Chemistry:Fluperlapine

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Short description: Chemical compound
Fluperlapine
Clinical data
ATC code
  • none
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC19H20FN3
Molar mass309.388 g·mol−1
3D model (JSmol)
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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.

Pharmacology

Binding profile[9]

Receptor Ki (nM)
5-HT2A 7.9
5-HT2C 18.2
5-HT6 29
5-HT7 4.6
M1 8.8
M2 71
M3 41
M4 14
M5 17
D1 85
D2 316.2
D3 254.7
D4 21

Synthesis

Patents:[10][11]

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

See also

References

  1. ↑ 1.0 1.1 Dictionary of pharmacological agents. CRC Press. 1997. p. 916. ISBN 978-0-412-46630-4. https://books.google.com/books?id=DeX7jgInYFMC&pg=PA916. Retrieved 15 September 2011. 
  2. ↑ "Fluperlapine in 104 schizophrenic patients. Open multicenter trial". Arzneimittel-Forschung 34 (1A): 125–30. 1984. PMID 6145428. 
  3. ↑ "Antipsychotic efficacy of fluperlapine. An open multicenter trial". Neuropsychobiology 11 (2): 116–20. 1984. doi:10.1159/000118064. PMID 6148712. 
  4. ↑ "The effect of fluperlapine in acute psychotic patients". Pharmacopsychiatry 17 (2): 57–60. March 1984. doi:10.1055/s-2007-1017408. PMID 6728910. 
  5. ↑ "Results of a multicenter AMDP study with fluperlapine in schizophrenic patients". Arzneimittel-Forschung 34 (1A): 122–4. 1984. PMID 6145427. 
  6. ↑ "Treatment of drug-induced exogenous psychosis in parkinsonism with clozapine and fluperlapine". European Archives of Psychiatry and Neurological Sciences 235 (1): 60–4. 1985. doi:10.1007/bf00380972. PMID 2864254. 
  7. ↑ "Medical treatment of dystonia". Dyskinesia. Psychopharmacology Supplementum. 2. 1985. pp. 111–7. doi:10.1007/978-3-642-70140-5_14. ISBN 978-3-642-70142-9. OCLC 10642795. 
  8. ↑ "Bioactivation and covalent binding of hydroxyfluperlapine in human neutrophils: implications for fluperlapine-induced agranulocytosis". Drug Metabolism and Disposition 28 (3): 255–63. March 2000. PMID 10681368. 
  9. ↑ "PDSP Ki Database". Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. 12 January 2011. http://pdsp.med.unc.edu/pdsp.php. 
  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).



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