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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 mass309.388 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 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. ^ a b Ganellin CR, Triggle DJ, 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. 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 from the original on 8 November 2013. Retrieved 3 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).
Retrieved from " https://en.wikipedia.org/?title=Fluperlapine&oldid=1193711609"
From Wikipedia, the free encyclopedia
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 mass309.388 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 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. ^ a b Ganellin CR, Triggle DJ, 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. 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 from the original on 8 November 2013. Retrieved 3 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).
Retrieved from " https://en.wikipedia.org/?title=Fluperlapine&oldid=1193711609"

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