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Practolol

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Practolol Basic information

Product Name:
Practolol
Synonyms:
  • DL-4'-[2-Hydroxy-3-(isopropylaMino)propoxy]acetanilide
  • dl-Practolol
  • rac Practolol
  • RaceMic Practolol
  • ici50172
  • n-(4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)phenyl)-acetamid
  • practalol
  • praktololu
CAS:
6673-35-4
MF:
C14H22N2O3
MW:
266.34
EINECS:
229-712-1
Product Categories:
  • Aromatics
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
6673-35-4.mol
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Practolol Chemical Properties

Melting point:
134-136° (BuOAc)
Boiling point:
409.54°C (rough estimate)
Density 
1.0807 (rough estimate)
refractive index 
1.5110 (estimate)
storage temp. 
Refrigerator
solubility 
DMSO (Slightly), Methanol (Slightly)
form 
Solid
pka
pKa 9.5 (Uncertain)
color 
White to Off-White
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Practolol Usage And Synthesis

Chemical Properties

N-[4-[2-HYDROXY-3-[(1-METHYLETHYL)AMINO]PROPOXY]PHENYL]ACETAMIDE is White Solid

Originator

Eraldin, I.C.I. ,UK,1970

Uses

Practolol is a selective adrenergic β-receptor blocking drug with antihyperstensive activity. Practolol has been used in the emergency treatment of cardiac arrhythmias.

Uses

N-[4-[2-HYDROXY-3-[(1-METHYLETHYL)AMINO]PROPOXY]PHENYL]ACETAMIDE is a selective adrenergic β-receptor blocking drug with antihyperstensive activity. N-[4-[2-HYDROXY-3-[(1-METHYLETHYL)AMINO]PROPOXY]PHENYL]ACETAMIDE has been used in the emergency treatment of cardiac arrhythmias.

Definition

ChEBI: N-(4-Hydroxyphenyl)acetamide in which the hydrogen of the phenolic hydroxy group is substituted by a 3-(isopropylaminoamino)-2-hydroxypropyl group. A selective beta blocker, it has been used in the emergency treatment of cardiac arrhythm as.

Manufacturing Process

The 1-(4-acetamidophenoxy)-2,3-epoxypropane used as starting material may be obtained as follows. To a solution of 4.5 parts of 4-acetamidophenol and 1.5 parts of sodium hydroxide in 50 parts of water at 15°C, there is added 3.5 parts of epichlorohydrin. The mixture is stirred for 16 hours at ambient temperature, filtered and the solid residue is washed with water. There is thus obtained 1-(4-acetamidophenoxy)-2,3-epoxypropane, MP 110°C.
A mixture of 2 parts of 1-(4-acetamidophenoxy)-2,3-epoxypropane and 10 parts of isopropylamine is stirred at ambient temperature for 16 hours. The resulting solution is evaporated to dryness under reduced pressure and the residue is crystallized from butyl acetate. There is thus obtained 1-(4acetamidophenoxy)-3-isopropylamino-2-propanol, MP 134° to 136°C.

brand name

A 25;Cardiol;Cordialina;Eraldina;Pralon;Teranol.

Therapeutic Function

Antiarrhythmic

World Health Organization (WHO)

Practolol, a beta-adrenoreceptor antagonist, was introduced in 1970 for the treatment of angina and cardiac dysrhythmias. By 1974 long-term use had been associated with serious delayed idiosyncratic reactions (oculomucocutaneous syndrome) and this led to the withdrawal of oral preparations by the major manufacturer on a worldwide basis. There is no evidence to suggest that other beta-adrenoreceptor antagonist are associated with this risk. Intravenous preparations of practolol remain available in many countries for the emergency treatment of selected cardiac dysrhythmias.

Biological Activity

Practolol is a potent and selective β1 adrenergic receptor antagonist. It can be used in the study of cardiac arrhythmias.

in vitro

Practolol (10 μM; 30 min) preferentially antagonizes the relaxant effects produced by R0363 in spontaneously contracted tracheal preparations from the guinea-pig.Practolol (10 nM-100 μM) blocks the progesterone production induced by (-)epinephrine in a dose-dependent manner in granulosa cells.

in vivo

Practolol (0.5 mg/kg; i.v.) decreases heart rate, left ventricular dP/dt max , myocardial blood flow and cardiac output in intact close-chest dogs.Practolol (0.5 mg/kg; i.v.) decreases normal myocardial blood flow but flow in the ischaemic area remains unchanged after coronary artery ligation.

PractololSupplier

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