Details of the Drug

General Information of Drug (ID: DMS9R43)

Drug Name

Ecopipam

Synonyms

Sch-39166; Sch 39166; 112108-01-7; Ecopipam [INN]; Sch39166; UNII-0X748O646K; CHEMBL298406; 0X748O646K; DSSTox_RID_80075; DSSTox_CID_23814; 6,7,7a,8,9,13b-Hexahydro-3-chloro-2-hydroxy-N-methyl-5H-benzo(d)naphtho(2,1b)azepine; DSSTox_GSID_43814; 5H-Benzo(d)naphth(2,1-b)azepin-12-ol, 11-chloro-6,6a,7,8,9,13b-hexahydro-7-methyl-, trans-(-)-; (6aS,13bR)-11-chloro-7-methyl-6,6a,7,8,9,13b-hexahydro-5H-benzo[d]naphtho[2,1-b]azepin-12-ol; 5H-Benzo[d]naphth[2,1-b]azepin-12-ol,; ecopipam (controlled-release, Lesch Nyhan syndrome/Tourette's syndrome/compulsive gambling). Psyadon Pharmaceuticals

Indication

Disease Entry	ICD 11	Status	REF
Cocaine addiction	6C45.2	Phase 3	[1], [2]
Tourette syndrome	8A05.00	Phase 2	[3]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

313.8

Topological Polar Surface Area (xlogp)

4.4

Rotatable Bond Count (rotbonds)

0

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

2

Chemical Identifiers

Formula: C19H20ClNO
IUPAC Name: (6aS,13bR)-11-chloro-7-methyl-5,6,6a,8,9,13b-hexahydronaphtho[1,2-a][3]benzazepin-12-ol
Canonical SMILES: CN1CCC2=CC(=C(C=C2[C@@H]3[C@@H]1CCC4=CC=CC=C34)O)Cl
InChI: 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
InChIKey: DMJWENQHWZZWDF-PKOBYXMFSA-N

Cross-matching ID

PubChem CID: 107930
ChEBI ID: CHEBI:93645
CAS Number: 112108-01-7
DrugBank ID: DB12273
TTD ID: D0Y6HW

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Dopamine D1 receptor (D1R)	TTZFYLI	DRD1_HUMAN	Modulator	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Cocaine addiction

ICD Disease Classification

6C45.2

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Dopamine D1 receptor (D1R)	DTT	DRD1	8.99E-01	-0.06	-0.3

Molecular Expression Atlas (MEA)

MEA Detail

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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 3304).
2	ClinicalTrials.gov (NCT01751802) Ecopipam Treatment of Self-Injurious Behavior in Subjects With Lesch-Nyhan Disease. U.S. National Institutes of Health.
3	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
4	A D1 receptor antagonist, ecopipam, for treatment of tics in Tourette syndrome.Clin Neuropharmacol.2014 Jan-Feb;37(1):26-30.
5	Dopamine/serotonin receptor ligands. 9. Oxygen-containing midsized heterocyclic ring systems and nonrigidized analogues. A step toward dopamine D5 ... J Med Chem. 2004 Aug 12;47(17):4155-8.
6	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
7	Reinforcement in an in vitro analog of appetitive classical conditioning of feeding behavior in Aplysia: blockade by a dopamine antagonist. Learn Mem. 2005 May-Jun;12(3):216-20.
8	Etiology of iodinated radiocontrast nephrotoxicity and its attenuation by beraprost. Yakugaku Zasshi. 2008 Jul;128(7):1023-9.
9	Clinical pipeline report, company report or official report of Lundbeck.
10	Adrogolide HCl (ABT-431; DAS-431), a prodrug of the dopamine D1 receptor agonist, A-86929: preclinical pharmacology and clinical data. CNS Drug Rev. 2001 Fall;7(3):305-16.
11	trans-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline: synthesis, resolution, and preliminary pharmacological characterization o... J Med Chem. 2006 Nov 16;49(23):6848-57.
12	Therapeutic effects of dopamine D1/D2 receptor agonists on detrusor hyperreflexia in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-lesioned parkinso... J Pharmacol Exp Ther. 1998 Jul;286(1):228-33.
13	The D-1 dopamine receptor partial agonist, CY 208-243, exhibits antiparkinsonian activity in the MPTP-treated marmoset. Eur J Pharmacol. 1988 Nov 1;156(2):197-206.
14	Effect of zelandopam, a dopamine D1-like receptor agonist, in puromycin aminonucleoside nephrosis rats. Eur J Pharmacol. 2005 Mar 7;510(1-2):121-6.