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Perlapine

From Wikipedia, the free encyclopedia
Sedative and hypnotic medication

Pharmaceutical compound
Perlapine
Clinical data
Trade namesHypnodine, Pipnodine
Other namesAW-14233; HF-2333; MP-11; PLP 100-127; 6-(4-Methyl-1-piperazinyl)morphanthridine
Identifiers
  • 6-(4-Methylpiperazin-1-yl)-11H-benzo[c][1]benzazepine
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.241.831Edit this at Wikidata
Chemical and physical data
FormulaC19H21N3
Molar mass291.398 g·mol−1
3D model (JSmol)
  • CN1CCN(CC1)C2=NC3=CC=CC=C3CC4=CC=CC=C42
  • InChI=1S/C19H21N3/c1-21-10-12-22(13-11-21)19-17-8-4-2-6-15(17)14-16-7-3-5-9-18(16)20-19/h2-9H,10-14H2,1H3
  • Key:PWRPUAKXMQAFCJ-UHFFFAOYSA-N

Perlapine, sold under the brand namesHypnodine andPipnodine, is ahypnotic andsedative of thetricyclic group which is marketed inJapan.[1] It acts primarily as apotentantihistamine,[2] and also hasanticholinergic,[2]antiserotonergic,[3]antiadrenergic, and someantidopaminergic activity.[3][4][5][6] The drug has relatively weakaffinity for thedopamineD2 receptor (IC50Tooltip Half-maximal inhibitory concentration = 1,803 nM) and, in accordance, is said to be ineffective as anantipsychotic.[6][7] However, it retains higher affinity for the dopamineD1 receptor (IC50 = 198 nM).[6] ItsIC50 values are 19 nM for theα1-adrenergic receptor, 4,945 nM for theα2-adrenergic receptor, and 70 nM for theserotonin5-HT2A receptor.[6] Perlapine is closely related toclotiapine,clozapine,fluperlapine,loxapine, andtilozepine.[6]

Perlapine has been suggested as a potential ligand for certainDREADDs.[8][9]

References

[edit]
  1. ^Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 811–.ISBN 978-3-88763-075-1.
  2. ^abLeysen JE, Niemegeers CJ (1985)."Neuroleptics". In Lajtha A (ed.).Alterations of Metabolites in the Nervous System. Boston, MA.: Springer Science & Business Media. pp. 331–361.ISBN 978-1-4757-6740-7.
  3. ^abMegens AA, Kennis LE (1996). "Risperidone and related 5HT2/D2 antagonists: a new type of antipsychotic agent?".Progress in Medicinal Chemistry.33:185–232.doi:10.1016/s0079-6468(08)70306-0.ISBN 9780444823106.PMID 8776944.
  4. ^Hathway DE (31 October 2007).Foreign Compound Metabolism in Mammals. Royal Society of Chemistry. pp. 302–.ISBN 978-1-84755-608-0.
  5. ^Liegeois JF, Bruhwyler J, Rogister F, Delarge J (April 1995)."Diarylazepine derivatives as potent atypical neuroleptic drugs: recent advances".Current Medicinal Chemistry.1 (6). Bentham Science Publishers:471–501.doi:10.2174/092986730106220216114910.S2CID 87829622.
  6. ^abcdeBarnes TR (22 October 2013).Antipsychotic Drugs and Their Side-Effects. Elsevier Science. pp. 28, 34.ISBN 978-1-4832-8810-9.
  7. ^American College of Neuropsychopharmacology (1978).Psychopharmacology: a generation of progress. Raven Press. p. 514.ISBN 978-0-89004-191-8.
  8. ^Thompson KJ, Khajehali E, Bradley SJ, Navarrete JS, Huang XP, Slocum S, et al. (September 2018)."DREADD Agonist 21 Is an Effective Agonist for Muscarinic-Based DREADDsin Vitro andin Vivo".ACS Pharmacology & Translational Science.1 (1):61–72.doi:10.1021/acsptsci.8b00012.PMC 6407913.PMID 30868140.
  9. ^Chen X, Choo H, Huang XP, Yang X, Stone O,Roth BL, Jin J (March 2015)."The first structure-activity relationship studies for designer receptors exclusively activated by designer drugs".ACS Chemical Neuroscience.6 (3):476–484.doi:10.1021/cn500325v.PMC 4368042.PMID 25587888.
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