Metoprolol

Metoprolol
Clinical data
Pronunciation/mɛˈtprlɑːl/ , /mɛtˈprlɑːl/
Trade namesLopressor, others
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
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability50% (single dose)
70% (repeated administration)
Protein binding12%
MetabolismLiver via CYP2D6, CYP3A4
Elimination half-life3–7 hours
ExcretionKidney
Identifiers
  • (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)
  • O(c1ccc(cc1)CCOC)CC(O)CNC(C)C
  • 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 name Lopressor among others, is a medication used to treat angina, high blood pressure 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 a beta blocker, specifically a selective β1 receptor blocker, and is taken by mouth or is given intravenously.

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. The metabolism of metoprolol can vary widely among patients, often as a result of hepatic impairment or CYP2D6 polymorphism.

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