Tiospirone

Overview

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.[1–6] WP

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.[7–12] WP

Binding profile[13] WP⚠ A table follows this text in the source and is not copied here. Open the source to see it.

Chemistry

Formula

C24H32N4O2S PC

CAS number

87691-91-6 PC

Molar mass (g/mol)

440.6 PC

IUPAC name (computed by PubChem)

8-[4-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]butyl]-8-azaspiro[4.5]decane-7,9-dione PC

SMILES

C1CCC2(C1)CC(=O)N(C(=O)C2)CCCCN3CCN(CC3)C4=NSC5=CC=CC=C54 PC

InChIKey

ZFZPJDFBJFHYIV-UHFFFAOYSA-N PC

PubChem CID

55752

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Yevich JP, New JS, Smith DW, Lobeck WG, Catt JD, Minielli JL, Eison MS, Taylor DP, Riblet LA, Temple DL. 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. March 1986. doi:10.1021/jm00153a010 · PMID 2869146
2. Journal / agency Jain AK, Kelwala S, Moore N, Gershon S. A controlled clinical trial of tiaspirone in schizophrenia. International Clinical Psychopharmacology. April 1987. doi:10.1097/00004850-198704000-00006 · PMID 2885367
3. Journal / agency Moore NC, Meyendorff E, Yeragani V, LeWitt PA, Gershon S. Tiaspirone in schizophrenia. Journal of Clinical Psychopharmacology. April 1987. doi:10.1097/00004714-198704000-00010 · PMID 3294920
4. Journal / agency Borison RL, Sinha D, Haverstock S, McLarnon MC, Diamond BI. Efficacy and safety of tiospirone vs. haloperidol and thioridazine in a double-blind, placebo-controlled trial. Psychopharmacology Bulletin. 1989. PMID 2574893
5. Other Nasrallah HA, Shriqui CL. Contemporary issues in the treatment of schizophrenia. 1995
6. Journal / agency Ishizumi K, Kojima A, Antoku F, Saji I, Yoshigi M. 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. December 1995. doi:10.1248/cpb.43.2139 · PMID 8582016
7. Journal / agency Sumiyoshi T, Suzuki K, Sakamoto H, Yamaguchi N, Mori H, Shiba K, Yokogawa K. Atypicality of several antipsychotics on the basis of in vivo dopamine-D2 and serotonin-5HT2 receptor occupancy. Neuropsychopharmacology. February 1995. doi:10.1016/0893-133X(94)00064-7 · PMID 7766287
8. Journal / agency Roth BL, Tandra S, Burgess LH, Sibley DR, Meltzer HY. D4 dopamine receptor binding affinity does not distinguish between typical and atypical antipsychotic drugs. Psychopharmacology. August 1995. doi:10.1007/BF02311185 · PMID 8524985
9. Journal / agency Weiner DM, Burstein ES, Nash N, Croston GE, Currier EA, Vanover KE, Harvey SC, Donohue E, Hansen HC, Andersson CM, Spalding TA, Gibson DF, Krebs-Thomson K, Powell SB, Geyer MA, Hacksell U, Brann MR. 5-hydroxytryptamine2A receptor inverse agonists as antipsychotics. The Journal of Pharmacology and Experimental Therapeutics. October 2001. PMID 11561089
10. Journal / agency Herrick-Davis K, Grinde E, Teitler M. Inverse agonist activity of atypical antipsychotic drugs at human 5-hydroxytryptamine2C receptors. The Journal of Pharmacology and Experimental Therapeutics. October 2000. PMID 10991983
11. Journal / agency Rauly-Lestienne I, Boutet-Robinet E, Ailhaud MC, Newman-Tancredi A, Cussac D. 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. October 2007. doi:10.1007/s00210-007-0182-6 · PMID 17786406
12. Journal / agency Newman-Tancredi A, Assié MB, Leduc N, Ormière AM, Danty N, Cosi C. 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. September 2005. doi:10.1017/S1461145704005000 · PMID 15707540
13. Other Roth BL, Driscol J. PDSP Kᵢ Database. 12 January 2011

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.