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(O)C(CC)=CC(Cl)=C2OC

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 2849	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 2849	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 2849	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 2849	0.134 nM [Ki]
Dopamine D4 receptor 76 Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7475902 \| http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=biology&ligandId=966	Antagonist 2849	7.0 null [pKi]

PubMed

Title	Date	PubMed
Dopamine induces growth inhibition and vascular normalization through reprogramming M2-polarized macrophages in rat C6 glioma.	2015-07-15	25818600
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015-01-05	25455453
Amphetamine up-regulates activator of G-protein signaling 1 mRNA and protein levels in rat frontal cortex: the role of dopamine and glucocorticoid receptors.	2010-06-16	20298760
Attenuation of cocaine's reinforcing and discriminative stimulus effects via muscarinic M1 acetylcholine receptor stimulation.	2010-03	19996296
The role of peripheral and central sodium channels in mediating brain temperature fluctuations induced by intravenous cocaine.	2006-10-30	16956595
Dopamine-2 receptors in the arcuate nucleus modulate cocaine-seeking behavior.	2006-10-23	17001283
Acute amphetamine down-regulates RGS4 mRNA and protein expression in rat forebrain: distinct roles of D1 and D2 dopamine receptors.	2006-03	16539683
Effects of intra-nucleus accumbens shell administration of dopamine agonists and antagonists on cocaine-taking and cocaine-seeking behaviors in the rat.	2005-11	16163523
Dopamine D1 and D2 receptor contributions to L-DOPA-induced dyskinesia in the dopamine-depleted rat.	2005-08	16023708
Glutamic acid decarboxylase 67 mRNA regulation in two globus pallidus neuron populations by dopamine and the subthalamic nucleus.	2004-03-24	15044549
Effects of dopamine antagonists on alfentanil-induced locomotor activity in horses.	2003-07	14498848
Opposite regulation by typical and atypical anti-psychotics of ERK1/2, CREB and Elk-1 phosphorylation in mouse dorsal striatum.	2003-07	12871586
Role of dopamine D2-like receptors in cocaine self-administration: studies with D2 receptor mutant mice and novel D2 receptor antagonists.	2002-04-01	11923462
Differential effects of D1- and D2-like compounds on cocaine self-administration in Lewis and Fischer 344 inbred rats.	2001-11	11602661
The effects of benzamide analogues on cocaine self-administration in rhesus monkeys.	1999-11	10591881
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.	1999-01-01	9890435
Involvement of dopamine D2 receptors in the effect of cocaine on sexual behaviour and stretching-yawning of male rats.	1997-06	9225304
Bromocriptine transcriptionally activates the multidrug resistance gene (pgp2/mdr1b) by a novel pathway.	1997-04-25	9111066
Cerebrocortical Fos expression following dopaminergic stimulation: D1/D2 synergism and its breakdown.	1996-07-22	8864302
Is clozapine selective for the dopamine D4 receptor?	1995	7475902
Characterization of the human dopamine D3 receptor expressed in transfected cell lines.	1994-01-01	7907989
Pharmacological and functional characterization of D2, D3 and D4 dopamine receptors in fibroblast and dopaminergic cell lines.	1994-01	8301592
Role of the central nervous system in hemodynamic and sympathoadrenal responses to cocaine in rats.	1990-10	2213551

Name

Type

Language

ETICLOPRIDE

Official Name

English

eticlopride [INN]

Preferred 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