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
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
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 |
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New 5-HT1A receptor agonists possessing 1,4-benzoxazepine scaffold exhibit highly potent anti-ischemic effects. | 2001 Feb 26 |
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Other neuroprotective therapies on trial in acute stroke. | 2006 |
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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 |
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Population pharmacokinetics of the selective serotonin 5-HT1A receptor partial agonist piclozotan. | 2009 Mar-Apr |
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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 |
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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 |
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New serotonin 5-HT(1A) receptor agonists with neuroprotective effect against ischemic cell damage. | 2011 Dec 8 |
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NCI_THESAURUS |
C47794
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FQE44HS7AH
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PICLOZOTAN
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C90944
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DB12361
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CHEMBL345237
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)