Metoprolol

Metoprolol
Clinical data
Pronunciation/mɛˈtoʊproʊlɑːl/ ⓘ, /mɛtoʊˈproʊlɑːl/
Trade namesLopressor (metoprolol tartrate), Toprol-XL (metoprolol succinate)
AHFS/Drugs.comMonograph
MedlinePlusa682864
License data
Pregnancy
category
  • AU: C
Routes of
administration		By mouth, intravenous
Drug classBeta blocker
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability50% (single dose)[3]
70% (repeated administration)[4]
Protein binding12%
MetabolismLiver via CYP2D6, CYP3A4
Elimination half-life3–7 hours
ExcretionKidney
Identifiers
IUPAC name
  • (RS)-1-[4-(2-Methoxyethyl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.051.952
Chemical and physical data
FormulaC15H25NO3
Molar mass267.369 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Melting point120 °C (248 °F)
SMILES
  • O(c1ccc(cc1)CCOC)CC(O)CNC(C)C
InChI
  • InChI=1S/C15H25NO3/c1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3/h4-7,12,14,16-17H,8-11H2,1-3H3 Y
  • Key:IUBSYMUCCVWXPE-UHFFFAOYSA-N Y
  (verify)

Metoprolol, sold under the brand names Lopressor and Toprol-XL among others, is a medication used to treat angina, high blood pressure and a number of conditions involving an abnormally fast heart rate.[5] It is also used to prevent further heart problems after myocardial infarction and to prevent headaches in those with migraines.[5] It is a beta blocker, specifically a selective β1 receptor blocker, and is taken by mouth or is given intravenously.[5]

Common side effects include trouble sleeping, feeling tired, feeling faint, and abdominal discomfort.[5] Large doses may cause serious toxicity.[6][7] Risk in pregnancy has not been ruled out.[5][8] It appears to be safe in breastfeeding.[9] The metabolism of metoprolol can vary widely among patients, often as a result of hepatic impairment[10] or CYP2D6 polymorphism.[11]

Metoprolol was first made in 1969, patented in 1970, and approved for medical use in 1978.[12][13][14] It is on the World Health Organization's List of Essential Medicines.[15] It is available as a generic medication.[5] In 2022, it was the sixth most commonly prescribed medication in the United States, with more than 65 million prescriptions.[16][17]

  1. ^ "Lopressor Product information". Health Canada. 22 October 2009. Retrieved 20 June 2023.
  2. ^ "Lopressor- metoprolol tartrate tablet". DailyMed. 14 September 2023. Retrieved 17 April 2025.
  3. ^ "Metolar 25/50 (metoprolol tartrate) tablet" (PDF). U.S. Food and Drug Administration (FDA). Archived (PDF) from the original on 3 March 2016. Retrieved 5 May 2015.
  4. ^ Jasek W, ed. (2007). Austria-Codex (in German) (62nd ed.). Vienna: Österreichischer Apothekerverlag. pp. 916–919. ISBN 978-3852001814.
  5. ^ a b c d e f "Metoprolol". The American Society of Health-System Pharmacists. Archived from the original on 12 March 2014. Retrieved 21 April 2014.
  6. ^ Pillay VV (2012). "Diuretics, Antihypertensives, and Antiarrhythmics". Modern Medical Toxicology. Jaypee Brothers Publishers. p. 303. ISBN 978-9350259658. Archived from the original on 7 July 2017.
  7. ^ Marx JA (2014). "Chapter 152: Cardiovascular Drugs". Rosen's emergency medicine : concepts and clinical practice (8th ed.). Philadelphia: Elsevier/Saunders. ISBN 978-1455706051.
  8. ^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
  9. ^ Medical Toxicology. Lippincott Williams & Wilkins. 2004. p. 684. ISBN 978-0781728454. Archived from the original on 7 July 2017.
  10. ^ Regårdh CG, Jordö L, Ervik M, Lundborg P, Olsson R, Rönn O (1981). "Pharmacokinetics of metoprolol in patients with hepatic cirrhosis". Clinical Pharmacokinetics. 6 (5): 375–388. doi:10.2165/00003088-198106050-00004. PMID 7333059. S2CID 1042204.
  11. ^ Blake CM, Kharasch ED, Schwab M, Nagele P (September 2013). "A meta-analysis of CYP2D6 metabolizer phenotype and metoprolol pharmacokinetics". Clinical Pharmacology and Therapeutics. 94 (3): 394–399. doi:10.1038/clpt.2013.96. PMC 3818912. PMID 23665868.
  12. ^ Cite error: The named reference Lopressor: FDA-Approved Drugs was invoked but never defined (see the help page).
  13. ^ Carlsson B, ed. (1997). Technological systems and industrial dynamics. Dordrecht: Kluwer Academic. p. 106. ISBN 978-0792399728. Archived from the original on 3 March 2017.
  14. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 461. ISBN 978-3527607495.
  15. ^ 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. Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  16. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  17. ^ "Metoprolol Drug Usage Statistics, United States, 2013–2022". ClinCalc. Retrieved 30 August 2024.
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.