ECOPIPAM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H20ClNO
Molecular Weight	313.821
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CCC3=CC=CC=C3[C@]1([H])C4=CC(O)=C(Cl)C=C4CCN2C

InChI

InChIKey=DMJWENQHWZZWDF-PKOBYXMFSA-N

InChI=1S/C19H20ClNO/c1-21-9-8-13-10-16(20)18(22)11-15(13)19-14-5-3-2-4-12(14)6-7-17(19)21/h2-5,10-11,17,19,22H,6-9H2,1H3/t17-,19+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H20ClNO
Molecular Weight	313.821
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2905002 | https://www.ncbi.nlm.nih.gov/pubmed/26922636 | https://www.ncbi.nlm.nih.gov/pubmed/26922636 | https://adisinsight.springer.com/drugs/800000645 | https://www.ncbi.nlm.nih.gov/pubmed/7862709 | https://www.ncbi.nlm.nih.gov/pubmed/26946382

Ecopipam (SCH-39166) is a selective D1 dopamine receptor antagonist both in vitro and in vivo. Additionally, it exhibits saturable, high-affinity binding to D5 receptors. Ecopipam was studied clinically for a variety of indications, including schizophrenia, drug abuse, and obesity, but in each case undesirable effects were observed. Currently, ecopipam is in clinical trials for the treatment of Lesch-Nyhan and Gilles de la Tourette's syndromes.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D1 receptor 101 Target ID: CHEMBL2056 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1973733\|https://www.ncbi.nlm.nih.gov/pubmed/1531365\|https://www.ncbi.nlm.nih.gov/pubmed/1535318\|https://www.ncbi.nlm.nih.gov/pubmed/24434529	Antagonist 2778		1.9 nM [Ki]

PubMed

Title	Date	PubMed
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1.	1991 Apr 18	1826762
Pharmacologic evaluation of SCH-39166, A-69024, NO-0756, and SCH-23390 in neonatal-6-OHDA-lesioned rats. Further evidence that self-mutilatory behavior induced by L-dopa is related to D1 dopamine receptors.	1992 Sep	1418306
Characterization of the binding of SCH 39166 to the five cloned dopamine receptor subtypes.	1994 Nov	7862709
Selective putaminal excitotoxic lesions in non-human primates model the movement disorder of Huntington disease.	1995 Feb	7753372
Zinc allosterically modulates antagonist binding to cloned D1 and D2 dopamine receptors.	1997 May	9109525
Attenuation of the euphoric effects of cocaine by the dopamine D1/D5 antagonist ecopipam (SCH 39166).	1999 Dec	10591286
Altered activity of midbrain dopamine neurons following 7-day withdrawal from chronic cocaine abuse is normalized by D2 receptor stimulation during the early withdrawal phase.	1999 Jul	10379527
Cocaine-predictive stimulus induces drug-seeking behavior and neural activation in limbic brain regions after multiple months of abstinence: reversal by D(1) antagonists.	2001 Feb 13	11172061
Effects of ecopipam, a selective dopamine D1 antagonist, on smoked cocaine self-administration by humans.	2001 Jun	11441422
Enduring resistance to extinction of cocaine-seeking behavior induced by drug-related cues.	2001 Sep	11522464
Amphetamine-evoked c-fos mRNA expression in the caudate-putamen: the effects of DA and NMDA receptor antagonists vary as a function of neuronal phenotype and environmental context.	2003 Jul	12807422

Patents

Sample Use Guides

In Vivo Use Guide

Phase I study of safety and tolerability of ecopipam in patients with Lesch-Nyhan disease: Patients were administered ecopipam on an escalated dosing schedule over 11 days starting at 12.5 mg/day and increasing to the maximal tolerated dose or to 200 mg/day.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:29:52 UTC 2023` Edited by `admin` on `Fri Dec 15 15:29:52 UTC 2023`
Record UNII	0X748O646K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ECOPIPAM

Official Name

English

(-)-(6AS,13BR)-11-CHLORO-6,6A,7,8,9,13B-HEXAHYDRO-7-METHYL-5H-BENZO(D)NAPHTH(2,1-B)AZEPIN-12-OL

Common Name

English

ecopipam [INN]

Common Name

English

Ecopipam [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197