Chemistry:Setiptiline

Setiptiline
Clinical data
Trade names	Tecipul
Other names	Teciptiline; delta(13b,4a),4a-Carba-mianserin; MO-8282; ORG-8282
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name 2-methyl-2,3,4,9-tetrahydro-1H-dibenzo[3,4:6,7]cyclohepta[1,2-c]pyridine;
CAS Number	57262-94-9 ;
PubChem CID	5205;
DrugBank	DB09304 ;
ChemSpider	5016 ;
UNII	7L38105Z6E;
KEGG	D08511 ;
ChEBI	CHEBI:135076;
Chemical and physical data
Formula	C19H19N
Molar mass	261.368 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c42c(\C3=C(/c1ccccc1C2)CN(C)CC3)cccc4;
	InChI InChI=1S/C19H19N/c1-20-11-10-18-16-8-4-2-6-14(16)12-15-7-3-5-9-17(15)19(18)13-20/h2-9H,10-13H2,1H3 ; Key:GVPIXRLYKVFFMK-UHFFFAOYSA-N ;
	(what is this?) (verify)

Short description: Antidepressant drug

Setiptiline (brand name Tecipul), also known as teciptiline, is a tetracyclic antidepressant (TeCA) that acts as a noradrenergic and specific serotonergic antidepressant (NaSSA). It was launched in 1989 for the treatment of depression in Japan by Mochida.^[1]^[2]

Pharmacology

Pharmacodynamics

Site	K_i (nM)	Species	Ref
NET	220 (IC₅₀)	Rat	^[3]
DAT	>10,000 (IC₅₀)	Rat	^[3]
5-HT_1A	ND	ND	ND
5-HT_2A	ND	ND	ND
5-HT_2C	ND	ND	ND
α₁	ND	ND	ND
α₂	24.3 (IC₅₀)	Rat	^[4]
H₁	ND	ND	ND
mACh	ND	ND	ND
Values are K_i (nM), unless otherwise noted. The smaller the value, the more strongly the drug binds to the site.

Setiptiline acts as a norepinephrine reuptake inhibitor,^[3] α₂-adrenergic receptor antagonist,^[4] and serotonin receptor antagonist,^[5] likely at the 5-HT₂ subtypes,^{[citation needed]} as well as an H₁ receptor inverse agonist/antihistamine.^[3]^{[additional citation(s) needed]}

Chemistry

Setiptiline has a tetracyclic structure and is a close analogue of mianserin and mirtazapine, with setiptiline being delta(13b,4a),4a-carba-mianserin, and mirtazapine being 6-azamianserin.

References

↑ "Chemistry: Tricyclic and tetracyclic antidepressants". Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. 1. Wiley VCH. 2007. p. 248. doi:10.1002/9783527619337.ch5. ISBN 978-3-527-31058-6. https://books.google.com/books?id=yXD4QA-Y_Z0C&pg=PA248.
↑ Swiss Pharmaceutical Society, ed (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 942. ISBN 3-88763-075-0. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA942.
↑ ^3.0 ^3.1 ^3.2 ^3.3 Cite error: Invalid <ref> tag; no text was provided for refs named pmid3792961
↑ ^4.0 ^4.1 "[Pharmacological studies of MO-8282, a new antidepressant]" (in ja). Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica 88 (6): 457–466. December 1986. doi:10.1254/fpj.88.457. PMID 2881854.
↑ "The lack of antidepressant properties and a potent central antiserotonin activity of Org 8282". Polish Journal of Pharmacology and Pharmacy 38 (4): 377–384. 1986. PMID 3774630.

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

[1] "Chemistry: Tricyclic and tetracyclic antidepressants". Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. 1. Wiley VCH. 2007. p. 248. doi:10.1002/9783527619337.ch5. ISBN 978-3-527-31058-6. https://books.google.com/books?id=yXD4QA-Y_Z0C&pg=PA248.

[IndexNominum-2] Swiss Pharmaceutical Society, ed (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 942. ISBN 3-88763-075-0. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA942.

[pmid3792961-3] 3.0 ^3.1 ^3.2 ^3.3 Cite error: Invalid <ref> tag; no text was provided for refs named pmid3792961

[pmid2881854-4] 4.0 ^4.1 "[Pharmacological studies of MO-8282, a new antidepressant]" (in ja). Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica 88 (6): 457–466. December 1986. doi:10.1254/fpj.88.457. PMID 2881854.

[pmid3774630-5] "The lack of antidepressant properties and a potent central antiserotonin activity of Org 8282". Polish Journal of Pharmacology and Pharmacy 38 (4): 377–384. 1986. PMID 3774630.

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v t e Anxiolytics (N05B)
5-HT_1AR agonists	Buspirone Gepirone^† Tandospirone
GABA_AR PAMs	Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam^# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam^# Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem^‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Chlormezanone^‡ Ethanol (alcohol) Etifoxine Imepitoin; Herbs: Kava Skullcap Valerian
Gabapentinoids (α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Pregabalin
Antidepressants	SSRIs (e.g., escitalopram) SNRIs (e.g., duloxetine) SARIs (e.g., trazodone) TCAs (e.g., clomipramine^#) TeCAs (e.g., mirtazapine) MAOIs (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)
Others	Benzoctamine Cannabidiol Cycloserine Fabomotizole Hydroxyzine Kanna Lavender Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#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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