SETIPTILINE MALEATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H19N.C4H4O4
Molecular Weight	377.433
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C/C(O)=O.CN1CCC2=C(C1)C3=C(CC4=C2C=CC=C4)C=CC=C3

InChI

InChIKey=AVPIBVPBCWBXIU-BTJKTKAUSA-N

InChI=1S/C19H19N.C4H4O4/c1-20-11-10-18-16-8-4-2-6-14(16)12-15-7-3-5-9-17(15)19(18)13-20;5-3(6)1-2-4(7)8/h2-9H,10-13H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

Molecular Formula	C19H19N
Molecular Weight	261.3609
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

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 828
Adrenergic receptor alpha-2 113 Target ID: CHEMBL2095158 Sources: http://www.ncbi.nlm.nih.gov/pubmed/2881854	Antagonist 2778
Adrenergic receptor alpha-1 169 Target ID: CHEMBL2094251 Sources: http://www.genome.jp/dbget-bin/www_bget?D02034	Antagonist 2778
Serotonin 2 (5-HT2) receptor 87 Target ID: CHEMBL2095200 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3774630	Antagonist 2778
Adrenergic receptor alpha-2 113 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 2778
Adrenergic receptor alpha-1 169 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 2778
Serotonin 2a (5-HT2a) receptor 231 Target ID: CHEMBL224 Sources: http://link.springer.com/referenceworkentry/10.1007%2F978-3-540-68706-1_1842	Antagonist 2778
Serotonin 2c (5-HT2c) receptor 124 Target ID: CHEMBL225 Sources: http://link.springer.com/referenceworkentry/10.1007%2F978-3-540-68706-1_1842	Antagonist 2778
Serotonin 3 (5-HT3) receptor 59 Target ID: CHEMBL2094132 Sources: http://link.springer.com/referenceworkentry/10.1007%2F978-3-540-68706-1_1842	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7516085	Primary	Approved 8429	Tecipul Approved Use Antidepressant Launch Date 8.525088E11
Depression 235 Sources: http://www.drugbank.ca/drugs/DB09304	Primary	Approved 8429	Tecipul Approved Use For the treatment of depression. Launch Date 8.525088E11
Depression 235 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=36605	Primary	Approved 8429	Setiptiline maleate Approved Use Setiptiline maleate is used to treat depression or depressive state Launch Date 5.9952962E11

PubMed

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

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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:37:34 UTC 2023` Edited by `admin` on `Sat Dec 16 01:37:34 UTC 2023`
Record UNII	9VOZ30EO2Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SETIPTILINE MALEATE

Common Name

English

BISOPOOL

Brand Name

English

SETIPTILINE MALEATE [MI]

Common Name

English

TECIPUL

Brand Name

English

MO-8282

Code

English

2,3,4,9-TETRAHYDRO-2-METHYL-1H-DIBENZO(3,4:6,7)CYCLOHEPTA(1,2-C)PYRIDYL MALEATE

Systematic Name

English

Setiptiline maleate [WHO-DD]

Common Name

English

SETIPTILINE MALEATE [JAN]

Common Name

English

Code System Code Type Description

EVMPD

SUB21582