CHEBI:6343 - labetalol

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ChEBI Name labetalol
ChEBI ID CHEBI:6343
Definition A secondary amino compound formally derived from ammonia by replacing two of the hydrogens by 2-(3-carbamoyl-4-hydroxyphenyl)-2-hydroxyethyl and 4-phenylbutan-2-yl groups. It is an adrenergic antagonist used to treat high blood pressure.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C19H24N2O3
Net Charge 0
Average Mass 328.40554
Monoisotopic Mass 328.179
InChI InChI=1S/C19H24N2O3/c1-13(7-8-14-5-3-2-4-6-14)21-12-18(23)15-9-10-17(22)16(11-15)19(20)24/h2-6,9-11,13,18,21-23H,7-8,12H2,1H3,(H2,20,24)
InChIKey SGUAFYQXFOLMHL-UHFFFAOYSA-N
SMILES CC(CCc1ccccc1)NCC(O)c1ccc(O)c(c1)C(N)=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): sympatholytic agent
Any compound which inhibits the postganglionic functioning of the sympathetic nervous system (SNS).
alpha-adrenergic antagonist
An agent that binds to but does not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
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): 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).
alpha-adrenergic antagonist
An agent that binds to but does not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
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 labetalol (CHEBI:6343) has role α-adrenergic antagonist (CHEBI:37890)
labetalol (CHEBI:6343) has role β-adrenergic antagonist (CHEBI:35530)
labetalol (CHEBI:6343) has role antihypertensive agent (CHEBI:35674)
labetalol (CHEBI:6343) has role sympatholytic agent (CHEBI:66991)
labetalol (CHEBI:6343) is a benzamides (CHEBI:22702)
labetalol (CHEBI:6343) is a secondary amino compound (CHEBI:50995)
IUPAC Name
2-hydroxy-5-{1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl}benzamide
INNs Sources
labétalol ChEBI
labetalol ChEBI
labetalolum ChEBI
Synonyms Sources
3-Carboxamido-4-hydroxy-alpha-((1-methyl-3-phenylpropylamino)methyl)benzyl alcohol ChemIDplus
5-(1-Hydroxy-2-(1-methyl-3-phenylpropylamino)ethyl)salicylamide ChemIDplus
kabetalol
Note: (2017-06-19) Misnomer used in PMID:28166217.
ChEBI
Labetalol KEGG COMPOUND
Manual Xrefs Databases
1531 DrugCentral
C07063 KEGG COMPOUND
D08106 KEGG DRUG
DB00598 DrugBank
DE2032642 Patent
HMDB0014736 HMDB
Labetalol Wikipedia
LSM-1282 LINCS
US4012444 Patent
View more database links
Registry Numbers Types Sources
2948416 Reaxys Registry Number Reaxys
2948416 Beilstein Registry Number Beilstein
36894-69-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
21908132 PubMed citation Europe PMC
22300487 PubMed citation Europe PMC
22528277 PubMed citation Europe PMC
23055089 PubMed citation Europe PMC
28166217 PubMed citation Europe PMC
Last Modified
19 June 2017