Amlodipine

Amlodipine, sold under the brand name Norvasc among others, is a calcium channel blocker medication used to treat high blood pressure, coronary artery disease (CAD) and variant angina (also called Prinzmetal angina or coronary artery vasospasm, among other names). It is taken orally (swallowed by mouth).

Amlodipine
Clinical data
Pronunciation/æmˈloʊdɪˌpiːn/
Trade namesNorvasc, Istin, Norliqva, others
AHFS/Drugs.comMonograph
MedlinePlusa692044
License data
Pregnancy
category
  • AU: C
Routes of
administration		Oral
Drug classCalcium channel blocker
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability64–90%
Protein binding93%
MetabolismLiver
MetabolitesVarious inactive pyrimidine metabolites
Onset of actionHighest availability 6–12 hours after oral dose
Elimination half-life30–50 hours
Duration of actionAt least 24 hours
ExcretionUrine
Identifiers
  • (RS)-3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.102.428
Chemical and physical data
FormulaC20H25ClN2O5
Molar mass408.88 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
SMILES
  • Clc1ccccc1C2/C(C(=O)OC)=C(/C)N/C(COCCN)=C2/C(=O)OCC
  • InChI=1S/C20H25ClN2O5/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)16(19(24)26-3)17(18)13-7-5-6-8-14(13)21/h5-8,17,23H,4,9-11,22H2,1-3H3 Y
  • Key:HTIQEAQVCYTUBX-UHFFFAOYSA-N Y
  (verify)

Common side effects include swelling, feeling tired, abdominal pain, and nausea. Serious side effects may include low blood pressure or heart attack. Whether use is safe during pregnancy or breastfeeding is unclear. When used by people with liver problems, and in elderly individuals, doses should be reduced. Amlodipine works partly by vasodilation (relaxing the arteries and increasing their diameter). It is a long-acting calcium channel blocker of the dihydropyridine type.

Amlodipine was patented in 1982, and approved for medical use in 1990. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2021, it was the fifth most commonly prescribed medication in the United States, with more than 73 million prescriptions.

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