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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;
CompTox Dashboard (EPA)	DTXSID50205886 ;
ECHA InfoCard	100.055.123
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 ;
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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

Setiptiline^[3]
Site	K_i (nM)	Species	Ref
SERTTooltip Serotonin transporter	>10,000 (IC₅₀)	Rat	^[4]
NETTooltip Norepinephrine transporter	220 (IC₅₀)	Rat	^[4]
DATTooltip Dopamine transporter	>10,000 (IC₅₀)	Rat	^[4]
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	^[5]
H₁	ND	ND	ND
mAChTooltip Muscarinic acetylcholine receptor	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,^[4] α₂-adrenergic receptor antagonist,^[5] and serotonin receptor antagonist,^[6] likely at the 5-HT₂ subtypes,^{[citation needed]} as well as an H₁ receptor inverse agonist/antihistamine.^[4]^{[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

^ Holenz J, Díaz JL, Buschmann H (2007). "Chemistry: Tricyclic and tetracyclic antidepressants". In Buschmann H, Torrens A, Vela JM (eds.). Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Vol. 1. Wiley VCH. p. 248. doi:10.1002/9783527619337.ch5. ISBN 978-3-527-31058-6.^{[permanent dead link‍]}
^ Swiss Pharmaceutical Society, ed. (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 942. ISBN 3-88763-075-0.
^ Roth BL, Driscol J. "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. Retrieved 14 August 2017.
^ ^a ^b ^c ^d ^e Niho T, Ito C, Shibutani Y, Hashizume H, Yamaguchi K (October 1986). "[Pharmacological properties of MO-8282, a novel antidepressant]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica (in Japanese). 88 (4): 309–320. doi:10.1254/fpj.88.309. PMID 3792961.
^ ^a ^b Mizota M, Oikawa Y, Nakayama K, Mizuguchi K, Takarada T, Kojima M, et al. (December 1986). "[Pharmacological studies of MO-8282, a new antidepressant]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica (in Japanese). 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.