Fluoromedroxyprogesterone acetate

Fluoromedroxyprogesterone acetate
Clinical data
Other namesFMPA; 9α-Fluoromedroxyprogesterone acetate; 9α-FMPA; 9α-Fluoro-6α-methyl-17α-hydroxyprogesterone acetate; 17α-Acetoxy-9α-fluoro-6α-methylpregn-4-ene-3,20-dione; 9α-Fluoro-6α-methyl-3,20-dioxopregn-4-en-17-yl acetate
Routes of
administration		By mouth
Drug classAngiogenesis inhibitor; Progestogen; Progestogen ester; Progestin; Glucocorticoid
Identifiers
  • [(6S,8S,9R,10S,13S,14S,17R)-17-Acetyl-9-fluoro-6,10,13-trimethyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC24H33FO4
Molar mass404.522 g·mol−1
3D model (JSmol)
  • C[C@H]1C[C@H]2[C@@H]3CC[C@@]([C@]3(CC[C@@]2([C@@]4(C1=CC(=O)CC4)C)F)C)(C(=O)C)OC(=O)C
  • InChI=1S/C24H33FO4/c1-14-12-20-18-7-9-24(15(2)26,29-16(3)27)22(18,5)10-11-23(20,25)21(4)8-6-17(28)13-19(14)21/h13-14,18,20H,6-12H2,1-5H3/t14-,18-,20-,21-,22-,23+,24-/m0/s1
  • Key:OITYTGLRWMEVSQ-XDBMOVBSSA-N

Fluoromedroxyprogesterone acetate (FMPA, 9α-fluoromedroxyprogesterone acetate, or 9α-FMPA) is a synthetic steroid medication which was under development by Meiji Dairies Corporation in the 1990s and 2000s for the potential treatment of cancers but was never marketed.[1][2][3][4][5][6][7] It is described as an antiangiogenic agent, with about two orders of magnitude greater potency for inhibition of angiogenesis than its parent compound medroxyprogesterone acetate.[2][4][5] FMPA showed about the same affinities for the progesterone and glucocorticoid receptors as MPA.[4] It reached the preclinical phase of research prior to the discontinuation of its development.[1]

  1. ^ a b "FMPA - AdisInsight".
  2. ^ a b Sugino E, Fujimori S, Hibino S, Choshi T, Ichihara Y, Sato Y, Yamaji T, Tsuboi H, Murata N, Uchida M, Shimamura M, Oikawa T (February 1997). "Synthesis of a new potent anti-angiogenic agent, 17 alpha-acetoxy-9 alpha-fluoro-6 alpha-methylprogesterone (9 alpha-fluoromedroxyprogesterone acetate [FMPA])". Chem. Pharm. Bull. 45 (2): 421–3. doi:10.1002/chin.199737217. PMID 9118456.
  3. ^ Kozutsumi D, Kawashima A, Sugimoto T, Kotohda Y, Fujimori S, Takami M, Kohno T, Oikawa T, Sugino E, Choshi T, Hibino S (September 1999). "Pharmacokinetics of 9alpha-fluoromedroxyprogesterone acetate in rats: comparison with medroxyprogesterone acetate". Biopharm Drug Dispos. 20 (6): 277–84. doi:10.1002/(SICI)1099-081X(199909)20:6<277::AID-BDD186>3.0.CO;2-T. PMID 10701698. S2CID 8879650.
  4. ^ a b c Yamaji T, Tsuboi H, Murata N, Uchida M, Kohno T, Sugino E, Hibino S, Shimamura M, Oikawa T (October 1999). "Anti-angiogenic activity of a novel synthetic agent, 9alpha-fluoromedroxyprogesterone acetate". Cancer Lett. 145 (1–2): 107–14. doi:10.1016/S0304-3835(99)00239-6. PMID 10530777.
  5. ^ a b Uchida M, Tsuboi H, Yamaji T, Murata N, Kohno T, Sugino E, Hibino S, Shimamura M, Oikawa T (June 2000). "Inhibition by 9alpha-fluoromedoroxyprogesterone acetate (FMPA) against mammary carcinoma induced by dimethylbenz[a]anthracene in rats and angiogenesis in the rabbit cornea - comparison with medroxyprogesterone acetate (MPA)". Cancer Lett. 154 (1): 63–9. doi:10.1016/S0304-3835(00)00375-X. PMID 10799740.
  6. ^ Murata N, Fujimori S, Ichihara Y, Sato Y, Yamaji T, Tsuboi H, Uchida M, Suzuki H, Yamada M, Oikawa T, Nemoto H, Nobuhiro J, Choshi T, Hibino S (November 2006). "Synthesis and anti-tumor activity of a fluorinated analog of medroxyprogesterone acetate (MPA), 9alpha-fluoromedroxyprogesterone acetate (FMPA)". Chem. Pharm. Bull. 54 (11): 1567–70. doi:10.1248/cpb.54.1567. PMID 17077554.
  7. ^ Murata N, Yamaji T, Uchida M, Tsuboi H, Suzuki H, Yamada M, Oikawa T, Nobuhiro J, Choshi T, Hibino S (December 2006). "Suppression of laser-induced choroidal neovascularization by subconjunctival injection of 9alpha-fluoromedroxyprogesterone acetate (FMPA), an anti-angiogenic agent, in rats". Biol. Pharm. Bull. 29 (12): 2410–4. doi:10.1248/bpb.29.2410. PMID 17142973.