Details
Stereochemistry | RACEMIC |
Molecular Formula | C14H22N2O3 |
Molecular Weight | 266.3361 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1
InChI
InChIKey=DURULFYMVIFBIR-UHFFFAOYSA-N
InChI=1S/C14H22N2O3/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)
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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Practolol and bendrofluazide in treatment of hypertension. | 1974 Sep |
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Method for the production of severe ventricular dysrhythmias in small laboratory animals. | 1975 |
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Effect of beta-adrenoceptor blocking drugs, physostigmine, and atropine on the toxicity of doxepin in mice. | 1975 Aug |
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The use of clonidine and practolol in the treatment of hypertension. | 1976 Feb |
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Comparison of verapamil and practolol in paroxysmal supraventricular tachycardia. | 1976 Mar |
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Intermittent claudication complicating beta-blockade. | 1976 May 8 |
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Influence of several anesthetic agents on the effect of delta9-tetrahydrocannabinol on the heart rate and blood pressure of the mongrel dog. | 1977 Jul 1 |
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Adverse reactions to practolol in hospitalized patients: a report from the Boston Collaborative Drug Surveillance Program. | 1977 Nov 14 |
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Peripheral neuropathy with disopyramide. | 1978 Feb 11 |
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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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Investigation into the cardioregulatory properties of the alpha 1-adrenoceptor blocker indoramin. | 1986 Feb |
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Central action of beta-adrenoceptor antagonists on blood pressure after acute administration in rats. | 1986 Jan-Mar |
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Atenolol-induced cutaneous vasculitis. | 1989 Mar |
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[Enantiomeric separation of drugs based on macrocyclic antibiotics]. | 2001 Jul |
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Modulatory effect of the adrenergic system upon fibroblast proliferation: participation of beta 3-adrenoceptors. | 2002 Jun |
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Data-mining analyses of pharmacovigilance signals in relation to relevant comparison drugs. | 2002 Oct |
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Putting theory into practice: James Black, receptor theory and the development of the beta-blockers at ICI, 1958-1978. | 2006 Jan |
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Experiences with carrier-mediated transport in liquid-phase microextraction. | 2006 Jul |
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Tuberculous abdominal cocoon--a report of 6 cases and review of the Literature. | 2006 Jun 27 |
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Beta-blockers use in patients with chronic obstructive pulmonary disease and concomitant cardiovascular conditions. | 2007 |
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A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling. | 2007 Oct 16 |
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Simulation-based cheminformatic analysis of organelle-targeted molecules: lysosomotropic monobasic amines. | 2008 Sep |
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Clinical consequences of asbestos-related diffuse pleural thickening: A review. | 2008 Sep 8 |
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Bench-to-bedside review: Beta-adrenergic modulation in sepsis. | 2009 |
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Beta-adrenergic stimulation and myocardial function in the failing heart. | 2009 Dec |
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Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project. | 2010 |
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Beta3-adrenoceptor agonists: possible role in the treatment of overactive bladder. | 2010 Dec |
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A problem encapsulated - role of CT. | 2010 Mar 15 |
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Comparison of esmolol and labetalol, in low doses, for attenuation of sympathomimetic response to laryngoscopy and intubation. | 2010 Sep |
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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Classification Tree | Code System | Code | ||
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WHO-ATC |
C07AB01
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WHO-VATC |
QC07AB01
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NCI_THESAURUS |
C29576
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100000081372
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SUB09986MIG
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DB01297
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C76556
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8620
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2832
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D011217
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m9088
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PRACTOLOL
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SUG9176GRW
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229-712-1
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555
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CHEMBL6995
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4883
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)