IPSAPIRONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H23N5O3S
Molecular Weight	401.483
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1N(CCCCN2CCN(CC2)C3=NC=CC=N3)S(=O)(=O)C4=CC=CC=C14

InChI

InChIKey=TZJUVVIWVWFLCD-UHFFFAOYSA-N

InChI=1S/C19H23N5O3S/c25-18-16-6-1-2-7-17(16)28(26,27)24(18)11-4-3-10-22-12-14-23(15-13-22)19-20-8-5-9-21-19/h1-2,5-9H,3-4,10-15H2

HIDE SMILES / InChI

Molecular Formula	C19H23N5O3S
Molecular Weight	401.483
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1981264 | https://www.ncbi.nlm.nih.gov/pubmed/7903326 | https://www.ncbi.nlm.nih.gov/pubmed/1978371

IPSAPIRONE, an azapirone derivative structurally unrelated to the benzodiazepines, is a selective 5-HT1A serotonin receptor agonist. It has antidepressant and anxiolytic effects. IPSAPIRONE was studied in several clinical trials for depression and generalized anxiety disorder.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 1a (5-HT1a) receptor 177 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9873561\|https://www.ncbi.nlm.nih.gov/pubmed/1981264\|https://www.ncbi.nlm.nih.gov/pubmed/16722631	Partial Agonist 297		67.61 nM [EC50]

