ANPIRTOLINE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H13ClN2S
Molecular Weight	228.742
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClC1=CC=CC(SC2CCNCC2)=N1

InChI

InChIKey=GGALEXMXDMUMDM-UHFFFAOYSA-N

InChI=1S/C10H13ClN2S/c11-9-2-1-3-10(13-9)14-8-4-6-12-7-5-8/h1-3,8,12H,4-7H2

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16631081 | https://adisinsight.springer.com/drugs/800000671 | https://www.ncbi.nlm.nih.gov/pubmed/7881726

Anpirtoline [D 16949] is a dichloropyridine derivative with antinociceptive and antidepressant activity. Anpirtoline has been described as an agonist at 5-HT1B and 5-HT1D receptors with a relatively high potency. It also acts as an agonist at 5-HT1A receptors, but has a lower potency than at the 5-HT1B sites. In addition, Anpirtoline acts as an antagonist at 5-HT3 receptors. The drug was in phase I clinical trials with ASTA Medica in Germany for the treatment of pain and depression, but development was suspended.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 1b (5-HT1b) receptor 46 Target ID: CHEMBL1898 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7881726	Agonist 2678
Serotonin 3 (5-HT3) receptor 59 Target ID: CHEMBL2111332 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7881726	Antagonist 2778		7.53 null [pKi]

PubMed

Title	Date	PubMed
Specific labelling of serotonin 5-HT(1B) receptors in rat frontal cortex with the novel, phenylpiperazine derivative, [3H]GR125,743. A pharmacological characterization.	2002 Apr	11888550
DARPP-32 mediates serotonergic neurotransmission in the forebrain.	2002 Mar 5	11880652
Neuronal expression and regulation of CGRP promoter activity following viral gene transfer into cultured trigeminal ganglia neurons.	2004 Jan 30	14715155

Sample Use Guides

In Vivo Use Guide

The pain relieving properties of imipramine (100 mg orally), tramadol (150 mg orally), and anpirtoline (60 mg orally) were compared in 16 healthy subjects in a cross-over, double-blind, randomized, and placebo-controlled study.

Route of Administration: Oral

In Vitro Use Guide

Binding assays with rat brain membranes have shown that anpirtoline bound with a much higher affinity to 5-HT1B receptor (Ki = 28 nM) than to 5-HT1A (Ki = 150 nM) and 5-HT2 (Ki = 1.49 uM) receptors.

Name

Type

Language

ANPIRTOLINE

Official Name

English

anpirtoline [INN]

Common Name

English

4-((6-CHLORO-2-PYRIDYL)THIO)PIPERIDINE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47794