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Mepindolol

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From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

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
PubChemCID	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-selectivebeta blocker. It is used to treatglaucoma.^[1]

Synthesis

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The first reported synthesis of mepindolol in 1971 used 4-hydroxy-2-methylindole {9) withepichlorohydrin and thenisopropylamine to add the sidechain which was known to produce beta blockers, by analogy with drugs discovered byImperial Chemical Industries, such aspropanolol.^[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

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^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. Retrieved2024-06-30.

v t e Beta blockers (C07)
β, non-selective	Alprenolol Bopindolol Bupranolol Carteolol Cloranolol Mepindolol 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

Drugs used forglaucoma preparations andmiosis (S01E)

Sympathomimetics

Parasympathomimetics

muscarinic	Aceclidine Pilocarpine
muscarinic/nicotinic	Acetylcholine Carbachol
acetylcholinesterase inhibitors	Demecarium Ecothiopate Stigmine (Fluostigmine Neostigmine Physostigmine) Paraoxon