Mepindolol
{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| image = Mepindolol.svg
| width =
| chirality = Racemic mixture
| IUPAC_name = (RS)-1-[(2-Methyl-1H-indol-4-yl)oxy]-3-(propan-2-ylamino)propan-2-ol
| UNII = 00Q31ER368
| CAS_number=23694-81-7
| PubChem=71698
| KEGG = D07181
| smiles=CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)C)O
| ATC_prefix = C07
| ATC_suffix = AA14
| ChemSpiderID = 64750
| C=15|H=22|N=2|O=2
| StdInChI = 1S/C15H22N2O2/c1-10(2)16-8-12(18)9-19-15-6-4-5-14-13(15)7-11(3)17-14/h4-7,10,12,16-18H,8-9H2,1-3H3
| StdInChIKey = NXWGWUVGUSFQJC-UHFFFAOYSA-N
}}
Mepindolol (Betagon) is a non-selective beta blocker. It is used to treat glaucoma.{{cite journal | vauthors = Schmid MG, Gecse O, Szabo Z, Kilár F, Gübitz G, Ali I, Aboul-Enein HY |title = Comparative study of the chiral resolution of β-blockers on cellulose tris (3,5-dimethyl-phenylcarbamate) phases in normal and reversed phase modes |journal = Journal of Liquid Chromatography & Related Technologies |volume = 24 |issue = 16 |doi = 10.1081/JLC-100105955 |pages = 2493–2504 | date = September 2001 }}
Synthesis
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.{{cite book| vauthors = Lednicer D |title=Strategies for Organic Drug Synthesis and Design|year=1998|publisher=John Wiley & Sons|location=Canada|isbn=0-471-19657-6|pages=37–41}} 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.{{cite journal |doi=10.1002/hlca.19710540805 |title=Beiträge zur Chemie der 4-Hydroxyindol-Verbindungen 10. Mitteilung über synthetische indolverbindungen |trans-title=Contributions to the chemistry of 4-hydroxyindole compounds 10. Report on synthetic indole compounds |date=1971 | vauthors = Seemann F, Wiskott E, Niklaus P, Troxler F |journal=Helvetica Chimica Acta |volume=54 |issue=8 |pages=2411–2419 |language=DE }}{{cite web |url=https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-13-0054 |title=Mepindolol | work = Pharmaceutical Substances |publisher=Georg Thieme Verlag KG |access-date=2024-06-30 }}
See also
References
{{Reflist}}
{{Beta blockers}}
{{Antiglaucoma preparations and miotics}}
{{Adrenergic receptor modulators}}
Category:Indole ethers at the benzene ring
Category:N-isopropyl-phenoxypropanolamines
{{Antihypertensive-stub}}