Mepindolol

Mepindolol
Clinical data
ATC code	C07AA14 (WHO) ;
Identifiers
	IUPAC name (RS)-1-[(2-Methyl-1H-indol-4-yl)oxy]-3-(propan-2-ylamino)propan-2-ol;
CAS Number	23694-81-7;
PubChem CID	71698;
ChemSpider	64750;
UNII	00Q31ER368;
KEGG	D07181;
CompTox Dashboard (EPA)	DTXSID40865110 ;
ECHA InfoCard	100.041.650
Chemical and physical data
Formula	C15H22N2O2
Molar mass	262.353 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)C)O;
	InChI InChI=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; Key:NXWGWUVGUSFQJC-UHFFFAOYSA-N;

Mepindolol (Betagon) is a non-selective beta blocker. It is used to treat glaucoma.^[1]

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.^[2] 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.^[3]^[4]

References

^ Schmid MG, Gecse O, Szabo Z, Kilár F, Gübitz G, Ali I, et al. (September 2001). "Comparative study of the chiral resolution of β-blockers on cellulose tris (3,5-dimethyl-phenylcarbamate) phases in normal and reversed phase modes". Journal of Liquid Chromatography & Related Technologies. 24 (16): 2493–2504. doi:10.1081/JLC-100105955.
^ Lednicer D (1998). Strategies for Organic Drug Synthesis and Design. Canada: John Wiley & Sons. pp. 37–41. ISBN 0-471-19657-6.
^ Seemann F, Wiskott E, Niklaus P, Troxler F (1971). "Beiträge zur Chemie der 4-Hydroxyindol-Verbindungen 10. Mitteilung über synthetische indolverbindungen" [Contributions to the chemistry of 4-hydroxyindole compounds 10. Report on synthetic indole compounds]. Helvetica Chimica Acta (in German). 54 (8): 2411–2419. doi:10.1002/hlca.19710540805.
^ "Mepindolol". Pharmaceutical Substances. Georg Thieme Verlag KG. Retrieved 2024-06-30.

[1] Schmid MG, Gecse O, Szabo Z, Kilár F, Gübitz G, Ali I, et al. (September 2001). "Comparative study of the chiral resolution of β-blockers on cellulose tris (3,5-dimethyl-phenylcarbamate) phases in normal and reversed phase modes". Journal of Liquid Chromatography & Related Technologies. 24 (16): 2493–2504. doi:10.1081/JLC-100105955.

[2] Lednicer D (1998). Strategies for Organic Drug Synthesis and Design. Canada: John Wiley & Sons. pp. 37–41. ISBN 0-471-19657-6.

[3] Seemann F, Wiskott E, Niklaus P, Troxler F (1971). "Beiträge zur Chemie der 4-Hydroxyindol-Verbindungen 10. Mitteilung über synthetische indolverbindungen" [Contributions to the chemistry of 4-hydroxyindole compounds 10. Report on synthetic indole compounds]. Helvetica Chimica Acta (in German). 54 (8): 2411–2419. doi:10.1002/hlca.19710540805.

[4] "Mepindolol". Pharmaceutical Substances. Georg Thieme Verlag KG. Retrieved 2024-06-30.

[1]

[2]

[3]

[4]

Beta blockers (C07)
β, non-selective	Alprenolol Bopindolol Bupranolol Carteolol Cloranolol Nadolol Oxprenolol Penbutolol Pindolol/Iodopindolol Propranolol^# Sotalol Tertatolol Timolol^#
β₁-selective	Acebutolol Atenolol Betaxolol Bevantolol Bisoprolol^# Celiprolol Epanolol Esmolol Landiolol Metoprolol Nebivolol Practolol Talinolol
β₂-selective	Butaxamine
α₁- + β-selective	Arotinolol Carvedilol Labetalol
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Synthesis

See also

References