FLESINOXAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H26FN3O4
Molecular Weight	415.4579
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=NYSDRDDQELAVKP-SFHVURJKSA-N

InChI=1S/C22H26FN3O4/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)/t18-/m0/s1

HIDE SMILES / InChI

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 177 Target ID: CHEMBL273 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9022796	Partial Agonist 297		1.7 nM [Ki]

PubMed

Title	Date	PubMed
Rocuronium-induced neuromuscular block after long pretreatment of clonidine in rabbits.	2010-09	20877704
5-HT1A receptor blockade reverses GABA(A) receptor alpha3 subunit-mediated anxiolytic effects on stress-induced hyperthermia.	2010-08	20535452
Chronic thromboembolic pulmonary hypertension.	2010-04	20376164
Peripheral 5-HT1A and 5-HT7 serotonergic receptors modulate parasympathetic neurotransmission in long-term diabetic rats.	2010	21403818
Modifying 5-HT1A Receptor Gene Expression as a New Target for Antidepressant Therapy.	2010	20661455
A pilot study of rizatriptan and visually-induced motion sickness in migraineurs.	2009-08-06	19680473
Flesinoxan challenge suggests that chronic treatment with paroxetine in rats does not desensitize receptors controlling 5-HT synthesis.	2008-12	18786747
Activation of 5-HT1A autoreceptors in the dorsal raphe nucleus reduces the behavioral consequences of social defeat.	2008-10	18692968
Assessing the neuronal serotonergic target-based antidepressant stratagem: impact of in vivo interaction studies and knockout models.	2008-09	19506722
Stress-induced hyperthermia and basal body temperature are mediated by different 5-HT(1A) receptor populations: a study in SERT knockout rats.	2008-08-20	18606402
The roles of dopamine and serotonin, and of their receptors, in regulating sleep and waking.	2008	18772053
Acute flesinoxan treatment produces a different effect on rat brain serotonin synthesis than chronic treatment: an alpha-methyl-l-tryptophan autoradiographic study.	2007-12	17574706
Allometric scaling of pharmacodynamic responses: application to 5-Ht1A receptor mediated responses from rat to man.	2007-11	17541734
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.	2007-01	16710314
Delay aversion: effects of 7-OH-DPAT, 5-HT1A/1B-receptor stimulation and D-cycloserine.	2006-12	17208285
Rapid desensitization of somatodendritic 5-HT1A receptors by chronic administration of the high-efficacy 5-HT1A agonist, F13714: a microdialysis study in the rat.	2006-09	16921393
5-HT1A receptor agonist affects fear conditioning through stimulations of the postsynaptic 5-HT1A receptors in the hippocampus and amygdala.	2006-02-17	16460727
Contractile effects of 5-hydroxytryptamine and 5-carboxamidotryptamine in the equine jejunum.	2006-01	16230998
Early response and 8-week treatment outcome in GAD.	2006	16845651
5-Hydroxytryptamine 1A receptors, major depression, and suicidal behavior.	2005-12-01	16139805
Differential ion current activation by human 5-HT(1A) receptors in Xenopus oocytes: evidence for agonist-directed trafficking of receptor signalling.	2005-12	15964603
The effect of a 5-HT1A receptor agonist on striatal dopamine release.	2005-08	15906386
Effects of serotonin and serotonergic agonists and antagonists on the production of tumor necrosis factor alpha and interleukin-6.	2005-04-30	15892984
Behavioral and physiological mouse models for anxiety: effects of flesinoxan in 129S6/SvEvTac and C57BL/6J mice.	2004-06-21	15194450
Effects of repeated testing in two inbred strains on flesinoxan dose-response curves in three mouse models for anxiety.	2004-06-21	15194449
Influence of 5-HT1 receptor agonists on feline stomach relaxation.	2004-05-25	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.	2004-05-05	15084431
Occupancy of agonist drugs at the 5-HT1A receptor.	2004-05	14985704
Hormonal and temperature responses to flesinoxan in normal volunteers: an antagonist study.	2004-03	15013031
Mechanism-based pharmacokinetic-pharmacodynamic modeling of 5-HT1A receptor agonists: estimation of in vivo affinity and intrinsic efficacy on body temperature in rats.	2004-03	14718609
In vivo characterization of 5-HT1A receptor-mediated gastric relaxation in conscious dogs.	2003-11	14517177
Ca2+ responses in Chinese hamster ovary-K1 cells demonstrate an atypical pattern of ligand-induced 5-HT1A receptor activation.	2003-11	12970382
Differential effects of the 5-HT1A receptor agonist flesinoxan given locally or systemically on REM sleep in the rat.	2003-10-08	14575796
Comparison of hippocampal G protein activation by 5-HT(1A) receptor agonists and the atypical antipsychotics clozapine and S16924.	2003-09	12923612
Modulation of 5-HT(1A) receptor-mediated Ca(2+) responses by co-expression with various recombinant G(alpha) proteins in CHO-K1 cells.	2003-08	12879209
Evaluation of the ocular hypotensive response of serotonin 5-HT1A and 5-HT2 receptor ligands in conscious ocular hypertensive cynomolgus monkeys.	2003-07	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.	2003-06	12726819
Modulation of passive avoidance in mice by the 5-HT1A receptor agonist flesinoxan: comparison with the benzodiazepine receptor agonist diazepam.	2003-04	12655311
Nad-299 antagonises 5-HT-stimulated and spiperone-inhibited [35S]GTPgammaS binding in cloned 5-HT1A receptors.	2002-12-31	12503636
Hormonal and temperature responses to the 5-HT1A receptor agonist flesinoxan in normal volunteers.	2002-10	12373416
Neuroendocrine evaluation of 5-HT1A function in male alcoholic patients.	2002-10	12183221
Psychopharmacology of anxiety disorders.	2002-09	22033867
Autonomic changes associated with enhanced anxiety in 5-HT(1A) receptor knockout mice.	2002-09	12225695
5-HT1A dysfunction in borderline personality disorder.	2002-07	12171388
Pharmacokinetic-pharmacodynamic modelling of the hypothermic and corticosterone effects of the 5-HT1A receptor agonist flesinoxan.	2002-06-07	12065193
The interaction between the locus coeruleus and dorsal raphe nucleus studied with dual-probe microdialysis.	2002-06-07	12065192
[Effect of (+/-)-pindolol on the central 5-HT1A receptor by the use of in vivo microdialysis and hippocampal slice preparations].	2002-06	12166089
[Participation of 5-HT1A-receptors in regulating various types of aggressive behavior].	2002-03-02	11871034
Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study.	1998-08-21	9760039
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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:49:37 GMT 2025` Edited by `admin` on `Mon Mar 31 18:49:37 GMT 2025`
Record UNII	3V574S89E1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLESINOXAN

Official Name

English

(+)-(S)-P-FLUORO-N-(2-(4-(2-(HYDROXYMETHYL)-1,4-BENZODIOXAN-5-YL)-1-PIPERAZINYL)ETHYL)BENZAMIDE

Preferred Name

English

flesinoxan [INN]

Common Name

English

FLESINOXAN [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47794