| Identification | More | [Name]
Metoprolol tartrate | [CAS]
56392-17-7 | [Synonyms]
1-(isopropylamino)-3-(p-(2-methoxyethyl)phenoxy)-2-propanol (2:1) dextro-tartrate salt
1-[ISOPROPYLAMINO]-3-[P-(BETA-METHOXY-ETHYL)PHENOXY]-2-PROPANOL(+)-TARTRATE SALT
METOPROLOL TARTARIC ACID
METOPROLOL TARTRATE
(+/-)-METOPROLOL (+)-TARTRATE SALT
(+-)-1-(isopropylamino)-3-(p-(2-methoxyethyl)phenoxy)-2-propanolhemi-l-tartr
(+-)-1-(isopropylamino)-3-(p-(2-methoxyethyl)phenoxy)-2-propanoltartrate(2:
1-(4-(2-methoxyethyl)phenoxy)-3-((1-methylethyl)amino)-2-propano(+-)-2-propanot
1-(isopropylamino)-3-(p-(2-methoxyethyl)phenoxy)-2-propano(+-)-2-propanotartrate
artrate(2:1)
beloc
betaloc
h93/26
lopresor
lopressor
metoprololhemitartrate
metoprololtartrate(2:1)
seloken
slowlopresor
METOPROLOL TARTRATE CRYSTALLINE POWDER | [EINECS(EC#)]
260-148-9 | [Molecular Formula]
C19H31NO9 | [MDL Number]
MFCD00941460 | [Molecular Weight]
417.45 | [MOL File]
56392-17-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Powder | [Melting point ]
120℃ | [Boiling point ]
695.37°C (rough estimate) | [density ]
1.1946 (rough estimate) | [refractive index ]
1.5300 (estimate) | [Fp ]
9℃ | [storage temp. ]
2-8°C | [solubility ]
H2O: soluble50mg/mL | [form ]
powder | [color ]
white to off-white | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Water Solubility ]
Soluble in water (>1000 mg/ml), methanol (>500 mg/ml), chloroform (496 mg/ml), ethanol (31 mg/ml at 25°C), and DMSO (100 mg/ml at 25°C). | [Usage]
A ? selective aryloxypropanolamine andrenergic antagonist. Used in the treatment of a variety of cardiovascular disorder.
Antihypertensive; antianginal; antiarrhythmic (class II) | [λmax]
223nm(H2O)(lit.) | [Merck ]
14,6151 | [BCS Class]
1 | [CAS DataBase Reference]
56392-17-7(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
Metoprolol (tartrate) (Item No. 21165) is an analytical reference standard categorized as a β1-adrenergic receptor blocker.1 This product is intended for use in analytical forensic applications. Metoprolol (succinate) is available as a general research tool (Item No. 15429). | [Chemical Properties]
White or almost white, crystalline powder or colourless crystals. | [Originator]
Betaloc,Astra,UK,1975 | [Manufacturing Process]
The starting material 1,2-epoxy-3-[p-(β-methoxyethyl)phenoxy]-propane was
obtained from p-(β-methoxyethyl)-phenol which was reacted with
epichlorohydrin whereafter the reaction product was distilled at 118°C to
128°C at a pressure of 0.35mm Hg.
1,2-Epoxy-3-[p-(β-methoxyethyl)-phenoxy]-propane (16.7g) was dissolved in
50 ml isopropanol and mixed with 20 ml isopropylamine. The mixture was
heated in an autoclave on boiling water-bath overnight, whereafter it was
evaporated and the remainder dissolved in 2 N HCI. The solution was
extracted first with ether and thereafter with methylene chloride. After
evaporating the methylene chloride phase, the hydrochloride of 1-
isopropylamino-3-[p(β-methoxyethyl)-phenoxy] -propanol-2 was obtained
which, after recrystallization from ethyl acetate, weighed 10.4 g. Melting point
83°C. Equivalent weight: found 304.0, calculated 303.8.
