FLESINOXAN HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H26FN3O4.ClH
Molecular Weight	451.919
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.OC[C@H]1COC2=C(C=CC=C2O1)N3CCN(CCNC(=O)C4=CC=C(F)C=C4)CC3

InChI

InChIKey=LZBWQEXVQZCBDJ-FERBBOLQSA-N

InChI=1S/C22H26FN3O4.ClH/c23-17-6-4-16(5-7-17)22(28)24-8-9-25-10-12-26(13-11-25)19-2-1-3-20-21(19)29-15-18(14-27)30-20;/h1-7,18,27H,8-15H2,(H,24,28);1H/t18-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Molecular Formula	C22H26FN3O4
Molecular Weight	415.4579
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8263314 | https://www.ncbi.nlm.nih.gov/pubmed/8614706 | https://adisinsight.springer.com/drugs/800001126

FLESINOXAN, a phenylpiperazine derivative, is a selective agonist for 5-HT1A receptors. It is an antidepressant agent which clinical development was stopped.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL273 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9022796	Partial Agonist 290		1.7 nM [Ki]

PubMed

Title	Date	PubMed
Differential cardiovascular effects of 8-hydroxy-2-(di-n-propylamino) tetralin (8-OH-DPAT), flesinoxan, 5-methyl-urapidil and MDL 75,608A in conscious spontaneously hypertensive rats.	1993	7906241
Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study.	1998 Aug 21	9760039
HPA axis dysfunction in major depression: relationship to 5-HT(1A) receptor activity.	2001	11490174
Stress-induced hyperthermia in the 5-HT(1A) receptor knockout mouse is normal.	2001 Apr 1	11297713
Effects of serotonergic compounds on aqueous humor dynamics in monkeys.	2001 Aug	11840350
Active efflux of the 5-HT(1A) receptor agonist flesinoxan via P-glycoprotein at the blood-brain barrier.	2001 Aug	11457654
Corticosterone responses in 5-HT1B receptor knockout mice to stress or 5-HT1A receptor activation are normal.	2001 Feb	11243496
The release of noradrenaline in the locus coeruleus and prefrontal cortex studied with dual-probe microdialysis.	2001 Jul 6	11430860
Generalization of serotonin (5-HT)1A agonists and the antipsychotics, clozapine, ziprasidone and S16924, but not haloperidol, to the discriminative stimuli elicited by PD128,907 and 7-OH-DPAT.	2001 Jun	11378160
Increased REM sleep after intra-dorsal raphe nucleus injection of flesinoxan or 8-OHDPAT: prevention with WAY 100635.	2002 Feb	11788240
Nad-299 antagonises 5-HT-stimulated and spiperone-inhibited [35S]GTPgammaS binding in cloned 5-HT1A receptors.	2002 Feb-Nov	12503636
The light-enhanced startle paradigm as a putative animal model for anxiety: effects of chlordiazepoxide, flesinoxan and fluvoxamine.	2002 Jan	11862346
Relationship between arterial distensibility and low-frequency power spectrum of blood pressure in spontaneously hypertensive rats.	2002 Jan	11743232
5-HT(1B) receptor knockout mice show no adaptive changes in 5-HT(1A) receptor function as measured telemetrically on body temperature and heart rate responses.	2002 Jan 1	11827741
[Effect of (+/-)-pindolol on the central 5-HT1A receptor by the use of in vivo microdialysis and hippocampal slice preparations].	2002 Jun	12166089
Pharmacokinetic-pharmacodynamic modelling of the hypothermic and corticosterone effects of the 5-HT1A receptor agonist flesinoxan.	2002 Jun 7	12065193
Neuroendocrine evaluation of 5-HT1A function in male alcoholic patients.	2002 Oct	12183221
Psychopharmacology of anxiety disorders.	2002 Sep	22033867
Modulation of 5-HT(1A) receptor-mediated Ca(2+) responses by co-expression with various recombinant G(alpha) proteins in CHO-K1 cells.	2003 Aug	12879209
Evaluation of the ocular hypotensive response of serotonin 5-HT1A and 5-HT2 receptor ligands in conscious ocular hypertensive cynomolgus monkeys.	2003 Jul	12676887
In vivo characterization of 5-HT1A receptor-mediated gastric relaxation in conscious dogs.	2003 Nov	14517177
Ca2+ responses in Chinese hamster ovary-K1 cells demonstrate an atypical pattern of ligand-induced 5-HT1A receptor activation.	2003 Nov	12970382
Differential effects of the 5-HT1A receptor agonist flesinoxan given locally or systemically on REM sleep in the rat.	2003 Oct 8	14575796
Comparison of hippocampal G protein activation by 5-HT(1A) receptor agonists and the atypical antipsychotics clozapine and S16924.	2003 Sep	12923612
Behavioral and physiological mouse models for anxiety: effects of flesinoxan in 129S6/SvEvTac and C57BL/6J mice.	2004 Jun 21	15194450
Mechanism-based pharmacokinetic-pharmacodynamic modeling of 5-HT1A receptor agonists: estimation of in vivo affinity and intrinsic efficacy on body temperature in rats.	2004 Mar	14718609
Influence of 5-HT1 receptor agonists on feline stomach relaxation.	2004 May 25	15178373
Effects of the 5-HT1A receptor ligands flesinoxan and WAY 100635 given systemically or microinjected into the laterodorsal tegmental nucleus on REM sleep in the rat.	2004 May 5	15084431
Early response and 8-week treatment outcome in GAD.	2006	16845651
Delay aversion: effects of 7-OH-DPAT, 5-HT1A/1B-receptor stimulation and D-cycloserine.	2006 Dec	17208285
5-HT1A receptor agonist affects fear conditioning through stimulations of the postsynaptic 5-HT1A receptors in the hippocampus and amygdala.	2006 Feb 17	16460727
Contractile effects of 5-hydroxytryptamine and 5-carboxamidotryptamine in the equine jejunum.	2006 Jan	16230998
SLV313 (1-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-4- [5-(4-fluoro-phenyl)-pyridin-3-ylmethyl]-piperazine monohydrochloride): a novel dopamine D2 receptor antagonist and 5-HT1A receptor agonist potential antipsychotic drug.	2007 Jan	16710314
Peripheral 5-HT1A and 5-HT7 serotonergic receptors modulate parasympathetic neurotransmission in long-term diabetic rats.	2010	21403818

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:37:15 UTC 2023` Edited by `admin` on `Fri Dec 15 15:37:15 UTC 2023`
Record UNII	8HV9S83FNY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLESINOXAN HYDROCHLORIDE

Common Name

English

FLESINOXAN HYDROCHLORIDE [MI]

Common Name

English

DU-29373

Code

English

(+)-N-(2-(4-(2,3-DIHYDRO-2-HYDROXYMETHYL-1,4-BENZODIOXAN-5-YL)-1-PIPERAZINYL)-ETHYL)-4-FLUOROBENZAMIDE HYDROCHLORIDE

Common Name

English

BENZAMIDE, N-(2-(4-((2R)-2,3-DIHYDRO-2-(HYDROXYMETHYL)-1,4-BENZODIOXIN-5-YL)-1-PIPERAZINYL)ETHYL)-4-FLUORO-, HYDROCHLORIDE (1:1)

Systematic Name

English

FLESINOXAN HCL

Common Name

English

Code System Code Type Description

FDA UNII

8HV9S83FNY