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Additional information about the drug Metoprolol

Metoprolol, marketed under the tradename Lopressor among others, is a medication of the selective β 1 receptor blocker type.
Metoprolol is sold in formulations that can be taken by mouth or given intravenously.
Common side effects include trouble sleeping, feeling tired, feeling faint, and abdominal discomfort.
Metoprolol was first made in 1969.
1 Medical uses
1.1 Available forms
2 Adverse effects
2.1 Precautions
2.2 Pregnancy and breastfeeding
3 Overdose
4 Pharmacology
4.1 Mechanism of action
4.2 Pharmacokinetics
5 Chemistry
5.1 Stereochemistry
6 History
7 Society and culture
8 Legal status
8.1 Legislation
8.2 In sport
8.3 Lawsuit
9 References
10 External links
Medical uses
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.
Treatment of heart failure
Vasovagal syncope
Adjunct in treatment of hyperthyroidism
Long QT syndrome, especially for patients with asthma, as metoprolol’s β1 selectivity tends to interfere less with asthma drugs, which are often β2-adrenergic receptor-agonist drugs
Prevention of relapse into atrial fibrillation (controlled-release/extended-release form)
Due to its selectivity in blocking the beta 1 receptors in the heart, metoprolol is also prescribed for off-label use in performance anxiety, social anxiety disorder, and other anxiety disorders.
Available forms
Metoprolol is sold in formulations that can be taken by mouth or given intravenously.
Adverse effects
Side effects, especially with higher doses, include dizziness, drowsiness, fatigue, diarrhea, unusual dreams, trouble sleeping, depression, and vision problems. Metoprolol may also reduce blood flow to the hands or feet, causing them to feel numb and cold; smoking may worsen this effect.
Serious side effects that are advised to be reported immediately include symptoms of bradycardia (resting heart rate slower than 60 beats per minute), persistent symptoms of dizziness, fainting and unusual fatigue, bluish discoloration of the fingers and toes, numbness/tingling/swelling of the hands or feet, sexual dysfunction, erectile dysfunction, hair loss, mental/mood changes, depression, breathing difficulty, cough, dyslipidemia and increased thirst. Consuming alcohol while taking metoprolol may cause mild body rashes and is not advised.
Metoprolol may worsen the symptoms of heart failure in some patients, who may experience chest pain or discomfort, dilated neck veins, extreme fatigue, irregular breathing, an irregular heartbeat, shortness of breath, swelling of the face, fingers, feet, or lower legs, weight gain, or wheezing.
This medicine may cause changes in blood sugar levels or cover up signs of low blood sugar, such as a rapid pulse rate.
Greater care is required with use in those with liver problems or asthma.
Pregnancy and breastfeeding
Risk for the fetus has not been ruled out, per being rated pregnancy category C in the United States.
Excessive doses of metoprolol can cause severe hypotension, bradycardia, metabolic acidosis, seizures, and cardiorespiratory arrest. Blood or plasma concentrations may be measured to confirm a diagnosis of overdose or poisoning in hospitalized patients or to assist in a medicolegal death investigation. Plasma levels are usually less than 200 μg/l during therapeutic administration, but can range from 1–20 mg/l in overdose victims.
General pharmacological principles of metoprolol:
beta-1 selective
moderately lipophilic
without intrinsic sympathomimetic activity
with weak membrane stabilizing activity
decreases heart rate, contractility, and cardiac output, therefore decreasing blood pressure
Mechanism of action
Metoprolol blocks β1 adrenergic receptors in heart muscle cells, thereby decreasing the slope of phase 4 in the nodal action potential (reducing Na + uptake) and prolonging repolarization of phase 3 (slowing down K + release).
Metoprolol has a short half-life of 3 to 7 hours, so is taken at least twice daily or as a slow-release preparation.
It undergoes α-hydroxylation and O-demethylation as a substrate of the cytochrome liver enzymes CYP2D6 and a small percentage by CYP3A4, resulting in inactive metabolites.
Metoprolol has a very low melting point; around 120 °C (248 °F) for the tartrate, and around 136 °C (277 °F) for the succinate. Because of this, metoprolol is always manufactured in a salt-based solution, as drugs with low melting points are difficult to work with in a manufacturing environment. The free base exists as a waxy white solid, and the tartrate salt is finer crystalline material.
The active substance metoprolol is employed either as metoprolol succinate or as metoprolol tartrate (where 100 mg metoprolol tartrate corresponds to 95 mg metoprolol succinate). The tartrate is an immediate-release formulation and the succinate is an extended-release formulation.
Metoprolol contains a stereocenter and consists of two enantiomers. This is a racemate, i.e. a 1:1 mixture of ( R )- and the ( S )-form:
Enantiomers of metoprolol
CAS-Nummer: 81024-43-3
CAS-Nummer: 81024-42-2
Metoprolol was first made in 1969.
Society and culture
Metoprolol is on the World Health Organization’s List of Essential Medicines, the most important medications needed in a basic health system.
Legal status
Within the UK metoprolol is classified as a prescription-only drug in the beta blocker class and is regulated by the Medicines and Healthcare Products Regulatory Agency (MHRA). The MHRA is a government body set up in 2003 and is responsible for regulating medicines, medical devices, and equipment used in healthcare. The MHRA acknowledges that no product is completely risk free but takes into account research and evidence to ensure that any risks associated are minimal.
The use of beta blockers such as metoprolol was approved in the US by the FDA (Food and Drug Administration) in 1967. The FDA has approved beta blockers for the treatment of cardiac arrhythmias, hypertension, migraines, and others. Prescribers may choose to prescribe beta blockers for other treatments if there is just cause even though it is not approved by the FDA. Drug manufacturers, however, are unable to advertise beta blockers for other purposes that have not been approved by the FDA. Since the FDA does not regulate the practice of medicine after the drug has been approved, it is legal to prescribe beta blockers for other treatments such as performance anxiety.
The MHRA granted the Intas Pharmaceuticals Limited Marketing Authorisation (licences) for metoprolol tartrate (50mg and 100mg tablets) for medicinal prescription only on September 23rd 2011; this was after it was established that there was no new or unexpected safety concerns and that the benefits of metoprolol tartrate were greater than the risks. Metoprolol tartrate is a generic version of Lopressor, which was licensed and authorised on June 6th 1997 to Novartis Pharmaceuticals.
In sport
Metoprolol is a beta blocker and is banned by the world anti-doping agency in some sports. Beta blockers can be used to reduce heart rate and minimize tremors, which can enhance performance in sports such as archery.
To detect if beta blockers have been used trace analysis of human urine is analysed. Uncharged drugs and/or metabolites of beta blockers can be analysed by gas-chromatography-mass spectrometry in selected ion monitoring (GC-MS-SIM). However, in modern times it is increasingly difficult to detect the presence of beta blockers used for sports doping purposes. A disadvantage to using GC-MS-SIM is that prior knowledge of the molecular structure of the target drugs/metabolites is required. Modern times have shown a variance in structures and hence novel beta blockers can go undetected.
In 2012, an $11 million settlement was reached with Toprol XL (time-release formula version of metoprolol) and its generic equivalent metoprolol. The lawsuit involved the pharmaceuticals companies AstraZeneca AB, AstraZeneca LP, AstraZeneca Pharmaceuticals LP, and Aktiebolaget Hassle. The claims of the lawsuit advise that the manufacturers violated antitrust and consumer protection law. Claiming that to increase profits, lower cost generic versions of Toprol XL were intentionally kept off the market. This claim was subsequently denied by the defendants.

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