OXPRENOLOL HYDROCHLORIDE Chemical Properties

Melting point:

91-93°C

storage temp. 

Store at +4°C

solubility 

Very soluble in water, freely soluble in alcohol.

form 

Solid

color 

White to off-white

CAS DataBase Reference

6452-73-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

RIDADR 

UN 2811 6.1 / PGIII

RTECS 

UA5277000

HazardClass 

IRRITANT

HS Code 

2922190900

Toxicity

LD50 oral in rat: 214mg/kg

OXPRENOLOL HYDROCHLORIDE Usage And Synthesis

Description

Oxprenolol is an orally bioavailable β-adrenergic receptor (β-AR) antagonist (K_i = 7.10 nM in a radioligand binding assay using rat heart tissue). It is non-selective and binds to both β₁- and β₂-ARs (K_ds = 2.09 and 1.35 nM in isolated rat heart and uterus, respectively). Oxprenolol is selective for β-ARs over serotonin (5-HT) receptors in rat sarcolemmal membrane preparations (IC₅₀s = 4.13 and 23,300 nM, respectively), but it binds to 5-HT_1A receptors in rat hippocampus and 5-HT_1B in rat striatum (K_is = 94.2 and 642 nM, respectively). Formulations containing oxprenolol have been used to treat hypertension and angina pectoris.

Chemical Properties

White Solid

Originator

Trasicor,Ciba Geigy ,Italy,1970

Uses

Antihypertensive;Adrenergic receptor antagonist

Uses

β-Adrenergic blocker. Antihypertensive, antianginal, antiarrhythmic.

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

Biological Activity

Non-selective β -adrenergic antagonist.

Clinical Use

Beta-1 adrenoceptor blocker:
Hypertension
Angina
Arrhythmias
Anxiety

Drug interactions

Potentially hazardous interactions with other drugs
Anaesthetics: enhanced hypotensive effect.
Analgesics: NSAIDs antagonise hypotensive effect.
Anti-arrhythmics: increased risk of myocardial depression and bradycardia; increased risk of bradycardia, myocardial depression and AV block with amiodarone; increased risk of myocardial depression and bradycardia with flecainide.
Antidepressants: enhanced hypotensive effect with MAOIs.
Antihypertensives: enhanced hypotensive effect; increased risk of first dose hypotensive effect with post-synaptic alpha-blockers such as prazosin; increased risk of withdrawal hypertension with clonidine; increased risk of bradycardia and AV block with diltiazem; severe hypotension and heart failure occasionally with nifedipine; asystole, severe hypotension and heart failure with verapamil.
Antimalarials: increased risk of bradycardia with mefloquine.
Antipsychotics: enhanced hypotensive effect with phenothiazines.
Cytotoxics: possible increased risk of bradycardia with crizotinib.
Diuretics: enhanced hypotensive effect.
Fingolimod: possibly increased risk of bradycardia.
Moxisylyte: possibly severe postural hypotension.
Sympathomimetics: severe hypertension with adrenaline and noradrenaline (especially with nonselective beta-blockers) and possibly with dopamine.

Metabolism

Oxprenolol is extensively metabolised in the liver, direct O-glucuronidation being the major metabolic pathway and oxidative reactions minor ones. Oxprenolol is excreted chiefly in the urine (almost exclusively in the form of inactive metabolites).

OXPRENOLOL HYDROCHLORIDE(6452-73-9)Related Product Information

• 3-AMINO-1-PHENOXY-2-PROPANOL HYDROCHLORIDE, 98
• bucumolol hydrochloride
• oxprenolol
• OXPRENOLOL HYDROCHLORIDE
• 2-(Allyloxy)phenol
• moprolol
• 2-(2-HYDROXYETHOXY)PHENOL
• ALPRENOLOL HYDROCHLORIDE
• Alprenolol
• N-methyl-N-(3-phenoxypropyl)amine
• 1-AMINO-3-PHENOXY-PROPAN-2-OL
• 1-ALLYLOXY-2-METHOXY-BENZENE
• 1-AMINO-3-(2-METHOXY-PHENOXY)-PROPAN-2-OL
• 3-phenoxy-1-propanamine
• [3-(2-METHOXY-PHENOXY)-PROPYL]-METHYL-AMINE
• 3-(2-methoxyphenoxy)propan-1-amine
• 1-(2-METHOXYPHENOXY)-2-PROPANOL
• 3-(ISOPROPYLAMINO)-1,2-PROPANEDIOL