LITOXETINE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H19NO
Molecular Weight	241.3282
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C(OC1CCNCC1)C2=CC=C3C=CC=CC3=C2

InChI

InChIKey=MJJDYOLPMGIWND-UHFFFAOYSA-N

InChI=1S/C16H19NO/c1-2-4-15-11-13(5-6-14(15)3-1)12-18-16-7-9-17-10-8-16/h1-6,11,16-17H,7-10,12H2

HIDE SMILES / InChI

Molecular Formula	C16H19NO
Molecular Weight	241.3282
Charge	0
Count

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

Description
Sources: https://adisinsight.springer.com/drugs/800001264 | http://ixaltis.com/litoxetine-ixa-001/ | https://www.ncbi.nlm.nih.gov/pubmed/10392309

Litoxetine is a selective serotonin (5-HT) reuptake inhibitor (SSRI) and mixed serotonin agonist-antagonist, which makes it particularly appropriate for treating continence dysfunctions. Litoxetine at concentrations without antimuscarinic properties (10 nM-1 microM) caused concentration-dependent relaxations in the rat isolated oesophageal muscularis mucosae, which reduced carbachol tone up to 37%. Higher litoxetine concentrations (3 microM-300 microM) were associated with marked relaxation up to the abolition of carbachol tone. The antimuscarinic activity of litoxetine, previously demonstrated in the isolated guinea-pig intestine, played a role in the rat isolated oesophageal muscularis mucosae at concentrations greater than 1 microM. The 5-HT-releasing action of litoxetine could account for the potentation by litoxetine of 5-HT-induced relaxation in tissues from untreated rats, which was reversed by pCPA treatment. Litoxetine is in phase II clinical trial for the treatment of urinary incontinence.

Originator

Approval Year

PubMed

Title	Date	PubMed
Design and optimisation of selective serotonin re-uptake inhibitors with high synthetic accessibility: part 2.	2009-10-15	19740658
Design and optimization of selective serotonin re-uptake inhibitors with high synthetic accessibility. Part 1.	2009-04-15	19282174
Induction of hyperlocomotion in mice exposed to a novel environment by inhibition of serotonin reuptake. A pharmacological characterization of diverse classes of antidepressant agents.	2002-04	11888558
Influence of fluoxetine and litoxetine on 5-HT4 receptor-mediated relaxation in the rat isolated oesophagus.	1999	10392309
Pharmacological characterization of the cloned human 5-hydroxytryptamine transporter.	1996-05-03	8645336
The psychomotor and cognitive effects of litoxetine in young and middle aged volunteers.	1995-08	8562293
The interaction of antidepressant drugs with central and peripheral (enteric) 5-HT3 and 5-HT4 receptors.	1995-03	7780635
EEG profile of litoxetine after single and repeated administration in healthy volunteers.	1994-02	8186061
Litoxetine: a selective 5-HT uptake inhibitor with concomitant 5-HT3 receptor antagonist and antiemetic properties.	1993-03-02	8385615
Activity of litoxetine and other serotonin uptake inhibitors in the tail suspension test in mice.	1992-05	1528946
Advances in sodium-ion coupled biogenic amine transporters.	1992	1501510
A common binding site for tricyclic and nontricyclic 5-hydroxytryptamine uptake inhibitors at the substrate recognition site of the neuronal sodium-dependent 5-hydroxytryptamine transporter.	1989-11-01	2532013
Anorectic activities of serotonin uptake inhibitors: correlation with their potencies at inhibiting serotonin uptake in vivo and 3H-mazindol binding in vitro.	1988	3261828

Sample Use Guides

In Vivo Use Guide

2.5 mg, 5 mg, 10 mg, 25 mg or placebo twice daily on days 1-4 and once on day 5

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:11:14 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:14 GMT 2025`
Record UNII	9980ST005G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

litoxetine [INN]

Preferred Name

English

LITOXETINE

Official Name

English

4-(2-NAPHTHYLMETHOXY)PIPERIDINE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C265