oxprenolol Chemical Properties

Melting point:

78-80°

Boiling point:

408.57°C (rough estimate)

Density 

1.0479 (rough estimate)

refractive index 

1.5000 (estimate)

solubility 

Dichloromethane (Slightly), Methanol (Slightly)

form 

Solid

pka

13.89±0.20(Predicted)

color 

White to Off-White

Stability:

Stable under recommended storage conditions., Stable Under Recommended Storage C

oxprenolol Usage And Synthesis

Description

Oxprenolol induced contact dermatitis in a worker at a pharmaceutical plant, in the division for drug synthesis. Epichlorhydrin was also used for the production of both propranolol and oxprenolol.

Originator

Trasicor,Ciba Geigy ,Italy,1970

Uses

Oxprenolol is a free base of Oxprenolol Hydrochloride(O870500) which is a β-Adrenergic blocker. Antihypertensive, antianginal, antiarrhythmic.

Uses

Vasodilator(coronary).

Definition

ChEBI: 1-(propan-2-ylamino)-3-(2-prop-2-enoxyphenoxy)-2-propanol is an aromatic ether.

Manufacturing Process

75 grams of pyrocatechol monoallyl ether, 75 grams of epichlorohydrin, 75 grams of potassium carbonate and 400 ml of acetone are stirred and heated at the boil for 12 hours. The potassium carbonate is then filtered off. The solvent is distilled off in a water-jet vacuum. The residual oil is dissolved in ether and agitated with 2 N sodium hydroxide solution. The ether is separated, dried and distilled off. The residue is distilled in a water-jet vacuum. 3-(ortho-allyloxy-phenoxy)-1,2-epoxypropane passes over at 145° to 157°C under 11 mm Hg pressure. A solution of 15 grams of 3-(ortho-allyloxyphenoxy)-1,2-epoxypropane and 15 grams of isopropylamine in 20 ml of ethanol is refluxed for 4 hours. The excess amine and the alcohol are then distilled off under vacuum, to leave 1-isopropylamino-2-hydroxy-3-(orthoallyloxy-phenoxy)-propane which melts at 75° to 80°C after recrystallization from hexane.

brand name

Trasicor (Novartis).

Therapeutic Function

Antiarrhythmic

Contact allergens

The beta-blocker oxprenolol induced contact dermatitis in a worker at a pharmaceutical plant, in a division for drug synthesis. Epichlorhydrin was also used for the production of drugs propranolol and oxprenolol.

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