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Fluoromedroxyprogesterone acetate

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
PubChemCID
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, or9α-FMPA) is asyntheticsteroid medication which was under development by Meiji Dairies Corporation in the 1990s and 2000s for the potential treatment ofcancers but was never marketed.[1][2][3][4][5][6][7] It is described as anantiangiogenic agent, with about two orders of magnitude greaterpotency for inhibition ofangiogenesis than itsparent compoundmedroxyprogesterone acetate.[2][4][5] FMPA showed about the sameaffinities for theprogesterone andglucocorticoid receptors as MPA.[4] It reached thepreclinical phase of research prior to the discontinuation of its development.[1]

See also

[edit]

References

[edit]
  1. ^ab"FMPA - AdisInsight".
  2. ^abSugino 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. ^abcYamaji 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. ^abUchida 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.

External links

[edit]
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
GRTooltip Glucocorticoid receptor
Agonists
Mixed
(SEGRMsTooltip Selective glucocorticoid receptor agonists)
Antagonists
Others


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