ChEBI Name verapamil
ChEBI ID CHEBI:9948
Definition A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C27H38N2O4
Net Charge 0
Average Mass 454.60160
Monoisotopic Mass 454.28316
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): calcium channel blocker
One of a class of drugs that acts by selective inhibition of calcium influx through cell membranes or on the release and binding of calcium in intracellular pools.
EC 1.2.3.1 (aldehyde oxidase) inhibitor
An EC 1.2.3.* (oxidoreductase acting on donor aldehyde/oxo group with oxygen as acceptor) inhibitor which interferes with the action of aldehyde oxidase (EC 1.2.3.1).
EC 3.4.24.18 (meprin A) inhibitor
An EC 3.4.24.* (metalloendopeptidase) inhibitor that inhibits the action of meprin A (EC 3.4.24.18).
EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor
An EC 3.4.24.* (metalloendopeptidase) inhibitor that interferes with the action of anthrax lethal factor endopeptidase (EC 3.4.24.83).
EC 3.6.3.1 (phospholipid-translocating ATPase) inhibitor
An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of phospholipid-translocating ATPase (EC 3.6.3.1).
EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor
An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of xenobiotic-transporting ATPase (EC 3.6.3.44).
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): anti-arrhythmia drug
A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
vasodilator agent
A drug used to cause dilation of the blood vessels.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing verapamil (CHEBI:9948) has part (S)-verapamil (CHEBI:77736)
verapamil (CHEBI:9948) has part dexverapamil (CHEBI:77734)
verapamil (CHEBI:9948) has role anti-arrhythmia drug (CHEBI:38070)
verapamil (CHEBI:9948) has role antihypertensive agent (CHEBI:35674)
verapamil (CHEBI:9948) has role calcium channel blocker (CHEBI:38215)
verapamil (CHEBI:9948) has role EC 1.2.3.1 (aldehyde oxidase) inhibitor (CHEBI:62872)
verapamil (CHEBI:9948) has role EC 3.4.24.18 (meprin A) inhibitor (CHEBI:77745)
verapamil (CHEBI:9948) has role EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor (CHEBI:77255)
verapamil (CHEBI:9948) has role EC 3.6.3.1 (phospholipid-translocating ATPase) inhibitor (CHEBI:77747)
verapamil (CHEBI:9948) has role EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor (CHEBI:77748)
verapamil (CHEBI:9948) has role environmental contaminant (CHEBI:78298)
verapamil (CHEBI:9948) has role vasodilator agent (CHEBI:35620)
verapamil (CHEBI:9948) has role xenobiotic (CHEBI:35703)
verapamil (CHEBI:9948) is a racemate (CHEBI:60911)
IUPAC Name
rac-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
INNs Sources
verapamil ChemIDplus
vérapamil WHO MedNet
verapamilo ChemIDplus
verapamilum ChemIDplus
Synonym Source
Verapamil KEGG COMPOUND
Manual Xrefs Databases
C07188 KEGG COMPOUND
D02356 KEGG DRUG
DB00661 DrugBank
HMDB0001850 HMDB
Verapamil Wikipedia
View more database links
Registry Numbers Types Sources
2825000 Reaxys Registry Number Reaxys
2825000 Beilstein Registry Number Beilstein
52-53-9 CAS Registry Number ChemIDplus
52-53-9 CAS Registry Number NIST Chemistry WebBook
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Last Modified
22 February 2017
General Comment
2014-09-04 Verapamil can be found in blood and urine samples of individuals who have taken this drug.
 
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