Structure via PubChem · Public domain (PubChem)
epanolol
Sign in to saveAlso known as ICI 141292
Epanolol is a beta blocker. developed by Imperial Chemical Industries. ==Synthesis== upright=2 The ester methyl 4-benzyloxyphenylacetate (1) is treated with ethylenediamine to give the amide (3). Separately, 2-cyanophenol (4) is reacted with epichlorohydrin and sodium hydroxide to produce the benzonitrile derivative (5). Combination of (3) and (5) by heating in propanol gives (6). Lastly, catalytic hydrogenation removes the benzyl protecting group and yields epanolol.
Chemical data
- Formula
- C20H23N3O4
- Molecular weight
- 369.4 g/mol
- IUPAC name
- N-[2-[[3-(2-cyanophenoxy)-2-hydroxypropyl]amino]ethyl]-2-(4-hydroxyphenyl)acetamide
- SMILES
- C1=CC=C(C(=C1)C#N)OCC(CNCCNC(=O)CC2=CC=C(C=C2)O)O
- InChIKey
- YARKMNAWFIMDKV-UHFFFAOYSA-N
- XLogP
- 0.9
- Polar surface area
- 115 Ų
- H-bond donors
- 4
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- cardiovascular disease
via ChEMBL · EBI
Research
58 papers- Clinical pharmacology of epanolol. Pharmacodynamic aspects.Drugs · 1989
- An overview of clinical trial experience with epanolol.Drugs · 1989
- Epanolol. A new once-daily antianginal agent: dose finding and long term efficacy.Drugs · 1989
- Efficacy of epanolol versus metoprolol in angina pectoris: report from a Swedish multicentre study of exercise tolerance.Journal of internal medicine · 1992
- Effects of epanolol and metoprolol on the heart measured by 24-hour holter monitoring.Drugs · 1989
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 369.169
Show 3 more facts
- canonical SMILES
- C1=CC=C(C(=C1)C#N)OCC(CNCCNC(=O)CC2=CC=C(C=C2)O)O
- chemical formula
- C₂₀H₂₃N₃O₄
- subject has role
- beta blocker
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Synthesis
- See also
- References
Epanolol is a beta blocker. developed by Imperial Chemical Industries. ==Synthesis== upright=2 The ester methyl 4-benzyloxyphenylacetate (1) is treated with ethylenediamine to give the amide (3). Separately, 2-cyanophenol (4) is reacted with epichlorohydrin and sodium hydroxide to produce the benzonitrile derivative (5). Combination of (3) and (5) by heating in propanol gives (6). Lastly, catalytic hydrogenation removes the benzyl protecting group and yields epanolol.
==See also== Bunitrolol Bucindolol
Excerpted from Wikipedia’s “epanolol” article, available under the CC BY-SA 4.0 licence.