Metoprolol

Metoprolol

Clinical data
Pronunciation	/mɛˈtoʊproʊlɑːl/, /mɛtoʊˈproʊlɑːl/
Trade names	Lopressor, Metolar XR
AHFS/Drugs.com	Monograph
MedlinePlus	a682864
License data	US FDA: Metoprolol
Pregnancy category	AU: C US: C (Risk not ruled out)
Routes of administration	By mouth, IV
ATC code	C07AB02 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	50% (single dose) 70% (repeated administration)
Protein binding	12%
Metabolism	Liver via CYP2D6, CYP3A4
Biological half-life	3–7 hours
Excretion	Kidney
Identifiers
IUPAC name (RS)-1-(Isopropylamino)-3-[4-(2-methoxyethyl)phenoxy]propan-2-ol
CAS Number	51384-51-1 Y
PubChem CID	4171
IUPHAR/BPS	553
DrugBank	DB00264 Y
ChemSpider	4027 Y
UNII	GEB06NHM23
KEGG	D02358 Y
ChEBI	CHEBI:6904 Y
ChEMBL	CHEMBL13 Y
ECHA InfoCard	100.048.603
Chemical and physical data
Formula	C15H25NO3
Molar mass	267.364 g/mol
3D model (Jmol)	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 Y Key:IUBSYMUCCVWXPE-UHFFFAOYSA-N Y

50% (single dose)

Metoprolol, marketed under the tradename Lopressor among others, is a selective β₁ receptor blocker medication. It is used to treat high blood pressure, chest pain due to poor blood flow to the heart, and a number of conditions involving an abnormally fast heart rate. It is also used to prevent further heart problems after myocardial infarction and to prevent headaches in those with migraines.

It is sold in formulations that can be taken by mouth or given intravenously. The medication is often taken twice a day. The extended-release formulation is take once per day. Metoprolol may be combined with hydrochlorothiazide in a single tablet.

Common side effects include trouble sleeping, feeling tired, feeling faint, and abdominal discomfort. Large doses may cause serious toxicity. Risk in pregnancy has not been ruled out. It appears to be safe in breastfeeding. Greater care is required with use in those with liver problems or asthma. Stopping this drug should be done slowly to decrease the risk of further health problems.

Metoprolol was first made in 1969. It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system. It is available as a generic drug. In 2013, metoprolol was the 19th-most prescribed medication in the United States.

Metoprolol is used for a number of conditions, including hypertension, angina, acute myocardial infarction, supraventricular tachycardia, ventricular tachycardia, congestive heart failure, and prevention of migraine headaches.