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

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 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
S 14506: novel receptor coupling at 5-HT(1A) receptors.	2001 Mar	11166326
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
Rapid tryptophan depletion plus a serotonin 1A agonist: competing effects on sleep in healthy men.	2001 Nov	11682272
Kava pyrones exert effects on neuronal transmission and transmembraneous cation currents similar to established mood stabilizers--a review.	2001 Nov	11642654
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
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
Effects of ethanol and ipsapirone on the development of midline raphe glial cells and astrocytes.	2003 Apr	12798971
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
5-HT1A responsivity in patients with panic disorder before and after treatment with aerobic exercise, clomipramine or placebo.	2003 May	12729940
Additive neuroprotective effect of Ketanserin and Ipsapirone on the hippocampal damage after transient forebrain ischemia in the Mongolian gerbil.	2003 May 15	12727309
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
5-HT1A and 5-HT1B receptor agonists and aggression: a pharmacological challenge of the serotonin deficiency hypothesis.	2005 Dec 5	16310183
Efficient single nucleotide polymorphism discovery in laboratory rat strains using wild rat-derived SNP candidates.	2005 Nov 29	16316463
The 5-HT1A receptor and the stimulus effects of LSD in the rat.	2005 Oct	16025319
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
Azapirones for generalized anxiety disorder.	2006 Jul 19	16856115
Gateways to clinical trials.	2006 Jun	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 May 30	16687129
Temperature regulation in depression: functional 5HT1A receptor adaptation differentiates antidepressant response.	2006 Oct	16641936
Prediction and prevention of suicide in patients with unipolar depression and anxiety.	2007 Sep 5	17803824
Chronic voluntary ethanol intake hypersensitizes 5-HT(1A) autoreceptors in C57BL/6J mice.	2008 Dec	19094059
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-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
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	18992726
Cannabis and schizophrenia spectrum disorders: a review of clinical studies.	2009 Jul	21938097
5-Hydroxytryptamine Receptor Subtypes and their Modulators with Therapeutic Potentials.	2009 Jun	22505971
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
Cortisol responses to ipsapirone challenge correlate with aggression, while basal cortisol levels correlate with impulsivity, in personality disorder and healthy volunteer subjects.	2010 Oct	20378126

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:29:11 UTC 2023` Edited by `admin` on `Fri Dec 15 15:29:11 UTC 2023`
Record UNII	6J9B11MN0K
Record Status	`Validated (UNII)`
Record Version

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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