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Butofilolol

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Chemical compound

Pharmaceutical compound
Butofilolol
Clinical data
Other namesCM-6805
ATC code
  • none
Identifiers
IUPAC name
  • (RS)-1--5-fluorophenyl]butan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.055.892 Edit this at Wikidata
Chemical and physical data
FormulaC17H26FNO3
Molar mass311.397 g·mol
3D model (JSmol)
SMILES
  • Fc1ccc(OCC(O)CNC(C)(C)C)c(c1)C(=O)CCC
InChI
  • InChI=1S/C17H26FNO3/c1-5-6-15(21)14-9-12(18)7-8-16(14)22-11-13(20)10-19-17(2,3)4/h7-9,13,19-20H,5-6,10-11H2,1-4H3
  • Key:NMBNQRJDEPOXCP-UHFFFAOYSA-N

Butofilolol (trade name Cafide) is a beta-blocker drug for the treatment of essential hypertension (high blood pressure). It is not known to be marketed anywhere.

It is an example of a butyrophenone.

Synthesis

The Fries rearrangement of the ester formed by 4-fluorophenol (1) and butryryl chloride (2) gives 5'-fluoro-2'-hydroxybutyrophenone (3). Treatment with epichlorohydrin in the presence of base leads to 1-butan-1-one (4). Lastly, reaction with tert-butylamine gives butofilolol.

References

  1. Houin G, Barre J, Jeanniot JP, Ledudal P, Cautreels W, Tillement JP (1984). "Pharmacokinetics of butofilolol (CAFIDE) after repeated oral administration in man". International Journal of Clinical Pharmacology Research. 4 (3): 175–83. PMID 6149195.
  2. Toussain P, Gay G, Debry G (June 1983). "". Annales de Cardiologie et d'Angeiologie. 32 (4): 277–83. PMID 6412614.
  3. Mercier C, Youmans P (1996). "4-fluorophenol: A key intermediate for agrochemicals and pharmaceuticals". The Roots of Organic Development. Industrial Chemistry Library. Vol. 8. pp. 293–300. doi:10.1016/S0926-9614(96)80020-7. ISBN 978-0-444-82434-9.
  4. Castañer J, Neuman M (1982). "Butofilolol". Drugs of the Future. 7 (2): 96. doi:10.1358/dof.1982.007.02.199366.
  5. US 4252825, Demarne H, "ompositions for treatment of cardiovascular conditions associated with overproduction of catecholamines", issued 24 February 1981, assigned to C. M. Industries )
Adrenergic receptor modulators
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
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