Amlodipine

Amlodipine
Clinical data
Pronunciation/æmˈloʊdɪˌpiːn/ ⓘ[1]
Trade namesNorvasc, others
AHFS/Drugs.comMonograph
MedlinePlusa692044
License data
Pregnancy
category
Routes of
administration		Oral
Drug classCalcium channel blocker
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability64–90%
Protein binding93%[7]
MetabolismLiver
MetabolitesVarious inactive pyrimidine metabolites
Onset of actionHighest availability 6–12 hours after oral dose[10]
Elimination half-life30–50 hours
Duration of actionAt least 24 hours[10]
ExcretionUrine[10]
Identifiers
IUPAC name
  • (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
  • 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)

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)[10] and variant angina (also called Prinzmetal angina or coronary artery vasospasm, among other names).[11] It is taken orally (swallowed by mouth).[10]

Common side effects include swelling, feeling tired, abdominal pain, and nausea.[10] Serious side effects may include low blood pressure or heart attack.[10] Whether use is safe during pregnancy or breastfeeding is unclear.[2][10] When used by people with liver problems, and in elderly individuals, doses should be reduced.[10] Amlodipine works partly by vasodilation (relaxing the arteries and increasing their diameter).[10] It is a long-acting calcium channel blocker of the dihydropyridine type.[10]

Amlodipine was patented in 1982, and approved for medical use in 1990.[12] It is on the World Health Organization's List of Essential Medicines.[13] It is available as a generic medication.[10][14] In 2022, it was the fifth most commonly prescribed medication in the United States, with more than 70 million prescriptions.[15][16] In Australia, it was one of the top 10 most prescribed medications between 2017 and 2023.[17]

  1. ^ "Medical Definition of Amlodipine". www.merriam-webster.com. Archived from the original on 8 November 2016. Retrieved 5 July 2017.
  2. ^ a b "Amlodipine Use During Pregnancy". Drugs.com. 28 October 2019. Archived from the original on 28 December 2019. Retrieved 29 December 2019.
  3. ^ "Poisons Standard June 2017". legislation.gov.au. 29 May 2017. Archived from the original on 13 December 2020. Retrieved 7 January 2018.
  4. ^ "Norvasc Product and Consumer Medicine Information Licence". TGA eBS. Archived from the original on 20 June 2022. Retrieved 19 June 2022.
  5. ^ "Norvasc product information". Health Canada. 25 April 2012. Archived from the original on 20 June 2022. Retrieved 19 June 2022.
  6. ^ Cite error: The named reference Istin SmPC was invoked but never defined (see the help page).
  7. ^ a b Cite error: The named reference Norvasc FDA label was invoked but never defined (see the help page).
  8. ^ "Norliqva- amlodipine solution". DailyMed. 28 February 2022. Archived from the original on 20 June 2022. Retrieved 19 June 2022.
  9. ^ "Amlodipine" (PDF). List of nationally authorised medicinal products. European Medicines Agency. Archived (PDF) from the original on 3 March 2022. Retrieved 20 June 2022.
  10. ^ a b c d e f g h i j k l "Amlodipine Besylate". Drugs.com. American Society of Hospital Pharmacists. Archived from the original on 4 June 2016. Retrieved 22 July 2016.
  11. ^ Boden WE (2012). Goldman's Cecil Medicine (24th ed.). Saunders. ISBN 978-1-4377-1604-7. Archived from the original on 26 August 2023. Retrieved 26 August 2023.
  12. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 465. ISBN 9783527607495. Archived from the original on 27 August 2021. Retrieved 1 June 2020.
  13. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  14. ^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.
  15. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  16. ^ "Amlodipine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  17. ^ "Medicines in the health system". Australian Institute of Health and Welfare. 2 July 2024. Retrieved 30 September 2024.
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