CHEBI:6438 - levobunolol

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ChEBI Name levobunolol
ChEBI ID CHEBI:6438
Definition A cyclic ketone that is 3,4-dihydronaphthalen-1-one substituted at position 5 by a 3-(tert-butylamino)-2-hydroxypropoxy group (the S-enantiomer). A non-selective β-adrenergic antagonist used (as its hydrochloride salt) for treatment of glaucoma.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C17H25NO3
Net Charge 0
Average Mass 291.38534
Monoisotopic Mass 291.183
InChI InChI=1S/C17H25NO3/c1-17(2,3)18-10-12(19)11-21-16-9-5-6-13-14(16)7-4-8-15(13)20/h5-6,9,12,18-19H,4,7-8,10-11H2,1-3H3/t12-/m0/s1
InChIKey IXHBTMCLRNMKHZ-LBPRGKRZSA-N
SMILES CC(C)(C)NC[C@H](O)COc1cccc2C(=O)CCCc12
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): antiglaucoma drug
Any drug which can be used to prevent or alleviate glaucoma, a disease in which the optic nerve is damaged, resulting in progressive, irreversible loss of vision. It is often, though not always, associated with increased pressure of the fluid in the eye.
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.
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ChEBI Ontology
Outgoing levobunolol (CHEBI:6438) has parent hydride tetralin (CHEBI:35008)
levobunolol (CHEBI:6438) has role β-adrenergic antagonist (CHEBI:35530)
levobunolol (CHEBI:6438) has role antiglaucoma drug (CHEBI:39456)
levobunolol (CHEBI:6438) is a aromatic ether (CHEBI:35618)
levobunolol (CHEBI:6438) is a cyclic ketone (CHEBI:3992)
levobunolol (CHEBI:6438) is a propanolamine (CHEBI:35533)
levobunolol (CHEBI:6438) is conjugate acid of levobunolol(1+) (CHEBI:72567)
Incoming dihydrolevobunolol (CHEBI:30268) has functional parent levobunolol (CHEBI:6438)
levobunolol(1+) (CHEBI:72567) is conjugate base of levobunolol (CHEBI:6438)
IUPAC Name
5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydronaphthalen-1(2H)-one
INN Source
levobunololum ChemIDplus
Synonyms Sources
(-)-Bunolol KEGG COMPOUND
(S)-5-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)-3,4-dihydro-1(2H)-naphthalenone ChemIDplus
Levobunolol KEGG COMPOUND
Manual Xrefs Databases
431 DrugCentral
C07914 KEGG COMPOUND
D08115 KEGG DRUG
DB01210 DrugBank
HMDB0015341 HMDB
Levobunolol Wikipedia
LSM-6578 LINCS
US2011263638 Patent
US2011275617 Patent
WO2008002929 Patent
WO2011140194 Patent
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Registry Numbers Types Sources
47141-42-4 CAS Registry Number KEGG COMPOUND
47141-42-4 CAS Registry Number ChemIDplus
6484587 Beilstein Registry Number Beilstein
6484587 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
11 August 2017