File:Metoprolol_chemical_structure.svg · Wikimedia Commons · See Wikimedia Commons
(RS)-metoprolol
Sign in to saveAlso known as CGP-2175C, GP-2175E, H-93/26, Lopressor®, Toprol®, Seloken, Lopresor
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. 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.
OverviewAI-generated
(RS)-metoprolol is a chemical compound with the formula C₁₅H₂₅NO₃. Its IUPAC name is 1-[4-(2-methoxyethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol. The substance has a molecular mass of 267.183444 and a weight of 267.36. It possesses a charge of 0, an xlogp value of 1.9, and a topological polar surface area of 50.7.
The molecule contains two hydrogen bond donors and four hydrogen bond acceptors. Its canonical SMILES notation is CC(C)NCC(COC1=CC=C(C=C1)CCOC)O. A search for (RS)-metoprolol in PubMed yields 9,531 results. The compound is referenced by 758 other encyclopedia articles.
Synthesized by Vinony from 17 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.O
- 3
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 459444186
- Drug.image
- Metoprolol structure.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Metoprolol_ball-and-stick.png
- Drug.image_class2
- bg-transparent
- Drug.chirality
- Racemic mixture
- Drug.pronounce
- ,
- Drug.tradename
- Lopressor (metoprolol tartrate), Toprol-XL (metoprolol succinate)
- Drug.MedlinePlus
- a682864
- Drug.DailyMedID
- Metoprolol
- Drug.pregnancy_AU
- C
- Drug.routes_of_administration
- By mouth, intravenous
- Drug.class
- Beta blocker
- Drug.ATC_prefix
- C07
- Drug.ATC_suffix
- AB02
- Drug.legal_AU
- S4
via Wikipedia infobox
Chemical data
- Formula
- C15H25NO3
- Molecular weight
- 267.36 g/mol
- IUPAC name
- 1-[4-(2-methoxyethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol
- SMILES
- CC(C)NCC(COC1=CC=C(C=C1)CCOC)O
- InChIKey
- IUBSYMUCCVWXPE-UHFFFAOYSA-N
- XLogP
- 1.9
- Polar surface area
- 50.7 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1978
- Admin. routes
- oral, parenteral
- Indications
- Beta-thalassemia, cardiovascular disease, atrial fibrillation, hypertension
via ChEMBL · EBI
Research
9,531 papers- Drug therapy: metoprolol.The New England journal of medicine · 1979
- Metoprolol overdose.Annals of emergency medicine · 1985
- Metoprolol overdose.Annals of emergency medicine · 1981
- Metoprolol (Lopressor).The Medical letter on drugs and therapeutics · 1978
- Understanding variation in metoprolol response: CYP2D6, drug interactions, and phenoconversion.Pharmacogenomics · 2025
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 267.183444
- Manufacturer
- Pfizer
- Has use
- medication
Show 9 more facts
- chemical formula
- C₁₅H₂₅NO₃
- subject has role
- essential medicine
- route of administration
- intravenous infusion and defusion
- Commons category
- Metoprolol
- medical condition treated
- ventricular tachycardia
- canonical SMILES
- CC(C)NCC(COC1=CC=C(C=C1)CCOC)O
- physically interacts with
- adrenoceptor beta 2
- found in taxon
- Carica papaya
- significant drug interaction
- lidocaine
via Wikidata · CC0
~11 min read
Encyclopedic overview
17 sectionsContents
- Medical uses
- Adverse effects
- Precautions
- Pregnancy and breastfeeding
- Overdose
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Chemistry
- Stereochemistry
- Formulations
- Society and culture
- Legal status
- Economics
- Sports
- References
- Further reading
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. 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.
Excerpted from Wikipedia’s “(RS)-metoprolol” article, available under the CC BY-SA 4.0 licence.