LERISETRON

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H20N4
Molecular Weight	292.3782
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C(N1C(=NC2=C1C=CC=C2)N3CCNCC3)C4=CC=CC=C4

InChI

InChIKey=PWWDCRQZITYKDV-UHFFFAOYSA-N

InChI=1S/C18H20N4/c1-2-6-15(7-3-1)14-22-17-9-5-4-8-16(17)20-18(22)21-12-10-19-11-13-21/h1-9,19H,10-14H2

HIDE SMILES / InChI

Description
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug/def/lerisetron | https://adisinsight.springer.com/drugs/800002865 | https://www.ncbi.nlm.nih.gov/pubmed/14619411

Lerisetron is a 5-hydroxytryptamine3 receptor antagonist. It was under development by FAES Farma for the potential treatment of emesis resulting from chemotherapy. Lerisetron specifically binds to 5-HT3 receptors, located peripherally on vagus nerve terminals and centrally in the chemoreceptor trigger zone (CTZ) of the area postrema, which may result in suppression of chemotherapy-induced nausea and vomiting. Lerisetron had been in phase III clinical trials for the treatment of emesis. However, this study was discontinued.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 3 (5-HT3) receptor 59 Target ID: CHEMBL2094116 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9046349 \| https://www.ncbi.nlm.nih.gov/pubmed/11782896	Antagonist 2778		9.2 null [pKi]
Serotonin 3a (5-HT3a) receptor 46 Target ID: CHEMBL1899 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11514154	Antagonist 2778		0.36 nM [Ki]

PubMed

Title	Date	PubMed
Effects of lerisetron, a new 5-HT3 receptor antagonist, on ipecacuanha-induced emesis in healthy volunteers.	2002	12404884
Identification of critical residues in loop E in the 5-HT3ASR binding site.	2002 Jun 13	12079500
Lerisetron. FAES.	2003 Jul	14619411
Age-related changes in pharmacokinetics and pharmacodynamics of lerisetron in the rat: a population pharmacokinetic model.	2003 Jul-Aug	12792155
Subunit rotation models activation of serotonin 5-HT3AB receptors by agonists.	2004 Oct	15849995
Pharmacokinetic-pharmacodynamic modeling of the hydroxy lerisetron metabolite L6-OH in rats: an integrated parent-metabolite model.	2005 Nov	16158214

Patents

Sample Use Guides

In Vivo Use Guide

Single dose intravenous - 18 mg oral - 20 mg

Route of Administration: Other

Name

Type

Language

LERISETRON

Official Name

English

Lerisetron [WHO-DD]

Common Name

English

1-BENZYL-2-(1-PIPERAZINYL)BENZIMIDAZOLE

Systematic Name

English

lerisetron [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C267