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ranolazine   Click here for help

GtoPdb Ligand ID: 7291

Synonyms: CVT-303 | Ranexa® | RS-43285 | RS-43285-003
Approved drug
ranolazine is an approved drug (FDA (2006), EMA (2008))
Compound class: Synthetic organic
Comment: The mechanism of action of ranolazine is largely unknown, but may have some antianginal effects by inhibition of the late sodium current in cardiac cells.
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ranolazine is commercially available from our sponsors

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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Click here for structure editor
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 5
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 77.76
Molecular weight 427.25
XLogP 1.9
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 COc1ccccc1OCC(CN1CCN(CC1)CC(=Nc1c(C)cccc1C)O)O
Isomeric SMILES COc1ccccc1OCC(CN1CCN(CC1)CC(=Nc1c(C)cccc1C)O)O
InChI InChI=1S/C24H33N3O4/c1-18-7-6-8-19(2)24(18)25-23(29)16-27-13-11-26(12-14-27)15-20(28)17-31-22-10-5-4-9-21(22)30-3/h4-10,20,28H,11-17H2,1-3H3,(H,25,29)
InChI Key XKLMZUWKNUAPSZ-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 chronic angina pectoris.
A Phase 3 clinical trial evaluating ranolazine in patients with incomplete revascularization post-PCI (percutaneous coronary intervention) is underway.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The precise mechanism by which this drug works is unknown. However, ChEMBL lists the sodium channel type IV and V alpha subunits (SCN4A and SCN5A respectively) as the molecular targets of this drug. These proteins mediate voltage-dependent sodium ion permeability of excitable membranes [1]. SCN4A is also known as the skeletal muscle sodium channel isoform and SCN5A is known as the cardiac sodium channel isoform. So SCN5A is potentially responsible for the drug's cardiac effects.
External links Click here for help
For extended ADME data see the following:

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