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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Attenuation of the euphoric effects of cocaine by the dopamine D1/D5 antagonist ecopipam (SCH 39166).	1999 Dec	10591286
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

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 16:42:40 GMT 2023` Edited by `admin` on `Fri Dec 15 16:42:40 GMT 2023`
Record UNII	5X1J3190JI
Record Status	`Validated (UNII)`
Record Version

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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