CHEBI:2379 - acebutolol

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ChEBI Name acebutolol
ChEBI ID CHEBI:2379
Definition An ether that is the 2-acetyl-4-(butanoylamino)phenyl ether of the primary hydroxy group of 3-(propan-2-ylamino)propane-1,2-diol.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H28N2O4
Net Charge 0
Average Mass 336.42600
Monoisotopic Mass 336.20491
InChI InChI=1S/C18H28N2O4/c1-5-6-18(23)20-14-7-8-17(16(9-14)13(4)21)24-11-15(22)10-19-12(2)3/h7-9,12,15,19,22H,5-6,10-11H2,1-4H3,(H,20,23)
InChIKey GOEMGAFJFRBGGG-UHFFFAOYSA-N
SMILES CCCC(=O)Nc1ccc(OCC(O)CNC(C)C)c(c1)C(C)=O
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.
sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
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.
sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing acebutolol (CHEBI:2379) has role β-adrenergic antagonist (CHEBI:35530)
acebutolol (CHEBI:2379) has role anti-arrhythmia drug (CHEBI:38070)
acebutolol (CHEBI:2379) has role antihypertensive agent (CHEBI:35674)
acebutolol (CHEBI:2379) has role sympathomimetic agent (CHEBI:35524)
acebutolol (CHEBI:2379) is a aromatic amide (CHEBI:62733)
acebutolol (CHEBI:2379) is a ethanolamines (CHEBI:23981)
acebutolol (CHEBI:2379) is a ether (CHEBI:25698)
acebutolol (CHEBI:2379) is a monocarboxylic acid amide (CHEBI:29347)
acebutolol (CHEBI:2379) is a propanolamine (CHEBI:35533)
acebutolol (CHEBI:2379) is a secondary amino compound (CHEBI:50995)
acebutolol (CHEBI:2379) is conjugate base of acebutolol(1+) (CHEBI:62101)
Incoming acebutolol(1+) (CHEBI:62101) is conjugate acid of acebutolol (CHEBI:2379)
IUPAC Name
N-{3-acetyl-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl}butanamide
INNs Sources
acebutolol ChemIDplus
acebutololum ChEBI
acetobutolol ChemIDplus
Synonyms Sources
(±)-acebutolol ChemIDplus
3'-acetyl-4'-(2-hydroxy-3-(isopropylamino)propoxy)butyranilide ChemIDplus
5'-butyramido-2'-(2-hydroxy-3-isopropylaminopropoxy)acetophenone ChemIDplus
Acebutolol KEGG COMPOUND
N-(3-acetyl-4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl)butanamide NIST Chemistry WebBook
N-[3-acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]butanamide NIST Chemistry WebBook
Manual Xrefs Databases
40 DrugCentral
Acebutolol Wikipedia
C06803 KEGG COMPOUND
D02338 KEGG DRUG
DB01193 DrugBank
LSM-4384 LINCS
US3857952 Patent
ZA6808345 Patent
View more database links
Registry Numbers Types Sources
2162244 Beilstein Registry Number ChemIDplus
2179873 Gmelin Registry Number Gmelin
37517-30-9 CAS Registry Number KEGG COMPOUND
37517-30-9 CAS Registry Number NIST Chemistry WebBook
37517-30-9 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
1378852 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2011-05-16 A cardioselective beta-blocker, acebutolol is used as the hydrochloride salt for the management of hypertension, angina pectoris, and cardiac arrhythmias.