U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of IPSAPIRONE

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
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study.
1998 Aug 21
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
Serotonergic dysregulation in bipolar disorders: a literature review of serotonergic challenge studies.
2002 Dec
Effects of ethanol and 5-HT1A agonists on astroglial S100B.
2002 Dec 15
Neuroendocrine response to meta-chlorophenylpiperazine and ipsapirone in relation to anxiety and aggression.
2002 Dec 15
Nad-299 antagonises 5-HT-stimulated and spiperone-inhibited [35S]GTPgammaS binding in cloned 5-HT1A receptors.
2002 Feb-Nov
Effects of short-term administration of valproate on serotonin-1A and dopamine receptor function in healthy human subjects.
2002 Nov
Effects of ethanol and ipsapirone on the development of midline raphe glial cells and astrocytes.
2003 Apr
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
Effects of chronic treatment with ipsapirone and buspirone on the C57BL/6J strain mice under social stress.
2003 Feb 14
5-HT1A responsivity in patients with panic disorder before and after treatment with aerobic exercise, clomipramine or placebo.
2003 May
Additive neuroprotective effect of Ketanserin and Ipsapirone on the hippocampal damage after transient forebrain ischemia in the Mongolian gerbil.
2003 May 15
Ca2+ responses in Chinese hamster ovary-K1 cells demonstrate an atypical pattern of ligand-induced 5-HT1A receptor activation.
2003 Nov
Effects of serotonin 5-HT(1/2) receptor agonists in a limited-access operant food intake paradigm in the rat.
2003 Oct
The serotonin-1A agonist ipsapirone prevents ethanol-associated death of total rhombencephalic neurons and prevents the reduction of fetal serotonin neurons.
2004 Jun 21
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
Differential effects of the novel antidepressant agomelatine (S 20098) versus fluoxetine on 5-HT1A receptors in the rat brain.
2004 Sep
Efficacy of open-label venlafaxine in subjects with major depressive disorder: associations with neuroendocrine response to serotonergic and noradrenergic probes.
2004 Sep 30
Sustained pharmacological blockade of NK1 substance P receptors causes functional desensitization of dorsal raphe 5-HT 1A autoreceptors in mice.
2005 Dec
5-HT1A and 5-HT1B receptor agonists and aggression: a pharmacological challenge of the serotonin deficiency hypothesis.
2005 Dec 5
Gender-specific 5-HT1A receptor changes in BrdU nuclear labeling patterns in neonatal dentate gyrus.
2005 Jun 9
Efficient single nucleotide polymorphism discovery in laboratory rat strains using wild rat-derived SNP candidates.
2005 Nov 29
Ipsapirone and ketanserin protects against circulatory shock, intracranial hypertension, and cerebral ischemia during heatstroke.
2005 Oct
The 5-HT1A receptor and the stimulus effects of LSD in the rat.
2005 Oct
Differential effects of acute diazepam on emotional and neutral memory tasks in acutely hospitalized depressed patients.
2005 Sep
Updated overview of the putative role of the serotoninergic system in obsessive-compulsive disorder.
2005 Sep
Signaling pathways involved with serotonin1A agonist-mediated neuroprotection against ethanol-induced apoptosis of fetal rhombencephalic neurons.
2005 Sep 8
Blunted hormone responses to Ipsapirone are associated with trait impulsivity in personality disorder patients.
2006 Jan
Azapirones for generalized anxiety disorder.
2006 Jul 19
Gateways to clinical trials.
2006 Jun
Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat.
2006 Mar 27
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 May 30
Temperature regulation in depression: functional 5HT1A receptor adaptation differentiates antidepressant response.
2006 Oct
A pharmacological analysis of mice with a targeted disruption of the serotonin transporter.
2007 Dec
Prediction and prevention of suicide in patients with unipolar depression and anxiety.
2007 Sep 5
Chronic voluntary ethanol intake hypersensitizes 5-HT(1A) autoreceptors in C57BL/6J mice.
2008 Dec
Differential long-term effects of MDMA on the serotoninergic system and hippocampal cell proliferation in 5-HTT knock-out vs. wild-type mice.
