DU-24565

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H14N4O2
Molecular Weight	258.2759
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[O-][N+](=O)C1=CC=C2N=C(C=CC2=C1)N3CCNCC3

InChI

InChIKey=GGDBEAVVGFNWIA-UHFFFAOYSA-N

InChI=1S/C13H14N4O2/c18-17(19)11-2-3-12-10(9-11)1-4-13(15-12)16-7-5-14-6-8-16/h1-4,9,14H,5-8H2

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6973481 | https://www.ncbi.nlm.nih.gov/pubmed/3110297 | https://www.ncbi.nlm.nih.gov/pubmed/7776439

Du-24565 is a potent and selective inhibitor of the synaptosomal uptake of serotonin. At higher concentration, it affects the uptake of norepinephrine and dopamine. It is a potential antidepressant and can be useful as a pharmacological tool to study the role of 5-HT in the central nervous system. DU-24565 had little effect on serotonin or tyrosine accumulation in human melanoma cells but suppressed the uptake of extracellular Dopa. In vitro, DU-24565 inhibited the proliferation of PC-3, DU-145 and LNCaP human prostate carcinoma cells in a dose-dependent manner.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
serotonin uptake 20 Target ID: GO:0051610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6973481	Inhibitor 8297	0.045 µM [IC50]
norepinephrine uptake 18 Target ID: GO:0051620 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6973481	Inhibitor 8297	66.0 µM [IC50]
dopamine uptake 14 Target ID: GO:0090494 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6973481	Inhibitor 8297	41.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Prostate cancer 178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7776439	Primary		Basic research	Unknown Approved Use Unknown
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15723351 https://www.ncbi.nlm.nih.gov/pubmed/6973481	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Synthesis, radiolabeling and preliminary biological evaluation of radiolabeled 5-methyl-6-nitroquipazine, a potential radioligand for the serotonin transporter.	2002 Dec 16	12443787
Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 2: 4-substituted 6-nitroquipazines.	2002 Mar 11	11859009
Presynaptic modulation of 5-HT release in the rat septal region.	2007 May 11	17383104
Synthesis and biological evaluation of one novel technetium-99m-labeled nitroquipazine derivative as an imaging agent for serotonin transporter.	2008 Dec	18684634
Effects of serotonergic agents on survival and hemolymph composition of the larval mosquito Aedes aegypti (Diptera: Culicidae, L.) in vivo: does serotonin regulate hemolymph acid-base homeostasis?	2009 Nov	19880735
Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands.	2009 Oct 23	19725810

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 1 mg/kg

Route of Administration: Oral

In Vitro Use Guide

DU-24565 at concentrations of 10(-8) and 10(-9) M was a potent inhibitor of serotonin uptake by rat blood platelets.

Name

Type

Language

DU-24565

Common Name

English

6-NITRO-2-PIPERAZIN-1-YL-QUINOLINE

Systematic Name

English

Code System Code Type Description

FDA UNII

28M0X094BH