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

Molecular Formula	C17H25ClN2O3
Molecular Weight	340.845
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
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
Role of dopamine D2-like receptors in cocaine self-administration: studies with D2 receptor mutant mice and novel D2 receptor antagonists.	2002 Apr 1	11923462
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
Dopamine-2 receptors in the arcuate nucleus modulate cocaine-seeking behavior.	2006 Oct 23	17001283

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:28:45 GMT 2023` Edited by `admin` on `Fri Dec 15 16:28:45 GMT 2023`
Record UNII	J8M468HBH4
Record Status	`Validated (UNII)`
Record Version

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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