Chemistry:Fluperlapine

Fluperlapine
Clinical data
ATC code	none;
Identifiers
	IUPAC name 3-fluoro-6-(4-methylpiperazin-1-yl)-11H-dibenzo[b,e]azepine;
CAS Number	67121-76-0 ;
PubChem CID	49381;
ChemSpider	44882 ;
UNII	EWG253M961;
ChEMBL	ChEMBL63756 ;
Chemical and physical data
Formula	C19H20FN3
Molar mass	309.388 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:OBWGMKKHCLHVIE-UHFFFAOYSA-N ;
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Short description: Chemical compound

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	K_i (nM)
5-HT_2A	7.9
5-HT_2C	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

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Patents:^[10]^[11]

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

References

↑ ^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.
↑ "Fluperlapine in 104 schizophrenic patients. Open multicenter trial". Arzneimittel-Forschung 34 (1A): 125–30. 1984. PMID 6145428.
↑ "Antipsychotic efficacy of fluperlapine. An open multicenter trial". Neuropsychobiology 11 (2): 116–20. 1984. doi:10.1159/000118064. PMID 6148712.
↑ "The effect of fluperlapine in acute psychotic patients". Pharmacopsychiatry 17 (2): 57–60. March 1984. doi:10.1055/s-2007-1017408. PMID 6728910.
↑ "Results of a multicenter AMDP study with fluperlapine in schizophrenic patients". Arzneimittel-Forschung 34 (1A): 122–4. 1984. PMID 6145427.
↑ "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.
↑ "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.
↑ "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.
↑ "PDSP K_i 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.
↑ Fritz Hunziker, Rudolf Fischer, U.S. Patent 4,308,207 (1981 to Sandoz Ltd.).
↑ Fritz Hunziker & Rudolf Fischer, U.S. Patent 4,406,900 (1983 to Fidelity Union Bank).

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Original source: https://en.wikipedia.org/wiki/Fluperlapine. Read more

[Ganellin-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.

[pmid6145428-2] "Fluperlapine in 104 schizophrenic patients. Open multicenter trial". Arzneimittel-Forschung 34 (1A): 125–30. 1984. PMID 6145428.

[pmid6148712-3] "Antipsychotic efficacy of fluperlapine. An open multicenter trial". Neuropsychobiology 11 (2): 116–20. 1984. doi:10.1159/000118064. PMID 6148712.

[pmid6728910-4] "The effect of fluperlapine in acute psychotic patients". Pharmacopsychiatry 17 (2): 57–60. March 1984. doi:10.1055/s-2007-1017408. PMID 6728910.

[pmid6145427-5] "Results of a multicenter AMDP study with fluperlapine in schizophrenic patients". Arzneimittel-Forschung 34 (1A): 122–4. 1984. PMID 6145427.

[pmid2864254-6] "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.

[pmid2860654-7] "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.

[pmid10681368-8] "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 K_i 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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v t e Antipsychotics (N05A)
Typical	Butyrophenones: Benperidol Bromperidol Droperidol Haloperidol^# Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines: Fluspirilene Penfluridol Pimozide Phenothiazines: Acetophenazine Butaperazine Carphenazine (carfenazine)^‡ Chlorpromazine Cyamemazine Dixyrazine Fluphenazine Levomepromazine (methotrimeprazine) Mesoridazine Perazine Periciazine Perphenazine Piperacetazine Pipotiazine Prochlorperazine Promazine Sulforidazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes: Chlorprothixene Clopenthixol Flupentixol Tiotixene (thiothixene) Zuclopenthixol
Disputed	Benzamides: Amisulpride Levosulpiride Nemonapride Remoxipride^‡ Sulpiride Sultopride Tiapride Veralipride^‡ Butyrophenones: Melperone Tricyclics: Carpipramine Clocapramine Clorotepine Clotiapine Loxapine Mosapramine Others: Molindone
Atypical	Benzisoxazole/benzisothiazoles: Iloperidone Lurasidone Paliperidone Paliperidone palmitate Perospirone Risperidone^# Ziprasidone Butyrophenones: Lumateperone^† Phenylpiperazines/quinolinones: Aripiprazole Aripiprazole lauroxil Brilaroxazine^† Brexpiprazole Cariprazine Tricyclics: Asenapine Clozapine^# Olanzapine Quetiapine Zotepine Others: Blonanserin Pimavanserin Sertindole
Others	Azacyclonol Cannabidiol Oxypertine Reserpine Tetrabenazine
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

