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(±)-Bupranolol

(±)-Bupranolol structure

CAS No:
14556-46-8
Formula:
C14H22ClNO2
Chemical Name:
(±)-Bupranolol
Synonyms:
2-Propanol,1-(2-chloro-5-methylphenoxy)-3-[(1,1-dimethylethyl)amino]-;2-Propanol,1-(tert-butylamino)-3-[(6-chloro-m-tolyl)oxy]-;1-(2-Chloro-5-methylphenoxy)-3-[(1,1-dimethylethyl)amino]-2-propanol;Bupranolol;(±)-Bupranolol;Ophtorenin;Bupranol;1-(tert-Butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol;70578-42-6
Categories:
Organic Chemistry > Amides

Description

Solid

Bupranolol is an aromatic ether.|Bupranolol is a non-selective beta blocker with potency similar to [propanolol]. It does not have intrinsic sympathomimetic activity (ISA), but does have strong membrane stabilizing activity.|An adrenergic-beta-2 antagonist that has been used for cardiac arrhythmia, angina pectoris, hypertension, glaucoma, and as an antithrombotic.

(±)-Bupranolol Basic Attributes

Molecular Weight：

271.785

Exact Mass：

271.78

DSSTox ID：

DTXSID7022704

ATC Code：

C - Cardiovascular system

HScode：

2922509090

Characteristics

PSA：

41.5

XLogP3：

3.16710

Appearance：

Solid

Density：

1.098g/cm3

Melting Point：

220-222 °C

Boiling Point：

396.3ºC at 760mmHg

Flash Point：

193.5ºC

Refractive Index：

1.522

Toxicity

Toxicity Summary：

Symptoms of overdose include bradycardia, cardiac failure, hypotension, and brochospasm.

Protein Binding：

76%

Drug Information

Drug Indication：

Used to manage hypertension and tachycardia. Also used to treat glaucoma.

Pharmacology：

Bupranolol is a competitive, nonselective beta-blocker similar to propanolol without intrinsic sympathomimetic activity.

MeSH：

Drugs that bind to but do not activate beta-adrenergic receptors thereby blocking the actions of beta-adrenergic agonists. Adrenergic beta-antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches, and anxiety. (See all compounds classified as Adrenergic beta-Antagonists.)|Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)|Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

Absorption：

Quickly and completely absorbed from the gut with less than 10% oral bioavailability.

Metabolism/Metabolites：

Over 90% undergoes first-pass metabolism. The main metabolite is carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid, of which 88% are eliminated renally within 24 hours.

Biological Half-Life：

2-4 hours

Mechanism of Action：

Bupranolol competes with sympathomimetic neurotransmitters such as catecholamines for binding at beta(1)-adrenergic receptors in the heart, inhibiting sympathetic stimulation. This results in a reduction in resting heart rate, cardiac output, systolic and diastolic blood pressure, and reflex orthostatic hypotension.

MeSH Entry Terms：

Betadrenol

(±)-Bupranolol Use and Manufacturing

Uses

Bupranolol is an antagonist at the cardiostimulatory low-affinity state of b(1)-adrenoceptors and is known to treat hypertension and tachycardia.

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:271.78
XLogP3:2.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:271.1339066
Monoisotopic Mass:271.1339066
Topological Polar Surface Area:41.5
Heavy Atom Count:18
Complexity:242
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes