Fluperlapine

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Fluperlapine
Clinical data
ATC code
  • none
Identifiers
  • 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 mass309.381 g/mol 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 as fluoroperlapine, is a tricyclic 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.

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

See also

References

  1. ^ a b 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, K. A. (1984). "Fluperlapine in 104 schizophrenic patients. Open multicenter trial". Arzneimittel-Forschung. 34 (1A): 125–130. PMID 6145428.
  3. ^ Woggon, B.; Angst, J.; Bartels, M.; Heinrich, K.; Hippius, H.; Koukkou, M.; Krebs, E.; Küfferle, B.; Müller-Oerlinghausen, B.; Pöldinger, W.; rÜTher, E.; Schied, H. W. (1984). "Antipsychotic efficacy of fluperlapine. An open multicenter trial". Neuropsychobiology. 11 (2): 116–120. doi:10.1159/000118064. PMID 6148712.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ Dieterle, D.; Eben, E.; Einhäupl, K.; Hippius, H.; Klein, H.; Rüther, E.; Schmauß, M. (2008). "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, H. W. (1984). "Results of a multicenter AMDP study with fluperlapine in schizophrenic patients". Arzneimittel-Forschung. 34 (1A): 122–124. 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): 60–64. doi:10.1007/bf00380972. PMID 2864254.
  7. ^ Pakkenberg, H.; Pedersen, B. (1985). "Medical treatment of dystonia". Psychopharmacology. Supplementum. 2: 111–117. doi:10.1007/978-3-642-70140-5_14. ISSN 0179-8456. OCLC 10642795. PMID 2860654.
  8. ^ Lai, W. G.; Gardner, I.; Zahid, N.; Uetrecht, J. P. (2000). "Bioactivation and covalent binding of hydroxyfluperlapine in human neutrophils: Implications for fluperlapine-induced agranulocytosis". Drug metabolism and disposition: the biological fate of chemicals. 28 (3): 255–263. 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. Retrieved 3 December 2013.{{cite web}}: CS1 maint: multiple names: authors list (link)
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