Antrafenine Explained

Antrafenine (Stakane) is a phenylpiperazine derivative drug invented in 1979.^[1] It acts as an analgesic and anti-inflammatory drug with similar efficacy to naproxen,^[2] but is not widely used as it has largely been replaced by newer drugs.

Synthesis

Method E: The reaction between 2-[4-[3-(trifluoromethyl)phenyl]-1-piperazinyl]ethanol [40004-29-3] (1) and Isatoic anhydride [118-48-9] (2) goes on to give 4-(3-(Trifluoromethyl)phenyl)piperazine-1-ethyl 2-aminobenzoate [51941-08-3] (3).

Method G: Alkylation with 4-chloro-7-(trifluoromethyl)quinoline [346-55-4] (4) completed the synthesis of antrafenine (5).

See also

• Phenylpiperazine
• Trifluoromethylphenylpiperazine

Notes and References

1. Manoury PM, Dumas AP, Najer H, Branceni D, Prouteau M, Lefevre-Borg FM . Synthesis and analgesic activities of some (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates . Journal of Medicinal Chemistry . 22 . 5 . 554–9 . May 1979 . 458805 . 10.1021/jm00191a017 .
2. Leatham PA, Bird HA, Wright V, Seymour D, Gordon A . A double blind study of antrafenine, naproxen and placebo in osteoarthrosis . European Journal of Rheumatology and Inflammation . 6 . 2 . 209–11 . 1983 . 6673985 .