Setiptiline

Setiptiline
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	none
Legal status
Legal status	℞ (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
ECHA InfoCard	100.055.123
Chemical and physical data
Formula	C19H19N
Molar mass	261.36 g/mol
3D model (Jmol)	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 ;
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Setiptiline (Tecipul), also known as teciptiline, is a tetracyclic antidepressant (TeCA) which 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]

Chemistry[edit]

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-aza-mianserin.

Pharmacology[edit]

Setiptiline acts as a norepinephrine reuptake inhibitor,^[3] α₂-adrenergic receptor antagonist,^[4] and serotonin receptor antagonist,^[5] likely at the 5-HT_2A, 5-HT_2C, and/or 5-HT₃ subtypes, as well as an H₁ receptor inverse agonist/antihistamine.^[3]

References[edit]

^ Buschmann, H.; Torrens, A.; Vela, J. M. (2007). Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. 1. Wiley VCH. p. 248. ISBN 978-3-527-31058-6.
^ Swiss Pharmaceutical Society, ed. (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 942. ISBN 3-88763-075-0.
^ ^a ^b Niho, T.; Ito, C.; Shibutani, Y.; Hashizume, H.; Yamaguchi, K. (1986). "Pharmacological Properties of MO-8282, a Novel Antidepressant". Nihon yakurigaku zasshi. Folia Pharmacologica Japonica. 88 (4): 309–320. doi:10.1254/fpj.88.309. PMID 3792961.
^ Mizota, M.; Oikawa, Y.; Nakayama, K.; Mizuguchi, K.; Takarada, T.; Kojima, M.; Kanehiro, H.; Funato, H.; Kayamoto, M.; Sato, M.; Niho, T. (1986). "Pharmacological Studies of MO-8282, a New Antidepressant". Nihon yakurigaku zasshi. Folia Pharmacologica Japonica. 88 (6): 457–466. doi:10.1254/fpj.88.457. PMID 2881854.
^ Przegaliński, E.; Baran, L.; Siwanowicz, J.; Rawłów, A. (1986). "The Lack of Antidepressant Properties and a Potent Central Antiserotonin Activity of Org 8282". Polish Journal of Pharmacology and Pharmacy. 38 (4): 377–384. PMID 3774630.

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[1] Buschmann, H.; Torrens, A.; Vela, J. M. (2007). Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. 1. Wiley VCH. p. 248. ISBN 978-3-527-31058-6.

[IndexNominum-2] Swiss Pharmaceutical Society, ed. (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 942. ISBN 3-88763-075-0.

[pmid3792961-3] Niho, T.; Ito, C.; Shibutani, Y.; Hashizume, H.; Yamaguchi, K. (1986). "Pharmacological Properties of MO-8282, a Novel Antidepressant". Nihon yakurigaku zasshi. Folia Pharmacologica Japonica. 88 (4): 309–320. doi:10.1254/fpj.88.309. PMID 3792961.

[4] Mizota, M.; Oikawa, Y.; Nakayama, K.; Mizuguchi, K.; Takarada, T.; Kojima, M.; Kanehiro, H.; Funato, H.; Kayamoto, M.; Sato, M.; Niho, T. (1986). "Pharmacological Studies of MO-8282, a New Antidepressant". Nihon yakurigaku zasshi. Folia Pharmacologica Japonica. 88 (6): 457–466. doi:10.1254/fpj.88.457. PMID 2881854.

[5] Przegaliński, E.; Baran, L.; Siwanowicz, J.; Rawłów, A. (1986). "The Lack of Antidepressant Properties and a Potent Central Antiserotonin Activity of Org 8282". Polish Journal of Pharmacology and Pharmacy. 38 (4): 377–384. PMID 3774630.

[1]

[2]

[3]

[4]

[5]

v t e Anxiolytics (N05B)

5-HT_1A agonists	Buspirone 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 Carbamates Chlormezanone^‡ Ethanol Etifoxine; Herbs: Kava Skullcap Valerian

α₂δ VDCC blockers	Gabapentin Gabapentin enacarbil Phenibut Pregabalin

Antidepressants	SSRIs SNRIs SARIs TCAs TeCAs MAOIs; Others: Agomelatine Bupropion Vilazodone Vortioxetine

Sympatholytics	Beta blockers (e.g., propranolol) Clonidine Dexmedetomidine Guanfacine Prazosin

Others	Benzoctamine Cannabidiol Cycloserine Fabomotizole Hydroxyzine Kanna Lavender Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum

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 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 Nortriptyline Noxiptiline Octriptyline Opipramol Oxaprotiline Pipofezine Pirandamine Propizepine Protriptyline Quinupramine Setiptiline/Teciptiline Spiroxepin Tandamine Tampramine Tianeptine Tienopramine Trimipramine

Antihistamines	Azatadine 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 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 Carvedilol Cidoxepin Cyclobenzaprine Damotepine Darenzepine Elanzepine Methylene blue Monatepil Nuvenzepine Oxetorone Perlapine P7C3 Pinadoline Pirenzepine Pirolate Pitrazepin Pizotifen Profenamine Serazapine Siltenzepine Telenzepine Tipindole Tropatepine Zolenzepine

Setiptiline

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Chemistry[edit]

Pharmacology[edit]

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Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	none
Legal status
Legal status	℞ (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^N
PubChem (CID)	5205
DrugBank	DB09304^N
ChemSpider	5016^Y
UNII	7L38105Z6E^Y
KEGG	D08511^Y
ECHA InfoCard	100.055.123
Chemical and physical data
Formula	C₁₉H₁₉N
Molar mass	261.36 g/mol
3D model (Jmol)	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^Y Key:GVPIXRLYKVFFMK-UHFFFAOYSA-N^Y
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