ranolazine

Also known as CVT-303, Ranexa®, RS-43285, RS-43285-003, N-(2,6-Dimethylphenyl)-2-[4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl]acetamide

Ranolazine, sold under the brand name Ranexa among others, is a medication used to treat heart related chest pain. Typically it is used together with other medications when those are insufficient. Therapeutic benefits appear smaller in females than males. It is taken by mouth.

Chemical data

Formula: C24H33N3O4
Molecular weight: 427.5 g/mol
IUPAC name: N-(2,6-dimethylphenyl)-2-[4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl]acetamide
SMILES: CC1=C(C(=CC=C1)C)NC(=O)CN2CCN(CC2)CC(COC3=CC=CC=C3OC)O
InChIKey: XKLMZUWKNUAPSZ-UHFFFAOYSA-N
XLogP: 2.7
Polar surface area: 74.3 Å²
H-bond donors: 2
H-bond acceptors: 6
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2006
Admin. routes: oral
Indications: dilated cardiomyopathy, atrial fibrillation, acute coronary syndrome, irritable bowel syndrome

via ChEMBL · EBI

Research

1,329 papers

Ranolazine: a potential anti-metastatic drug targeting voltage-gated sodium channels.British journal of cancer · 2024
Ranolazine: A Contemporary Review.Journal of the American Heart Association · 2016
Ranolazine in Cardiac Arrhythmia.Clinical cardiology · 2016
Ranolazine and its Antiarrhythmic Actions.Cardiovascular & hematological agents in medicinal chemistry · 2015
Ranolazine: An Established Anti-anginal Drug with Emerging Antidiabetic Potential Supported by Preclinical and Clinical Evidence.Cardiovascular & hematological disorders drug targets · 2025

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 427.247107
Has use: medication

Show 6 more facts

chemical formula: C₂₄H₃₃N₃O₄
canonical SMILES: CC1=C(C(=CC=C1)C)NC(=O)CN2CCN(CC2)CC(COC3=CC=CC=C3OC)O
defined daily dose: 1.5
Commons category: Ranolazine
subject has role: sodium channel blocker
significant drug interaction: ketoconazole

Sources (5)

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Encyclopedic overview

10 sections

Contents

Medical uses
Contraindications
Side effects
Drug interactions
Mechanism of action
History
Society and culture
Legal status
Commercial aspects
References

Common side effects include constipation, headache, nausea, and dizziness. Serious side effects may include QT prolongation. Ranolazine is contraindicated (not recommended) in those with liver cirrhosis. How it works is not clear but may involve adenosine triphosphate.

Excerpted from Wikipedia’s “ranolazine” article, available under the CC BY-SA 4.0 licence.

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