Bopindolol

Bopindolol (INNTooltip International Nonproprietary Name), 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]

Bopindolol

Clinical data
Trade names	Sandonorm
Other names	LT 31-200
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
Drug class	Beta blocker
ATC code	C07AA17 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (RS)-1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoate
CAS Number	62658-63-3 Y
PubChem CID	44112
DrugBank	DB08807 Y
ChemSpider	40146 Y
UNII	KT304VZO57
KEGG	D07537 N
ChEBI	CHEBI:76749
ChEMBL	ChEMBL357995 Y
CompTox Dashboard (EPA)	DTXSID6022684
Chemical and physical data
Formula	C23H28N2O3
Molar mass	380.488 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3
InChI InChI=1S/C23H28N2O3/c1-16-13-19-20(25-16)11-8-12-21(19)27-15-18(14-24-23(2,3)4)28-22(26)17-9-6-5-7-10-17/h5-13,18,24-25H,14-15H2,1-4H3 Y Key:UUOJIACWOAYWEZ-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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-HT_1A 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).

Thieme Patent:^[8] Starting amnine:^[9]

History

Bopindolol is related to and was developed as a successor to pindolol.^[4] It was first described in the literature by at least 1977.^[1]