Setiptiline

Setiptiline
Clinical data
Trade namesTecipul
Other namesTeciptiline; delta(13b,4a),4a-Carba-mianserin; MO-8282; ORG-8282
AHFS/Drugs.comInternational 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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.055.123 Edit this at Wikidata
Chemical and physical data
FormulaC19H19N
Molar mass261.368 g·mol−1
3D model (JSmol)
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 checkY
  • Key:GVPIXRLYKVFFMK-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Setiptiline (brand name 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]

Pharmacology

Pharmacodynamics

Setiptiline[3]
SiteKi (nM)SpeciesRef
SERT>10,000 (IC50)Rat[4]
NET220 (IC50)Rat[4]
DAT>10,000 (IC50)Rat[4]
5-HT1ANDNDND
5-HT2ANDNDND
5-HT2CNDNDND
α1NDNDND
α224.3 (IC50)Rat[5]
H1NDNDND
mAChNDNDND
Values are Ki (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, as well as an H1 receptor inverse agonist/antihistamine.[4]

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.

See also

References

  1. ↑ Buschmann, H.; Torrens, A.; Vela, J. M. (2007). Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Vol. 1. Wiley VCH. p. 248. ISBN 978-3-527-31058-6.
  2. ↑ Swiss Pharmaceutical Society, ed. (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 942. ISBN 3-88763-075-0.
  3. ↑ Roth, BL; Driscol, J. "PDSP Ki 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.
  4. 1 2 3 4 5 Niho T, Ito C, Shibutani Y, Hashizume H, Yamaguchi K (1986). "[Pharmacological properties of MO-8282, a novel antidepressant]". Nippon Yakurigaku Zasshi (in Japanese). 88 (4): 309–20. doi:10.1254/fpj.88.309. PMID 3792961.
  5. 1 2 Mizota M, Oikawa Y, Nakayama K, Mizuguchi K, Takarada T, Kojima M, Kanehiro H, Funato H, Kayamoto M, Sato M (1986). "[Pharmacological studies of MO-8282, a new antidepressant]". Nippon Yakurigaku Zasshi (in Japanese). 88 (6): 457–66. doi:10.1254/fpj.88.457. PMID 2881854.
  6. ↑ Przegaliński E, Baran L, Siwanowicz J, Rawłów A (1986). "The lack of antidepressant properties and a potent central antiserotonin activity of Org 8282". Pol J Pharmacol Pharm. 38 (4): 377–84. PMID 3774630.


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