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)
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2903243 |
|||
Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2903243 |
|||
Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6146718 |
251.19 nM [Kd] |
PubMed
Title | Date | PubMed |
---|---|---|
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
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:00:27 UTC 2023
by
admin
on
Fri Dec 15 19:00:27 UTC 2023
|
Record UNII |
SUG9176GRW
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ENANTIOMER -> RACEMATE | |||
|
ENANTIOMER -> RACEMATE | |||
|
SALT/SOLVATE -> PARENT | |||
|
SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |