LITOXETINE

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=CC3=C(C=CC=C3)C=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

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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
Advances in sodium-ion coupled biogenic amine transporters.	1992	1501510
Activity of litoxetine and other serotonin uptake inhibitors in the tail suspension test in mice.	1992 May	1528946
Litoxetine: a selective 5-HT uptake inhibitor with concomitant 5-HT3 receptor antagonist and antiemetic properties.	1993 Mar 2	8385615
EEG profile of litoxetine after single and repeated administration in healthy volunteers.	1994 Feb	8186061
Design and optimisation of selective serotonin re-uptake inhibitors with high synthetic accessibility: part 2.	2009 Oct 15	19740658

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

Name

Type

Language

LITOXETINE

Official Name

English

4-(2-NAPHTHYLMETHOXY)PIPERIDINE

Systematic Name

English

litoxetine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C265