Buflomedil

Buflomedil, sold under the brand name Loftyl, is a vasoactive drug used to treat claudication or the symptoms of peripheral arterial disease. It is currently not approved by the Food and Drug Administration (FDA) for use in the United States.

Buflomedil

Names
Preferred IUPAC name 4-(Pyrrolidin-1-yl)-1-(2,4,6-trimethoxyphenyl)butan-1-one
Identifiers
CAS Number	55837-25-7 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL188921 Y
ChemSpider	2373 Y
ECHA InfoCard	100.054.393
PubChem CID	2467
UNII	V7I71DQ432 Y
CompTox Dashboard (EPA)	DTXSID5022697
InChI InChI=1S/C17H25NO4/c1-20-13-11-15(21-2)17(16(12-13)22-3)14(19)7-6-10-18-8-4-5-9-18/h11-12H,4-10H2,1-3H3 Y Key: OWYLAEYXIQKAOL-UHFFFAOYSA-N Y InChI=1/C17H25NO4/c1-20-13-11-15(21-2)17(16(12-13)22-3)14(19)7-6-10-18-8-4-5-9-18/h11-12H,4-10H2,1-3H3 Key: OWYLAEYXIQKAOL-UHFFFAOYAG
SMILES O=C(c1c(OC)cc(OC)cc1OC)CCCN2CCCC2
Properties
Chemical formula	C17H25NO4
Molar mass	307.38 g/mol
Pharmacology
ATC code	C04AX20 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Toxicity

This drug has been suspended from marketing in the European Union, because of concerns about severe neurological and cardiac toxicity.^[1][2] In its press release dated 17 November 2011 EMA suggested that doctors "should stop using buflomedil and consider alternative treatment options". The European Commission advised all member states to revoke marketing authorisation.^[3]

Various adverse effects have been reported to the FDA.^[4]

Synthesis

Patent:^[5] China1 China2

Acylation between 1,3,5-trimethoxybenzene [621-23-8] (1) and 4-pyrrolidinobutyronitrile [35543-25-0] (2) occurs in chlorobenzene solvent in the presence of gaseous hydrochloric acid to give Bufomedil (3). This is a demonstration of the Hoesch reaction.