ivabradine   Click here for help

GtoPdb Ligand ID: 2357

Synonyms: Corlanor® | Corlentor® | Procoralan® | S-16257
Approved drug PDB Ligand
ivabradine is an approved drug (EMA (2005), FDA (2015))
Compound class: Synthetic organic
Comment: Marketed drugs contain ivabradine hydrochloride (PubChem CID 3045381).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: ivabradine

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 0
Rotatable bonds 10
Topological polar surface area 60.47
Molecular weight 468.26
XLogP 2.41
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 COc1cc2CC(c2cc1OC)CN(CCCN1CCc2c(CC1=O)cc(c(c2)OC)OC)C
Isomeric SMILES COc1cc2C[C@@H](c2cc1OC)CN(CCCN1CCc2c(CC1=O)cc(c(c2)OC)OC)C
InChI InChI=1S/C27H36N2O5/c1-28(17-21-11-20-14-25(33-4)26(34-5)16-22(20)21)8-6-9-29-10-7-18-12-23(31-2)24(32-3)13-19(18)15-27(29)30/h12-14,16,21H,6-11,15,17H2,1-5H3/t21-/m1/s1
InChI Key ACRHBAYQBXXRTO-OAQYLSRUSA-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
Across Europe, ivabradine has EMA approval for the symptomatic treatment of stable angina and chronic heart failure (HF) in patients with elevated heart rates. In August 2014 the US FDA granted priority review designation for ivabradine for the treatment of chronic HF, and in April 2015 granted approval for use of the drug in cases of worsening heart failure to reduce hospitalisation.
ivabradine has been tested for heart rate-lowering efficacy in patients with postural orthostatic tachycardia syndrome (POTS) [3]. The benefit of ivabradine over beta blockers is that it doesn't depress blood pressure, but it is not approved for treating POTS. In addition to postural orthostatic tachycardia, POTS patients also suffer from fatigue, weakness and brain fog, a set of symptoms that are experienced by 'long-COVID' patients. In view of the similar symptomology, it has been proposed that ivabradine may offer potential for managing such post-viral abnormalities in long-COVID patients.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Ivabradine inhibits the If current in the sinoatrial node (cardiac pacemaker) [2]. The heart rate is slowed down without any negative effects on myocardial contractility or ventricular repolarization.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03182725 Effect of Ivabradine on Patients With Postural Orthostatic Tachycardia Syndrome Phase 3 Interventional University of California, San Diego
External links Click here for help
For extended ADME data see the following:

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