PubMed

Title	Date	PubMed
Cellular and mitochondrial effects of alcohol consumption.	2010-12	21318009
Cortisol responses to ipsapirone challenge correlate with aggression, while basal cortisol levels correlate with impulsivity, in personality disorder and healthy volunteer subjects.	2010-10	20378126
A systematic, updated review on the antidepressant agomelatine focusing on its melatonergic modulation.	2010-09	21358978
Serotonin synthesis, release and reuptake in terminals: a mathematical model.	2010-08-19	20723248
Buspirone improves haloperidol-induced Parkinson disease in mice through 5-HT(1A) recaptors.	2010	22615592
Oppositional effects of serotonin receptors 5-HT1a, 2, and 2c in the regulation of adult hippocampal neurogenesis.	2010	20721314
Modifying 5-HT1A Receptor Gene Expression as a New Target for Antidepressant Therapy.	2010	20661455
Emotional reactivity and cognitive performance in aversively motivated tasks: a comparison between four rat strains.	2009-12-15	20003525
Cannabis and schizophrenia spectrum disorders: a review of clinical studies.	2009-07	21938097
5-Hydroxytryptamine Receptor Subtypes and their Modulators with Therapeutic Potentials.	2009-06	22505971
5-HT7 receptor deletion enhances REM sleep suppression induced by selective serotonin reuptake inhibitors, but not by direct stimulation of 5-HT1A receptor.	2009-02	18948124
Effects of ethanol and ipsapirone on the expression of genes encoding anti-apoptotic proteins and an antioxidant enzyme in ethanol-treated neurons.	2009-01-16	18992726
Antiaversive effects of cannabinoids: is the periaqueductal gray involved?	2009	19096514
Chronic voluntary ethanol intake hypersensitizes 5-HT(1A) autoreceptors in C57BL/6J mice.	2008-12	19094059
Differential long-term effects of MDMA on the serotoninergic system and hippocampal cell proliferation in 5-HTT knock-out vs. wild-type mice.	2008-12	18611291
A pharmacological analysis of mice with a targeted disruption of the serotonin transporter.	2007-12	17712549
Prediction and prevention of suicide in patients with unipolar depression and anxiety.	2007-09-05	17803824
Temperature regulation in depression: functional 5HT1A receptor adaptation differentiates antidepressant response.	2006-10	16641936
Azapirones for generalized anxiety disorder.	2006-07-19	16856115
Gateways to clinical trials.	2006-06	16845450
The effects of ethanol and the serotonin(1A) agonist ipsapirone on the expression of the serotonin(1A) receptor and several antiapoptotic proteins in fetal rhombencephalic neurons.	2006-05-30	16687129
Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat.	2006-03-27	16545797
Blunted hormone responses to Ipsapirone are associated with trait impulsivity in personality disorder patients.	2006-01	16123761
5-HT1A and 5-HT1B receptor agonists and aggression: a pharmacological challenge of the serotonin deficiency hypothesis.	2005-12-05	16310183
Sustained pharmacological blockade of NK1 substance P receptors causes functional desensitization of dorsal raphe 5-HT 1A autoreceptors in mice.	2005-12	16219031
Efficient single nucleotide polymorphism discovery in laboratory rat strains using wild rat-derived SNP candidates.	2005-11-29	16316463
Ipsapirone and ketanserin protects against circulatory shock, intracranial hypertension, and cerebral ischemia during heatstroke.	2005-10	16205318
The 5-HT1A receptor and the stimulus effects of LSD in the rat.	2005-10	16025319
Signaling pathways involved with serotonin1A agonist-mediated neuroprotection against ethanol-induced apoptosis of fetal rhombencephalic neurons.	2005-09-08	16081165
Differential effects of acute diazepam on emotional and neutral memory tasks in acutely hospitalized depressed patients.	2005-09	18568105
Updated overview of the putative role of the serotoninergic system in obsessive-compulsive disorder.	2005-09	18568072
Gender-specific 5-HT1A receptor changes in BrdU nuclear labeling patterns in neonatal dentate gyrus.	2005-06-09	15939086
Efficacy of open-label venlafaxine in subjects with major depressive disorder: associations with neuroendocrine response to serotonergic and noradrenergic probes.	2004-09-30	15488964
Differential effects of the novel antidepressant agomelatine (S 20098) versus fluoxetine on 5-HT1A receptors in the rat brain.	2004-09	15380370
The serotonin-1A agonist ipsapirone prevents ethanol-associated death of total rhombencephalic neurons and prevents the reduction of fetal serotonin neurons.	2004-06-21	15158072
New arylpiperazine 5-HT(1A) receptor ligands containing the pyrimido[2,1-f]purine fragment: synthesis, in vitro, and in vivo pharmacological evaluation.	2004-05-06	15115407
Ca2+ responses in Chinese hamster ovary-K1 cells demonstrate an atypical pattern of ligand-induced 5-HT1A receptor activation.	2003-11	12970382
Effects of serotonin 5-HT(1/2) receptor agonists in a limited-access operant food intake paradigm in the rat.	2003-10	12957332
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
Additive neuroprotective effect of Ketanserin and Ipsapirone on the hippocampal damage after transient forebrain ischemia in the Mongolian gerbil.	2003-05-15	12727309
5-HT1A responsivity in patients with panic disorder before and after treatment with aerobic exercise, clomipramine or placebo.	2003-05	12729940
Effects of ethanol and ipsapirone on the development of midline raphe glial cells and astrocytes.	2003-04	12798971
Effects of chronic treatment with ipsapirone and buspirone on the C57BL/6J strain mice under social stress.	2003-02-14	12535712
Nad-299 antagonises 5-HT-stimulated and spiperone-inhibited [35S]GTPgammaS binding in cloned 5-HT1A receptors.	2002-12-31	12503636
Effects of ethanol and 5-HT1A agonists on astroglial S100B.	2002-12-15	12480124
Neuroendocrine response to meta-chlorophenylpiperazine and ipsapirone in relation to anxiety and aggression.	2002-12-15	12467943
Serotonergic dysregulation in bipolar disorders: a literature review of serotonergic challenge studies.	2002-12	12519094
Effects of short-term administration of valproate on serotonin-1A and dopamine receptor function in healthy human subjects.	2002-11	12491576
Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study.	1998-08-21	9760039
Labelling of recombinant human and native rat serotonin 5-HT1A receptors by a novel, selective radioligand, [3H]-S 15535: definition of its binding profile using agonists, antagonists and inverse agonists.	1998-03	9550290

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:58:44 GMT 2025` Edited by `admin` on `Mon Mar 31 17:58:44 GMT 2025`
Record UNII	6J9B11MN0K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IPSAPIRONE

Official Name

English

IPSAPIRONE [MI]

Preferred Name

English

1,2-BENZISOTHIAZOL-3(2H)-ONE, 2-(4-(4-(2-PYRIMIDINYL)-1-PIPERAZINYL)BUTYL)-, 1,1-DIOXIDE

Systematic Name

English

ipsapirone [INN]

Common Name

English

2-(4-(4-(2-PYRIMIDINYL)-1-PIPERAZINYL)BUTYL)-1,2-BENZISOTHIAZOLIN-3-ONE 1,1-DIOXIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47794