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Details

Stereochemistry RACEMIC
Molecular Formula C14H22N2O3.ClH.H2O
Molecular Weight 320.812
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRACTOLOL HYDROCHLORIDE MONOHYDRATE

SMILES

O.Cl.CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1

InChI

InChIKey=JRRAXNNFIAXBSQ-UHFFFAOYSA-N
InChI=1S/C14H22N2O3.ClH.H2O/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;1H2

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C14H22N2O3
Molecular Weight 266.3361
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Targets

PubMed

PubMed

TitleDatePubMed
Beta3-adrenoceptor agonists: possible role in the treatment of overactive bladder.
2010-12
Comparison of esmolol and labetalol, in low doses, for attenuation of sympathomimetic response to laryngoscopy and intubation.
2010-09
A problem encapsulated - role of CT.
2010-03-15
Chiral separations of some beta-adrenergic agonists and antagonists on AmyCoat column by HPLC.
2010-01
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.
2010
Beta-adrenergic stimulation and myocardial function in the failing heart.
2009-12
Bench-to-bedside review: Beta-adrenergic modulation in sepsis.
2009
Clinical consequences of asbestos-related diffuse pleural thickening: A review.
2008-09-08
Simulation-based cheminformatic analysis of organelle-targeted molecules: lysosomotropic monobasic amines.
2008-09
Abdominal cocoon secondary to tuberculosis.
2008-07
An instructive example of a long-latency adverse drug reaction--sclerosing peritonitis due to practolol.
2007-11
A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling.
2007-10-16
Cutaneous vasculitis induced by carvedilol.
2007-08
Beta-blockers use in patients with chronic obstructive pulmonary disease and concomitant cardiovascular conditions.
2007
Carvedilol in the treatment of chronic heart failure: lessons from the Carvedilol Or Metoprolol European Trial.
2007
Experiences with carrier-mediated transport in liquid-phase microextraction.
2006-07
Computational approaches for modeling human intestinal absorption and permeability.
2006-07
Tuberculous abdominal cocoon--a report of 6 cases and review of the Literature.
2006-06-27
Testing times: the emergence of the practolol disaster and its challenge to British drug regulation in the modern period.
2006-04
An unusual and difficult diagnosis of intestinal obstruction: The abdominal cocoon. Case report and review of the literature.
2006-03-24
Putting theory into practice: James Black, receptor theory and the development of the beta-blockers at ICI, 1958-1978.
2006-01
A ranked presentation of the MHRA/CSM (Medicines & Health Care Regulatory Agency/Committee on Safety of Medicines) Drug Analysis Print (DAP) data on practolol.
2005-10
Liquid-phase microextraction based on carrier mediated transport combined with liquid chromatography-mass spectrometry. New concept for the determination of polar drugs in a single drop of human plasma.
2005-04-22
Modeling the electrophoretic mobility of beta-blockers in capillary electrophoresis using artificial neural networks.
2005-03
Clinical characteristics of dialysis related sclerosing encapsulating peritonitis: multi-center experience in Korea.
2005-02-28
The selectivity of beta-adrenoceptor antagonists at the human beta1, beta2 and beta3 adrenoceptors.
2005-02
[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications].
2004-02-20
Application of data mining techniques in pharmacovigilance.
2004-02
Improvement of peak shape and separation performance of beta-blockers in conventional reversed-phase columns using solvent modifiers.
2003-08
Data-mining analyses of pharmacovigilance signals in relation to relevant comparison drugs.
2002-10
Calculation of electrophoretic mobility in mixed solvent buffers in capillary zone electrophoresis using a mixture response surface method.
2002-09
Norepinephrine elicits beta2-receptor-mediated dilation of isolated human coronary arterioles.
2002-07-30
Modulatory effect of the adrenergic system upon fibroblast proliferation: participation of beta 3-adrenoceptors.
2002-06
From toxic precursors to safe drugs. Mechanisms and relevance of idiosyncratic drug reactions.
2002
Modern doctoring.
2001-09-06
Atenolol-induced cutaneous vasculitis.
1989-03
Investigation into the cardioregulatory properties of the alpha 1-adrenoceptor blocker indoramin.
1986-02
Central action of beta-adrenoceptor antagonists on blood pressure after acute administration in rats.
1986-01-01
Effects of beta-adrenergic blocking drugs in hypertensive rats.
1980-01
The role of beta1- and beta2-adrenoceptors in the inhibition of gastric acid secretion in the dog.
1978-09
Peripheral neuropathy with disopyramide.
1978-02-11
Adverse reactions to practolol in hospitalized patients: a report from the Boston Collaborative Drug Surveillance Program.
1977-11-14
Influence of several anesthetic agents on the effect of delta9-tetrahydrocannabinol on the heart rate and blood pressure of the mongrel dog.
1977-07-01
Intermittent claudication complicating beta-blockade.
1976-05-08
Letter: Propranolol and the nephrotic syndrome.
1976-04-17
Comparison of verapamil and practolol in paroxysmal supraventricular tachycardia.
1976-03
The use of clonidine and practolol in the treatment of hypertension.
1976-02
Effect of beta-adrenoceptor blocking drugs, physostigmine, and atropine on the toxicity of doxepin in mice.
1975-08
Method for the production of severe ventricular dysrhythmias in small laboratory animals.
1975
Practolol and bendrofluazide in treatment of hypertension.
1974-09
Patents

Sample Use Guides

In Vivo Use Guide
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
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 23:44:47 GMT 2025
Edited
by admin
on Mon Mar 31 23:44:47 GMT 2025
Record UNII
ILY56C703Y
Record Status Validated (UNII)
Record Version
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Name Type Language
PRACTOLOL HYDROCHLORIDE MONOHYDRATE [MI]
Preferred Name English
PRACTOLOL HYDROCHLORIDE MONOHYDRATE
MI  
Common Name English
ACETAMIDE, N-(4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)PHENYL)-, HYDROCHLORIDE, HYDRATE (1:1:1)
Systematic Name English
Code System Code Type Description
PUBCHEM
139033100
Created by admin on Mon Mar 31 23:44:47 GMT 2025 , Edited by admin on Mon Mar 31 23:44:47 GMT 2025
PRIMARY
FDA UNII
ILY56C703Y
Created by admin on Mon Mar 31 23:44:47 GMT 2025 , Edited by admin on Mon Mar 31 23:44:47 GMT 2025
PRIMARY
MERCK INDEX
m9088
Created by admin on Mon Mar 31 23:44:47 GMT 2025 , Edited by admin on Mon Mar 31 23:44:47 GMT 2025
PRIMARY
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ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY