ecopipam

Ecopipam (development codes SCH-39166, EBS-101, and PSYRX-101) is a dopamine antagonist which is under development for the treatment of Lesch–Nyhan syndrome, Tourette syndrome, speech disorders, and restless legs syndrome. It is taken by mouth.

Chemical data

Formula: C19H20ClNO
Molecular weight: 313.8 g/mol
IUPAC name: (6aS,13bR)-11-chloro-7-methyl-5,6,6a,8,9,13b-hexahydronaphtho[1,2-a][3]benzazepin-12-ol
SMILES: CN1CCC2=CC(=C(C=C2[C@@H]3[C@@H]1CCC4=CC=CC=C34)O)Cl
InChIKey: DMJWENQHWZZWDF-PKOBYXMFSA-N
XLogP: 4.4
Polar surface area: 23.5 Å²
H-bond donors: 1
H-bond acceptors: 2
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 3
Molecule type: Small molecule
Indications: gambling behaviour, Tourette syndrome, restless legs syndrome, Lesch-Nyhan syndrome

via ChEMBL · EBI

Wikidata facts

Subclass of: chemical compound
Mass: 313.123

Show 5 more facts

chemical formula: C₁₉H₂₀ClNO
isomeric SMILES: CN1CCC2=CC(=C(C=C2[C@@H]3[C@@H]1CCC4=CC=CC=C34)O)Cl
canonical SMILES: CN1CCC2=CC(=C(C=C2C3C1CCC4=CC=CC=C34)O)Cl
subject has role: dopamine antagonist
Commons category: Ecopipam

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Encyclopedic overview

6 sections

Contents

Pharmacology
Pharmacodynamics
Research
Chemistry
See also
References

Ecopipam acts as a selective dopamine D1 and D5 receptor antagonist. It is orally active, has an elimination half-life of 10hours, crosses the blood–brain barrier, and substantially occupies brain dopamine receptors. Side effects of ecopipam may include depression, anxiety, fatigue, sedation, somnolence, insomnia, headaches, muscle twitching, and suicidal ideation, among others. It appears to lack the typical extrapyramidal effects like tardive dyskinesia that occur with D2 receptor antagonists.

Excerpted from Wikipedia’s “ecopipam” article, available under the CC BY-SA 4.0 licence.

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