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Encyclopedia > Metoprolol
Systematic (IUPAC) name
CAS number 37350-58-6
ATC code C07AB02
PubChem 4171
DrugBank APRD00208
Chemical data
Formula C15H25NO3 
Mol. mass 267.364 g/mol
Pharmacokinetic data
Bioavailability 12%
Metabolism Hepatic
Half life 3-7 hours
Excretion Renal
Therapeutic considerations
Pregnancy cat.

C(AU) C(US) Image File history File links No higher resolution available. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... This article or section does not cite any references or sources. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... BIC pen cap, about 1 gram. ... The mole (symbol: mol) is the SI base unit that measures an amount of substance. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ present in vertebrates and some other animals. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... The kidneys filter wastes (such as urea) from the blood and excrete them, along with water, as urine. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... Anthem Advance Australia Fair Royal anthem: God Save the Queen Capital Canberra Largest city Sydney Official languages English (de facto 1) Government Federal constitutional monarchy and parliamentary democracy  -  Queen Elizabeth II  -  Governor-General Michael Jeffery  -  Prime Minister John Howard Independence from the United Kingdom   -  Constitution 1 January 1901   -  Statute of... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Legal status

Prescription only The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...

Routes oral iv

Metoprolol is a selective beta1 receptor blocker used in treatment of several diseases of the cardiovascular system, especially hypertension. It is marketed under the brand name Lopressor by Novartis, and Toprol-XL (in the USA); Seleken or Selokeen (elsewhere); as Minax by Alphapharm (in Australia), as Betaloc by AstraZeneca and as Corvitol by Berlin-Chemie AG. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... Spoiler warning: Minax was a fictional evil enchantress in the second Ultima game and one of its main villains. ... Beta blockers or beta-adrenergic blocking agents are a class of drugs used to treat a variety of cardiovascular conditions and some other diseases. ... Novartis Suffern Yes plant is the Swiss companys sole pharmaceutical production facility in the U.S. Novartis International AG is a multinational pharmaceutical company based in Basel, Switzerland that manufactures mainstream products such as Benefiber (a fiber supplement) and Lamisil (a foot fungus medicine). ... // Company Overview Alpharma is a producer of specialty antibiotics, animal health feed additives for poultry and livestock, and vaccines for farmed fish. ... AstraZeneca PLC (LSE: AZN, NYSE: AZN), is a large Anglo-Swedish pharmaceutical company formed on 6 April 1999 by the merger of Swedish Astra AB and British Zeneca Group. ...

It should be noted that Lopressor refers to metoprolol tartrate, while Toprol-XL refers to metoprolol succinate, the sustained release formulation. A tartrate is a salt or ester of the organic compound tartaric acid, a dicarboxylic acid. ... Succinic acid, originally called spirit of amber, is a carboxylic acid with the formula: HOOC-CH2-CH2-COOH At room temperature, pure succinic acid is a solid that forms colorless, odorless prisms. ... Sustained-release (SR), extended-release (ER, XR, or XL), time-release or timed-release, controlled-release (CR), or continuous-release (CR or Contin) pills are tablets or capsules formulated to dissolve slowly and release a drug over time. ...


Physical properties

Metoprolol is very low melting. Its melting point is around 45 degrees Celsius (as determined by Differential scanning calorimetry). For this reason metoprolol is always manufactured in salt form, as drugs with melting points below 100 degrees Celsius are difficult to work with in a manufacturing environment. The free base exists as a waxy white solid, where the tartrate salt is finer crystalline material. Differential scanning calorimetry (DSC) is a thermoanalytical technique in which the difference in the amount of heat required to increase the temperature of a sample and reference are measured as a function of temperature. ...


  • Cardioselective
  • Lipophilic
  • Without intrinsic sympathomimetic activity (ISA)
  • Without membrane stabilizing activity
  • Short half-life must be taken at least twice daily or as an SR preparation.

This article or section does not cite its references or sources. ... Sympathomimetics are a class of drugs whose properties mimic those of a stimulated sympathetic nervous system. ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ...


Essential hypertension is a subtype of arterial hypertension in which no one specific etiology can be isolated as the cause of increased blood pressure. ... This article or section does not adequately cite its references or sources. ... The latin word angina refers to a painful constriction or tightness somewhere in the body. ... Acute myocardial infarction (AMI or MI), commonly known as a heart attack, is a disease state that occurs when the blood supply to a part of the heart is interrupted. ... Prophylaxis refers to any medical or public health procedure whose purpose is to prevent, rather than treat or cure, disease. ... Hyperthyroidism (or overactive thyroid gland) is the clinical syndrome caused by an excess of circulating free thyroxine (T4) or free triiodothyronine (T3), or both. ...

Side effects

Transient effects include dizziness, lightheadedness, drowsiness, tiredness, diarrhea, unusual dreams, ataxia, trouble sleeping, and vision problems. If negative symptoms become worse or are persistent, then they may be a sign of something more serious. This drug may reduce blood flow to the hands and feet, causing them to feel cold. Smoking may worsen this effect. Ataxia (from Greek ataxiā, meaning failure to put in order) is unsteady and clumsy motion of the limbs or torso due to a failure of the gross coordination of muscle movements. ...

Serious but unlikely side effects that are not to be tolerated for any length of time include: symptoms of a very slow heartbeat (e.g.,persistent dizziness, fainting, unusual fatigue), bluish discoloration of the fingers and toes(which means that there is not enough oxygen going to the extremeties), numbness/tingling/swelling of the hands or feet, decreased sexual ability, reversible hair loss, mental/mood changes, trouble breathing, cough, unexplained or sudden weight gain, increased thirst, increased urination. Even more highly unlikely are: easy bruising or bleeding, persistent sore throat or fever, yellowing skin or eyes, stomach pain, dark urine, persistent nausea. Symptoms of an allergic reaction include: rash, itching, swelling, severe dizziness.


  1. ^ (June 12 1999) "Effect of metoprolol CR/XL in chronic heart failure: Metoprolol CR/XL Randomised Intervention Trial in Congestive Heart Failure (MERIT-HF)". Lancet 353 (9169): 2001-7. PMID 10376614. 

External links

  • AstraZeneca's page for Toprol-XL®
  • Links to external chemical sources

  Results from FactBites:
Parkinsn's List Drug DataBase metoprolol / Lopressor,Topro-XL (2697 words)
Metoprolol is widely distributed throughout the body, crosses the blood-brain barrier and the placenta, and is concentrated in breast milk.
Metoprolol should be used with caution in patients with diabetes mellitus because the drug can mask symptoms of hypoglycemia such as tachycardia, palpitations, blood pressure changes, tremor, and anxiety.
Metoprolol is relatively contraindicated in severe hepatic disease because of possible decreased clearance of the drug, since it is principally metabolized by the liver.
  More results at FactBites »



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