Details
Stereochemistry | RACEMIC |
Molecular Formula | C14H22N2O3.ClH |
Molecular Weight | 302.797 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1
InChI
InChIKey=UEWORNJBQXFYSM-UHFFFAOYSA-N
InChI=1S/C14H22N2O3.ClH/c1-10(2)15-8-13(18)9-19-14-6-4-12(5-7-14)16-11(3)17;/h4-7,10,13,15,18H,8-9H2,1-3H3,(H,16,17);1H
Practolol is a beta-adrenergic antagonist that has been used in the emergency treatment of cardiac arrhythmias. Practolol is a cardio-selective beta-blocking agent with an intrinsic sympathomimetic action, but devoid of local anaesthetic effect. It has been found effective in post infarction arrhythmias. In early infarction it reduces the area of necrosis as measured by surface ST segment mapping. Practolol has also been shown to be an effective drug in treating angina. Long-term treatment revealed advantageous effects of practolol on the incidence of anginal attacks and the number of nitroglycerin tablets consumed in daily life. There was also a noticeable improvement in the ECG. The results obtained in a double-blind trial, with placebo, proved the effectiveness of the drug. The treatment enabled the patients to lead appreciably more active lives. A marked increase in work performance, depending on the dose applied, was confirmed in exercise tolerance tests. No side-effects which would call for discontinuance of the treatment were seen during long-term administration with doses up to 800 mg daily. Like other beta-adrenergic antagonists, practolol competes with adrenergic neurotransmitters such as catecholamines for binding at sympathetic receptor sites. Practolol binds at beta(1)-adrenergic receptors in the heart and vascular smooth muscle, inhibiting the effects of the catecholamines epinephrine and norepinephrine and decreasing heart rate, cardiac output, and systolic and diastolic blood pressure. Practolol, discovered in 1966, was removed from the market due to severe side effects including conjunctival scarring, fibrosis, and metaplasia.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2903243 |
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Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2903243 |
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Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6146718 |
251.19 nM [Kd] |
PubMed
Title | Date | PubMed |
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Intermittent claudication complicating beta-blockade. | 1976 May 8 |
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The role of beta1- and beta2-adrenoceptors in the inhibition of gastric acid secretion in the dog. | 1978 Sep |
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Improvement of peak shape and separation performance of beta-blockers in conventional reversed-phase columns using solvent modifiers. | 2003 Aug |
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Application of data mining techniques in pharmacovigilance. | 2004 Feb |
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The selectivity of beta-adrenoceptor antagonists at the human beta1, beta2 and beta3 adrenoceptors. | 2005 Feb |
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Computational approaches for modeling human intestinal absorption and permeability. | 2006 Jul |
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An unusual and difficult diagnosis of intestinal obstruction: The abdominal cocoon. Case report and review of the literature. | 2006 Mar 24 |
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Beta-blockers use in patients with chronic obstructive pulmonary disease and concomitant cardiovascular conditions. | 2007 |
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Beta3-adrenoceptor agonists: possible role in the treatment of overactive bladder. | 2010 Dec |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8096673
Curator's Comment: In a controlled double-blind study practolol, a new cardioselective beta-blocking drug, was given to 15 patients with angina pectoris, and compared with propranolol 80 mg. q.d.s. The dose of practolol ranged from 200 to 600 mg.b.d. and was decided by initial open titration in individual patients. https://www.ncbi.nlm.nih.gov/pubmed/4392983
Idiopathic dilated congestive cardiomyopathy (DCCM): 50-400 mg twice daily, for 2-12 months
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2843784
Curator's Comment: The subclass of beta-adrenergic receptors mediating glycogenolysis in slices from cerebral cortex of the mouse, incubated in the presence of [3H]glucose, was identified by comparing the relative potencies of agonists and the inhibition constants of antagonists to those found on reference systems. (+/-)Isoprenaline, (-)adrenaline and (-)noradrenaline produced a concentration-related glycogenolysis with Kact values of 2.2 x 10(-8) M, 2.8 x 10(-7) M and 3.6 x 10(-7) M, respectively.
The predominantly beta 1-adrenergic receptor antagonists, practolol and metoprolol shifted the concentration-response curve to noradrenaline to the right, with apparent Ki values of 8.0 x 10(-7) M and 7.6 x 10(-8) M, respectively, close to those reported in the rat heart.
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3083993
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DBSALT002280
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DTXSID20990217
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AT88RXS5AE
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6996-43-6
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230-270-7
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ACTIVE MOIETY
SUBSTANCE RECORD