ECOPIPAM

Investigational

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

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

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

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
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1.	1991 Apr 18	1826762
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

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

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

Preferred Name

English

ECOPIPAM

Official Name

English

ecopipam [INN]

Common Name

English

Ecopipam [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197