Tìm theo
Penbutolol
Các tên gọi khác (8 ) :
  • (2S)-1-(tert-butylamino)-3-(2-cyclopentylphenoxy)propan-2-ol
  • 1-(tert-Butylamino)-3-(o-cyclopentylphenoxy)propan-2-ol
  • 2-Propanol, 1-(2-cyclopentylphenoxy)-3-((1,1-dimethylethyl)amino)-, (S)-
  • HOE 893
  • HOE 893D
  • Levatol
  • Penbutolol
  • Penbutololum
antihypertensive agents, adrenergic beta antagonists
Thuốc Gốc
Small Molecule
CAS: 36507-48-9
ATC: C07AA23
ĐG : Schwarz Pharma Inc.
CTHH: C18H29NO2
PTK: 291.4284
Penbutolol is a drug in the beta-blocker class used to treat hypertension. Penbutolol binds both beta-1 and beta-2 adrenergic receptors, rendering it a non-selective beta-blocker. Penbutolol can act as a partial agonist at beta adrenergic receptors, since it is a sympathomimetric drug. Penbutolol also demonstrates high binding affinity to the 5-hydroxytryptamine receptor 1A with antagonistic effects. This binding characteristic of penbutolol is being investigated for its implications in Antidepressant Therapy. Penbutolol is contraindicated in patients with cardiogenic shock, sinus bradycardia, second and third degree atrioventricular conduction block, bronchial asthma, and those with known hypersensitivity.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
Phân tử khối
291.4284
Monoisotopic mass
291.219829177
InChI
InChI=1S/C18H29NO2/c1-18(2,3)19-12-15(20)13-21-17-11-7-6-10-16(17)14-8-4-5-9-14/h6-7,10-11,14-15,19-20H,4-5,8-9,12-13H2,1-3H3/t15-/m0/s1
InChI Key
InChIKey=KQXKVJAGOJTNJS-HNNXBMFYSA-N
IUPAC Name
tert-butyl[(2S)-3-(2-cyclopentylphenoxy)-2-hydroxypropyl]amine
Traditional IUPAC Name
penbutolol
SMILES
CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1
Độ sôi
438.2
Độ hòa tan
2.12e-02 g/l
logP
4.15
logS
-4.1
pKa (strongest acidic)
14.09
pKa (Strongest Basic)
9.76
PSA
41.49 Å2
Refractivity
86.6 m3·mol-1
Polarizability
34.58 Å3
Rotatable Bond Count
7
H Bond Acceptor Count
3
H Bond Donor Count
2
Physiological Charge
1
Number of Rings
2
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Penbutolol is a ß-1, ß-2 (nonselective) adrenergic receptor antagonist. Experimental studies showed a dose-dependent increase in heart rate in reserpinized (norepinephrine-depleted) rats given penbutolol intravenously at doses of 0.25 to 1.0 mg/kg, suggesting that penbutolol has some intrinsic sympathomimetic activity. In human studies, however, heart rate decreases have been similar to those seen with propranolol.
Cơ Chế Tác Dụng : Penbutolol is a drug in the beta-blocker class used to treat hypertension. Penbutolol binds both beta-1 and beta-2 adrenergic receptors, rendering it a non-selective beta-blocker. Penbutolol can act as a partial agonist at beta adrenergic receptors, since it is a sympathomimetric drug. Penbutolol also demonstrates high binding affinity to the 5-hydroxytryptamine receptor 1A with antagonistic effects. This binding characteristic of penbutolol is being investigated for its implications in Antidepressant Therapy. Penbutolol is contraindicated in patients with cardiogenic shock, sinus bradycardia, second and third degree atrioventricular conduction block, bronchial asthma, and those with known hypersensitivity. Penbutolol acts on the β1 adrenergic receptors in both the heart and the kidney. When β1 receptors are activated by catecholamines, they stimulate a coupled G protein that leads to the conversion of adenosine triphosphate (ATP) to cyclic adenosine monophosphate (cAMP). The increase in cAMP leads to activation of protein kinase A (PKA), which alters the movement of calcium ions in heart muscle and increases the heart rate. Penbutolol blocks the catecholamine activation of β1 adrenergic receptors and decreases heart rate, which lowers blood pressure.
