Setiptiline

Last updated

Setiptiline
Setiptiline 2D structure.svg
Clinical data
Trade names Tecipul
Other namesTeciptiline; 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
  • 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 InfoCard 100.055.123 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H19N
Molar mass 261.368 g·mol−1
3D model (JSmol)
  • c42c(\C3=C(/c1ccccc1C2)CN(C)CC3)cccc4
  • 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 Yes check.svgY
  • Key:GVPIXRLYKVFFMK-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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]

Contents

Pharmacology

Pharmacodynamics

Setiptiline [3]
SiteKi (nM)SpeciesRef
SERT Tooltip Serotonin transporter>10,000 (IC50)Rat [4]
NET Tooltip Norepinephrine transporter220 (IC50)Rat [4]
DAT Tooltip Dopamine transporter>10,000 (IC50)Rat [4]
5-HT1A NDNDND
5-HT2A NDNDND
5-HT2C NDNDND
α1 NDNDND
α2 24.3 (IC50)Rat [5]
H1 NDNDND
mACh Tooltip Muscarinic acetylcholine receptorNDNDND
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,[ 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.

See also

References

  1. ↑ 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 ]
  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 (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.
  5. 1 2 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.
  6. ↑ 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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