Butofilolol

Butofilolol
Clinical data
Other names	CM-6805
ATC code	none;
Identifiers
	IUPAC name (RS)-1-[2-[3-(tert-butylamino)-2-hydroxypropoxy]-5-fluorophenyl]butan-1-one;
CAS Number	58930-32-8 ;
PubChem CID	68838;
ChemSpider	62071 ;
UNII	4AZC6Y5A8G;
ChEMBL	ChEMBL157443 ;
CompTox Dashboard (EPA)	DTXSID30867082 ;
ECHA InfoCard	100.055.892
Chemical and physical data
Formula	C17H26FNO3
Molar mass	311.397 g·mol−1
3D model (JSmol)	Interactive image;
	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).^[1]^[2] 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)^[3] and butryryl chloride (2) gives 5'-fluoro-2'-hydroxybutyrophenone (3). Treatment with epichlorohydrin in the presence of base leads to 1-[5-fluoro-2-(oxiranylmethoxy)phenyl]butan-1-one (4). Lastly, reaction with tert-butylamine gives butofilolol.^[4]^[5]

References

^ 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.
^ Toussain P, Gay G, Debry G (June 1983). "[Long-term hypotensive treatment by butofilolol]". Annales de Cardiologie et d'Angeiologie. 32 (4): 277–83. PMID 6412614.
^ 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.
^ Castañer J, Neuman M (1982). "Butofilolol". Drugs of the Future. 7 (2): 96. doi:10.1358/dof.1982.007.02.199366.
^ US 4252825, Demarne H, "ompositions for treatment of cardiovascular conditions associated with overproduction of catecholamines", issued 24 February 1981, assigned to C. M. Industries )

[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). "[Long-term hypotensive treatment by butofilolol]". 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 )

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