出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/25 11:36:31」(JST)
| Systematic (IUPAC) name | |
|---|---|
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(RS)-1-(Isopropylamino)-3-[4-(2-methoxyethyl)phenoxy]propan-2-ol
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| Clinical data | |
| Pronunciation | /mɛˈtoʊproʊlɑːl/, /mɛtoʊˈproʊlɑːl/ |
| Trade names | Lopressor, Metolar XR |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a682864 |
| Licence data | US FDA:link |
| Pregnancy category |
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| Legal status |
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| Routes of administration |
Oral, IV |
| Pharmacokinetic data | |
| Bioavailability | 50%[1] |
| Protein binding | 12% |
| Metabolism | Liver via CYP2D6, CYP3A4 |
| Biological half-life | 3-7 hours |
| Excretion | Kidney |
| Identifiers | |
| CAS Number | 51384-51-1 Y |
| ATC code | C07AB02 |
| PubChem | CID: 4171 |
| IUPHAR/BPS | 553 |
| DrugBank | DB00264 Y |
| ChemSpider | 4027 Y |
| UNII | GEB06NHM23 Y |
| KEGG | D02358 Y |
| ChEBI | CHEBI:6904 Y |
| ChEMBL | CHEMBL13 Y |
| Chemical data | |
| Formula | C15H25NO3 |
| Molecular mass | 267.364 g/mol |
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SMILES
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InChI
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| Physical data | |
| Melting point | 120 °C (248 °F) |
| (verify) | |
Metoprolol, marketed under the tradename Lopressor among others, is a selective β1 receptor blocker medication.[2] 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.[2]
It comes in formulations that can be taken by mouth or given intravenously. The medication is often taken twice a day. There is an extended release formulation that is once per day. Metoprolol may be combined with hydrochlorothiazide in a single tablet.[2]
Common side effects include trouble sleeping, feeling tired, feeling faint, and abdominal discomfort.[2] Large doses may cause serious toxicity.[3][4] Risk in pregnancy has not been ruled out.[2][5] It appears to be safe in breastfeeding.[6] Greater care is required with use in those with liver problems or asthma.[2] If stopped this should be done slowly to decrease the risk of further health problems.[2]
Metoprolol was first made in 1969.[7] It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.[8] It is available as a generic drug.[2] In 2013, metoprolol was the 19th most prescribed medication in the United States.[9]
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.[10]
Due to its selectivity in blocking the beta1 receptors in the heart, metoprolol is also prescribed for off-label use in performance anxiety, social anxiety disorder, and other anxiety disorders.
Side effects, especially with higher doses, include dizziness, drowsiness, fatigue, diarrhea, unusual dreams, ataxia, trouble sleeping, depression, and vision problems. It may also reduce blood flow to the hands and feet, causing them to feel numb and cold; smoking may worsen this effect.[16] Due to the high penetration across the blood-brain barrier, lipophilic beta blockers such as propranolol and metoprolol are more likely than other less lipophilic beta blockers to cause sleep disturbances such as insomnia and vivid dreams and nightmares.[17]
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 (impotence), hair loss, mental/mood changes, depression, trouble breathing, cough, dyslipidemia, and increased thirst. Taking it with alcohol might cause mild body rashes, so is not recommended.[16]
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.[18]
This medicine may cause changes in blood sugar levels or cover up signs of low blood sugar, such as a rapid pulse rate.[18] It also may cause some people to become less alert than they are normally, making it dangerous for them to drive or use machines.[18]
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.[19][20][21]
It is pregnancy category C in the United States and category C in Australia, meaning evidence of harm is possible.[2][5]
Metoprolol has a very low melting point, the tartrate's is around 120 °C (248 °F), and the succinate's around 136 °C (277 °F). 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.[22]
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 and the succinate is an extended-release formulation.[23]
Metoprolol undergoes a-hydroxylation and O-demethylation as a substrate of the cytochrome liver enzymes CYP2D6[24][25] and a small percentage by CYP3A4.
It is marketed under the brand name Lopressor by Novartis, and Toprol-XL (in the USA); Selokeen (in the Netherlands); as Minax by Alphapharm and Metrol by Arrow Pharmaceuticals (in Australia), as Betaloc by AstraZeneca, as Bloxan by Krka (company) (in Slovenia), as Neobloc by Unipharm (in Israel), Presolol by Hemofarm (in Serbia), and Corvitol by Berlin-Chemie AG (in Germany). In India, this drug is available under the brand names Met-XL, Metolar, Starpress, and Restopress. A number of generic products are available, as well.
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| リンク元 | 「メトプロロール」「metoprolol fumarate」「metoprolol succinate」 |
| 関連記事 | 「tartrate」 |