paliperidone   Click here for help

GtoPdb Ligand ID: 7258

Synonyms: 9-hydroxyrisperidone | Invega® | Ro-76477 | Ro-92670
Approved drug
paliperidone is an approved drug (FDA (2006), EMA (2007))
Compound class: Synthetic organic
Comment: Paliperidone is an atypical antipsychotic. Mechanistically it is a dopamine receptor and 5-HT2A receptor antagonist.
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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 4
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 84.39
Molecular weight 426.21
XLogP 2.96
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 Fc1ccc2c(c1)onc2C1CCN(CC1)CCc1c(C)nc2n(c1=O)CCCC2O
Isomeric SMILES Fc1ccc2c(c1)onc2C1CCN(CC1)CCc1c(C)nc2n(c1=O)CCCC2O
InChI InChI=1S/C23H27FN4O3/c1-14-17(23(30)28-9-2-3-19(29)22(28)25-14)8-12-27-10-6-15(7-11-27)21-18-5-4-16(24)13-20(18)31-26-21/h4-5,13,15,19,29H,2-3,6-12H2,1H3
InChI Key PMXMIIMHBWHSKN-UHFFFAOYSA-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 psychotic or manic symptoms of schizophrenia.
In November 2014, the US FDA granted a supplemental New Drug Application (sNDA) for paliperidone palmitate (PubChem CID 9852746) as a treatment for schizoaffective disorder as either monotherapy or adjunctive therapy. This sNDA will be scrutinised under priority review, a mechanism whereby drugs may be approved more quickly, if they are found to offer significant improvement in the treatment of serious conditions, over currently available therapies. Following publication of results from a Phase 3 clinical trial [1], the FDA formally approved the use of paliperidone palmitate (trade named Invega Trinza) as a long-acting schizophrenia medication in May 2015. Invega Trinza has a dosing interval of three months.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The most likely molecular mechanism of action (MMOA) of this drug is via antagonism of dopamine D2 and serotonin 5-HT2A receptors. The full MMOA remains to be determined.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)