Bopindolol


Bopindolol, sold under the brand name Sandonorm among others, is a beta blocker used to treat hypertension. It has been marketed in a number of countries throughout the world, for instance in Europe.

Pharmacology

Bopindolol is an ester prodrug of mepindolol. It acts as a non-selective or dual β1- and β2-adrenergic receptor antagonist. Bopindolol has intrinsic sympathomimetic activity and membrane-stabilizing activity. Besides the β1- and β2-adrenergic receptors, bopindolol shows very low affinity for the β3-adrenergic receptor and interacts with certain serotonin receptors such as the serotonin 5-HT1A receptor with strong affinity.

Chemistry

The predicted log P of bopindolol ranges from 4.45 to 4.7. It showed the highest predicted lipophilicity of 30clinically relevant beta blockers, with the second most lipophilic beta blocker predicted to be the better-known penbutolol.

Synthesis

The reaction of 4-Hydroxy-2-methylindole with epichlorohydrin in the presence of lye led to 2-methyl-4--1H-indole . Addition of tert-butylamine led to 4--2-methylindole . Ester formation with benzoic anhydride in the presence of hexamethylphosphoric acid triamide completed the synthesis of Bopindolol.

History

Bopindolol is related to and was developed as a successor to pindolol. It was first described in the literature by at least 1977.