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=C1C=CC=C4

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

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 172 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 290		67.61 nM [EC50]

PubMed

Title	Date	PubMed
Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study.	1998 Aug 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 Mar	9550290
Functional consequences of 5-HT transporter gene disruption on 5-HT(1a) receptor-mediated regulation of dorsal raphe and hippocampal cell activity.	2001 Mar 15	11245702
Serotonergic dysregulation in bipolar disorders: a literature review of serotonergic challenge studies.	2002 Dec	12519094
Neuroendocrine response to meta-chlorophenylpiperazine and ipsapirone in relation to anxiety and aggression.	2002 Dec 15	12467943
Nad-299 antagonises 5-HT-stimulated and spiperone-inhibited [35S]GTPgammaS binding in cloned 5-HT1A receptors.	2002 Feb-Nov	12503636
Dissociable hormonal, cognitive and mood responses to neuroendocrine challenge: evidence for receptor-specific serotonergic dysregulation in depressed mood.	2002 Mar	11850150
Effects of ethanol and ipsapirone on the development of midline raphe glial cells and astrocytes.	2003 Apr	12798971
Effects of chronic treatment with ipsapirone and buspirone on the C57BL/6J strain mice under social stress.	2003 Feb 14	12535712
5-HT1A responsivity in patients with panic disorder before and after treatment with aerobic exercise, clomipramine or placebo.	2003 May	12729940
Ca2+ responses in Chinese hamster ovary-K1 cells demonstrate an atypical pattern of ligand-induced 5-HT1A receptor activation.	2003 Nov	12970382
Effects of serotonin 5-HT(1/2) receptor agonists in a limited-access operant food intake paradigm in the rat.	2003 Oct	12957332
The serotonin-1A agonist ipsapirone prevents ethanol-associated death of total rhombencephalic neurons and prevents the reduction of fetal serotonin neurons.	2004 Jun 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 May 6	15115407
Sustained pharmacological blockade of NK1 substance P receptors causes functional desensitization of dorsal raphe 5-HT 1A autoreceptors in mice.	2005 Dec	16219031
Efficient single nucleotide polymorphism discovery in laboratory rat strains using wild rat-derived SNP candidates.	2005 Nov 29	16316463
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
Blunted hormone responses to Ipsapirone are associated with trait impulsivity in personality disorder patients.	2006 Jan	16123761
Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat.	2006 Mar 27	16545797
Temperature regulation in depression: functional 5HT1A receptor adaptation differentiates antidepressant response.	2006 Oct	16641936
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
Antiaversive effects of cannabinoids: is the periaqueductal gray involved?	2009	19096514
Emotional reactivity and cognitive performance in aversively motivated tasks: a comparison between four rat strains.	2009 Dec 15	20003525
5-Hydroxytryptamine Receptor Subtypes and their Modulators with Therapeutic Potentials.	2009 Jun	22505971
Modifying 5-HT1A Receptor Gene Expression as a New Target for Antidepressant Therapy.	2010	20661455

Name

Type

Language

IPSAPIRONE

Official 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

IPSAPIRONE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47794