Metoprolol

Metoprolol
Clinical data
Pronunciation	/mɛˈtoʊproʊlɑːl/, /mɛtoʊˈproʊlɑːl/
Trade names	Lopressor, Metolar XR, Toprol XL, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682864
License data	US DailyMed: Metoprolol;
Pregnancy; category	AU: C; ;
Routes of; administration	By mouth, intravenous
Drug class	Beta blocker
ATC code	C07AB02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	50% (single dose); 70% (repeated administration)
Protein binding	12%
Metabolism	Liver via CYP2D6, CYP3A4
Elimination half-life	3–7 hours
Excretion	Kidney
Identifiers
	IUPAC name (RS)-1-[4-(2-Methoxyethyl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol;
CAS Number	51384-51-1 ;
PubChem CID	4171;
IUPHAR/BPS	553;
DrugBank	DB00264 ;
ChemSpider	4027 ;
UNII	GEB06NHM23;
KEGG	D02358 ;
ChEBI	CHEBI:6904 ;
ChEMBL	ChEMBL13 ;
CompTox Dashboard (EPA)	DTXSID2023309 ;
ECHA InfoCard	100.051.952
Chemical and physical data
Formula	C15H25NO3
Molar mass	267.369 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
Melting point	120 °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 ; Key:IUBSYMUCCVWXPE-UHFFFAOYSA-N ;
	(verify)

Metoprolol, sold under the brand name Lopressor among others, is a medication used to treat high blood pressure, angina, and a number of conditions involving an abnormally fast heart rate.^[4] It is also used to prevent further heart problems after myocardial infarction and to prevent headaches in those with migraines.^[4] It is a selective β₁ receptor blocker medication.^[4] It is taken by mouth or is given intravenously.^[4]

Common side effects include trouble sleeping, feeling tired, feeling faint, and abdominal discomfort.^[4] Large doses may cause serious toxicity.^[5]^[6] Risk in pregnancy has not been ruled out.^[4]^[7] It appears to be safe in breastfeeding.^[8] The metabolism of metoprolol can vary widely among patients, often as a result of hepatic impairment^[9] or CYP2D6 polymorphism.^[10]

Metoprolol was first made in 1969, patented in 1970, and approved for medical use in 1978.^[11]^[12]^[13] It is on the World Health Organization's List of Essential Medicines.^[14] It is available as a generic medication.^[4] In 2021, it was the sixth most commonly prescribed medication in the United States, with more than 65 million prescriptions.^[15]^[16]

^ "Lopressor Product information". Health Canada. 22 October 2009. Retrieved 20 June 2023.
^ "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.
^ Jasek W, ed. (2007). Austria-Codex (in German) (62nd ed.). Vienna: Österreichischer Apothekerverlag. pp. 916–919. ISBN 978-3852001814.
^ ^a ^b ^c ^d ^e ^f ^g "Metoprolol". The American Society of Health-System Pharmacists. Archived from the original on 12 March 2014. Retrieved 21 April 2014.
^ 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.
^ Marx JA (2014). "Chapter 152: Cardiovascular Drugs". Rosen's emergency medicine : concepts and clinical practice (8th ed.). Philadelphia, PA: Elsevier/Saunders. ISBN 978-1455706051.
^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
^ Medical Toxicology. Lippincott Williams & Wilkins. 2004. p. 684. ISBN 978-0781728454. Archived from the original on 7 July 2017.
^ 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.
^ 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): 394–9. doi:10.1038/clpt.2013.96. PMC 3818912. PMID 23665868.
^ Cite error: The named reference Lopressor: FDA-Approved Drugs was invoked but never defined (see the help page).
^ 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.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 461. ISBN 978-3527607495.
^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
^ "Metoprolol – Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

[1] "Lopressor Product information". Health Canada. 22 October 2009. Retrieved 20 June 2023.

[2] "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.

[Austria-Codex-3] Jasek W, ed. (2007). Austria-Codex (in German) (62nd ed.). Vienna: Österreichischer Apothekerverlag. pp. 916–919. ISBN 978-3852001814.

[AHFS2014-4] ^ ^a ^b ^c ^d ^e ^f ^g "Metoprolol". The American Society of Health-System Pharmacists. Archived from the original on 12 March 2014. Retrieved 21 April 2014.

[5] 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.

[Rosen2014-6] Marx JA (2014). "Chapter 152: Cardiovascular Drugs". Rosen's emergency medicine : concepts and clinical practice (8th ed.). Philadelphia, PA: Elsevier/Saunders. ISBN 978-1455706051.

[Australian_Government-7] "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.

[Medical_Toxicology-8] Medical Toxicology. Lippincott Williams & Wilkins. 2004. p. 684. ISBN 978-0781728454. Archived from the original on 7 July 2017.

[pmid7333059-9] 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.

[pmid23665868-10] 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): 394–9. doi:10.1038/clpt.2013.96. PMC 3818912. PMID 23665868.

[Lopressor:_FDA-Approved_Drugs-11] Cite error: The named reference Lopressor: FDA-Approved Drugs was invoked but never defined (see the help page).

[Kluwer_Academic-12] 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.

[13] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 461. ISBN 978-3527607495.

[WHO22nd-14] World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.

[15] "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.

[16] "Metoprolol – Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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