Structure via PubChem · Public domain (PubChem)
mepindolol
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Mepindolol (Betagon) is a non-selective beta blocker. It is used to treat glaucoma. ==Synthesis== upright=2 The first reported synthesis of mepindolol in 1971 used 4-hydroxy-2-methylindole {9) with epichlorohydrin and then isopropylamine to add the sidechain which was known to produce beta blockers, by analogy with drugs discovered by Imperial Chemical Industries, such as propanolol. The requisite intermediate was synthesized in a multi-step procedure from 4-benzyloxyindole-2-carboxylic acid (1) which was converted into (9) by conventional chemistry.
Chemical data
- Formula
- C15H22N2O2
- Molecular weight
- 262.35 g/mol
- IUPAC name
- 1-[(2-methyl-1H-indol-4-yl)oxy]-3-(propan-2-ylamino)propan-2-ol
- SMILES
- CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)C)O
- InChIKey
- NXWGWUVGUSFQJC-UHFFFAOYSA-N
- XLogP
- 2.3
- Polar surface area
- 57.3 Ų
- H-bond donors
- 3
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- cardiovascular disease
via ChEMBL · EBI
Research
87 papers- Mepindolol reduces myocardial necrosis in rats with coronary artery occlusion.Journal of cardiovascular pharmacology · 1985
- [Mepindolol reduction of the degradation of phospholipids and the necrosis induced by myocardial ischemia].Giornale italiano di cardiologia · 1985
- Multicenter evaluation of mepindolol and of mepindolol plus hydrochlorothiazide in essential hypertension.International journal of clinical pharmacology, therapy, and toxicology · 1982
- Effects of (+/-)- (+)- and (-)-metoprolol, (+/-)- (+)- and (-)-pindolol, (+/-)-mepindolol and (+/-)-bopindolol on the rat left atria and portal vein.General pharmacology · 1991
- Determination of plasma mepindolol levels by high-performance liquid chromatography and electrochemical detection.Journal of chromatography · 1980
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 262.168
Show 5 more facts
- canonical SMILES
- CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)C)O
- chemical formula
- C₁₅H₂₂N₂O₂
- subject has role
- beta blocker
- Commons category
- Mepindolol
- defined daily dose
- 5
Sources (3)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Synthesis
- See also
- References
Mepindolol (Betagon) is a non-selective beta blocker. It is used to treat glaucoma. ==Synthesis== upright=2 The first reported synthesis of mepindolol in 1971 used 4-hydroxy-2-methylindole {9) with epichlorohydrin and then isopropylamine to add the sidechain which was known to produce beta blockers, by analogy with drugs discovered by Imperial Chemical Industries, such as propanolol. The requisite intermediate was synthesized in a multi-step procedure from 4-benzyloxyindole-2-carboxylic acid (1) which was converted into (9) by conventional chemistry.
== See also == Pindolol Bopindolol
Excerpted from Wikipedia’s “mepindolol” article, available under the CC BY-SA 4.0 licence.