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| Trade names | Sandonorm |
| Other names | LT 31-200 |
| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Oral |
| Drug class | Beta blocker |
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| Chemical and physical data | |
| Formula | C23H28N2O3 |
| Molar mass | 380.488 g·mol−1 |
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Bopindolol (INNTooltip International Nonproprietary Name), sold under the brand nameSandonorm among others, is abeta blocker used to treathypertension.[1][2][3][4] It has been marketed in a number of countries throughout the world, for instance inEurope.[2]
Bopindolol is anesterprodrug ofmepindolol.[3][4] It acts as anon-selective or dualβ1- andβ2-adrenergic receptorantagonist.[4] Bopindolol hasintrinsic sympathomimetic activity (ISA) andmembrane-stabilizing activity (MSA).[4] Besides the β1- and β2-adrenergic receptors, bopindolol shows very lowaffinity for theβ3-adrenergic receptor and interacts with certainserotonin receptors such as theserotonin5-HT1A receptor with strong affinity.[4]
The predictedlog P of bopindolol ranges from 4.45 to 4.7.[5][6] It showed the highest predictedlipophilicity of 30 clinically relevant beta blockers, with the second most lipophilic beta blocker predicted to be the better-knownpenbutolol.[7]
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).
Bopindolol is related to and was developed as a successor topindolol.[4] It was first described in the literature by at least 1977.[1]
