zuclopenthixol   Click here for help

GtoPdb Ligand ID: 7559

Synonyms: Acuphase® | cis(Z)-cloflupentixol | Cisordinol® | Clopixol® | NSC 64087 | NSC169185
Approved drug
zuclopenthixol is an approved drug
Compound class: Synthetic organic
Comment: Zuclopenthixol is a thioxanthene class typical antipsychotic. Chemically it is the cis-isomer of clopenthixol. The CAS registry number (53772-83-1) submitted with the WHO INN record for zuclopenthixol maps to PubChem CID 5311507.
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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 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 52.01
Molecular weight 400.14
XLogP 4.12
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 OCCN1CCN(CC1)CCC=C1c2ccccc2Sc2c1cc(Cl)cc2
Isomeric SMILES OCCN1CCN(CC1)CC/C=C\1/c2ccccc2Sc2c1cc(Cl)cc2
InChI InChI=1S/C22H25ClN2OS/c23-17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)27-22)5-3-9-24-10-12-25(13-11-24)14-15-26/h1-2,4-8,16,26H,3,9-15H2/b18-5-
InChI Key WFPIAZLQTJBIFN-DVZOWYKESA-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/)
No information available.
Summary of Clinical Use Click here for help
Used to treat schizophrenia and acute mania. There is no information regarding approval for clinical use of this drug on the US FDA or European Medicines Agency (EMA) websites. Individual national approval agencies may have granted marketing authorisation. See Drugs.com for a list of countries where this drug may be in use. In the UK three salt formulations of zuclopenthixol are approved; acetate (PubChem CID 6436640, injectable form), decanoate (PubChem CID 6450333, injectable form) and dihydrochloride (PubChem CID 6433208), tablet form).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Zuclopenthixol is an antagonist of the dopamine D1 and D2 receptor subtypes. Drug treatment induces sedation and improves psychotic symptoms.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)