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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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 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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (2006)  |  EMA (2008)
IUPAC Name Click here for help
N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}ethanimidic acid
International Nonproprietary Names Click here for help
INN number INN
5946 ranolazine
Synonyms Click here for help
CVT-303 | Ranexa® | RS-43285 | RS-43285-003
Database Links Click here for help
CAS Registry No. 95635-55-5
ChEMBL Ligand CHEMBL1404
DrugBank Ligand DB00243
DrugCentral Ligand 2359
GtoPdb PubChem SID 178103865
PubChem CID 56959
Search Google for chemical match using the InChIKey XKLMZUWKNUAPSZ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone XKLMZUWKNUAPSZ
Search PubMed clinical trials ranolazine
Search PubMed titles ranolazine
Search PubMed titles/abstracts ranolazine
UniChem Compound Search for chemical match using the InChIKey XKLMZUWKNUAPSZ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XKLMZUWKNUAPSZ-UHFFFAOYSA-N
Wikipedia Ranolazine

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MedChemExpress
Ranolazine (links to external site)
Cat. No. HY-B0280