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





A persistent deficit of serotonin neurons in the offspring of ethanol-fed dams: protective effects of maternal ipsapirone treatment.	2001 Aug 23	11506862
Behavioral effect of 1A-serotonin receptor agonist ipsapirone in mice previously defeated in male-male encounters.	2001 Nov	11865336
5-HT(1A) receptor dysfunction in female patients with schizophrenia.	2001 Nov 15	11720694
Astrocyte-mediated trophic support of developing serotonin neurons: effects of ethanol, buspirone, and S100B.	2001 Nov 26	11718831
5-hydroxytryptamine (5-HT)1A autoreceptor adaptive changes in substance P (neurokinin 1) receptor knock-out mice mimic antidepressant-induced desensitization.	2001 Oct 15	11588191
Effects of ethanol and 5-HT1A agonists on astroglial S100B.	2002 Dec 15	12480124
Neuroendocrine response to meta-chlorophenylpiperazine and ipsapirone in relation to anxiety and aggression.	2002 Dec 15	12467943
Repeated treatment with antidepressants differentially alters 5-HT1A agonist-stimulated [35S]GTP gamma S binding in rat brain regions.	2002 Jun	12128004
5-HT1A receptor activation and anti-cataleptic effects: high-efficacy agonists maximally inhibit haloperidol-induced catalepsy.	2002 Oct 25	12398907
5-HT1A receptor-mediated regulation of mitogen-activated protein kinase phosphorylation in rat brain.	2002 Oct 4	12354565
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
Ca2+ responses in Chinese hamster ovary-K1 cells demonstrate an atypical pattern of ligand-induced 5-HT1A receptor activation.	2003 Nov	12970382
Gender-specific 5-HT1A receptor changes in BrdU nuclear labeling patterns in neonatal dentate gyrus.	2005 Jun 9	15939086
Differential effects of acute diazepam on emotional and neutral memory tasks in acutely hospitalized depressed patients.	2005 Sep	18568105
Updated overview of the putative role of the serotoninergic system in obsessive-compulsive disorder.	2005 Sep	18568072
A pharmacological analysis of mice with a targeted disruption of the serotonin transporter.	2007 Dec	17712549
Prediction and prevention of suicide in patients with unipolar depression and anxiety.	2007 Sep 5	17803824
5-HT7 receptor deletion enhances REM sleep suppression induced by selective serotonin reuptake inhibitors, but not by direct stimulation of 5-HT1A receptor.	2009 Feb	18948124
Modifying 5-HT1A Receptor Gene Expression as a New Target for Antidepressant Therapy.	2010	20661455

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