fluperlapine

{{Short description|Chemical compound}}

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{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 459444391

| IUPAC_name = 3-fluoro-6-(4-methylpiperazin-1-yl)-11H-dibenzo[b,e]azepine

| image = Fluperlapine.svg

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 67121-76-0

| ATC_prefix = none

| ATC_suffix =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = EWG253M961

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 63756

| PubChem = 49381

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 44882

| C = 19 | H = 20 | F = 1 | N = 3

| smiles = Fc4ccc3c(/N=C(/N1CCN(C)CC1)c2ccccc2C3)c4

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OBWGMKKHCLHVIE-UHFFFAOYSA-N

| bioavailability =

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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,

{{cite book | vauthors = Ganellin CR, Triggle DJ, Macdonald F | title = Dictionary of pharmacological agents | url = https://books.google.com/books?id=DeX7jgInYFMC&pg=PA916 | access-date = 15 September 2011 | year = 1997 | publisher = CRC Press | isbn = 978-0-412-46630-4 | page = 916 }} but despite demonstrating efficacy in the treatment of a variety of medical conditions including schizophrenia,

{{cite journal | vauthors = Fischer-Cornelssen KA | title = Fluperlapine in 104 schizophrenic patients. Open multicenter trial | journal = Arzneimittel-Forschung | volume = 34 | issue = 1A | pages = 125–30 | year = 1984 | pmid = 6145428 }}

{{cite journal | vauthors = Woggon B, Angst J, Bartels M, Heinrich K, Hippius H, Koukkou M, Krebs E, Küfferle B, Müller-Oerlinghausen B, Pöldinger W | display-authors = 6 | title = Antipsychotic efficacy of fluperlapine. An open multicenter trial | journal = Neuropsychobiology | volume = 11 | issue = 2 | pages = 116–20 | year = 1984 | pmid = 6148712 | doi = 10.1159/000118064 }}

{{cite journal | vauthors = Dieterle D, Eben E, Einhäupl K, Hippius H, Klein H, Rüther E, Schmauss M | title = The effect of fluperlapine in acute psychotic patients | journal = Pharmacopsychiatry | volume = 17 | issue = 2 | pages = 57–60 | date = March 1984 | pmid = 6728910 | doi = 10.1055/s-2007-1017408 | s2cid = 22264476 }}

{{cite journal | vauthors = Woggon B, Heinrich K, Küfferle B, Müller-Oerlinghausen B, Pöldinger W, Rüther E, Schied HW | title = Results of a multicenter AMDP study with fluperlapine in schizophrenic patients | journal = Arzneimittel-Forschung | volume = 34 | issue = 1A | pages = 122–4 | year = 1984 | pmid = 6145427 }} psychosis associated with Parkinson's disease,{{cite journal | vauthors = Scholz E, Dichgans J | title = Treatment of drug-induced exogenous psychosis in parkinsonism with clozapine and fluperlapine | journal = European Archives of Psychiatry and Neurological Sciences | volume = 235 | issue = 1 | pages = 60–4 | year = 1985 | pmid = 2864254 | doi = 10.1007/bf00380972 | s2cid = 23735955 }} depressive symptoms, and dystonia,

{{cite book | vauthors = Pakkenberg H, Pedersen B | title = Dyskinesia | chapter = Medical treatment of dystonia | volume = 2 | pages = 111–7 | year = 1985 | pmid = 2860654 | doi = 10.1007/978-3-642-70140-5_14 | isbn = 978-3-642-70142-9 | series = Psychopharmacology Supplementum | oclc = 10642795 }} it was never marketed.

This was perhaps due to its capacity for producing potentially life-threatening agranulocytosis, similarly to clozapine,{{cite journal | vauthors = Lai WG, Gardner I, Zahid N, Uetrecht JP | title = Bioactivation and covalent binding of hydroxyfluperlapine in human neutrophils: implications for fluperlapine-induced agranulocytosis | journal = Drug Metabolism and Disposition | volume = 28 | issue = 3 | pages = 255–63 | date = March 2000 | pmid = 10681368 }} which it closely resembles both structurally and pharmacologically.