:Setiptiline

{{Short description|Antidepressant drug}}

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{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 464389691

| IUPAC_name = 2-methyl-2,3,4,9-tetrahydro-1H-dibenzo[3,4:6,7]cyclohepta[1,2-c]pyridine

| image = Setiptiline 2D structure.svg

| width = 200px

| tradename = Tecipul

| Drugs.com = {{drugs.com|international|setiptiline}}

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 57262-94-9

| ATC_prefix = none

| ATC_suffix =

| ATC_supplemental =

| PubChem = 5205

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB09304

| ChEBI = 135076

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 5016

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 7L38105Z6E

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D08511

| synonyms = Teciptiline; delta(13b,4a),4a-Carba-mianserin; MO-8282; ORG-8282

| C=19 | H=19 | N=1

| SMILES = c42c(\C3=C(/c1ccccc1C2)CN(C)CC3)cccc4

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = 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.{{cite book | vauthors = Holenz J, Díaz JL, Buschmann H | chapter = Chemistry: Tricyclic and tetracyclic antidepressants | doi = 10.1002/9783527619337.ch5 | veditors = Buschmann H, Torrens A, Vela JM | chapter-url = https://books.google.com/books?id=yXD4QA-Y_Z0C&pg=PA248 | title = Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application | volume = 1 | page = 248 | publisher = Wiley VCH | year = 2007 | isbn = 978-3-527-31058-6 }}{{Dead link|date=March 2024 |bot=InternetArchiveBot |fix-attempted=yes }}{{ cite book | url = https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA942 | title = Index Nominum 2000: International Drug Directory | page = 942 | editor = Swiss Pharmaceutical Society | publisher = Medpharm Scientific Publishers | year = 2000 | isbn = 3-88763-075-0 }}

Pharmacology

=Pharmacodynamics=

{{See also|Pharmacology of antidepressants|Tetracyclic antidepressant#Binding profiles}}

class="wikitable floatleft" style="font-size:small;"

|+ Setiptiline{{cite web | title = PDSP Ki Database | work = Psychoactive Drug Screening Program (PDSP)|author1-link=Bryan Roth | vauthors = Roth BL, Driscol J | publisher = University of North Carolina at Chapel Hill and the United States National Institute of Mental Health | access-date = 14 August 2017 | url = https://kidbdev.med.unc.edu/databases/pdsp.php?knowID=0&kiKey=&receptorDD=&receptor=&speciesDD=&species=&sourcesDD=&source=&hotLigandDD=&hotLigand=&testLigandDD=&testFreeRadio=testFreeRadio&testLigand=setiptiline&referenceDD=&reference=&KiGreater=&KiLess=&kiAllRadio=all&doQuery=Submit+Query}}

SiteKi (nM)SpeciesRef
{{abbrlink|SERT|Serotonin transporter}}>10,000 (IC50)Rat{{cite journal | vauthors = Niho T, Ito C, Shibutani Y, Hashizume H, Yamaguchi K | title = [Pharmacological properties of MO-8282, a novel antidepressant] | language = ja | journal = Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica | volume = 88 | issue = 4 | pages = 309–320 | date = October 1986 | pmid = 3792961 | doi = 10.1254/fpj.88.309 | doi-access = free }}
{{abbrlink|NET|Norepinephrine transporter}}220 (IC50)Rat
{{abbrlink|DAT|Dopamine transporter}}>10,000 (IC50)Rat
5-HT1A{{abbr|ND|No data}}{{abbr|ND|No data}}{{abbr|ND|No data}}
5-HT2A{{abbr|ND|No data}}{{abbr|ND|No data}}{{abbr|ND|No data}}
5-HT2C{{abbr|ND|No data}}{{abbr|ND|No data}}{{abbr|ND|No data}}
α1{{abbr|ND|No data}}{{abbr|ND|No data}}{{abbr|ND|No data}}
α224.3 (IC50)Rat{{cite journal | vauthors = Mizota M, Oikawa Y, Nakayama K, Mizuguchi K, Takarada T, Kojima M, Kanehiro H, Funato H, Kayamoto M, Sato M | display-authors = 6 | title = [Pharmacological studies of MO-8282, a new antidepressant] | language = ja | journal = Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica | volume = 88 | issue = 6 | pages = 457–466 | date = December 1986 | pmid = 2881854 | doi = 10.1254/fpj.88.457 | doi-access = free }}
H1{{abbr|ND|No data}}{{abbr|ND|No data}}{{abbr|ND|No data}}
{{abbrlink|mACh|Muscarinic acetylcholine receptor}}{{abbr|ND|No data}}{{abbr|ND|No data}}{{abbr|ND|No data}}
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| colspan="4" style="width: 1px;" | 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, α2-adrenergic receptor antagonist, and serotonin receptor antagonist,{{cite journal | vauthors = Przegaliński E, Baran L, Siwanowicz J, Rawłów A | title = The lack of antidepressant properties and a potent central antiserotonin activity of Org 8282 | journal = Polish Journal of Pharmacology and Pharmacy | volume = 38 | issue = 4 | pages = 377–384 | year = 1986 | pmid = 3774630 }} likely at the 5-HT2 subtypes,{{Citation needed|date=September 2017}} as well as an H1 receptor inverse agonist/antihistamine.{{Additional citation needed|date=September 2017}}

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

{{Reflist}}

{{Antidepressants}}

{{Anxiolytics}}

{{Navboxes

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{{Adrenergic receptor modulators}}

{{Histamine receptor modulators}}

{{Monoamine reuptake inhibitors}}

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{{Tricyclics}}

Category:Alpha-2 blockers

Category:H1 receptor antagonists

Category:Noradrenergic and specific serotonergic antidepressants

Category:Piperidines

Category:Serotonin receptor antagonists

Category:Tetracyclic antidepressants

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