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Piquindone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Piquindone
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • (4aS,8aS)-3-ethyl-2,6-dimethyl-1,4a,5,6,7,8,8a,9-octahydro-4H-pyrrolo[2,3-g]isoquinolin-4-one
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC15H22N2O
Molar mass246.354 g·mol−1
3D model (JSmol)
  • O=C2c1c([nH]c(c1CC)C)C[C@H]3[C@H]2CN(CC3)C

Piquindone (Ro 22-1319) is anatypical antipsychotic with atricyclicstructure that was developed in the 1980s but was never marketed.[1][2][3] It acts as aselectiveD2 receptorantagonist,[4][5][6] though based on its effects profile its selectivity may be considered controversial. Unlike most other D2 receptor ligands, piquindone displaysNa+-dependentbinding, a property it shares withtropapride,zetidoline, andmetoclopramide.[7]

Inclinical trials piquindone was found to possess moderate efficacy in treatingpositive symptoms of schizophrenia, and notably, was also modestly effective fornegative symptoms, though this was just under statistical significance.[1] Additionally, relative tohaloperidol, it was found to possesses significantly fewerextrapyramidal symptoms and had a much lower propensity for inducingtardive dyskinesia, indicating itsatypical nature.[1][3] In addition topsychosis, piquindone has also been found to be effective in the treatment ofTourette's syndrome in numerous clinical studies.[8][9][10][11]

See also

[edit]

References

[edit]
  1. ^abcCohen JD, Van Putten T, Marder S, Berger PA, Stahl SM (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.7 (5):324–9.doi:10.1097/00004714-198710000-00006.PMID 2890671.
  2. ^Olson GL, Cheung HC, Morgan KD, et al. (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.24 (9):1026–34.doi:10.1021/jm00141a002.PMID 6116805.
  3. ^abDavidson AB, Boff E, MacNeil DA, Wenger J, Cook L (1983). "Pharmacological effects of Ro 22-1319: a new antipsychotic agent".Psychopharmacology.79 (1):32–9.doi:10.1007/BF00433013.PMID 6132425.S2CID 12070196.
  4. ^Nakajima T, Iwata K (November 1984)."[3H]Ro 22-1319 (piquindone) binds to the D2 dopaminergic receptor subtype in a sodium-dependent manner".Molecular Pharmacology.26 (3):430–8.PMID 6149457.
  5. ^Pugh MT, O'Boyle KM, Molloy AG, Waddington JL (1985). "Effects of the putative D-1 antagonist SCH 23390 on stereotyped behaviour induced by the D-2 agonist RU24213".Psychopharmacology.87 (3):308–12.doi:10.1007/BF00432713.PMID 2934758.S2CID 19324697.
  6. ^Molloy AG, O'Boyle KM, Pugh MT, Waddington JL (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.25 (1):249–53.doi:10.1016/0091-3057(86)90262-5.PMID 3529126.S2CID 7007444.
  7. ^Collin S, Vercauteren DP, Vanderveken D, Evrard G, Durant F (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.3 (1):39–53.Bibcode:1989JCAMD...3...39C.doi:10.1007/BF01590994.PMID 2715795.S2CID 13298150.
  8. ^Uhr SB, Berger PA, Pruitt B, Stahl SM (October 1984). "Treatment of Tourette's syndrome with RO22-1319, a D-2-receptor antagonist".The New England Journal of Medicine.311 (15): 989.doi:10.1056/NEJM198410113111517.PMID 6147753.
  9. ^Uhr SB, Pruitt B, Berger PA, Stahl SM (April 1986). "Case report of four patients with Tourette syndrome treated with piquindone, a D2 receptor antagonist".Journal of Clinical Psychopharmacology.6 (2):128–30.doi:10.1097/00004714-198604000-00028.PMID 2871057.
  10. ^Uhr SB, Pruitt B, Berger PA, Stahl SM (July 1986). "Improvement of symptoms in Tourette syndrome by piquindone, a novel dopamine-2 receptor antagonist".International Clinical Psychopharmacology.1 (3):216–20.doi:10.1097/00004850-198607000-00004.PMID 3549873.
  11. ^Jiménez-Jiménez FJ, García-Ruiz PJ (2001)."Pharmacological options for the treatment of Tourette's disorder".Drugs.61 (15):2207–20.doi:10.2165/00003495-200161150-00005.PMID 11772131.S2CID 44720189.[permanent dead link]
Typical
Disputed
Atypical
Others
D1-like
Agonists
PAMs
Antagonists
D2-like
Agonists
Antagonists
Classes
Antidepressants
(Tricyclic antidepressants(TCAs))
Antihistamines
Antipsychotics
Anticonvulsants
Anticholinergics
Others
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