title: Synthesis and anti-tumor activity of a fluorinated analog of medroxyprogesterone acetate (MPA), 9alpha-fluoromedroxyprogesterone acetate (FMPA).
abstract: We synthesized 9alpha-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-beta-cyclodextrin (DM-beta-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.
authors.affiliation: Pharmaceuticals Development Department, Meiji Dairies Corporation, Tokyo, Japan. natsuko_murata@meiji-milk.com
authors.forename: Natsuko
authors.initials: N
authors.lastname: Murata
authors.forename: Shiho
authors.initials: S
authors.lastname: Fujimori
authors.forename: Yoshitatsu
authors.initials: Y
authors.lastname: Ichihara
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Sato
authors.forename: Taketo
authors.initials: T
authors.lastname: Yamaji
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Tsuboi
authors.forename: Masayuki
authors.initials: M
authors.lastname: Uchida
authors.forename: Hiroto
authors.initials: H
authors.lastname: Suzuki
authors.forename: Masashi
authors.initials: M
authors.lastname: Yamada
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Oikawa
authors.forename: Hideo
authors.initials: H
authors.lastname: Nemoto
authors.forename: Junko
authors.initials: J
authors.lastname: Nobuhiro
authors.forename: Tominari
authors.initials: T
authors.lastname: Choshi
authors.forename: Satoshi
authors.initials: S
authors.lastname: Hibino
mesh_terms: D000284:Administration, Oral; D000818:Animals; D000970:Antineoplastic Agents / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000737:chemistry; D002277:Carcinoma / Q000188:drug therapy*; D004354:Drug Screening Assays, Antitumor; D005260:Female; D005461:Fluorine / Q000737:chemistry*; D008325:Mammary Neoplasms, Experimental / Q000188:drug therapy*; D017258:Medroxyprogesterone Acetate / Q000008:administration & dosage / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D051381:Rats; D017207:Rats, Sprague-Dawley; D013237:Stereoisomerism
chemical_list: C516643:9alpha-fluoromedroxyprogesterone acetate; D000970:Antineoplastic Agents; D005461:Fluorine; D017258:Medroxyprogesterone Acetate