Dược Động Học :
▧ Absorption :
>90%.
▧ Protein binding :
80-98% bound to plasma proteins. Extensively bound to Alpha-1-acid glycoprotein 1.
▧ Metabolism :
Metabolized in the liver by hydroxylation and glucuroconjugation forming a glucuronide metabolite and a semi-active 4-hydroxy metabolite.
▧ Route of Elimination :
The metabolites are excreted principally in the urine.
▧ Half Life :
Plasma= approximately 5h Conjugated= approximately 20h in healthy persons, 25h in healthy elderly persons, and 100h in patients on renal dialysis.
▧ Clearance :
Approximately 90% of the metabolites are excreted in the urine.
Độc Tính : Symptoms of overdose include drowsiness, vertigo, headache, and atriventricular block.
Chỉ Định : Penbutolol is indicated in the treatment of mild to moderate arterial hypertension. It may be used alone or in combination with other antihypertensive agents, especially thiazide-type diuretics.Penbutolol is contraindicated in patients with cardiogenic shock, sinus bradycardia, second and third degree atrioventricular conduction block, bronchial asthma, and those with known hypersensitivity.
Tương Tác Thuốc :
  • Aminophylline Antagonism of action and increased effect of theophylline
  • Chlorpropamide The beta-blocker, penbutolol, may decrease symptoms of hypoglycemia.
  • Clonidine Increased hypertension when clonidine stopped
  • Digoxin Both digitalis glycosides and beta-blockers slow atrioventricular conduction and decrease heart rate. Concomitant use can increase the risk of bradycardia.
  • Dihydroergotamine Ischemia with risk of gangrene
  • Disopyramide The beta-blocker, penbutolol, may increase the toxicity of disopyramide.
  • Epinephrine Hypertension, then bradycardia
  • Ergotamine Ischemia with risk of gangrene
  • Fenoterol Antagonism
  • Formoterol Antagonism
  • Gliclazide The beta-blocker, penbutolol, may decrease symptoms of hypoglycemia.
  • Glyburide The beta-blocker, penbutolol, may decrease symptoms of hypoglycemia.
  • Ibuprofen Risk of inhibition of renal prostaglandins
  • Indomethacin Risk of inhibition of renal prostaglandins
  • Insulin Glargine The beta-blocker, penbutolol, may decrease symptoms of hypoglycemia.
  • Lidocaine Penbutolol increases the volume of distribution of lidocaine in normal subjects. This could result in a requirement for higher loading doses of lidocaine.
  • Methyldopa Possible hypertensive crisis
  • Methysergide Ischemia with risk of gangrene
  • Orciprenaline Antagonism
  • Oxtriphylline Antagonism of action and increased effect of theophylline
  • Pipobroman Antagonism
  • Piroxicam Risk of inhibition of renal prostaglandins
  • Prazosin Risk of hypotension at the beginning of therapy
  • Repaglinide The beta-blocker, penbutolol, may decrease symptoms of hypoglycemia.
  • Terazosin Increased risk of hypotension. Initiate concomitant therapy cautiously.
  • Terbutaline Antagonism
  • Theophylline Antagonism of action and increased effect of theophylline
  • Treprostinil Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Liều Lượng & Cách Dùng : Tablet - Oral - 20 mg, yellow, oval.
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Levatol 20 mg tablet
    Giá bán buôn : USD >2.87
    Đơn vị tính : tablet
Nhà Sản Xuất
  • Công ty : Hoechst Ltd.
    Sản phẩm biệt dược : Betapressin
  • Công ty : Schwarz Pharma
    Sản phẩm biệt dược : Levatol
  • Công ty :
    Sản phẩm biệt dược : Levatolol
  • Công ty : Sanofi-Aventis
    Sản phẩm biệt dược : Lobeta
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