2008 Dec
Antiaversive effects of cannabinoids: is the periaqueductal gray involved?
2009
Emotional reactivity and cognitive performance in aversively motivated tasks: a comparison between four rat strains.
2009 Dec 15
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
Effects of ethanol and ipsapirone on the expression of genes encoding anti-apoptotic proteins and an antioxidant enzyme in ethanol-treated neurons.
2009 Jan 16
Cannabis and schizophrenia spectrum disorders: a review of clinical studies.
2009 Jul
5-Hydroxytryptamine Receptor Subtypes and their Modulators with Therapeutic Potentials.
2009 Jun
Buspirone improves haloperidol-induced Parkinson disease in mice through 5-HT(1A) recaptors.
2010
Oppositional effects of serotonin receptors 5-HT1a, 2, and 2c in the regulation of adult hippocampal neurogenesis.
2010
Modifying 5-HT1A Receptor Gene Expression as a New Target for Antidepressant Therapy.
2010
Serotonin synthesis, release and reuptake in terminals: a mathematical model.
2010 Aug 19
Cellular and mitochondrial effects of alcohol consumption.
2010 Dec
Cortisol responses to ipsapirone challenge correlate with aggression, while basal cortisol levels correlate with impulsivity, in personality disorder and healthy volunteer subjects.
2010 Oct
A systematic, updated review on the antidepressant agomelatine focusing on its melatonergic modulation.
2010 Sep
Name Type Language
IPSAPIRONE
INN   MI  
INN  
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
Created by admin on Fri Dec 15 15:29:11 GMT 2023 , Edited by admin on Fri Dec 15 15:29:11 GMT 2023
NCI_THESAURUS C28197
Created by admin on Fri Dec 15 15:29:11 GMT 2023 , Edited by admin on Fri Dec 15 15:29:11 GMT 2023
Code System Code Type Description
CAS
95847-70-4
Created by admin on Fri Dec 15 15:29:11 GMT 2023 , Edited by admin on Fri Dec 15 15:29:11 GMT 2023
PRIMARY
INN
5774
Created by admin on Fri Dec 15 15:29:11 GMT 2023 , Edited by admin on Fri Dec 15 15:29:11 GMT 2023
PRIMARY
MESH
C043077
Created by admin on Fri Dec 15 15:29:11 GMT 2023 , Edited by admin on Fri Dec 15 15:29:11 GMT 2023
PRIMARY
MERCK INDEX
m6395
Created by admin on Fri Dec 15 15:29:11 GMT 2023 , Edited by admin on Fri Dec 15 15:29:11 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID4045688
Created by admin on Fri Dec 15 15:29:11 GMT 2023 , Edited by admin on Fri Dec 15 15:29:11 GMT 2023
PRIMARY
FDA UNII
6J9B11MN0K
Created by admin on Fri Dec 15 15:29:11 GMT 2023 , Edited by admin on Fri Dec 15 15:29:11 GMT 2023
PRIMARY
SMS_ID
100000083148
Created by admin on Fri Dec 15 15:29:11 GMT 2023 , Edited by admin on Fri Dec 15 15:29:11 GMT 2023
PRIMARY
ChEMBL
CHEMBL8412
Created by admin on Fri Dec 15 15:29:11 GMT 2023 , Edited by admin on Fri Dec 15 15:29:11 GMT 2023
PRIMARY
WIKIPEDIA
IPSAPIRONE
Created by admin on Fri Dec 15 15:29:11 GMT 2023 , Edited by admin on Fri Dec 15 15:29:11 GMT 2023
PRIMARY
PUBCHEM
56971
Created by admin on Fri Dec 15 15:29:11 GMT 2023 , Edited by admin on Fri Dec 15 15:29:11 GMT 2023
PRIMARY
NCI_THESAURUS
C74391
Created by admin on Fri Dec 15 15:29:11 GMT 2023 , Edited by admin on Fri Dec 15 15:29:11 GMT 2023
PRIMARY
EVMPD
SUB08290MIG
Created by admin on Fri Dec 15 15:29:11 GMT 2023 , Edited by admin on Fri Dec 15 15:29:11 GMT 2023
PRIMARY