CHEBI:60917 - (2R,3S,2'R)-nadolol

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ChEBI Name (2R,3S,2'R)-nadolol
ChEBI ID CHEBI:60917
ChEBI ASCII Name (2R,3S,2'R)-nadolol
Definition An aromatic ether, being the (2R)-3-(tert-butylamino)-2-hydroxypropyl ether of the phenolic hydroxy group of (6R,7S)-5,6,7,8-tetrahydronaphthalene-1,6,7-triol.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C17H27NO4
Net Charge 0
Average Mass 309.40060
Monoisotopic Mass 309.19401
InChI InChI=1S/C17H27NO4/c1-17(2,3)18-9-12(19)10-22-16-6-4-5-11-7-14(20)15(21)8-13(11)16/h4-6,12,14-15,18-21H,7-10H2,1-3H3/t12-,14-,15+/m1/s1
InChIKey VWPOSFSPZNDTMJ-YUELXQCFSA-N
SMILES CC(C)(C)NC[C@@H](O)COc1cccc2C[C@@H](O)[C@@H](O)Cc12
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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): 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.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (2R,3S,2'R)-nadolol (CHEBI:60917) has role β-adrenergic antagonist (CHEBI:35530)
(2R,3S,2'R)-nadolol (CHEBI:60917) has role anti-arrhythmia drug (CHEBI:38070)
(2R,3S,2'R)-nadolol (CHEBI:60917) has role antihypertensive agent (CHEBI:35674)
(2R,3S,2'R)-nadolol (CHEBI:60917) is a aromatic ether (CHEBI:35618)
(2R,3S,2'R)-nadolol (CHEBI:60917) is a secondary amino compound (CHEBI:50995)
(2R,3S,2'R)-nadolol (CHEBI:60917) is a triol (CHEBI:27136)
(2R,3S,2'R)-nadolol (CHEBI:60917) is enantiomer of (2S,3R,2'S)-nadolol (CHEBI:60918)
Incoming nadolol (CHEBI:7444) has part (2R,3S,2'R)-nadolol (CHEBI:60917)
(2S,3R,2'S)-nadolol (CHEBI:60918) is enantiomer of (2R,3S,2'R)-nadolol (CHEBI:60917)
IUPAC Name
(2R,3S)-5-{[(2R)-3-(tert-butylamino)-2-hydroxypropyl]oxy}-1,2,3,4-tetrahydronaphthalene-2,3-diol
Registry Number Type Source
7518264 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
20945127 PubMed citation Europe PMC
Last Modified
10 January 2011
General Comment
2011-01-10 This is the most active diastereoisomer of nadolol, 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. 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.