CHEBI:7444 - nadolol

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ChEBI Name nadolol
ChEBI ID CHEBI:7444
Definition Nadolol is a diastereoisomeric mixture consisting of equimolar amounts of the four possible 2,3-cis-isomers of 5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol.
Stars This entity has been manually annotated by the ChEBI Team.
Roles Classification
Biological Role(s): sympatholytic agent
Any compound which inhibits the postganglionic functioning of the sympathetic nervous system (SNS).
beta-adrenergic antagonist
An agent that binds to but does not activate beta-adrenergic receptors thereby blocking the actions of endogenous or exogenous beta-adrenergic agonists. beta-Adrenergic antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches and anxiety.
Application(s): anti-arrhythmia drug
A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
sympatholytic agent
Any compound which inhibits the postganglionic functioning of the sympathetic nervous system (SNS).
beta-adrenergic antagonist
An agent that binds to but does not activate beta-adrenergic receptors thereby blocking the actions of endogenous or exogenous beta-adrenergic agonists. beta-Adrenergic antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches and anxiety.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing nadolol (CHEBI:7444) has part (2R,3S,2'R)-nadolol (CHEBI:60917)
nadolol (CHEBI:7444) has part (2R,3S,2'S)-nadolol (CHEBI:60922)
nadolol (CHEBI:7444) has part (2S,3R,2'R)-nadolol (CHEBI:60920)
nadolol (CHEBI:7444) has part (2S,3R,2'S)-nadolol (CHEBI:60918)
nadolol (CHEBI:7444) has role β-adrenergic antagonist (CHEBI:35530)
nadolol (CHEBI:7444) has role anti-arrhythmia drug (CHEBI:38070)
nadolol (CHEBI:7444) has role antihypertensive agent (CHEBI:35674)
nadolol (CHEBI:7444) has role sympatholytic agent (CHEBI:66991)
nadolol (CHEBI:7444) is a diastereoisomeric mixture (CHEBI:60915)
IUPAC Name
rac-(2R,3S)-5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol
INN Source
nadolol ChemIDplus
Synonyms Sources
1-(tert-butylamino)-3-[(5,6,7,8-tetrahydro-cis-6,7-dihydroxy-1-naphthyl)oxy]-2-propanol ChEBI
2,3-cis-1,2,3,4-tetrahydro-5-((2-hydroxy-3-tert-butylamino)propoxy)-2,3-naphthalenediol ChemIDplus
Brand Names Sources
Corgard KEGG DRUG
Solgol ChEBI
Database Links Databases
D00432 KEGG DRUG
DB01203 DrugBank
DE2258995 Patent
DE2421549 Patent
LSM-1879 LINCS
US3935267 Patent
View more database links
Registry Numbers Types Sources
2508986 Beilstein Registry Number Beilstein
42200-33-9 CAS Registry Number ChemIDplus
42200-33-9 CAS Registry Number NIST Chemistry WebBook
Last Modified
24 February 2016
General Comments
2011-01-10 A non-cardioselective beta-blocker, nadolol is used in the management of cardiac arrhythmias, angina pectoris, and hypertension. It is also used in the prophylactic treatment of migraine, and as an adjunct in the treatment of hyperthyroidism.
2011-01-10 Nadolol is administered as an equimolar mixture of the four possible 2,3-cis-diastereoisomers of 5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol; the 2R,3S,2'R-isomer is the most active.