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Namespace Prefixes

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Statements

Subject Item
n2:DB00264
rdf:type
n3:Drug
n3:description
Metoprolol is a cardioselective β1-adrenergic blocking agent used for acute myocardial infarction (MI), heart failure, angina pectoris and mild to moderate hypertension. It may also be used for supraventricular and tachyarrhythmias and prophylaxis for migraine headaches. Metoprolol is structurally similar to bisoprolol, acebutolol and atenolol in that it has two substituents in the <i>para</i> position of the benzene ring. The β1-selectivity of these agents is thought to be due in part to the large substituents in the <i>para</i> position. At low doses, metoprolol selectively blocks cardiac β1-adrenergic receptors with little activity against β2-adrenergic receptors of the lungs and vascular smooth muscle. Receptor selectivity decreases with higher doses. Unlike propranolol and pindolol, metoprolol does not exhibit membrane-stabilizing or intrinsic sympathomimetic activity. Membrane-stabilizing effects are only observed at doses much higher than those needed for β-adrenergic blocking activity. Metoprolol possesses a single chiral centre and is administered as a racemic mixture.
n3:dosage
n4:271B4333-363D-11E5-9242-09173F13E4C5 n4:271B4334-363D-11E5-9242-09173F13E4C5 n4:271B4335-363D-11E5-9242-09173F13E4C5 n4:271B4336-363D-11E5-9242-09173F13E4C5 n4:271B432F-363D-11E5-9242-09173F13E4C5 n4:271B4330-363D-11E5-9242-09173F13E4C5 n4:271B4331-363D-11E5-9242-09173F13E4C5 n4:271B4332-363D-11E5-9242-09173F13E4C5 n4:271B433B-363D-11E5-9242-09173F13E4C5 n4:271B433C-363D-11E5-9242-09173F13E4C5 n4:271B433D-363D-11E5-9242-09173F13E4C5 n4:271B433E-363D-11E5-9242-09173F13E4C5 n4:271B4337-363D-11E5-9242-09173F13E4C5 n4:271B4338-363D-11E5-9242-09173F13E4C5 n4:271B4339-363D-11E5-9242-09173F13E4C5 n4:271B433A-363D-11E5-9242-09173F13E4C5 n4:271B4325-363D-11E5-9242-09173F13E4C5 n4:271B4326-363D-11E5-9242-09173F13E4C5 n4:271B432B-363D-11E5-9242-09173F13E4C5 n4:271B432C-363D-11E5-9242-09173F13E4C5 n4:271B432D-363D-11E5-9242-09173F13E4C5 n4:271B432E-363D-11E5-9242-09173F13E4C5 n4:271B4327-363D-11E5-9242-09173F13E4C5 n4:271B4328-363D-11E5-9242-09173F13E4C5 n4:271B4329-363D-11E5-9242-09173F13E4C5 n4:271B432A-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# : Effect of metoprolol CR/XL in chronic heart failure: Metoprolol CR/XL Randomised Intervention Trial in Congestive Heart Failure (MERIT-HF) Lancet. 1999 Jun 12;353(9169):2001-7. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/10376614
n3:group
approved investigational
n3:halfLife
3-7 hours
n3:indication
For the management of acute myocardial infarction, angina pectoris, heart failure and mild to moderate hypertension. May be used to treat supraventricular and tachyarrhythmias and as prophylaxis for migraine headaches.
