Tìm theo
Metoprolol
Các tên gọi khác (3) :
  • (RS)-Metoprolol
  • 1-(isopropylamino)-3-[4-(2-methoxyethyl)phenoxy]propan-2-ol
  • Metoprolol
Thuốc tim mạch
Thuốc Gốc
Small Molecule
CAS: 37350-58-6
ATC: C07AB02, C07AB52
ĐG : Advanced Pharmaceutical Services Inc.
CTHH: C15H25NO3
PTK: 267.3639
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 para position of the benzene ring. The β1-selectivity of these agents is thought to be due in part to the large substituents in the para 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.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C15H25NO3
Phân tử khối
267.3639
Monoisotopic mass
267.183443671
InChI
InChI=1S/C15H25NO3/c1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3/h4-7,12,14,16-17H,8-11H2,1-3H3
InChI Key
InChIKey=IUBSYMUCCVWXPE-UHFFFAOYSA-N
IUPAC Name
{2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl}(propan-2-yl)amine
Traditional IUPAC Name
metoprolol
SMILES
COCCC1=CC=C(OCC(O)CNC(C)C)C=C1
Độ tan chảy
120 °C (tartarate salt)
Độ hòa tan
1.69E+004 mg/L (at 25 °C)
logP
1.88
logS
-2.8
pKa (strongest acidic)
14.09
pKa (Strongest Basic)
9.67
PSA
50.72 Å2
Refractivity
76.7 m3·mol-1
Polarizability
31.9 Å3
Rotatable Bond Count
9
H Bond Acceptor Count
4
H Bond Donor Count
2
Physiological Charge
1
Number of Rings
1
Bioavailability
1
Rule of Five
true
Ghose Filter
true
caco2 Permeability
-4.59
Dược Lực Học : Metoprolol, a competitive, beta1-selective (cardioselective) adrenergic antagonist, is similar to atenolol in its moderate lipid solubility, lack of intrinsic sympathomimetic activity (ISA), and weak membrane stabilizing activity (MSA).
Cơ Chế Tác Dụng : 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 para position of the benzene ring. The β1-selectivity of these agents is thought to be due in part to the large substituents in the para 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. 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.
Dược Động Học :
▧ Absorption :
Rapid and complete, 50%
▧ Protein binding :
12%
▧ Metabolism :
Primarily hepatic
▧ Route of Elimination :
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.
▧ Half Life :
3-7 hours
Độc Tính : LD50=5500 mg/kg (orally in rats), toxic effects include bradycardia, hypotension, bronchospasm, and cardiac failure. LD50=2090 mg/kg (orally in mice)
Chỉ Định : 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.
Tương Tác Thuốc :
  • Acetohexamide The beta-blocker, metoprolol, may decrease symptoms of hypoglycemia.
  • Chlorpropamide The beta-blocker, metoprolol, may decrease symptoms of hypoglycemia.
  • Cimetidine Cimetidine may increase the serum concentration of metoprolol by decreasing its metabolism.
  • Citalopram The SSRI, citalopram, may increase the bradycardic effect of the beta-blocker, metoprolol.
  • Clonidine Increased hypertension when clonidine stopped
  • Dihydroergotamine Ischemia with risk of gangrene
  • Diltiazem Increased risk of bradycardia
  • Disopyramide The beta-blocker, metoprolol, may increase adverse effects of disopyramide.
  • Dronedarone Metoprolol is a CYP2D6 substrate and because dronedarone inhibits this enzyme, will increase metoprolol exposure 1.6-fold. Lower dose of metoprolol.
  • Epinephrine Hypertension, then bradycardia
  • Ergonovine Ischemia with risk of gangrene
  • Ergotamine Ischemia with risk of gangrene
  • Escitalopram The SSRI, escitalopram, may increase the bradycardic effect of the beta-blocker, metoprolol.
  • Fenoterol Antagonism
  • Fluoxetine The SSRI, fluoxetine, may increase the bradycardic effect of the beta-blocker, metoprolol.
