 61-881 nM; Ki = 58-978 nM) that, unlike oxytocin (OT), displays antagonist instead of agonist activity toward vasopressin V1a receptor/V1aR (IC50 = 613 nM; Ki = 27-113 nM). WAY-267464 exhibits OT-like anxiolytic effects in assays measuring both behavioral (33% increase in punished crossing by 10 mg/mL ip or 10 μg/mouse icv in four-plate tests; 75% increased open quadrants stay by 3 μg/mouse icv in elevated zero maze) and autonomic (47% higher stress-induced hyperthermia by 10 μg/mouse icv) parameters of the anxiety response. Similar to the antipsychotic-like effects reported for OT, WAY-267464 also reverses disruption in prepulse inhibition of the acoustic startle reflex induced by either MK-801 or amphetamine. Unlike OT, WAY-267464 does not affect immobility in mouse tail suspension test.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Consulter la Bibliothèque de documents

Yamei Tang et al.
Neuropharmacology, 77, 277-284 (2013-10-24)
Oxytocin (OT) was reported to affect cognitive and emotional behavior by action in ventral tegmental area (VTA) and other brain areas. However, it is still unclear how OT activates VTA and related midline nucleus. Here, using patch-clamp recording, we studied
William T Jorgensen et al.
European journal of medicinal chemistry, 143, 1644-1656 (2017-11-12)
WAY-267,464 (1) and twelve conformationally rigid analogues (3a-f-4a-f) were synthesised, characterised and evaluated in cellular assays with the aim of systematically exploring interactions with the oxytocin receptor (OTR). Each analogue was evaluated in radioligand binding displacement assays at both human
William T Jorgensen et al.
European journal of medicinal chemistry, 108, 730-740 (2016-01-08)
A previously identified, non-peptidic oxytocin (OT) receptor agonist WAY-267,464 (1) and nine novel derivatives (3, 4a-7a, 4b-7b) were synthesised and evaluated in vitro with the aim of systematically exploring hydrogen bonding interactions and ligand flexibility. All analogues were subjected to competition
Nisrine Lahoud et al.
Psychoneuroendocrinology, 38(10), 2184-2195 (2013-09-17)
The oxytocinergic system promotes social behavior and reduces anxiety. The significant roles and functional interactions of the medial prefrontal cortex and the amygdala in the regulation of fear provide a unique experimental setting to examine the effects of oxytocin on
Emma J Campbell-Smith et al.
Learning & memory (Cold Spring Harbor, N.Y.), 22(5), 247-257 (2015-04-17)
The present study investigated how oxytocin (OT) signaling in the central (CeA) and basolateral (BLA) amygdala affects acquisition, expression, and extinction of context-conditioned fear (freezing) in rats. In the first set of experiments, acquisition of fear to a shocked context

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