Synthesis and Anti-tumor Activity of a Fluorinated Analog of Medroxyprogesterone Acetate (MPA), 9α-Fluoromedroxyprogesterone Acetate (FMPA)

Natsuko Murata; Shiho Fujimori; Yoshitatsu Ichihara; Yoshio Sato; Taketo Yamaji; Hiroshi Tsuboi; Masayuki Uchida; Hiroto Suzuki; Masashi Yamada; Tsutomu Oikawa; Hideo Nemoto; Junko Nobuhiro; Tominari Choshi; Satoshi Hibino

doi:10.1248/cpb.54.1567

Regular Articles

Synthesis and Anti-tumor Activity of a Fluorinated Analog of Medroxyprogesterone Acetate (MPA), 9α-Fluoromedroxyprogesterone Acetate (FMPA)

Natsuko Murata, Shiho Fujimori, Yoshitatsu Ichihara, Yoshio Sato, Taketo Yamaji, Hiroshi Tsuboi, Masayuki Uchida, Hiroto Suzuki, Masashi Yamada, Tsutomu Oikawa, Hideo Nemoto, Junko Nobuhiro, Tominari Choshi, Satoshi Hibino

Author information

Keywords: 9α-fluoromedroxyprogesterone acetate, synthesis, medroxyprogesterone acetate, anti-angiogenic agent, dimethylbenz[a]anthracene, mammary carcinoma

JOURNAL FREE ACCESS

2006 Volume 54 Issue 11 Pages 1567-1570

DOI https://doi.org/10.1248/cpb.54.1567

Details

Abstract

We synthesized 9α-fluoromedroxyprogesterone acetate (FMPA) in order to test whether it is a more potent anti-angiogenic agent than medroxyprogesterone acetate (MPA), which has been widely used as a therapeutic agent for breast and endometrium cancers. FMPA was previously synthesized in 10 steps (total yield: 1%). An efficient synthesis of FMPA has been achieved in 6 steps (total yield: 12%). We examined the anti-tumor effect of FMPA, complexed with dimethyl-β-cyclodextrin (DM-β-CyD), on rat mammary carcinomas induced by 7,12-dimethylbenz[a]anthracene (DMBA). FMPA showed great anti-tumor effect on DMBA-induced rat mammary carcinomas.

Corresponding author

Register with J-STAGE for free!