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Labetalol
Các tên gọi khác (5 ) :
  • 3-Carboxamido-4-hydroxy-alpha-((1-methyl-3-phenylpropylamino)methyl)benzyl alcohol
  • 5-(1-Hydroxy-2-(1-methyl-3-phenylpropylamino)ethyl)salicylamide
  • Labetalol
  • Labetalolum
  • Labetolol
antihypertensive agents, sympathomimetics, adrenergic alpha 1 receptor antagonists, adrenergic beta ant
Thuốc Gốc
Small Molecule
CAS: 36894-69-6
ATC: C07AG01
ĐG : Akorn Inc. , http://www.akorn.com
CTHH: C19H24N2O3
PTK: 328.4055
Blocker of both alpha- and beta-adrenergic receptors that is used as an antihypertensive. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C19H24N2O3
Phân tử khối
328.4055
Monoisotopic mass
328.178692644
InChI
InChI=1S/C19H24N2O3/c1-13(7-8-14-5-3-2-4-6-14)21-12-18(23)15-9-10-17(22)16(11-15)19(20)24/h2-6,9-11,13,18,21-23H,7-8,12H2,1H3,(H2,20,24)
InChI Key
InChIKey=SGUAFYQXFOLMHL-UHFFFAOYSA-N
IUPAC Name
2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide
Traditional IUPAC Name
labetalol
SMILES
CC(CCC1=CC=CC=C1)NCC(O)C1=CC(C(N)=O)=C(O)C=C1
Độ tan chảy
188 °C
Độ hòa tan
117 mg/L (at 25 °C)
logP
3.09
logS
-4.8
pKa (strongest acidic)
8.05
pKa (Strongest Basic)
9.8
PSA
95.58 Å2
Refractivity
94.72 m3·mol-1
Polarizability
36.83 Å3
Rotatable Bond Count
8
H Bond Acceptor Count
4
H Bond Donor Count
4
Physiological Charge
1
Number of Rings
2
Bioavailability
1
Rule of Five
true
Ghose Filter
true
caco2 Permeability
-5.03
Dược Lực Học : Labetalol is an selective alpha-1 and non-selective beta adrenergic blocker used to treat high blood pressure. It works by blocking these adrenergic receptors, which slows sinus heart rate, decreases peripheral vascular resistance, and decreases cardiac output. Labetalol has two asymmetric centers and therefore, exists as a molecular complex of two diastereoisomeric pairs. Dilevalol, the R,R' stereoisomer, makes up 25% of racemic labetalol.
Cơ Chế Tác Dụng : Blocker of both alpha- and beta-adrenergic receptors that is used as an antihypertensive. [PubChem] Labetalol HCl combines both selective, competitive, alpha-1-adrenergic blocking and nonselective, competitive, beta-adrenergic blocking activity in a single substance. In man, the ratios of alpha- to beta- blockade have been estimated to be approximately 1:3 and 1:7 following oral and intravenous (IV) administration, respectively. The principal physiologic action of labetalol is to competitively block adrenergic stimulation of β-receptors within the myocardium (β1-receptors) and within bronchial and vascular smooth muscle (β2-receptors), and α1-receptors within vascular smooth muscle. This causes a decrease in systemic arterial blood pressure and systemic vascular resistance without a substantial reduction in resting heart rate, cardiac output, or stroke volume, apparently because of its combined α- and β-adrenergic blocking activity.
Dược Động Học :
▧ Absorption :
Completely absorbed (100%) from the gastrointestinal tract with peak plasma levels occurring 1 to 2 hours after oral administration. The absolute bioavailability of labetalol is increased when administered with food.
▧ Protein binding :
50%
▧ Metabolism :
Primarily hepatic, undergoes significant first pass metabolism
▧ Route of Elimination :
These metabolites are present in plasma and are excreted in the urine, and via the bile, into the feces.
