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Buflomedil

From Wikipedia, the free encyclopedia

Buflomedil
Names
Preferred IUPAC name
4-(Pyrrolidin-1-yl)-1-(2,4,6-trimethoxyphenyl)butan-1-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard100.054.393Edit this at Wikidata
UNII
  • 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 checkY
    Key: OWYLAEYXIQKAOL-UHFFFAOYSA-N checkY
  • 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
  • O=C(c1c(OC)cc(OC)cc1OC)CCCN2CCCC2
Properties
C17H25NO4
Molar mass307.38 g/mol
Pharmacology
C04AX20 (WHO)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Buflomedil, sold under the brand nameLoftyl, is avasoactive drug used to treatclaudication or the symptoms ofperipheral arterial disease. It is currently not approved by theFood and Drug Administration (FDA) for use in the United States.

Toxicity

[edit]

This drug has been suspended from marketing in the European Union, because of concerns about severeneurological andcardiac 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]

Variousadverse effects have been reported to the FDA.[4]

Synthesis

[edit]
Patent:[5]China1China2

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 giveBufomedil (3). This is a demonstration of theHoesch reaction.

References

[edit]
  1. ^"Buflomedil-Containing Drugs May Be Suspended in EU". Medscape. Retrieved20 February 2023.
  2. ^Archived copy EMAArchived 23 January 2012 at theWayback Machine
  3. ^"Buflomedil durchf beschluss"(PDF).bfarm.de (in German). February 2012. Retrieved20 February 2023.
  4. ^"Drug cite". Archived fromthe original on 4 March 2016. Retrieved18 November 2011.
  5. ^DE2122144 idem Louis Lafon,U.S. patent 3,895,030 (1975 to Orsymonde);
Phenylethanolamine derivatives
Alpha blockers
Nicotinic acid and derivatives
Purine derivatives
Ergot alkaloids
Other peripheral vasodilators
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
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