Chemistry:Bopindolol

From HandWiki

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]

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:[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]

References

  1. ↑ 1.0 1.1 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. 2014. pp. 169. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA169. Retrieved 10 July 2025. 
  2. ↑ 2.0 2.1 Index Nominum: International Drug Directory. Index Nominum: International Drug Directory. Medpharm Scientific Publishers. 2004. pp. 154. ISBN 978-3-88763-101-7. https://books.google.com/books?id=EgeuA47Ocm4C&pg=PA154. Retrieved 10 July 2025. 
  3. ↑ 3.0 3.1 Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. 2012. pp. 53. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA53. Retrieved 10 July 2025. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 "Bopindolol: pharmacological basis and clinical implications". Cardiovascular Drug Reviews 19 (1): 9–24. Spring 2001. doi:10.1111/j.1527-3466.2001.tb00180.x. PMID 11314603. 
  5. ↑ "Bopindolol". PubChem. U.S. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/44112. 
  6. ↑ "Bopindolol: Uses, Interactions, Mechanism of Action". 20 October 2010. https://go.drugbank.com/drugs/DB08807. 
  7. ↑ "The impact of lipophilicity in drug research: a case report on beta-blockers". Mini Reviews in Medicinal Chemistry 5 (2): 197–205. February 2005. 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).




Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Bopindolol&oldid=4028152"