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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

Description

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

PubMed

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.