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

Natsuko Murata
Pharmaceuticals Development Department, Meiji Dairies Corporation
Shiho Fujimori
Pharmaceuticals Development Department, Meiji Dairies Corporation
Yoshitatsu Ichihara
Pharmaceuticals Development Department, Meiji Dairies Corporation
Yoshio Sato
Division of Research and Development, Meiji Dairies Corporation
Taketo Yamaji
Division of Research and Development, Meiji Dairies Corporation
Hiroshi Tsuboi
Division of Research and Development, Meiji Dairies Corporation
Masayuki Uchida
Division of Research and Development, Meiji Dairies Corporation
Hiroto Suzuki
Pharmaceuticals Development Department, Meiji Dairies Corporation
Masashi Yamada
Pharmaceuticals Development Department, Meiji Dairies Corporation
Tsutomu Oikawa
Faculty of Health and Social Work, Kanagawa University of Human Services
Hideo Nemoto
Faculty of Pharmaceutical Sciences, University of Toyama
Junko Nobuhiro
Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University
Tominari Choshi
Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University
Satoshi Hibino
Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University

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

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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.

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