Structure via PubChem · Public domain (PubChem)
norverapamil
Sign in to saveNorverapamil is a calcium channel blocker. It is the main active metabolite of verapamil. It contributes significantly to the therapeutic effects of verapamil, which include the treatment of hypertension, angina, and arrhythmias. Despite being a metabolite of verapamil, norverapamil retains much of the pharmacological activity of verapamil, particularly impacting the calcium ion flow through L-type calcium channels, leading to its therapeutic cardiovascular and vasodilation effects.
Chemical data
- Formula
- C26H36N2O4
- Molecular weight
- 440.6 g/mol
- IUPAC name
- 2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethylamino]-2-propan-2-ylpentanenitrile
- SMILES
- CC(C)C(CCCNCCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC
- InChIKey
- UPKQNCPKPOLASS-UHFFFAOYSA-N
- XLogP
- 3.3
- Polar surface area
- 72.7 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
281 papers- Verapamil and its metabolite norverapamil inhibit the Mycobacterium tuberculosis MmpS5L5 efflux pump to increase bedaquiline activity.Proceedings of the National Academy of Sciences of the United States of America · 2025
- Comparative pharmacokinetics of verapamil and norverapamil in normal and ulcerative colitis rats after oral administration of low and high dose verapamil by UPLC-MS/MS.Xenobiotica; the fate of foreign compounds in biological systems · 2020
- Determination of Verapamil Hydrochloride and Norverapamil Hydrochloride in Rat Plasma by Capillary Electrophoresis With End-Column Electrochemiluminescence Detection and Their Pharmacokinetics Study.Journal of chromatographic science · 2021
- Pharmacokinetics of verapamil and norverapamil from controlled release floating pellets in humans.European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V · 2002
- Verapamil, and its metabolite norverapamil, inhibit macrophage-induced, bacterial efflux pump-mediated tolerance to multiple anti-tubercular drugs.The Journal of infectious diseases · 2014
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 440.268
Show 3 more facts
- canonical SMILES
- CC(C)C(CCCNCCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC
- chemical formula
- C₂₆H₃₆N₂O₄
- subject has role
- calcium channel blocker
Sources (2)
via Wikidata · CC0
~4 min read
Encyclopedic overview
5 sectionsContents
- Pharmacodynamics
- Pharmacokinetics
- Interaction with P-Glycoprotein
- Factors that affect metabolism
- References
Norverapamil is a calcium channel blocker. It is the main active metabolite of verapamil. It contributes significantly to the therapeutic effects of verapamil, which include the treatment of hypertension, angina, and arrhythmias. Despite being a metabolite of verapamil, norverapamil retains much of the pharmacological activity of verapamil, particularly impacting the calcium ion flow through L-type calcium channels, leading to its therapeutic cardiovascular and vasodilation effects.
== Pharmacodynamics == Norverapamil inhibits L-type calcium channels located in the heart and blood vessels, leading to several pharmacological effects including vasodilation, negative inotropy, and negative dromotropy. Norverapamil relaxes the smooth muscles of blood vessels, reducing systemic vascular resistance and consequently lowering blood pressure. Also, by decreasing calcium influx into heart muscle cells, it is able to lower myocardial contractility. This makes it useful in reducing the workload of the heart, particularly in cardiovascular conditions such as angina. Norverapamil is also able to slow atrioventricular (AV) conduction, which is useful in controlling supra-ventricular arrhythmias by controlling the heart rate through reduced electrical conduction.
Excerpted from Wikipedia’s “norverapamil” article, available under the CC BY-SA 4.0 licence.