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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 of ECOPIPAM HYDROCHLORIDE

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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1.
1991 Apr 18
Characterization of the binding of SCH 39166 to the five cloned dopamine receptor subtypes.
1994 Nov
Selective putaminal excitotoxic lesions in non-human primates model the movement disorder of Huntington disease.
1995 Feb
Zinc allosterically modulates antagonist binding to cloned D1 and D2 dopamine receptors.
1997 May
Attenuation of the euphoric effects of cocaine by the dopamine D1/D5 antagonist ecopipam (SCH 39166).
1999 Dec
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
Patents

Sample Use Guides

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
USAN  
USAN  
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
Created by admin on Fri Dec 15 16:42:40 GMT 2023 , Edited by admin on Fri Dec 15 16:42:40 GMT 2023
FDA ORPHAN DRUG 308210
Created by admin on Fri Dec 15 16:42:40 GMT 2023 , Edited by admin on Fri Dec 15 16:42:40 GMT 2023
NCI_THESAURUS C66883
Created by admin on Fri Dec 15 16:42:40 GMT 2023 , Edited by admin on Fri Dec 15 16:42:40 GMT 2023
NCI_THESAURUS C28197
Created by admin on Fri Dec 15 16:42:40 GMT 2023 , Edited by admin on Fri Dec 15 16:42:40 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL298406
Created by admin on Fri Dec 15 16:42:40 GMT 2023 , Edited by admin on Fri Dec 15 16:42:40 GMT 2023
PRIMARY
FDA UNII
5X1J3190JI
Created by admin on Fri Dec 15 16:42:40 GMT 2023 , Edited by admin on Fri Dec 15 16:42:40 GMT 2023
PRIMARY
EPA CompTox
DTXSID50172488
Created by admin on Fri Dec 15 16:42:40 GMT 2023 , Edited by admin on Fri Dec 15 16:42:40 GMT 2023
PRIMARY
NCI_THESAURUS
C87494
Created by admin on Fri Dec 15 16:42:40 GMT 2023 , Edited by admin on Fri Dec 15 16:42:40 GMT 2023
PRIMARY
USAN
JJ-92
Created by admin on Fri Dec 15 16:42:40 GMT 2023 , Edited by admin on Fri Dec 15 16:42:40 GMT 2023
PRIMARY
PUBCHEM
170317
Created by admin on Fri Dec 15 16:42:40 GMT 2023 , Edited by admin on Fri Dec 15 16:42:40 GMT 2023
PRIMARY
EVMPD
SUB128274
Created by admin on Fri Dec 15 16:42:40 GMT 2023 , Edited by admin on Fri Dec 15 16:42:40 GMT 2023
PRIMARY
CAS
190133-94-9
Created by admin on Fri Dec 15 16:42:40 GMT 2023 , Edited by admin on Fri Dec 15 16:42:40 GMT 2023
PRIMARY
SMS_ID
100000153825
Created by admin on Fri Dec 15 16:42:40 GMT 2023 , Edited by admin on Fri Dec 15 16:42:40 GMT 2023
PRIMARY
DRUG BANK
DBSALT002167
Created by admin on Fri Dec 15 16:42:40 GMT 2023 , Edited by admin on Fri Dec 15 16:42:40 GMT 2023
PRIMARY
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