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

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
Anorectic activities of serotonin uptake inhibitors: correlation with their potencies at inhibiting serotonin uptake in vivo and 3H-mazindol binding in vitro.	1988	3261828
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 Nov 1	2532013
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
The psychomotor and cognitive effects of litoxetine in young and middle aged volunteers.	1995 Aug	8562293
The interaction of antidepressant drugs with central and peripheral (enteric) 5-HT3 and 5-HT4 receptors.	1995 Mar	7780635
Pharmacological characterization of the cloned human 5-hydroxytryptamine transporter.	1996 May 3	8645336
Influence of fluoxetine and litoxetine on 5-HT4 receptor-mediated relaxation in the rat isolated oesophagus.	1999	10392309
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 Apr	11888558
Design and optimization of selective serotonin re-uptake inhibitors with high synthetic accessibility. Part 1.	2009 Apr 15	19282174
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:51:41 GMT 2023` Edited by `admin` on `Fri Dec 15 15:51:41 GMT 2023`
Record UNII	9980ST005G
Record Status	`Validated (UNII)`
Record Version

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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