v t e Tricyclics
Classes	Acridine Anthracene Dibenzazepine Dibenzocycloheptene Dibenzodiazepine Dibenzothiazepine Dibenzothiepin Dibenzoxazepine Dibenzoxepin Phenothiazine Pyridazinobenzoxazine Pyridinobenzodiazepine Thioxanthene
Antidepressants (TCAs and TeCAs)	7-OH-Amoxapine Amezepine Amineptine Amitriptyline Amitriptylinoxide Amoxapine Aptazapine Azepindole Azipramine Batelapine Butriptyline Cianopramine Ciclazindol Ciclopramine Cidoxepin Clomipramine Cotriptyline Cyanodothiepin Demexiptiline Depramine (balipramine) Desipramine (desmethylimipramine) Desmethylclomipramine Desmethyltrimipramine Dibenzepin Dimetacrine Dosulepin (dothiepin) Doxepin Enprazepine Esmirtazapine Fantridone Fluotracen Hepzidine Homopipramol Imipramine Imipraminoxide Intriptyline Iprindole Ketipramine Litracen Lofepramine Losindole Loxapine Maprotiline Mariptiline Mazindol Melitracen Metapramine Mezepine Mianserin Mirtazapine Monometacrine Naranol Nitroxazepine Norbutriptyline Nordoxepin Northiaden (nordosulepin) Nortriptyline (noramitriptyline) Noxiptiline Octriptyline Opipramol Oxaprotiline Pipofezine Pirandamine Propizepine Protriptyline Quinupramine Setiptiline (teciptiline) Spiroxepin Tandamine Tampramine Tianeptine Tienopramine Trimipramine
Antihistamines	Azatadine Bisulepin Clobenzepam Cyproheptadine Dacemazine Deptropine Desloratadine Epinastine Etymemazine Fenethazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Ketotifen Latrepirdine Loratadine Mebhydrolin Mequitazine Methdilazine Olopatadine Oxomemazine Phenindamine Pimethixene Promethazine Propiomazine Rupatadine Thiazinamium
Antipsychotics	Acetophenazine Alimemazine Amoxapine Asenapine Butaclamol Butaperazine Carfenazine (carphenazine) Carpipramine Chlorpromazine Chlorprothixene Ciclindole Citatepine Clocapramine Clomacran Clorotepine Clotiapine Clozapine Cyanothepin Doclothepin Docloxythepin Erizepine Flucindole Flumezapine Fluotracen Flupentixol Fluphenazine Gevotroline Homopipramol Isofloxythepin Levomepromazine/Methotrimeprazine Loxapine Lurasidone Maroxepin Meperathiepin Mesoridazine Metiapine Metitepine Metoxepin Mosapramine Naranol Octomethothepin Olanzapine Oxyclothepin Oxyprothepin Pentiapine Peradithiepin Perathiepin Perazine Perphenazine Periciazine Pinoxepin Piperacetazine Pipotiazine Piquindone Prochlorperazine Promazine Prothipendyl Quetiapine Savoxepin/Cipazoxapine Sulforidazine Tenilapine Thiethylperazine Thiopropazate Thioridazine Thiothixene Tilozepine Traboxopine Trifluoperazine Triflupromazine Trifluthepin Zotepine Zuclopenthixol
Anticonvulsants	Carbamazepine Dizocilpine Eslicarbazepine Eslicarbazepine acetate Etazepine Licarbazepine Oxcarbazepine Oxitriptyline Rispenzepine
Others	Adosopine Aminopromazine Atiprosin Beloxepin Benzoctamine Carvedilol Cidoxepin Cyclobenzaprine Damotepine Darenzepine Elanzepine Fluradoline Methylene blue Monatepil Nuvenzepine Oxetorone Perlapine P7C3 Pinadoline Pirenzepine Pirolate Pitrazepin Pizotifen Profenamine Serazapine Siltenzepine Telenzepine Tipindole Tropatepine Zolenzepine

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Clinical data

ATC code	none
Identifiers
IUPAC name 3-fluoro-6-(4-methylpiperazin-1-yl)-11H-dibenzo[b,e]azepine
CAS Number	67121-76-0^N
PubChem CID	49381
ChemSpider	44882^Y
UNII	EWG253M961
ChEMBL	ChEMBL63756^Y
Chemical and physical data
Formula	C₁₉H₂₀FN₃
Molar mass	309.388 g·mol⁻¹
3D model (JSmol)	Interactive image
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
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