ETICLOPRIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H25ClN2O3
Molecular Weight	340.845
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN1CCC[C@H]1CNC(=O)C2=C(OC)C(Cl)=CC(CC)=C2O

InChI

InChIKey=AADCDMQTJNYOSS-LBPRGKRZSA-N

InChI=1S/C17H25ClN2O3/c1-4-11-9-13(18)16(23-3)14(15(11)21)17(22)19-10-12-7-6-8-20(12)5-2/h9,12,21H,4-8,10H2,1-3H3,(H,19,22)/t12-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8301592 | https://www.ncbi.nlm.nih.gov/pubmed/18801115 | https://www.ncbi.nlm.nih.gov/pubmed/9108576

Eticlopride {2S(−)-3-chloro-5-ethyl-N-[(1-ethyl-2-pyrrolidinyl)methyl]-6-hydroxy-2-methoxybenzamide} is an antagonist at dopamine D2 and D3 receptors. It is widely used for in vivo, in vitro, and ex vivo examination of D2/D3 receptors densities and function. Eticlopride exerts antipsychotic activity in animals.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
dopamine receptor D2 4 Target ID: 694181.0 Gene Symbol: DRD2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16631246 \| https://www.ncbi.nlm.nih.gov/pubmed/10591881	Antagonist 2778	0.5 nM [Ki]
dopamine receptor D3 2 Target ID: 1.00425048E8 Gene Symbol: DRD3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16631246 \| https://www.ncbi.nlm.nih.gov/pubmed/10591881	Antagonist 2778	0.16 nM [Ki]
D(2) dopamine receptor 58 Target ID: P14416 Gene ID: 1813.0 Gene Symbol: DRD2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21097933 \| https://www.ncbi.nlm.nih.gov/pubmed/8301592	Antagonist 2778	0.08 nM [Ki]
D(3) dopamine receptor 16 Target ID: P35462 Gene ID: 1814.0 Gene Symbol: DRD3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21097933 \| https://www.ncbi.nlm.nih.gov/pubmed/8301592	Antagonist 2778	0.134 nM [Ki]
Dopamine D4 receptor 71 Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7475902 \| http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=biology&ligandId=966	Antagonist 2778	7.0 null [pKi]

PubMed

Title	Date	PubMed
Role of the central nervous system in hemodynamic and sympathoadrenal responses to cocaine in rats.	1990 Oct	2213551
Pharmacological and functional characterization of D2, D3 and D4 dopamine receptors in fibroblast and dopaminergic cell lines.	1994 Jan	8301592
Characterization of the human dopamine D3 receptor expressed in transfected cell lines.	1994 Jan 1	7907989
Is clozapine selective for the dopamine D4 receptor?	1995	7475902
Cerebrocortical Fos expression following dopaminergic stimulation: D1/D2 synergism and its breakdown.	1996 Jul 22	8864302
Bromocriptine transcriptionally activates the multidrug resistance gene (pgp2/mdr1b) by a novel pathway.	1997 Apr 25	9111066
Involvement of dopamine D2 receptors in the effect of cocaine on sexual behaviour and stretching-yawning of male rats.	1997 Jun	9225304
Effects of single and multiple treatments with L-dihydroxyphenylalanine (L-DOPA) on dopamine receptor-G protein interactions and supersensitive immediate early gene responses in striata of rats after reserpine treatment or with unilateral nigrostriatal lesions.	1999 Jan 1	9890435
Effects of dopamine antagonists on alfentanil-induced locomotor activity in horses.	2003 Jul	14498848
Glutamic acid decarboxylase 67 mRNA regulation in two globus pallidus neuron populations by dopamine and the subthalamic nucleus.	2004 Mar 24	15044549
Dopamine D1 and D2 receptor contributions to L-DOPA-induced dyskinesia in the dopamine-depleted rat.	2005 Aug	16023708
Effects of intra-nucleus accumbens shell administration of dopamine agonists and antagonists on cocaine-taking and cocaine-seeking behaviors in the rat.	2005 Nov	16163523
Acute amphetamine down-regulates RGS4 mRNA and protein expression in rat forebrain: distinct roles of D1 and D2 dopamine receptors.	2006 Mar	16539683
Dopamine-2 receptors in the arcuate nucleus modulate cocaine-seeking behavior.	2006 Oct 23	17001283
The role of peripheral and central sodium channels in mediating brain temperature fluctuations induced by intravenous cocaine.	2006 Oct 30	16956595
Amphetamine up-regulates activator of G-protein signaling 1 mRNA and protein levels in rat frontal cortex: the role of dopamine and glucocorticoid receptors.	2010 Jun 16	20298760
Attenuation of cocaine's reinforcing and discriminative stimulus effects via muscarinic M1 acetylcholine receptor stimulation.	2010 Mar	19996296
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015 Jan 5	25455453
Dopamine induces growth inhibition and vascular normalization through reprogramming M2-polarized macrophages in rat C6 glioma.	2015 Jul 15	25818600

Name

Type

Language

ETICLOPRIDE

Official Name

English

eticlopride [INN]

Common Name

English

(-)-(S)-5-CHLORO-3-ETHYL-N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-6-METHOXYSALICYLAMIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66883