▧ Half Life :
6-8 hours
Độc Tính : LD50 = 66 mg/kg (Rat, IV). Side effects or adverse reactions include dizziness when standing up, very low blood pressure, severely slow heartbeat, weakness, diminished sexual function, fatigue
Chỉ Định : For the management of hypertension (alone or in combination with other classes of antihypertensive agents), as well as chronic stable angina pectoris and sympathetic overactivity syndrome associated with severe tetanus. Labetalol is used parenterally for immediate reduction in blood pressure in severe hypertension or in hypertensive crises when considered an emergency, for the control of blood pressure in patients with pheochromocytoma and pregnant women with preeclampsia, and to produce controlled hypotension during anesthesia to reduce bleeding resulting from surgical procedures.
Tương Tác Thuốc :
  • Acetohexamide The beta-blocker, labetalol, may decrease symptoms of hypoglycemia.
  • Chlorpropamide The beta-blocker, labetalol, may decrease symptoms of hypoglycemia.
  • Cimetidine Cimetidine may increase the serum concentration of labetolol by decreasing its metabolism.
  • Clonidine Increased hypertension when clonidine stopped
  • Dihydroergotamine Ischemia with risk of gangrene
  • Disopyramide The beta-blocker, labetolol, may increase the toxicity of disopyramide.
  • Enflurane Monitor arterial pressure closely
  • Epinephrine Hypertension, then bradycardia
  • Ergonovine Ischemia with risk of gangrene
  • Ergotamine Ischemia with risk of gangrene
  • Fenoterol Antagonism
  • Formoterol Antagonism
  • Gliclazide The beta-blocker, labetalol, may decrease symptoms of hypoglycemia.
  • Glipizide The beta-blocker, labetalol, may decrease symptoms of hypoglycemia.
  • Glisoxepide The beta-blocker, labetalol, may decrease symptoms of hypoglycemia.
  • Glyburide The beta-blocker, labetalol, may decrease symptoms of hypoglycemia.
  • Glycodiazine The beta-blocker, labetalol, may decrease symptoms of hypoglycemia.
  • Halothane Monitor arterial pressure closely
  • Ibuprofen Risk of inhibition of renal prostaglandins
  • Indomethacin Risk of inhibition of renal prostaglandins
  • Insulin Glargine The beta-blocker, labetolol, may decrease symptoms of hypoglycemia.
  • Iobenguane May diminish the therapeutic effect and increase chances of producing a false negative imaging result of Iobenguane as it depletes or inhibit reuptake of noradrenaline stores
  • Isoflurane Monitor arterial pressure closely
  • Isoprenaline Antagonism
  • Lidocaine The beta-blocker, labetalol, may increase the effect and toxicity of lidocaine.
  • Methysergide Ischemia with risk of gangrene
  • Orciprenaline Antagonism
  • Pipobroman Antagonism
  • Pirbuterol Antagonism
  • Piroxicam Risk of inhibition of renal prostaglandins
  • Prazosin Risk of hypotension at the beginning of therapy
  • Procaterol Antagonism
  • Repaglinide The beta-blocker, labetalol, may decrease symptoms of hypoglycemia.
  • Salbutamol Antagonism
  • Salmeterol Antagonism
  • Terazosin Increased risk of hypotension. Initiate concomitant therapy cautiously.
  • Terbutaline Antagonism
  • Tolazamide The beta-blocker, labetalol, may decrease symptoms of hypoglycemia.
  • Tolbutamide The beta-blocker, labetalol, 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
Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Leiras
    Sản phẩm biệt dược : Albetol
  • Công ty : Standard
    Sản phẩm biệt dược : Latol
  • Công ty : GlaxoSmithKline
    Sản phẩm biệt dược : Normadate
  • Công ty : Schering
    Sản phẩm biệt dược : Normodyne
  • Công ty : GlaxoSmithKline
    Sản phẩm biệt dược : Trandate
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00598
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=3869
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505511
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07063
ChemSpider
http://www.chemspider.com/Chemical-Structure.3734.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=25758
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0172-4364-60
PharmGKB
http://www.pharmgkb.org/drug/PA164743150
Wikipedia
http://en.wikipedia.org/wiki/Labetalol
RxList
http://www.rxlist.com/cgi/generic2/labet.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/nor1301.shtml
Drugs.com
http://www.drugs.com/cdi/labetalol.html
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