Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C15H22N2O.ClH.2H2O |
| Molecular Weight | 318.839 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.Cl.[H][C@@]12CCN(C)C[C@@]1([H])C(=O)C3=C(C2)NC(C)=C3CC
InChI
InChIKey=GEAXXUIYNZBBLU-ZTALITPHSA-N
InChI=1S/C15H22N2O.ClH.2H2O/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;1H;2*1H2/t10-,12+;;;/m0.../s1
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C15H22N2O |
| Molecular Weight | 246.348 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Locomotor behaviors in response to new selective D-1 and D-2 dopamine receptor agonists, and the influence of selective antagonists. | 1986 Jul |
|
| The thermodynamics of agonist and antagonist binding to dopamine D-2 receptors. | 1986 Sep |
|
| Effects of D2-dopaminergic receptor stimulation on male rat sexual behavior. | 1987 |
|
| The dopamine D-2 antagonist, Ro 22-1319, inhibits the persistent behavioral syndrome induced by iminodipropionitrile (IDPN) in mice. | 1987 Jun |
|
| Crystallographic, theoretical and molecular modelling studies on the conformations of the salicylamide, raclopride, a selective dopamine-D2 antagonist. | 1987 Oct |
|
| The efficacy of piquindone, a new atypical neuroleptic, in the treatment of the positive and negative symptoms of schizophrenia. | 1987 Oct |
|
| Alterations in sleep polygraphy after neuroleptic withdrawal: a putative supersensitive dopaminergic mechanism. | 1989 Jan |
|
| Stereoelectronic study of zetidoline, a dopamine D2 receptor antagonist. | 1989 Jan |
|
| Structural requirements of Na+-dependent antidopaminergic agents: Tropapride, Piquindone, Zetidoline, and Metoclopramide. Comparison with Na+-independent ligands. | 1989 Mar |
|
| Optically active benzamides as predictive tools for mapping the dopamine D2 receptor. | 1990 Jul 31 |
|
| Dopamine D2 receptor model explains binding affinity of neuroleptics: piquindone and its structure activity relationships. | 1996 Apr |
|
| The incorporation of butyrophenones and related compounds into a pharmacophore for dopamine D2 antagonists. | 1997 Aug |
|
| A multiway 3D QSAR analysis of a series of (S)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-6-methoxybenzamides. | 1998 Jan |
|
| Pharmacological options for the treatment of Tourette's disorder. | 2001 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:33:04 GMT 2023
by
admin
on
Fri Dec 15 15:33:04 GMT 2023
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| Record UNII |
4IPC09W42Y
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| Record Status |
Validated (UNII)
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| Record Version |
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C166760
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DTXSID401003839
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11954264
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83784-19-4
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CHEMBL1192678
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4IPC09W42Y
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U-45
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PARENT -> SALT/SOLVATE | |||
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ANHYDROUS->SOLVATE |
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ACTIVE MOIETY |