PIQUINDONE

Details

Stereochemistry	RACEMIC
Molecular Formula	C15H22N2O
Molecular Weight	246.348
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CCN(C)C[C@@]1([H])C(=O)C3=C(C2)NC(C)=C3CC

InChI

InChIKey=PVZMYDPRVUCJKV-CMPLNLGQSA-N

InChI=1S/C15H22N2O/c1-4-11-9(2)16-13-7-10-5-6-17(3)8-12(10)15(18)14(11)13/h10,12,16H,4-8H2,1-3H3/t10-,12+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6132425 | https://www.ncbi.nlm.nih.gov/pubmed/2564788 | https://www.ncbi.nlm.nih.gov/pubmed/3549873 | https://www.ncbi.nlm.nih.gov/pubmed/2890671 | https://www.ncbi.nlm.nih.gov/pubmed/3699100 | https://www.ncbi.nlm.nih.gov/pubmed/6149457

Piquindone is an antipsychotic pyrroloisoquinoline derivative that binds to dopamine D2 receptors. It is a potent D-2 antagonist. It has a low potential for extrapyramidal effects and tardive dyskinesia. Piquindone exhibited relatively weaker cataleptogenic and antistereotypic activity than haloperidol, and had minimal activity in a rat chronic stereotypy model of receptor supersensitivity. Piquindone almost as potent as haloperidol, with fewer or less intense extrapyramidal effects and low potential for tardive dyskinesia. Piquindone led to moderate but significant improvements in the positive symptoms of schizophrenia and to improvements in negative symptoms just below the level of statistical significance. Therapeutic efficacy of a piquindone antagonist in Tourette Syndrome can be achieved without production of disabling extrapyramidal-side effects.

Approval Year

PubMed

Title	Date	PubMed
Improvement of symptoms in Tourette syndrome by piquindone, a novel dopamine-2 receptor antagonist.	1986 Jul	3549873
The thermodynamics of agonist and antagonist binding to dopamine D-2 receptors.	1986 Sep	2943980
Crystallographic, theoretical and molecular modelling studies on the conformations of the salicylamide, raclopride, a selective dopamine-D2 antagonist.	1987 Oct	2891816
The induction of grooming and vacuous chewing by a series of selective D-1 dopamine receptor agonists: two directions of D-1:D-2 interaction.	1989 Feb 7	2565818
Alterations in sleep polygraphy after neuroleptic withdrawal: a putative supersensitive dopaminergic mechanism.	1989 Jan	2563233
Stereoelectronic study of zetidoline, a dopamine D2 receptor antagonist.	1989 Jan	2521253
Structural requirements of Na+-dependent antidopaminergic agents: Tropapride, Piquindone, Zetidoline, and Metoclopramide. Comparison with Na+-independent ligands.	1989 Mar	2715795
The effect of dopamine receptor blockade on the development of sensitization to the locomotor activating effects of amphetamine and morphine.	1989 Oct 9	2679971
Optically active benzamides as predictive tools for mapping the dopamine D2 receptor.	1990 Jul 31	1977603
Dopamine D2 receptor model explains binding affinity of neuroleptics: piquindone and its structure activity relationships.	1996 Apr	8874043
The incorporation of butyrophenones and related compounds into a pharmacophore for dopamine D2 antagonists.	1997 Aug	9342550
A multiway 3D QSAR analysis of a series of (S)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-6-methoxybenzamides.	1998 Jan	9570091
Pharmacological options for the treatment of Tourette's disorder.	2001	11772131

Name

Type

Language

PIQUINDONE

Official Name

English

RO-22-1319

Code

English

(±)-TRANS-3-ETHYL-1,4A,5,6,7,8,8A,9-OCTAHYDRO-2,6-DIMETHYL-4H-PYRROLO(2,3-G)ISOQUINOLIN-4-ONE

Common Name

English

piquindone [INN]

Common Name

English

RO 22-1319

Code

English

4H-PYRROLO(2,3-G)ISOQUINOLIN-4-ONE, 3-ETHYL-1,4A,5,6,7,8,8A,9-OCTAHYDRO-2,6-DIMETHYL-, (±)-

Common Name

English

Code System Code Type Description

MESH

C032412