PICLOZOTAN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H24ClN3O2
Molecular Weight	409.909
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClC1=COC2=C(C=CC=C2)C(=O)N1CCCCN3CCC(=CC3)C4=NC=CC=C4

InChI

InChIKey=URMTUEWUIGOJBW-UHFFFAOYSA-N

InChI=1S/C23H24ClN3O2/c24-22-17-29-21-9-2-1-7-19(21)23(28)27(22)14-6-5-13-26-15-10-18(11-16-26)20-8-3-4-12-25-20/h1-4,7-10,12,17H,5-6,11,13-16H2

HIDE SMILES / InChI

Molecular Formula	C23H24ClN3O2
Molecular Weight	409.909
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/20858480 | https://www.ncbi.nlm.nih.gov/pubmed/19300037 | https://adisinsight.springer.com/drugs/800012319

Piclozotan (SUN N4057) is a 1,4-benzoxazepine derivative that exhibits sub-nanomolar affinity at serotonin 1A receptor with good selectivity over dopamine D2 and α1-adrenoceptors. Piclozotan reduced levodopa-induced forelimb hyperkinesia by 55% and 69%, respectively, at 1h relative to the control. Piclozotan significantly lengthened the duration of rotational behavior by 26% versus the control and attenuated the increase in striatal levodopa-derived extracellular dopamine levels. Piclozotan, a serotonin 1A agonist, can improve motor complications in patients with advanced Parkinson's disease. Piclozotan has been shown to be neuroprotective against ischemic neuronal damage in animal models. Piclozotan had been in phase II for the treatment of stroke. However, this research has been discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
New 5-HT1A receptor agonists possessing 1,4-benzoxazepine scaffold exhibit highly potent anti-ischemic effects.	2001 Feb 26	11229779
Other neuroprotective therapies on trial in acute stroke.	2006	16651823
Synthesis, SAR studies, and evaluation of 1,4-benzoxazepine derivatives as selective 5-HT1A receptor agonists with neuroprotective effect: Discovery of Piclozotan.	2006 Mar 15	16290165
Population pharmacokinetics of the selective serotonin 5-HT1A receptor partial agonist piclozotan.	2009 Mar-Apr	19300037
A systematic review of clinical trials of pharmacological interventions for acute ischaemic stroke (1955-2008) that were completed, but not published in full.	2010 Apr 22	20412562
Effects of piclozotan (SUN N4057), a partial serotonin 1A receptor agonist, on motor complications induced by repeated administration of levodopa in parkinsonian rats.	2010 Dec 15	20858480
New serotonin 5-HT(1A) receptor agonists with neuroprotective effect against ischemic cell damage.	2011 Dec 8	22029386

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:39:25 UTC 2023` Edited by `admin` on `Fri Dec 15 16:39:25 UTC 2023`
Record UNII	FQE44HS7AH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PICLOZOTAN

Official Name

English

3-CHLORO-4-(4-(1',2',3',6'-TETRAHYDRO-(2,4'-BIPYRIDIN)-1'-YL)BUTYL)-1,4-BENZOXAZEPIN-5(4H)-ONE

Systematic Name

English

piclozotan [INN]

Common Name

English

SUN-N-4057

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C47794