Bopindolol
Chemical compound
From Wikipedia, the free encyclopedia
Bopindolol (INN), sold under the brand name Sandonorm among others, is a beta blocker used to treat hypertension.[1][2][3][4] It has been marketed in a number of countries throughout the world, for instance in Europe.[2]
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| Trade names | Sandonorm |
| Other names | LT 31-200 |
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| Routes of administration | Oral |
| Drug class | Beta blocker |
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| Formula | C23H28N2O3 |
| Molar mass | 380.488 g·mol−1 |
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Pharmacology
Bopindolol is an ester prodrug of mepindolol.[3][4] It acts as a non-selective or dual β1- and β2-adrenergic receptor antagonist.[4] Bopindolol has intrinsic sympathomimetic activity (ISA) and membrane-stabilizing activity (MSA).[4] 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.[4]
Chemistry
The predicted log P of bopindolol ranges from 4.45 to 4.7.[5][6] 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.[7]
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).
