ECOPIPAM HYDROCHLORIDE

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

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 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
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

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

ECOPIPAM HYDROCHLORIDE

Official Name

English

SCH 39166

Code

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