Piquindone

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Chemical compound

title: "Piquindone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["atypical-antipsychotics", "pyrroloisoquinolines"] description: "Chemical compound" topic_path: "general/atypical-antipsychotics" source: "https://en.wikipedia.org/wiki/Piquindone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| IUPAC_name = (4aS,8aS)-3-ethyl-2,6-dimethyl-1,4a,5,6,7,8,8a,9-octahydro-4H-pyrrolo[2,3-g]isoquinolin-4-one | image = Piquindone.png | image_class = skin-invert-image

| tradename = | pregnancy_category = | legal_status = Uncontrolled | routes_of_administration = Oral

| bioavailability = | metabolism = | elimination_half-life = | excretion =

| C=15 | H=22 | N=2 | O=1 | smiles = O=C2c1c([nH]c(c1CC)C)C[C@H]3[C@H]2CN(CC3)C

Piquindone (Ro 22-1319) is an atypical antipsychotic with a tricyclic structure that was developed in the 1980s but was never marketed. It acts as a selective D2 receptor antagonist, though based on its effects profile its selectivity may be considered controversial. Unlike most other D2 receptor ligands, piquindone displays Na+-dependent binding, a property it shares with tropapride, zetidoline, and metoclopramide.

In clinical trials piquindone was found to possess moderate efficacy in treating positive symptoms of schizophrenia, and notably, was also modestly effective for negative symptoms, though this was just under statistical significance. Additionally, relative to haloperidol, it was found to possesses significantly fewer extrapyramidal symptoms and had a much lower propensity for inducing tardive dyskinesia, indicating its atypical nature. In addition to psychosis, piquindone has also been found to be effective in the treatment of Tourette's syndrome in numerous clinical studies.

References

(October 1987). "The efficacy of piquindone, a new atypical neuroleptic, in the treatment of the positive and negative symptoms of schizophrenia". Journal of Clinical Psychopharmacology.
(September 1981). "A dopamine receptor model and its application in the design of a new class of rigid pyrrolo[2,3-g]isoquinoline antipsychotics". Journal of Medicinal Chemistry.
(1983). "Pharmacological effects of Ro 22-1319: a new antipsychotic agent". Psychopharmacology.
(November 1984). "[3H]Ro 22-1319 (piquindone) binds to the D2 dopaminergic receptor subtype in a sodium-dependent manner". Molecular Pharmacology.
(1985). "Effects of the putative D-1 antagonist SCH 23390 on stereotyped behaviour induced by the D-2 agonist RU24213". Psychopharmacology.
(July 1986). "Locomotor behaviors in response to new selective D-1 and D-2 dopamine receptor agonists, and the influence of selective antagonists". Pharmacology Biochemistry and Behavior.
(March 1989). "Structural requirements of Na+-dependent antidopaminergic agents: Tropapride, Piquindone, Zetidoline, and Metoclopramide. Comparison with Na+-independent ligands". Journal of Computer-aided Molecular Design.
(October 1984). "Treatment of Tourette's syndrome with RO22-1319, a D-2-receptor antagonist". The New England Journal of Medicine.
(April 1986). "Case report of four patients with Tourette syndrome treated with piquindone, a D2 receptor antagonist". Journal of Clinical Psychopharmacology.
(July 1986). "Improvement of symptoms in Tourette syndrome by piquindone, a novel dopamine-2 receptor antagonist". International Clinical Psychopharmacology.
(May 2020). "Pharmacological options for the treatment of Tourette's disorder". Drugs.

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