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
Flesinoxan, a 5-HT1A receptor agonist/alpha 1-adrenoceptor antagonist, lowers intraocular pressure in NZW rabbits.	2001 Aug	11840354
Effects of serotonergic compounds on aqueous humor dynamics in monkeys.	2001 Aug	11840350
Effect of chronic administration of flesinoxan and fluvoxamine on freezing behavior induced by conditioned fear.	2001 Aug 3	11672573
[Participation of 5-HT1A-receptors in regulating various types of aggressive behavior].	2001 Nov-Dec	11871034
Nad-299 antagonises 5-HT-stimulated and spiperone-inhibited [35S]GTPgammaS binding in cloned 5-HT1A receptors.	2002 Feb-Nov	12503636
5-HT1A dysfunction in borderline personality disorder.	2002 Jul	12171388
[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
The interaction between the locus coeruleus and dorsal raphe nucleus studied with dual-probe microdialysis.	2002 Jun 7	12065192
Neuroendocrine evaluation of 5-HT1A function in male alcoholic patients.	2002 Oct	12183221
Modulation of passive avoidance in mice by the 5-HT1A receptor agonist flesinoxan: comparison with the benzodiazepine receptor agonist diazepam.	2003 Apr	12655311
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
Mutation in a protein kinase C phosphorylation site of the 5-HT1A receptor preferentially attenuates Ca2+ responses to partial as opposed to higher-efficacy 5-HT1A agonists.	2003 Jun	12726819
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
Hormonal and temperature responses to flesinoxan in normal volunteers: an antagonist study.	2004 Mar	15013031
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
Occupancy of agonist drugs at the 5-HT1A receptor.	2004 May	14985704
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
5-Hydroxytryptamine 1A receptors, major depression, and suicidal behavior.	2005 Dec 1	16139805
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
Rapid desensitization of somatodendritic 5-HT1A receptors by chronic administration of the high-efficacy 5-HT1A agonist, F13714: a microdialysis study in the rat.	2006 Sep	16921393
Acute flesinoxan treatment produces a different effect on rat brain serotonin synthesis than chronic treatment: an alpha-methyl-l-tryptophan autoradiographic study.	2007 Dec	17574706
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
Allometric scaling of pharmacodynamic responses: application to 5-Ht1A receptor mediated responses from rat to man.	2007 Nov	17541734
Stress-induced hyperthermia and basal body temperature are mediated by different 5-HT(1A) receptor populations: a study in SERT knockout rats.	2008 Aug 20	18606402
A pilot study of rizatriptan and visually-induced motion sickness in migraineurs.	2009 Aug 6	19680473
Modifying 5-HT1A Receptor Gene Expression as a New Target for Antidepressant Therapy.	2010	20661455
Chronic thromboembolic pulmonary hypertension.	2010 Apr	20376164
5-HT1A receptor blockade reverses GABA(A) receptor alpha3 subunit-mediated anxiolytic effects on stress-induced hyperthermia.	2010 Aug	20535452

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:37:15 GMT 2023` Edited by `admin` on `Fri Dec 15 15:37:15 GMT 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