The hydrochloride is then converted to the tartrate. | [Brand name]
Lopressor (Novartis). | [Therapeutic Function]
Beta-adrenergic blocker | [General Description]
A certified solution standard applicable for use in clinical toxicology or forensic analysis by LC-MS/MS or GC/MS. Metoprolol is used for the treatment of multiple heart conditions including hypertension, angina, and tachycardia. This beta blocker is sold under the trade names Lepressor and Toprol XL?. | [Biological Activity]
Selective β 1 -adrenoceptor antagonist (K i values are 47, 2960 and 10100 nM for β 1 , β 2 and β 3 adrenoceptors respectively). Inhibits spontaneous endothelin-1 production in vitro and displays antihypertensive and antianginal activity in vivo . | [Clinical Use]
Beta-adrenoceptor blocker:
Hypertension
Angina
Cardiac arrhythmias
Migraine prophylaxis
Hyperthyroidism | [Veterinary Drugs and Treatments]
Because metoprolol is relatively safe to use in animals with bronchospastic
disease,
it is often chosen over propranolol. It may be effective
in supraventricular tachyarrhythmias, premature ventricular
contractions (PVC’s, VPC’s), systemic hypertension, and treating
cats with hypertrophic cardiomyopathy. There is increasing interest
in using beta blockers in heart failure in dogs; one retrospective
study showed increased survival times when dogs were given
metoprolol, but definitive prospective, double-blinded studies have
not been reported documenting the benefit (increased survival) of
beta-blockers in dogs with heart failure. | [Drug interactions]
Potentially hazardous interactions with other drugs
Anaesthetics: enhanced hypotensive effect.
Analgesics: NSAIDs antagonise hypotensive effect.
Anti-arrhythmics: increased risk of myocardial
depression and bradycardia; increased risk of
bradycardia, myocardial depression and AV block
with amiodarone; increased risk of myocardial
depression and bradycardia with flecainide;
concentration increased by propafenone and
dronedarone.
Antibacterials: concentration reduced by rifampicin.
Antidepressants: enhanced hypotensive effect with
MAOIs; concentration increased by citalopram and
escitalopram and possibly by paroxetine - avoid.
Antihypertensives; enhanced hypotensive effect;
increased risk of withdrawal hypertension with
clonidine; increased risk of first dose hypotensive
effect with post-synaptic alpha-blockers such as
prazosin.
Antimalarials: increased risk of bradycardia with
mefloquine; avoid with artemether/lumefantrine.
Antipsychotics enhanced hypotensive effect with
phenothiazines.
Antivirals: avoid concomitant use with tipranavir in
heart failure.
Calcium-channel blockers: increased risk of
bradycardia and AV block with diltiazem;
hypotension and heart failure possible with
nifedipine and nisoldipine; asystole, severe
hypotension and heart failure with verapamil.
Cytotoxics: possible increased risk of bradycardia
with crizotinib.
Diuretics: enhanced hypotensive effect.
Fingolimod: possibly increased risk of bradycardia.
Moxisylyte: possible severe postural hypotension. | [Metabolism]
Extensively metabolised in the liver, mainly by the
cytochrome P450 isoenzyme CYP2D6, and undergoes
oxidative deamination, O-dealkylation followed by
oxidation, and aliphatic hydroxylation.
The metabolites are excreted in the urine with only small
amounts of unchanged metoprolol. | [storage]
Desiccate at RT |
| Questions And Answer | Back Directory | [β1 receptor blocker]
Metoprolol tartrate is a selective β1-adrenergic receptor blocker,oral absorption is rapid and complete,it is used for the treatment of hypertension, angina pectoris, myocardial infarction, hypertrophic cardiomyopathy, aortic dissection, cardiac arrhythmia, hyperthyroidism, cardiac neurosis and other diseases. In recent years, it is also used for ther treatment of heart failure, which can reduce mortality. In unstable/non-ST-segment elevation myocardial infarction and acute myocardial infarction control guiding principles developed by American Heart Association , effect of metoprolol tartrateare is clearly recognized. In the past, concerns about β-blocker therapy caused hypotension is too large, and for the consideration that there may be racial differences between Asians in β-blocker use and the West, patients with treatment of β-blockers in China is fewer , the use of β-blockers is in lower dose.
Metoprolol tartrate has a weaker membrane stability and it has no intrinsic sympathomimetic activity, and in comparison with similar drugs commonly used in clinical propranolol ,in addition to the advantages of β1-blocker on its pharmacodynamic,it also has its pharmacokinetic kinetics advantages, such as relatively weak first-pass effect compared with propranolol, simple metabolic pathways, most pharmacologically inactive metabolites and the like. | [Uses]
Hypertensive medication.
| [Hazards & Safety Information]
Category: toxic substances
Toxicity grading: Middle poisoning
Acute toxicity: oral -rat LD50: 5500 mg/kg; Oral-Mouse LD50: 1500 mg/kg
Flammability and hazard characteristics: It is combustible; fire decomposition produces toxic nitrogen oxide gases
Storage Characteristics: Ventilated, low-temperature ,dry storeroom.
Extinguishing agent: Water, carbon dioxide, dry powder, sandy soil. |
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