n3:manufacturer
n5:271B42D6-363D-11E5-9242-09173F13E4C5 n5:271B42D7-363D-11E5-9242-09173F13E4C5 n5:271B42D5-363D-11E5-9242-09173F13E4C5 n5:271B42DA-363D-11E5-9242-09173F13E4C5 n5:271B42DB-363D-11E5-9242-09173F13E4C5 n5:271B42D8-363D-11E5-9242-09173F13E4C5 n5:271B42D9-363D-11E5-9242-09173F13E4C5 n5:271B42DE-363D-11E5-9242-09173F13E4C5 n5:271B42DF-363D-11E5-9242-09173F13E4C5 n5:271B42DC-363D-11E5-9242-09173F13E4C5 n5:271B42DD-363D-11E5-9242-09173F13E4C5 n5:271B42E2-363D-11E5-9242-09173F13E4C5 n5:271B42E3-363D-11E5-9242-09173F13E4C5 n5:271B42E0-363D-11E5-9242-09173F13E4C5 n5:271B42E1-363D-11E5-9242-09173F13E4C5 n5:271B42E6-363D-11E5-9242-09173F13E4C5 n5:271B42E7-363D-11E5-9242-09173F13E4C5 n5:271B42E4-363D-11E5-9242-09173F13E4C5 n5:271B42E5-363D-11E5-9242-09173F13E4C5 n5:271B42EA-363D-11E5-9242-09173F13E4C5 n5:271B42EB-363D-11E5-9242-09173F13E4C5 n5:271B42E8-363D-11E5-9242-09173F13E4C5 n5:271B42E9-363D-11E5-9242-09173F13E4C5
owl:sameAs
n27:DB00264 n29:DB00264
dcterms:title
Metoprolol
adms:identifier
n9:6904 n10:4027 n11:25756 n12:553 n13:553 n14:DB00264 n15:58177-293-04 n17:4171 n18:C07202 n19:D02358 n20:46506211 n24:PA450480 n25:Metoprolol
n3:mechanismOfAction
Metoprolol competes with adrenergic neurotransmitters such as catecholamines for binding at beta(1)-adrenergic receptors in the heart. Beta(1)-receptor blockade results in a decrease in heart rate, cardiac output, and blood pressure.
n3:packager
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n3:routeOfElimination
Less than 5% of an oral dose of metoprolol is recovered unchanged in the urine; the rest is excreted by the kidneys as metabolites that appear to have no beta-blocking activity.
n3:synonym
(RS)-Metoprolol 1-(isopropylamino)-3-[4-(2-methoxyethyl)phenoxy]propan-2-ol Metoprolol
n3:toxicity
LD<sub>50</sub>=5500 mg/kg (orally in rats), toxic effects include bradycardia, hypotension, bronchospasm, and cardiac failure. LD<sub>50</sub>=2090 mg/kg (orally in mice)
n30:hasAHFSCode
n32:24-24-00
n3:foodInteraction
Take with food. Avoid natural licorice. Avoid alcohol.
n3:proteinBinding
12%
n3:salt
n3:synthesisReference
"DrugSyn.org":http://www.drugsyn.org/Metoprolol.htm
n21:hasConcept
n22:M0013686
foaf:page
n7:metoprolol.html n23:metopxl.htm
n3:IUPAC-Name
n16:271B4343-363D-11E5-9242-09173F13E4C5
n3:InChI
n16:271B4349-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n16:271B4348-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n16:271B4345-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n16:271B4346-363D-11E5-9242-09173F13E4C5
n3:SMILES
n16:271B4347-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n16:271B4359-363D-11E5-9242-09173F13E4C5 n16:271B4341-363D-11E5-9242-09173F13E4C5
n3:logP
n16:271B435B-363D-11E5-9242-09173F13E4C5 n16:271B4342-363D-11E5-9242-09173F13E4C5 n16:271B433F-363D-11E5-9242-09173F13E4C5
n3:logS
n16:271B4340-363D-11E5-9242-09173F13E4C5
n30:hasATCCode
n31:C07AB02
n3:H-Bond-Acceptor-Count
n16:271B434F-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n16:271B4350-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n16:271B434A-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n16:271B434B-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n16:271B434D-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n16:271B434C-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n16:271B434E-363D-11E5-9242-09173F13E4C5
n3:absorption
Rapid and complete, 50%
n3:affectedOrganism
Humans and other mammals
n3:caco2-Permeability
n16:271B435C-363D-11E5-9242-09173F13E4C5
n3:casRegistryNumber
37350-58-6
n3:category
n3:containedIn
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n3:Bioavailability
n16:271B4355-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n16:271B4357-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n16:271B4358-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n16:271B435A-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n16:271B4354-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n16:271B4353-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n16:271B4356-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n16:271B4344-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n16:271B4351-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n16:271B4352-363D-11E5-9242-09173F13E4C5