Synthesis of a new potent anti-angiogenic agent, 17α-acetoxy-9α-fluoro-6α-methylprogesterone (9α-fluoromedroxyprogesterone acetate [FMPA])

A new anti-angiogenic agent, 17α-acetoxy-9α-fluoro-6α-methylprogesterone (9α-fluoromedoroxyprogesterone acetate [FMPA, 9]) was synthesized in a 10-step sequence. FMPA (9) had about two orders of magnitude stronger anti-angiogenic activity than medroxyprogesterone acetate (MPA), as estimated in a bioassay involving chorioallantoic membranes of growing chick embryos.