IPSAPIRONE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H23N5O3S.ClH
Molecular Weight	437.944
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.O=C1N(CCCCN2CCN(CC2)C3=NC=CC=N3)S(=O)(=O)C4=C1C=CC=C4

InChI

InChIKey=USDUGJXCPKBJTN-UHFFFAOYSA-N

InChI=1S/C19H23N5O3S.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

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
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
A persistent deficit of serotonin neurons in the offspring of ethanol-fed dams: protective effects of maternal ipsapirone treatment.	2001 Aug 23	11506862
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
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
Smoking modulates neuroendocrine responses to ipsapirone in patients with panic disorder.	2002 Aug	12093600
Serotonergic dysregulation in bipolar disorders: a literature review of serotonergic challenge studies.	2002 Dec	12519094
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
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 short-term administration of valproate on serotonin-1A and dopamine receptor function in healthy human subjects.	2002 Nov	12491576
5-HT1A receptor activation and anti-cataleptic effects: high-efficacy agonists maximally inhibit haloperidol-induced catalepsy.	2002 Oct 25	12398907
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
Ca2+ responses in Chinese hamster ovary-K1 cells demonstrate an atypical pattern of ligand-induced 5-HT1A receptor activation.	2003 Nov	12970382
Efficacy of open-label venlafaxine in subjects with major depressive disorder: associations with neuroendocrine response to serotonergic and noradrenergic probes.	2004 Sep 30	15488964
Sustained pharmacological blockade of NK1 substance P receptors causes functional desensitization of dorsal raphe 5-HT 1A autoreceptors in mice.	2005 Dec	16219031
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
Signaling pathways involved with serotonin1A agonist-mediated neuroprotection against ethanol-induced apoptosis of fetal rhombencephalic neurons.	2005 Sep 8	16081165
Blunted hormone responses to Ipsapirone are associated with trait impulsivity in personality disorder patients.	2006 Jan	16123761
Azapirones for generalized anxiety disorder.	2006 Jul 19	16856115
Gateways to clinical trials.	2006 Jun	16845450
Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat.	2006 Mar 27	16545797
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
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
Chronic voluntary ethanol intake hypersensitizes 5-HT(1A) autoreceptors in C57BL/6J mice.	2008 Dec	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 Dec	18611291
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
Serotonin synthesis, release and reuptake in terminals: a mathematical model.	2010 Aug 19	20723248
Cellular and mitochondrial effects of alcohol consumption.	2010 Dec	21318009
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
A systematic, updated review on the antidepressant agomelatine focusing on its melatonergic modulation.	2010 Sep	21358978

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:20:29 UTC 2023` Edited by `admin` on `Fri Dec 15 16:20:29 UTC 2023`
Record UNII	08R5U8PYVO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IPSAPIRONE HYDROCHLORIDE

Official Name

English

IPSAPIRONE HYDROCHLORIDE [MI]

Common Name

English

BAY-Q-7821

Code

English

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

Common Name

English

IPSAPIRONE HCL

Common Name

English

IPSAPIRONE HYDROCHLORIDE [USAN]

Common Name

English

2-[4-[4-(2-Pyrimidinyl)-1-piperazinyl]butyl]-1,2-benzisothiazolin-3-one 1,1-dioxide, monohydrochloride

Common Name

English

IPSAPIRONE HYDROCHLORIDE [MART.]

Common Name

English

BAY Q 7821

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C28197