Setiptiline

Antidepressant drug

  • none
Legal statusLegal 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
  • 57262-94-9 ☒N
PubChem CID
  • 5205
DrugBank
  • DB09304 ☒N
ChemSpider
  • 5016 checkY
UNII
  • 7L38105Z6E
KEGG
  • D08511 checkY
ChEBI
  • CHEBI:135076
CompTox Dashboard (EPA)
  • DTXSID50205886 Edit this at Wikidata
ECHA InfoCard100.055.123 Edit this at WikidataChemical and physical dataFormulaC19H19NMolar mass261.368 g·mol−13D model (JSmol)
  • Interactive image
  • 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) 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 Ki (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-HT1A ND ND ND
5-HT2A ND ND ND
5-HT2C 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 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. ^ 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.
  5. ^ 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.
  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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SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
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NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants
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  • See also: Receptor/signaling modulators
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DATTooltip Dopamine transporter
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NETTooltip Norepinephrine transporter
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SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
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