ecopipam   Click here for help

GtoPdb Ligand ID: 3304

Synonyms: EBS-101 | PSYRX-101 | SCH 39166 | SCH-39166 | SCH39166
Compound class: Synthetic organic
Comment: Ecopipam is an orally bioactive, brain penetrant dopamine receptor antagonist [4], with selectivity for the D1/5 subtypes [1]. It is structurally related to benzazepine. Ecopipam has been utilised to demonstrate (in animal models) the potential of D1 receptor antagonism to rescue autistic-like behaviours that are associated with the lysosomal storage disorder mucopolysaccharidosis type IIIA-D (MPS-IIIA-D) [2].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 23.47
Molecular weight 313.12
XLogP 3.72
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CN1CCc2c(C3C1CCc1c3cccc1)cc(c(c2)Cl)O
Isomeric SMILES CN1CCc2c([C@@H]3[C@@H]1CCc1c3cccc1)cc(c(c2)Cl)O
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
InChI Key DMJWENQHWZZWDF-PKOBYXMFSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Chipkin RE, Iorio LC, Coffin VL, McQuade RD, Berger JG, Barnett A. (1988)
Pharmacological profile of SCH39166: a dopamine D1 selective benzonaphthazepine with potential antipsychotic activity.
J Pharmacol Exp Ther, 247 (3): 1093-102. [PMID:2905002]
2. De Risi M, Cusimano L, Bujanda Cundin X, Pizzo M, Gigante Y, Monaco M, Di Eugenio C, De Leonibus E. (2025)
D1 dopamine receptor antagonists as a new therapeutic strategy to treat autistic-like behaviours in lysosomal storage disorders.
Mol Psychiatry, [Epub ahead of print]. [PMID:39865184]
3. Gilbert DL, Dubow JS, Cunniff TM, Wanaski SP, Atkinson SD, Mahableshwarkar AR. (2023)
Ecopipam for Tourette Syndrome: A Randomized Trial.
Pediatrics, 151 (2). [PMID:36628546]
4. Karlsson P, Sedvall G, Halldin C, Swahn CG, Farde L. (1995)
Evaluation of SCH 39166 as PET ligand for central D1 dopamine receptor binding and occupancy in man.
Psychopharmacology (Berl), 121 (3): 300-8. [PMID:8584610]
5. Panda PK, Panda P, Dawman L, Mishra AS, Kumar V, Sharawat IK. (2025)
Safety and Efficacy of Ecopipam in Patients with Tourette Syndrome: A Systematic Review and Meta-analysis.
CNS Drugs, 39 (2): 127-142. [PMID:39730854]
6. Sunahara RK, Guan HC, O'Dowd BF, Seeman P, Laurier LG, Ng G, George SR, Torchia J, Van Tol HH, Niznik HB. (1991)
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1.
Nature, 350 (6319): 614-9. [PMID:1826762]
7. Tice MA, Hashemi T, Taylor LA, Duffy RA, McQuade RD. (1994)
Characterization of the binding of SCH 39166 to the five cloned dopamine receptor subtypes.
Pharmacol Biochem Behav, 49 (3): 567-71. [PMID:7862709]