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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
The use of clonidine and practolol in the treatment of hypertension.
1976 Feb
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
The role of beta1- and beta2-adrenoceptors in the inhibition of gastric acid secretion in the dog.
1978 Sep
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
[Enantiomeric separation of drugs based on macrocyclic antibiotics].
2001 Jul
From toxic precursors to safe drugs. Mechanisms and relevance of idiosyncratic drug reactions.
2002
Data-mining analyses of pharmacovigilance signals in relation to relevant comparison drugs.
2002 Oct
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
Putting theory into practice: James Black, receptor theory and the development of the beta-blockers at ICI, 1958-1978.
2006 Jan
Experiences with carrier-mediated transport in liquid-phase microextraction.
2006 Jul
Beta-blockers use in patients with chronic obstructive pulmonary disease and concomitant cardiovascular conditions.
2007
Abdominal cocoon secondary to tuberculosis.
2008 Jul
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
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
  • Download
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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ENANTIOMER -> RACEMATE
PARENT -> SALT/SOLVATE
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SOLVATE->ANHYDROUS
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