CHEBI:6897 - metipranolol

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ChEBI Name metipranolol
ChEBI ID CHEBI:6897
Definition 3-(Propan-2-ylamino)propane-1,2-diol in which the hydrogen of the primary hydroxy group is substituted by a 4-acetoxy-2,3,5-trimethylphenoxy group. A non-cardioselective beta-blocker, it is used to lower intra-ocular pressure in the management of open-angle glaucoma.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:355221
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Formula C17H27NO4
Net Charge 0
Average Mass 309.40060
Monoisotopic Mass 309.194
InChI InChI=1S/C17H27NO4/c1-10(2)18-8-15(20)9-21-16-7-11(3)17(22-14(6)19)13(5)12(16)4/h7,10,15,18,20H,8-9H2,1-6H3
InChIKey BQIPXWYNLPYNHW-UHFFFAOYSA-N
SMILES CC(C)NCC(O)COc1cc(C)c(OC(C)=O)c(C)c1C
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.
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.
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ChEBI Ontology
Outgoing metipranolol (CHEBI:6897) has role β-adrenergic antagonist (CHEBI:35530)
metipranolol (CHEBI:6897) has role anti-arrhythmia drug (CHEBI:38070)
metipranolol (CHEBI:6897) has role antiglaucoma drug (CHEBI:39456)
metipranolol (CHEBI:6897) has role antihypertensive agent (CHEBI:35674)
metipranolol (CHEBI:6897) is a acetate ester (CHEBI:47622)
metipranolol (CHEBI:6897) is a aromatic ether (CHEBI:35618)
metipranolol (CHEBI:6897) is a propanolamine (CHEBI:35533)
metipranolol (CHEBI:6897) is a secondary amino compound (CHEBI:50995)
IUPAC Name
4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-2,3,6-trimethylphenyl acetate
INNs Sources
metipranolol ChemIDplus
metipranololum ChemIDplus
Synonyms Sources
(±)-metipranolol ChEBI
Acetic acid 4-(2-hydroxy-3-isopropylamino-propoxy)-2,3,6-trimethyl-phenyl ester ChEMBL
Metipranolol KEGG COMPOUND
Manual Xrefs Databases
1779 DrugCentral
C07915 KEGG COMPOUND
D02374 KEGG DRUG
DB01214 DrugBank
Metipranolol Wikipedia
View more database links
Registry Numbers Types Sources
2152010 Reaxys Registry Number Reaxys
22664-55-7 CAS Registry Number ChemIDplus
Last Modified
22 February 2017