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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.054.393
PubChem CID
UNII
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
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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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.

References
  1. Medscape: http://www.medscape.com/viewarticle/753768
  2. EMA: http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/public_health_alerts/2011/11/human_pha_detail_000045.jsp&mid=WC0b01ac058001d126
  3. https://www.bfarm.de/SharedDocs/Downloads/DE/Arzneimittel/Pharmakovigilanz/Risikoinformationen/RisikoBewVerf/a-f/buflomedil_durchf_beschluss.pdf?__blob=publicationFile&v=3
  4. http://www.drugcite.com/?q=BUFLOMEDIL&s=&a=
  5. DE2122144 idem Louis Lafon, U.S. Patent 3,895,030 (1975 to Orsymonde);


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