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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
Structure of PRACTOLOL

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)

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 ( + / - )

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
Effect of beta-adrenoceptor blocking drugs, physostigmine, and atropine on the toxicity of doxepin in mice.
1975 Aug
Letter: Propranolol and the nephrotic syndrome.
1976 Apr 17
Comparison of verapamil and practolol in paroxysmal supraventricular tachycardia.
1976 Mar
Peripheral neuropathy with disopyramide.
1978 Feb 11
Quantitative structure-retention and retention-activity relationships of beta-blocking agents by micellar liquid chromatography.
2001 Apr 6
[Enantiomeric separation of drugs based on macrocyclic antibiotics].
2001 Jul
Norepinephrine elicits beta2-receptor-mediated dilation of isolated human coronary arterioles.
2002 Jul 30
Modulatory effect of the adrenergic system upon fibroblast proliferation: participation of beta 3-adrenoceptors.
2002 Jun
Data-mining analyses of pharmacovigilance signals in relation to relevant comparison drugs.
2002 Oct
Calculation of electrophoretic mobility in mixed solvent buffers in capillary zone electrophoresis using a mixture response surface method.
2002 Sep
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
Testing times: the emergence of the practolol disaster and its challenge to British drug regulation in the modern period.
2006 Apr
Putting theory into practice: James Black, receptor theory and the development of the beta-blockers at ICI, 1958-1978.
2006 Jan
Carvedilol in the treatment of chronic heart failure: lessons from the Carvedilol Or Metoprolol European Trial.
2007
Cutaneous vasculitis induced by carvedilol.
2007 Aug
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
Beta-adrenergic stimulation and myocardial function in the failing heart.
2009 Dec
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 Fri Dec 15 19:00:27 UTC 2023
Edited
by admin
on Fri Dec 15 19:00:27 UTC 2023
Record UNII
SUG9176GRW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRACTOLOL
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
ACETAMIDE, N-(4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)PHENYL)-
Systematic Name English
PRACTOLOL [USAN]
Common Name English
PRACTOLOL [MART.]
Common Name English
4'-(2-HYDROXY-3-(ISOPROPYLAMINO)PROPOXY)ACETANILIDE
Systematic Name English
ICI-50172
Code English
practolol [INN]
Common Name English
AY-21,011
Code English
DALZIC
Brand Name English
ERALDIN
Brand Name English
AY-21011
Code English
Practolol [WHO-DD]
Common Name English
PRACTOLOL [MI]
Common Name English
DL-4'-(2-HYDROXY-3-(ISOPROPYLAMINO)PROPOXY)ACETANILIDE
Systematic Name English
I.C.I.-50,172
Code English
I.C.I. 50,172
Code English
Classification Tree Code System Code
WHO-ATC C07AB01
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
WHO-VATC QC07AB01
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
NCI_THESAURUS C29576
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
Code System Code Type Description
SMS_ID
100000081372
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY
EVMPD
SUB09986MIG
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY
DRUG CENTRAL
3486
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY
CHEBI
258351
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY
CAS
6673-35-4
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY
DRUG BANK
DB01297
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY
NCI_THESAURUS
C76556
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY
RXCUI
8620
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY RxNorm
INN
2832
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY
EPA CompTox
DTXSID0021179
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY
MESH
D011217
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY
MERCK INDEX
m9088
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
PRACTOLOL
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY
FDA UNII
SUG9176GRW
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY
ECHA (EC/EINECS)
229-712-1
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY
IUPHAR
555
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY
ChEMBL
CHEMBL6995
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY
PUBCHEM
4883
Created by admin on Fri Dec 15 19:00:27 UTC 2023 , Edited by admin on Fri Dec 15 19:00:27 UTC 2023
PRIMARY
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