Buflomedil

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Buflomedil
Names
Preferred IUPAC name
4-(Pyrrolidin-1-yl)-1-(2,4,6-trimethoxyphenyl)butan-1-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.054.393 Edit 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 mass 307.38 g/mol
Pharmacology
C04AX20 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

Toxicity

[edit]

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

[edit]
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.

References

[edit]
  1. ^ "Buflomedil-Containing Drugs May Be Suspended in EU". Medscape. Retrieved 20 February 2023.
  2. ^ Archived copy EMA Archived 23 January 2012 at the Wayback Machine
  3. ^ "Buflomedil durchf beschluss" (PDF). bfarm.de (in German). February 2012. Retrieved 20 February 2023.
  4. ^ "Drug cite". Archived from the original on 4 March 2016. Retrieved 18 November 2011.
  5. ^ DE2122144 idem Louis Lafon, U.S. patent 3,895,030 (1975 to Orsymonde);


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