Fluperlapine

Fluperlapine (NB 106-689), also known as fluoroperlapine, is a morphanthridine (11H-dibenzo[b,e]azepine) atypical antipsychotic with additional antidepressant and sedative effects. It was first synthesized 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 of medical conditions including schizophrenia,[2][3][4][5] psychosis associated with Parkinson's disease,[6] depressive symptoms, and dystonia,[7] it was never marketed.[1] This was perhaps due to its capacity for producing potentially life-threatening agranulocytosis, similarly to clozapine,[8] which it closely resembles both structurally and pharmacologically.

Fluperlapine
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 3-fluoro-6-(4-methylpiperazin-1-yl)-11H-dibenzo[b,e]azepine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H20FN3
Molar mass309.388 g·mol−1
3D model (JSmol)
SMILES
  • Fc4ccc3c(/N=C(/N1CCN(C)CC1)c2ccccc2C3)c4
InChI
  • 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 Y
  • Key:OBWGMKKHCLHVIE-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Pharmacology

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

See also

References

  1. Ganellin, C. R.; Triggle, D. J.; Macdonald, F. (1997). Dictionary of pharmacological agents. CRC Press. p. 916. ISBN 978-0-412-46630-4. Retrieved 15 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.
  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 from the original on 8 November 2013. Retrieved 3 December 2013.
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