Tiospirone

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title: "Tiospirone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["abandoned-drugs", "antipsychotics", "azapirones", "piperazinylbenzisothiazoles"] description: "Atypical antipsychotic drug" topic_path: "arts/music" source: "https://en.wikipedia.org/wiki/Tiospirone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Atypical antipsychotic drug ::

| IUPAC_name = 8-[4-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]butyl]-8-azaspiro[4.5]decane-7,9-dione | image = Tiospirone.svg | image_class = skin-invert-image | width = 250px

| tradename = | pregnancy_category = | legal_status = Development terminated | routes_of_administration =

| bioavailability = | metabolism = Hepatic | elimination_half-life = 1.4 hours | excretion = Urine

| CAS_number = 87691-91-6 | ATC_prefix = none | ATC_suffix = | PubChem = 55752 | IUPHAR_ligand = 101 | ChemSpiderID = 50348 | UNII_Ref = | UNII = 35C6UMO5SR | ChEMBL = 35057

| C = 24 | H = 32 | N = 4 | O = 2 | S = 1

Tiospirone (BMY-13,859), also sometimes called tiaspirone or tiosperone, is an atypical antipsychotic of the azapirone class. It was investigated as a treatment for schizophrenia in the late 1980s and was found to have an effectiveness equivalent to those of typical antipsychotics in clinical trials but without causing extrapyramidal side effects. However, development was halted and it was not marketed. Perospirone, another azapirone derivative with antipsychotic properties, was synthesized and assayed several years after tiospirone. It was found to be both more potent and more selective in comparison and was commercialized instead.

Pharmacology

Pharmacodynamics

Tiospirone acts as a 5-HT1A receptor partial agonist, 5-HT2A, 5-HT2C, and 5-HT7 receptor inverse agonist, and D2, D4, and α1-adrenergic receptor antagonist.

Binding profile ::data[format=table]

Receptor	Ki (nM)
5-HT2A	0.06
5-HT2C	9.73
5-HT6	950
5-HT7	0.64
M1	630
M2	180
M3	1290
M4	480
M5	3900
D2	0.5
D4	13.6
::

References

References

1. (March 1986). "Synthesis and biological evaluation of 1-(1,2-benzisothiazol-3-yl)- and (1,2-benzisoxazol-3-yl)piperazine derivatives as potential antipsychotic agents". Journal of Medicinal Chemistry.
2. (April 1987). "A controlled clinical trial of tiaspirone in schizophrenia". International Clinical Psychopharmacology.
3. (April 1987). "Tiaspirone in schizophrenia". Journal of Clinical Psychopharmacology.
4. (1989). "Efficacy and safety of tiospirone vs. haloperidol and thioridazine in a double-blind, placebo-controlled trial". Psychopharmacology Bulletin.
5. (1995). "Contemporary issues in the treatment of schizophrenia". American Psychiatric Press.
6. (December 1995). "Succinimide derivatives. II. Synthesis and antipsychotic activity of N-[4-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]butyl]-1,2-cis- cyclohexanedicarboximide (SM-9018) and related compounds". Chemical & Pharmaceutical Bulletin.
7. (February 1995). "Atypicality of several antipsychotics on the basis of in vivo dopamine-D2 and serotonin-5HT2 receptor occupancy". Neuropsychopharmacology.
8. (August 1995). "D4 dopamine receptor binding affinity does not distinguish between typical and atypical antipsychotic drugs". Psychopharmacology.
9. (October 2001). "5-hydroxytryptamine2A receptor inverse agonists as antipsychotics". The Journal of Pharmacology and Experimental Therapeutics.
10. (October 2000). "Inverse agonist activity of atypical antipsychotic drugs at human 5-hydroxytryptamine2C receptors". The Journal of Pharmacology and Experimental Therapeutics.
11. (October 2007). "Differential profile of typical, atypical and third generation antipsychotics at human 5-HT7a receptors coupled to adenylyl cyclase: detection of agonist and inverse agonist properties". Naunyn-Schmiedeberg's Archives of Pharmacology.
12. (September 2005). "Novel antipsychotics activate recombinant human and native rat serotonin 5-HT1A receptors: affinity, efficacy and potential implications for treatment of schizophrenia". The International Journal of Neuropsychopharmacology.
13. (12 January 2011). "PDSP K_i Database". University of North Carolina at Chapel Hill and the United States National Institute of Mental Health.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::