  • Formoterol Antagonism
  • Gliclazide The beta-blocker, metoprolol, may decrease symptoms of hypoglycemia.
  • Glipizide The beta-blocker, metoprolol, may decrease symptoms of hypoglycemia.
  • Glisoxepide The beta-blocker, metoprolol, may decrease symptoms of hypoglycemia.
  • Glyburide The beta-blocker, metoprolol, may decrease symptoms of hypoglycemia.
  • Glycodiazine The beta-blocker, metoprolol, may decrease symptoms of hypoglycemia.
  • Hydralazine Increased effect of both drugs
  • Ibuprofen Risk of inhibition of renal prostaglandins
  • Indomethacin Risk of inhibition of renal prostaglandins
  • Insulin Glargine The beta-blocker, metoprolol, may decrease symptoms of hypoglycemia.
  • Isoprenaline Antagonism
  • Lidocaine The beta-blocker, metoprolol, may increase the effect and toxicity of lidocaine
  • Methysergide Ischemia with risk of gangrene
  • Mirabegron Mirabegron is a moderate CYP2D6 inhibitor and may cause an increase in exposure of CYP2D6 substrates. Monitor concomitant therapy closely.
  • Orciprenaline Antagonism
  • Paroxetine The SSRI increases the effect of the beta-blocker
  • Phenobarbital The barbiturate decreases the effect of the metabolized beta-blocker
  • Pipobroman Antagonism
  • Pirbuterol Antagonism
  • Piroxicam Risk of inhibition of renal prostaglandins
  • Prazosin Risk of hypotension at the beginning of therapy
  • Primidone The barbiturate decreases the effect of metabolized beta-blocker
  • Procaterol Antagonism
  • Propafenone Propafenone may increase the effect of beta-blocker, metoprolol.
  • Repaglinide The beta-blocker, metoprolol, may decrease symptoms of hypoglycemia.
  • Rifampicin Rifampin may decrease the serum concentration of metoprolol by increasing its metabolism.
  • Salbutamol Antagonism
  • Salmeterol Antagonism
  • Sertraline The SSRI increases the effect of the beta-blocker
  • Telithromycin Telithromycin may possibly increase metoprolol effect
  • Terazosin Increased risk of hypotension. Initiate concomitant therapy cautiously.
  • Terbinafine Terbinafine may reduce the metabolism and clearance of Metoprolol. Consider alternate therapy or monitor for therapeutic/adverse effects of Metoprolol if Terbinafine is initiated, discontinued or dose changed.
  • Terbutaline Antagonism
  • Tolazamide The beta-blocker, metoprolol, may decrease symptoms of hypoglycemia.
  • Tolbutamide The beta-blocker, metoprolol, may decrease symptoms of hypoglycemia.
  • Treprostinil Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
  • Verapamil Increased effect of both drugs
Liều Lượng & Cách Dùng : Liquid - Intravenous
Solution - Intravenous
Tablet - Oral
Tablet, extended release - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Corvitol
  • Công ty :
    Sản phẩm biệt dược : Dutoprol
  • Công ty : Novartis
    Sản phẩm biệt dược : Lopressor
  • Công ty :
    Sản phẩm biệt dược : Minax
  • Công ty :
    Sản phẩm biệt dược : Selokeen
  • Công ty :
    Sản phẩm biệt dược : TOPROL
  • Công ty :
    Sản phẩm biệt dược : Toprol-XL
  • Công ty :
    Sản phẩm biệt dược : TOPROLXL
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00264
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=4171
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506211
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07202
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D02358
ChemSpider
http://www.chemspider.com/Chemical-Structure.4027.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=25756
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/58177-293-04
PharmGKB
http://www.pharmgkb.org/drug/PA450480
Wikipedia
http://en.wikipedia.org/wiki/Metoprolol
RxList
http://www.rxlist.com/cgi/generic/metopxl.htm
Drugs.com
http://www.drugs.com/metoprolol.html
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