penbutolol

Also known as HOE-39-893d, HOE-893d, Levatol®, HOE 893D, HOE 893, Penbutololum, 2-Propanol, 1-(2-cyclopentylphenoxy)-3-((1,1-dimethylethyl)amino)-, (S)-

Penbutolol (brand names Levatol, Levatolol, Lobeta, Paginol, Hostabloc, Betapressin) is a medication in the class of beta blockers, used in the treatment of high blood pressure. Penbutolol is able to bind to both beta-1 adrenergic receptors and beta-2 adrenergic receptors (the two subtypes), thus making it a non-selective β blocker. Penbutolol is a sympathomimetic drug with properties allowing it to act as a partial agonist at β adrenergic receptors.

Chemical data

Formula: C18H29NO2
Molecular weight: 291.4 g/mol
IUPAC name: (2S)-1-(tert-butylamino)-3-(2-cyclopentylphenoxy)propan-2-ol
SMILES: CC(C)(C)NC[C@@H](COC1=CC=CC=C1C2CCCC2)O
InChIKey: KQXKVJAGOJTNJS-HNNXBMFYSA-N
XLogP: 4.2
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: Approved
Molecule type: Small molecule
First approval: 1987
Admin. routes: oral
Indications: cardiovascular disease

via ChEMBL · EBI

Research

273 papers

Penbutolol.2006
Penbutolol.2012
Penbutolol: a new beta-adrenergic blocking agent.DICP : the annals of pharmacotherapy · 1990
Penbutolol and carteolol: two new beta-adrenergic blockers with partial agonism.Journal of clinical pharmacology · 1990
Penbutolol: pharmacokinetics, effect on exercise tachycardia, and in vitro inhibition of radioligand binding.European journal of clinical pharmacology · 1988

via PubMed

Wikidata facts

Mass: 291.219829
Has use: medication

Show 9 more facts

Commons category: Penbutolol
chemical formula: C₁₈H₂₉NO₂
medical condition treated: arterial hypertension
World Health Organisation international non-proprietary name: penbutolol
canonical SMILES: CC(C)(C)NCC(COC1=CC=CC=C1C2CCCC2)O
isomeric SMILES: CC(C)(C)NC[C@@H](COC1=CC=CC=C1C2CCCC2)O
defined daily dose: 40
subject has role: antihypertensive drug
found in taxon: Caenorhabditis elegans

Sources (6)

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~4 min read

Encyclopedic overview

9 sections

Contents

Medical uses
Side effects
Pharmacology
Pharmacodynamics
Pharmacokinetics
Chemistry
Society and culture
Availability
References

It was approved by the FDA in 1987 and was withdrawn from the US market by January 2015.

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

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