Butofilolol
{{Short description|Chemical compound}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Drugbox
| IUPAC_name = (RS)-1-[2-[3-(tert-butylamino)-2-hydroxypropoxy]-5-fluorophenyl]butan-1-one
| image = Butofilolol skeletal.svg
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| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 58930-32-8
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| ATC_prefix = none
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| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 157443
| PubChem = 68838
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4AZC6Y5A8G
| synonyms = CM-6805
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 62071
| chemical_formula =
| C=17 | H=26 | F=1 | N=1 | O=3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NMBNQRJDEPOXCP-UHFFFAOYSA-N
| smiles = Fc1ccc(OCC(O)CNC(C)(C)C)c(c1)C(=O)CCC
}}
Butofilolol (trade name Cafide) is a beta-blocker drug for the treatment of essential hypertension (high blood pressure).{{cite journal | vauthors = Houin G, Barre J, Jeanniot JP, Ledudal P, Cautreels W, Tillement JP | title = Pharmacokinetics of butofilolol (CAFIDE) after repeated oral administration in man | journal = International Journal of Clinical Pharmacology Research | volume = 4 | issue = 3 | pages = 175–83 | year = 1984 | pmid = 6149195 }}{{cite journal | vauthors = Toussain P, Gay G, Debry G | title = [Long-term hypotensive treatment by butofilolol] | journal = Annales de Cardiologie et d'Angeiologie | volume = 32 | issue = 4 | pages = 277–83 | date = June 1983 | pmid = 6412614 }} 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){{cite book |doi=10.1016/S0926-9614(96)80020-7 |chapter=4-fluorophenol: A key intermediate for agrochemicals and pharmaceuticals |title=The Roots of Organic Development |series=Industrial Chemistry Library |date=1996 | vauthors = Mercier C, Youmans P |volume=8 |pages=293–300 |isbn=978-0-444-82434-9 }} 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.{{cite journal | title = Butofilolol
| vauthors = Castañer J, Neuman M | journal = Drugs of the Future | date = 1982 | volume = 7 | issue = 2 | page = 96 | doi = 10.1358/dof.1982.007.02.199366 }}{{cite patent | inventor = Demarne H | title = ompositions for treatment of cardiovascular conditions associated with overproduction of catecholamines | country = US | number = 4252825 | gdate = 24 February 1981 | assign = C. M. Industries | url = https://patents.google.com/patent/US4252825 }})