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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
Structure of PRACTOLOL HYDROCHLORIDE

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

HIDE SMILES / InChI

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
Practolol and bendrofluazide in treatment of hypertension.
1974 Sep
The use of practolol in supraventricular arrhythmias associated with acute illnesses.
1975 May
Letter: Propranolol and the nephrotic syndrome.
1976 Apr 17
The use of clonidine and practolol in the treatment of hypertension.
1976 Feb
Comparison of verapamil and practolol in paroxysmal supraventricular tachycardia.
1976 Mar
Intermittent claudication complicating beta-blockade.
1976 May 8
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
Adverse reactions to practolol in hospitalized patients: a report from the Boston Collaborative Drug Surveillance Program.
1977 Nov 14
Peripheral neuropathy with disopyramide.
1978 Feb 11
Effects of beta-adrenergic blocking drugs in hypertensive rats.
1980 Jan
Investigation into the cardioregulatory properties of the alpha 1-adrenoceptor blocker indoramin.
1986 Feb
Central action of beta-adrenoceptor antagonists on blood pressure after acute administration in rats.
1986 Jan-Mar
Quantitative structure-retention and retention-activity relationships of beta-blocking agents by micellar liquid chromatography.
2001 Apr 6
Modern doctoring.
2001 Mar-Apr
Improvement of peak shape and separation performance of beta-blockers in conventional reversed-phase columns using solvent modifiers.
2003 Aug
[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications].
2003 Oct-Dec
Application of data mining techniques in pharmacovigilance.
2004 Feb
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 Apr 22
The selectivity of beta-adrenoceptor antagonists at the human beta1, beta2 and beta3 adrenoceptors.
2005 Feb
Clinical characteristics of dialysis related sclerosing encapsulating peritonitis: multi-center experience in Korea.
2005 Feb 28
Experiences with carrier-mediated transport in liquid-phase microextraction.
2006 Jul
An unusual and difficult diagnosis of intestinal obstruction: The abdominal cocoon. Case report and review of the literature.
2006 Mar 24
Beta-blockers use in patients with chronic obstructive pulmonary disease and concomitant cardiovascular conditions.
2007
An instructive example of a long-latency adverse drug reaction--sclerosing peritonitis due to practolol.
2007 Nov
A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling.
2007 Oct 16
Simulation-based cheminformatic analysis of organelle-targeted molecules: lysosomotropic monobasic amines.
2008 Sep
Clinical consequences of asbestos-related diffuse pleural thickening: A review.
2008 Sep 8
Bench-to-bedside review: Beta-adrenergic modulation in sepsis.
2009
Beta-adrenergic stimulation and myocardial function in the failing heart.
2009 Dec
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.
2010
Chiral separations of some beta-adrenergic agonists and antagonists on AmyCoat column by HPLC.
2010 Jan
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 Sat Dec 16 11:17:27 GMT 2023
Edited
by admin
on Sat Dec 16 11:17:27 GMT 2023
Record UNII
AT88RXS5AE
Record Status Validated (UNII)
Record Version
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Name Type Language
PRACTOLOL HYDROCHLORIDE
Common Name English
ACETAMIDE, N-(4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)PHENYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
PRACTOLOL CHLORIDE
Common Name English
(±)-PRACTOLOL HYDROCHLORIDE
Common Name English
ACETAMIDE, N-(4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)PHENYL)-, MONOHYDROCHLORIDE
Systematic Name English
TERANOL HYDROCHLORIDE
Brand Name English
Code System Code Type Description
PUBCHEM
3083993
Created by admin on Sat Dec 16 11:17:28 GMT 2023 , Edited by admin on Sat Dec 16 11:17:28 GMT 2023
PRIMARY
DRUG BANK
DBSALT002280
Created by admin on Sat Dec 16 11:17:28 GMT 2023 , Edited by admin on Sat Dec 16 11:17:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID20990217
Created by admin on Sat Dec 16 11:17:28 GMT 2023 , Edited by admin on Sat Dec 16 11:17:28 GMT 2023
PRIMARY
FDA UNII
AT88RXS5AE
Created by admin on Sat Dec 16 11:17:28 GMT 2023 , Edited by admin on Sat Dec 16 11:17:28 GMT 2023
PRIMARY
CAS
6996-43-6
Created by admin on Sat Dec 16 11:17:28 GMT 2023 , Edited by admin on Sat Dec 16 11:17:28 GMT 2023
PRIMARY
ECHA (EC/EINECS)
230-270-7
Created by admin on Sat Dec 16 11:17:28 GMT 2023 , Edited by admin on Sat Dec 16 11:17:28 GMT 2023
PRIMARY
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