bupranolol

Also known as BRN 2272923, SK&F 16805-A

Bupranolol is a non-selective beta blocker without intrinsic sympathomimetic activity (ISA), but with strong membrane stabilizing activity. Its potency is similar to propranolol.

In the Vinony graph

Within Vinony's link graph, bupranolol is referenced by 573 other articles, and connects out to International Standard Book Number, arterial hypertension and chemical formula.

It is catalogued under topics including Antiarrhythmic agents, Beta blockers and Chloroarenes.

Its subject is documented across 12 Wikipedia language editions.

Key facts

Drug.Verifiedfields: changed
Drug.verifiedrevid: 460123491
Drug.IUPAC_name: (RS)-1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol
Drug.image: Bupranolol.svg
Drug.image_class: skin-invert-image
Drug.routes_of_administration: Oral, topical (eye drops)
Drug.bioavailability: < 10%
Drug.protein_bound: 76%
Drug.metabolism: First pass elimination > 90%
Drug.elimination_half life: 2-4 hours (plasma)
Drug.excretion: > 88% renal (as carboxybupranolol)
Drug.CAS_number: 14556-46-8
Drug.ATC_prefix: C07
Drug.ATC_suffix: AA19
Drug.ChEMBL: 305380
Drug.StdInChI: 1S/C14H22ClNO2/c1-10-5-6-12(15)13(7-10)18-9-11(17)8-16-14(2,3)4/h5-7,11,16-17H,8-9H2,1-4H3
Drug.StdInChIKey: HQIRNZOQPUAHHV-UHFFFAOYSA-N
Drug.PubChem: 2475

via Wikipedia infobox

Chemical data

Formula: C14H22ClNO2
Molecular weight: 271.78 g/mol
IUPAC name: 1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol
SMILES: CC1=CC(=C(C=C1)Cl)OCC(CNC(C)(C)C)O
InChIKey: HQIRNZOQPUAHHV-UHFFFAOYSA-N
XLogP: 2.8
Polar surface area: 41.5 Å²
H-bond donors: 2
H-bond acceptors: 3
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 2
Molecule type: Small molecule
Indications: cardiovascular disease

via ChEMBL · EBI

Research

338 papers

Long-acting isosorbide mononitrate.Drugs · 1999
Interactions of bupranolol with the polymorphic debrisoquine/sparteine monooxygenase (CYP2D6).European journal of clinical pharmacology · 1993
Differences in the Antinociceptive Effects and Binding Properties of Propranolol and Bupranolol Enantiomers.The journal of pain · 2015
Evidence that (+)-bupranolol interacts directly with myocardial beta-adrenoceptors. Control of optical purity with differential thermal analysis.Naunyn-Schmiedeberg's archives of pharmacology · 1980
Atypical cardiostimulant beta-adrenoceptor in the rat heart: stereoselective antagonism by bupranolol but lack of effect by some bupranolol analogues.British journal of pharmacology · 2003

via PubMed

Wikidata facts

Subclass of: medication
Mass: 271.133907

Show 5 more facts

chemical formula: C₁₄H₂₂ClNO₂
World Health Organisation international non-proprietary name: bupranolol
subject has role: beta blocker
canonical SMILES: CC1=CC(=C(C=C1)Cl)OCC(CNC(C)(C)C)O
physically interacts with: adrenoceptor beta 3

Sources (2)

via Wikidata · CC0

~1 min read

Encyclopedic overview

5 sections

Contents

Uses and dosage
Pharmacology
Adverse effects, contraindications, interactions
References
Further reading

Bupranolol is a non-selective beta blocker without intrinsic sympathomimetic activity (ISA), but with strong membrane stabilizing activity. Its potency is similar to propranolol.

==Uses and dosage== Like other beta blockers, oral bupranolol can be used to treat hypertension and tachycardia. The initial dose is 50 mg two times a day. It can be increased to 100 mg four times a day. Bupranolol eye drops (0.05%-0.5%) are used against glaucoma.

Excerpted from Wikipedia’s “bupranolol” article, available under the CC BY-SA 4.0 licence.