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

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 of TIOSPIRONE

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
4.65 nM [Ki]
74.0 nM [IC50]
950.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

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

Sample Use Guides

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
INN  
INN  
Official Name English
tiospirone [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C28197
Created by admin on Sat Dec 16 17:49:25 GMT 2023 , Edited by admin on Sat Dec 16 17:49:25 GMT 2023
Code System Code Type Description
WIKIPEDIA
Tiospirone
Created by admin on Sat Dec 16 17:49:25 GMT 2023 , Edited by admin on Sat Dec 16 17:49:25 GMT 2023
PRIMARY
ChEMBL
CHEMBL35057
Created by admin on Sat Dec 16 17:49:25 GMT 2023 , Edited by admin on Sat Dec 16 17:49:25 GMT 2023
PRIMARY
NCI_THESAURUS
C73303
Created by admin on Sat Dec 16 17:49:25 GMT 2023 , Edited by admin on Sat Dec 16 17:49:25 GMT 2023
PRIMARY
EVMPD
SUB11092MIG
Created by admin on Sat Dec 16 17:49:25 GMT 2023 , Edited by admin on Sat Dec 16 17:49:25 GMT 2023
PRIMARY
SMS_ID
100000077236
Created by admin on Sat Dec 16 17:49:25 GMT 2023 , Edited by admin on Sat Dec 16 17:49:25 GMT 2023
PRIMARY
CAS
87691-91-6
Created by admin on Sat Dec 16 17:49:25 GMT 2023 , Edited by admin on Sat Dec 16 17:49:25 GMT 2023
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MESH
C042709
Created by admin on Sat Dec 16 17:49:25 GMT 2023 , Edited by admin on Sat Dec 16 17:49:25 GMT 2023
PRIMARY
INN
6035
Created by admin on Sat Dec 16 17:49:25 GMT 2023 , Edited by admin on Sat Dec 16 17:49:25 GMT 2023
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PUBCHEM
55752
Created by admin on Sat Dec 16 17:49:25 GMT 2023 , Edited by admin on Sat Dec 16 17:49:25 GMT 2023
PRIMARY
EPA CompTox
DTXSID90236558
Created by admin on Sat Dec 16 17:49:25 GMT 2023 , Edited by admin on Sat Dec 16 17:49:25 GMT 2023
PRIMARY
FDA UNII
35C6UMO5SR
Created by admin on Sat Dec 16 17:49:25 GMT 2023 , Edited by admin on Sat Dec 16 17:49:25 GMT 2023
PRIMARY