Mepindolol

Chemical compound

C07AA14 (WHO)

Identifiers

(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 InfoCard100.041.650

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Chemical and physical dataFormulaC₁₅H₂₂N₂O₂Molar mass262.353 g·mol⁻¹3D model (JSmol)

Interactive image

ChiralityRacemic mixture

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]

See also

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.

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Beta blockers (C07)

β, non-selective

β₁-selective

β₂-selective

Butaxamine

α₁- + β-selective

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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Drugs used for glaucoma preparations and miosis (S01E)

Sympathomimetics

Parasympathomimetics

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

Carbonic anhydrase inhibitors/
(sulfonamides)

Beta blocking agents

Prostaglandin analogues (F_2α)

Other agents

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Adrenergic receptor modulators

α₁

Agonists

Antagonists

α₂

Agonists

Antagonists

Agonists

Antagonists

See also: Receptor/signaling modulators
Dopaminergics
Serotonergics
Monoamine reuptake inhibitors
Monoamine releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins

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