SETIPTILINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H19N
Molecular Weight	261.3609
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCC2=C(C1)C3=C(CC4=CC=CC=C24)C=CC=C3

InChI

InChIKey=GVPIXRLYKVFFMK-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.drugbank.ca/drugs/DB09304http://link.springer.com/referenceworkentry/10.1007%2F978-3-540-68706-1_1842 | http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=36605
Curator's Comment: Description was created based on several sources, including https://www.drugbank.ca/drugs/DB09304

Setiptiline Maleate is a tetracyclic antidepressant that has been used in the treatment of depression. It has antihistamine and hypnotic–sedative effects, but almost no anticholinergic effects. It is a weak inhibitor of norepinephrine reuptake in vitro and strongly stimulates the release of central norepinephrine by blocking presynaptic α2-adrenoceptors similar to mianserin. It also acts as a 5-HT2A, 5-HT2C, and 5-HT3 receptor antagonist. Unlike most conventional antidepressants, it has no efficacy as a serotonin reuptake inhibitor. It can induce drowsiness and thirst, but it displays low toxicity. Setiptiline Maleate was launched in 1989 for the treatment of depression in Japan.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
serotonin receptor signaling pathway 6 Target ID: GO:0007210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3774630	Modulator 846
Adrenergic receptor alpha-2 114 Target ID: CHEMBL2095158 Sources: http://www.ncbi.nlm.nih.gov/pubmed/2881854	Antagonist 2849
Adrenergic receptor alpha-1 171 Target ID: CHEMBL2094251 Sources: http://www.genome.jp/dbget-bin/www_bget?D02034	Antagonist 2849
Serotonin 2 (5-HT2) receptor 90 Target ID: CHEMBL2095200 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3774630	Antagonist 2849
Adrenergic receptor alpha-2 114 Target ID: CHEMBL2095158 Sources: http://link.springer.com/referenceworkentry/10.1007%2F978-3-540-68706-1_1842 \| http://www.genome.jp/dbget-bin/www_bget?D02034	Antagonist 2849
Adrenergic receptor alpha-1 171 Target ID: CHEMBL2094251 Sources: http://link.springer.com/referenceworkentry/10.1007%2F978-3-540-68706-1_1842 \| http://www.genome.jp/dbget-bin/www_bget?D02034	Antagonist 2849
Serotonin 2a (5-HT2a) receptor 237 Target ID: CHEMBL224 Sources: http://link.springer.com/referenceworkentry/10.1007%2F978-3-540-68706-1_1842	Antagonist 2849
Serotonin 2c (5-HT2c) receptor 131 Target ID: CHEMBL225 Sources: http://link.springer.com/referenceworkentry/10.1007%2F978-3-540-68706-1_1842	Antagonist 2849
Serotonin 3 (5-HT3) receptor 59 Target ID: CHEMBL2094132 Sources: http://link.springer.com/referenceworkentry/10.1007%2F978-3-540-68706-1_1842	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Schizophrenia 305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7516085	Primary	Approved 8583	Tecipul Approved Use Antidepressant Launch Date 1997
Depression 240 Sources: http://www.drugbank.ca/drugs/DB09304	Primary	Approved 8583	Tecipul Approved Use For the treatment of depression. Launch Date 1997
Depression 240 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=36605	Primary	Approved 8583	Setiptiline maleate Approved Use Setiptiline maleate is used to treat depression or depressive state Launch Date 1988

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.97 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7824756/	0.08 mg/kg 1 times / day steady-state, oral dose: 0.08 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered:		SETIPTILINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
6 mg 1 times / day multiple, oral Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7824756/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7824756/	Other AEs: Salivation, Drowsiness... Other AEs: Salivation (5.3%) Drowsiness (5.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/7824756/
6 mg 3 times / day multiple, oral Recommended Dose: 6 mg, 3 times / day Route: oral Route: multiple Dose: 6 mg, 3 times / day Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=36605	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=36605	Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=36605

AEs

AE	Significance	Dose	Population
Drowsiness	5.3%	6 mg 1 times / day multiple, oral Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7824756/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7824756/
Salivation	5.3%	6 mg 1 times / day multiple, oral Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7824756/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7824756/

PubMed

Title	Date	PubMed
Solid-phase extraction and analysis of 20 antidepressant drugs in human plasma by LC/MS with SSI method.	2006-10-16	16859851
Enhancing central noradrenergic function in depression: is there still a place for a new antidepressant?	2005-03	18568121
[Practical analysis of toxic substances useful of clinical toxicology -2- tricyclic and tetracyclic antidepressants].	2002-04	12108019
Carbamazepine treatment of corticosteroid-induced mood disorder.	2001-08	11511412
The effect of age on plasma level of setiptiline maleate in depressed patients.	1994-10	7824756
Effectiveness of concomitant setiptiline maleate (Tecipul) on negative symptoms of schizophrenia.	1994-03	7516085
[Behavioral effects of a new antidepressant, setiptiline].	1991-01	2045013
[Pharmacological properties of MO-8282, a novel antidepressant].	1986-10	3792961
The lack of antidepressant properties and a potent central antiserotonin activity of Org 8282.	1986-07-01	3774630

Patents

Sample Use Guides

In Vivo Use Guide

3-8 mg/day oral

Route of Administration: Oral

In Vitro Use Guide

100uM setiptiline inhibited about 60% of NMDA current in Xenopus oocytes injected with rat brain mRNA.

Name

Type

Language

ORG 8282

Preferred Name

English

SETIPTILINE

Official Name

English

setiptiline [INN]

Common Name

English

Setiptiline [WHO-DD]

Common Name

English

SETIPTILINE [MI]

Common Name

English

SETIPTILINE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C265