Bopindolol (INNTooltip International Nonproprietary Name), 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 (ISA) and membrane-stabilizing activity (MSA). 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 30 clinically 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 [35320-67-3] (1) with epichlorohydrin in the presence of lye led to 2-methyl-4-(oxiran-2-ylmethoxy)-1H-indole [62119-47-5] (2). Addition of tert-butylamine led to 4-(2-Hydroxy-3-tert-butylaminopropoxy)-2-methylindole [23869-98-9] (3). Ester formation with benzoic anhydride [93-97-0] (4) in the presence of hexamethylphosphoric acid triamide [680-31-9] completed the synthesis of Bopindolol (5).
History Bopindolol is related to and was developed as a successor to pindolol. It was first described in the literature by at least 1977.
References