Novel design and synthesis of modified structure of Carvedilol

Mehrnoosh Hashemzadeh, Mohammad R. Movahed, Wade A. Russu, Ladan Soroush, Diné N. Hill

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

β-adrenergic blocking agents have been in use for nearly 40 years. β-blockers have been more thoroughly studied in the past twenty years as they have become commonly prescribed to heart failure patients. The class of β-blockers has grown considerably and has many pharmaceutical applications in patients with heart failure. Carvedilol has been the most effective beta-blocker in the treatment of the systolic heart failure. Carvedilol is a non-selective β - and β -blocker enantiomer with antioxidant effects that are attributed to its carbazole moiety. Carvedilol is taken twice daily because it is extensively metabolized and therefore loses its effectiveness due to a short half-life. Recently a long acting carvedilol has become available, as Coreg CR. Coreg CR is available for once-a-day administration as controlled-release oral capsules containing 10, 20, 40, or 80 mg carvedilol phosphate. The subject of the current report is to design a new structural analog of carvedilol that incorporates a protecting group such as a fluorine atom at position 8 of the carbazole ring for the purpose of blocking a critical metabolic pathway thus increasing its half life. This will follow discussion regarding current carvedilol patents. We believe that carvedilol activity will remain unchanged. The synthesis of 8-Fluoro-1, 2, 3, 9-tetrahydro-4H-carbazol-4-one, a key synthetic intermediate of the designed carvedilol analog, was carried out and successfully characterized.

Original languageEnglish (US)
Pages (from-to)175-179
Number of pages5
JournalRecent Patents on Cardiovascular Drug Discovery
Volume6
Issue number3
DOIs
StatePublished - Sep 2011

Keywords

  • Acute coronary syndrome
  • Carvedilol
  • Coreg
  • Coreg cr
  • Heart failure
  • β-blocker

ASJC Scopus subject areas

  • Drug Discovery
  • Cardiology and Cardiovascular Medicine
  • Pharmacology (medical)

Fingerprint Dive into the research topics of 'Novel design and synthesis of modified structure of Carvedilol'. Together they form a unique fingerprint.

Cite this