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Fluperlapine

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Fluperlapine
Clinical data
ATC code
  • none
Identifiers
  • 3-fluoro-6-(4-methylpiperazin-1-yl)-11H-dibenzo[b,e]azepine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC19H20FN3
Molar mass309.388 g·mol−1
3D model (JSmol)
  • Fc4ccc3c(/N=C(/N1CCN(C)CC1)c2ccccc2C3)c4
  • InChI=1S/C19H20FN3/c1-22-8-10-23(11-9-22)19-17-5-3-2-4-14(17)12-15-6-7-16(20)13-18(15)21-19/h2-7,13H,8-12H2,1H3 checkY
  • Key:OBWGMKKHCLHVIE-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Fluperlapine (NB 106-689), also known asfluoroperlapine, is amorphanthridine (11H-dibenzo[b,e]azepine)atypical antipsychotic with additionalantidepressant andsedative effects. It was firstsynthesized in 1979, and then subsequently studied in animals and humans in 1984 and beyond,[1] but despite demonstrating efficacy in the treatment of a variety ofmedical conditions includingschizophrenia,[2][3][4][5]psychosis associated withParkinson's disease,[6]depressive symptoms, anddystonia,[7] it was never marketed.[1]This was perhaps due to its capacity for producing potentially life-threateningagranulocytosis, similarly to clozapine,[8] which it closely resembles bothstructurally andpharmacologically.

Pharmacology

[edit]

Binding profile[9]

ReceptorKi (nM)
5-HT2A7.9
5-HT2C18.2
5-HT629
5-HT74.6
M18.8
M271
M341
M414
M517
D185
D2316.2
D3254.7
D421

Synthesis

[edit]
Patents:[10][11]

3-fluoro-5,11-dihydro-6H-dibenz[b,e]azepin-6-one [62662-88-8] (3)

See also

[edit]

References

[edit]
  1. ^abGanellin CR, Triggle DJ, Macdonald F (1997).Dictionary of pharmacological agents.CRC Press. p. 916.ISBN 978-0-412-46630-4. Retrieved15 September 2011.
  2. ^Fischer-Cornelssen KA (1984). "Fluperlapine in 104 schizophrenic patients. Open multicenter trial".Arzneimittel-Forschung.34 (1A):125–30.PMID 6145428.
  3. ^Woggon B, Angst J, Bartels M, Heinrich K, Hippius H, Koukkou M, et al. (1984). "Antipsychotic efficacy of fluperlapine. An open multicenter trial".Neuropsychobiology.11 (2):116–20.doi:10.1159/000118064.PMID 6148712.
  4. ^Dieterle D, Eben E, Einhäupl K, Hippius H, Klein H, Rüther E, Schmauss M (March 1984). "The effect of fluperlapine in acute psychotic patients".Pharmacopsychiatry.17 (2):57–60.doi:10.1055/s-2007-1017408.PMID 6728910.S2CID 22264476.
  5. ^Woggon B, Heinrich K, Küfferle B, Müller-Oerlinghausen B, Pöldinger W, Rüther E, Schied HW (1984). "Results of a multicenter AMDP study with fluperlapine in schizophrenic patients".Arzneimittel-Forschung.34 (1A):122–4.PMID 6145427.
  6. ^Scholz E, Dichgans J (1985). "Treatment of drug-induced exogenous psychosis in parkinsonism with clozapine and fluperlapine".European Archives of Psychiatry and Neurological Sciences.235 (1):60–4.doi:10.1007/bf00380972.PMID 2864254.S2CID 23735955.
  7. ^Pakkenberg H, Pedersen B (1985). "Medical treatment of dystonia".Dyskinesia. Psychopharmacology Supplementum. Vol. 2. pp. 111–7.doi:10.1007/978-3-642-70140-5_14.ISBN 978-3-642-70142-9.OCLC 10642795.PMID 2860654.
  8. ^Lai WG, Gardner I, Zahid N, Uetrecht JP (March 2000). "Bioactivation and covalent binding of hydroxyfluperlapine in human neutrophils: implications for fluperlapine-induced agranulocytosis".Drug Metabolism and Disposition.28 (3):255–63.PMID 10681368.
  9. ^Roth BL, Driscol J (12 January 2011)."PDSP Ki Database".Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. Archived fromthe original on 8 November 2013. Retrieved3 December 2013.
  10. ^Fritz Hunziker, Rudolf Fischer,U.S. patent 4,308,207 (1981 to Sandoz Ltd.).
  11. ^Fritz Hunziker & Rudolf Fischer,U.S. patent 4,406,900 (1983 to Fidelity Union Bank).
Typical
Disputed
Atypical
Others
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
D1-like
Agonists
PAMs
Antagonists
D2-like
Agonists
Antagonists
H1
Agonists
Antagonists
H2
Agonists
Antagonists
H3
Agonists
Antagonists
H4
Agonists
Antagonists
mAChRsTooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(andprodrugs)
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT37
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Classes
Antidepressants
(Tricyclic antidepressants(TCAs))
Antihistamines
Antipsychotics
Anticonvulsants
Anticholinergics
Others
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