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Fluoromedroxyprogesterone acetate

April 12, 2024

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]

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
  • 171611-77-1 Y
PubChem CID
  • 9865941
ChemSpider
  • 8041632
UNII
  • 8Q7RBX3VSU
Chemical and physical data
FormulaC24H33FO4
Molar mass404.522 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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

See also edit

References edit

  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.

External links edit

  • Fluoromedroxyprogesterone acetate (FMPA) - AdisInsight


 

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April 12, 2024
fluoromedroxyprogesterone, acetate, fmpa, fluoromedroxyprogesterone, acetate, fmpa, synthetic, steroid, medication, which, under, development, meiji, dairies, corporation, 1990s, 2000s, potential, treatment, cancers, never, marketed, described, antiangiogenic,. Fluoromedroxyprogesterone acetate FMPA 9a fluoromedroxyprogesterone acetate or 9a 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 Fluoromedroxyprogesterone acetateClinical dataOther namesFMPA 9a Fluoromedroxy wbr progesterone acetate 9a FMPA 9a Fluoro 6a methyl 17a hydroxyprogesterone acetate 17a Acetoxy 9a fluoro 6a methylpregn 4 ene 3 20 dione 9a Fluoro 6a methyl 3 20 dioxopregn 4 en 17 yl acetateRoutes ofadministrationBy mouthDrug classAngiogenesis inhibitor Progestogen Progestogen ester Progestin GlucocorticoidIdentifiersIUPAC name 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 acetateCAS Number171611 77 1 YPubChem CID9865941ChemSpider8041632UNII8Q7RBX3VSUChemical and physical dataFormulaC 24H 33F O 4Molar mass404 522 g mol 13D model JSmol Interactive imageSMILES 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 CInChI 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 s1Key OITYTGLRWMEVSQ XDBMOVBSSA NSee also editAnecortave acetateReferences edit a b FMPA AdisInsight 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 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 lt 277 AID BDD186 gt 3 0 CO 2 T PMID 10701698 S2CID 8879650 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 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 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 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 editFluoromedroxyprogesterone acetate FMPA AdisInsight nbsp This article about a steroid is a stub You can help Wikipedia by expanding it vte nbsp This antineoplastic or immunomodulatory drug article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Fluoromedroxyprogesterone acetate amp oldid 1137998636, wikipedia, wiki, book, books, library,

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