ECOPIPAM HYDROCHLORIDE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H20ClNO.ClH
Molecular Weight	350.282
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CN1CCC2=CC(Cl)=C(O)C=C2[C@@H]3[C@@H]1CCC4=C3C=CC=C4

InChI

InChIKey=APFMVAHRFWBCDG-JUOYHRLASA-N

InChI=1S/C19H20ClNO.ClH/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;1H/t17-,19+;/m0./s1

HIDE SMILES / InChI

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 106 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 2849		1.9 nM [Ki]

PubMed

Title	Date	PubMed
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.	2003-07	12807422
Enduring resistance to extinction of cocaine-seeking behavior induced by drug-related cues.	2001-09	11522464
Effects of ecopipam, a selective dopamine D1 antagonist, on smoked cocaine self-administration by humans.	2001-06	11441422
Cocaine-predictive stimulus induces drug-seeking behavior and neural activation in limbic brain regions after multiple months of abstinence: reversal by D(1) antagonists.	2001-02-13	11172061
Attenuation of the euphoric effects of cocaine by the dopamine D1/D5 antagonist ecopipam (SCH 39166)	1999-12	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.	1999-07	10379527
Zinc allosterically modulates antagonist binding to cloned D1 and D2 dopamine receptors.	1997-05	9109525
Selective putaminal excitotoxic lesions in non-human primates model the movement disorder of Huntington disease.	1995-02	7753372
Characterization of the binding of SCH 39166 to the five cloned dopamine receptor subtypes.	1994-11	7862709
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.	1992-09	1418306
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1.	1991-04-18	1826762

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

Name

Type

Language

SCH 39166

Preferred Name

English

ECOPIPAM HYDROCHLORIDE

Official Name

English

ECOPIPAM HYDROCHLORIDE [USAN]

Common 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 HYDROCHLORIDE

Common Name

English

SCH-39166

Code

English

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

Common Name

English

ECOPIPAM HCL

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

284109