TIOSPIRONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H32N4O2S
Molecular Weight	440.601
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1CC2(CCCC2)CC(=O)N1CCCCN3CCN(CC3)C4=NSC5=C4C=CC=C5

InChI

InChIKey=ZFZPJDFBJFHYIV-UHFFFAOYSA-N

InChI=1S/C24H32N4O2S/c29-21-17-24(9-3-4-10-24)18-22(30)28(21)12-6-5-11-26-13-15-27(16-14-26)23-19-7-1-2-8-20(19)31-25-23/h1-2,7-8H,3-6,9-18H2

HIDE SMILES / InChI

Description
Sources: http://adisinsight.springer.com/drugs/800000562 | https://www.ncbi.nlm.nih.gov/pubmed/11007069 | https://www.ncbi.nlm.nih.gov/pubmed/2728088 | https://www.ncbi.nlm.nih.gov/pubmed/2885367 | https://www.ncbi.nlm.nih.gov/pubmed/2869146

Tiospirone (TSP) is an atypical antipsychotic drug. Tiaspirone appeared to be a promising antipsychotic agent as it didn`t cause extrapyramidal syndromes. It has 5HT-2 antagonistic properties as well as affinity for D2, 5HT-1a, 5HT-6 and sigma receptors. Tiospirone was in phase III clinical trials for the treatment of attention hyperactivity disorder with Mead Johnson in the USA but its development appears to have been discontinued.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11755134	Partial Agonist 290	4.65 nM [Ki]
Serotonin 2c (5-HT2c) receptor 124 Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10991983	Inverse Agonist 80	74.0 nM [IC50]
Serotonin 6 (5-HT6) receptor 45 Target ID: CHEMBL3371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8522988	Antagonist 2778	950.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3294920 https://www.ncbi.nlm.nih.gov/pubmed/2885367	Primary		Phase III 656	Unknown Approved Use Unknown
Psychotic disorder 26 Sources: http://adisinsight.springer.com/drugs/800000562	Primary		Phase III 656	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYPs 33

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYPs 33	substrate 3367 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1002/9780470571224.pse048	yes

Sourcing

Vendor/Aggregator	ID	URL
AOBIOUS INC	AOB5289	http://aobious.com/aobious/search?search_query=AOB5289
BOC Sciences	87691-91-6	http://www.bocsci.com/description.asp?cas=87691-91-6
Compound Cloud	55751
Compound Cloud	55752
Hangzhou Yuhao Chemical Technology	RT0936
MuseChem	R055594	https://www.musechem.com/product/R055594.html
Toronto Research Chemicals	T444810	https://www.trc-canada.com/product-detail/?CatNum=T444810
eMolecules	110043328	https://orderbb.emolecules.com/search/#?query=110043328
eMolecules	300666089	https://orderbb.emolecules.com/search/#?query=300666089
eMolecules	43552516	https://orderbb.emolecules.com/search/#?query=43552516

PubMed

Title	Date	PubMed
Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors.	1994 Mar	7908055
Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor.	1996 Jan	8522988
Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study.	1998 Aug 21	9760039
Inverse agonist activity of atypical antipsychotic drugs at human 5-hydroxytryptamine2C receptors.	2000 Oct	10991983

Patents

Sample Use Guides

In Vivo Use Guide

After a single 75 mg dose of tiospirone, demonstrable levels of dopamine binding activity were present. A variety of time points were sampled during the multiple dose study wherein subjects received 60 mg, t.i.d. for 28 days.

Route of Administration: Oral

In Vitro Use Guide

Tiaspirone was found to be a competitive, reversible inhibitor of the sodium-dependent high-affinity choline uptake (SDHACU) by crude hippocampal and striatal synaptosomal preparations, giving IC50 values of respectively 3.69 microM and 1.14 uM.

Name

Type

Language

TIOSPIRONE

Official Name

English

tiospirone [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197