NALUZOTAN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H38N4O3S
Molecular Weight	450.638
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)NC1=CC=CC(=C1)N2CCN(CCCCNS(=O)(=O)CC3CCCCC3)CC2

InChI

InChIKey=SPWZXWDPAWDKQE-UHFFFAOYSA-N

InChI=1S/C23H38N4O3S/c1-20(28)25-22-10-7-11-23(18-22)27-16-14-26(15-17-27)13-6-5-12-24-31(29,30)19-21-8-3-2-4-9-21/h7,10-11,18,21,24H,2-6,8-9,12-17,19H2,1H3,(H,25,28)

HIDE SMILES / InChI

Molecular Formula	C23H38N4O3S
Molecular Weight	450.638
Charge	0
Count

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

Description
Sources: https://adisinsight.springer.com/drugs/800019899 | https://www.ipgroupplc.com/media/portfolio-news/2010/2010-07-07

Naluzotan (PRX-00023), a small molecule, non-azapirone, dual serotonin (5-HT)1A receptor agonist and sigma-1 receptor antagonist, is under development with Proximagen for the treatment of epilepsy. In previous clinical trials, the compound was shown to be safe and well-tolerated in over 400 patients. Epilepsy patients with localisation-related epilepsy have reduced 5-HT1a receptor binding as indicated by positron emission tomography (PET scan). It is thought that by increasing neurotransmitter activity at 5-HT1a receptor sites, seizure incidence and severity may be decreased.

Originator

Approval Year

PubMed

Title	Date	PubMed
An integrated in silico 3D model-driven discovery of a novel, potent, and selective amidosulfonamide 5-HT1A agonist (PRX-00023) for the treatment of anxiety and depression.	2006 Jun 1	16722631
Drug evaluation: PRX-00023, a selective 5-HT1A receptor agonist for depression.	2007 Jan	17263189
Tolerability, pharmacokinetics, and neuroendocrine effects of PRX-00023, a novel 5-HT1A agonist, in healthy subjects.	2007 Jul	17495280
Effects of PRX-00023, a novel, selective serotonin 1A receptor agonist on measures of anxiety and depression in generalized anxiety disorder: results of a double-blind, placebo-controlled trial.	2008 Apr	18344738
Short-term tolerability of a nonazapirone selective serotonin 1A agonist in adults with generalized anxiety disorder: a 28-day, open-label study.	2008 Sep	18840371
PRX-00023, a selective serotonin 1A receptor agonist, reduces ultrasonic vocalizations in infant rats bred for high infantile anxiety.	2009 Nov	19576924

Patents

Sample Use Guides

In Vivo Use Guide

Generalized anxiety disorder: all subjects underwent a 1-week placebo run-in and were randomized to receive once-daily capsules containing either Naluzotan (80 mg/d) or placebo for an additional 8 weeks.

Route of Administration: Oral

In Vitro Use Guide

Naluzotan behaves as a full 5-HT1A agonist in an in vitro cell-based functional assay with an EC50 of 20 nM. Naluzotan has significant affinity in the guinea pig sigma receptor (Ki = 100 nM).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:50:23 UTC 2023` Edited by `admin` on `Sat Dec 16 17:50:23 UTC 2023`
Record UNII	LQ54E5B4EW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NALUZOTAN

Official Name

English

N-{3-[4-(4-{[(Cyclohexylmethyl)sulfonyl]amino}butyl)piperazin-1-yl]phenyl}acetamide

Systematic Name

English

naluzotan [INN]

Common Name

English

NALUZOTAN [USAN]

Common Name

English

PRX-00023

Code

English

ACETAMIDE, N-(3-(4-(4-(((CYCLOHEXYLMETHYL)SULFONYL)AMINO)BUTYL)-1-PIPERAZINYL)PHENYL)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66885