Bopindolol

Last updated
Bopindolol
Bopindolol.svg
Clinical data
Trade names Sandonorm
Other namesLT 31-200
AHFS/Drugs.com International Drug Names
Routes of
administration 		Oral
Drug class Beta blocker
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (RS)-1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C23H28N2O3
Molar mass 380.488 g·mol−1
3D model (JSmol)
  • CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)(C)C)OC(=O)C3=CC=CC=C3
  • 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 Yes check.svgY
  • Key:UUOJIACWOAYWEZ-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Bopindolol (INN Tooltip 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]

Contents

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).

Thieme Patent: Starting amnine: Bopindolol synthesis.svg
Thieme Patent: Starting amnine:

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]

References

  1. 1 2 Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 169. ISBN   978-1-4757-2085-3 . Retrieved 10 July 2025.
  2. 1 2 Schweizerischer Apotheker-Verein (2004). Index Nominum: International Drug Directory. Index Nominum: International Drug Directory. Medpharm Scientific Publishers. p. 154. ISBN   978-3-88763-101-7 . Retrieved 10 July 2025.
  3. 1 2 Morton, I.K.; Hall, J.M. (2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. p. 53. ISBN   978-94-011-4439-1 . Retrieved 10 July 2025.
  4. 1 2 3 4 5 6 Nagatomo T, Hosohata Y, Ohnuki T, Nakamura T, Hattori K, Suzuki J, Ishiguro M (Spring 2001). "Bopindolol: pharmacological basis and clinical implications". Cardiovascular Drug Reviews. 19 (1): 9–24. doi: 10.1111/j.1527-3466.2001.tb00180.x . PMID   11314603.
  5. ↑ "Bopindolol". PubChem. Retrieved 10 July 2025.
  6. ↑ "Bopindolol: Uses, Interactions, Mechanism of Action". DrugBank Online. 20 October 2010. Retrieved 10 July 2025.
  7. ↑ Mannhold R (February 2005). "The impact of lipophilicity in drug research: a case report on beta-blockers". Mini Rev Med Chem. 5 (2): 197–205. doi:10.2174/1389557053402701. PMID   15720289.
  8. ↑ DE2635209 idem Franz Troxler, Fritz Seemann, U.S. patent 4,434,176 (1984 to Sandoz Ltd.).
  9. ↑ Franz Dr Troxler & Albert Dr Hofmann, CH453363 (1968 to Sandoz AG).


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