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Fluoromedroxyprogesterone acetate

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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
IUPAC name
  • phenanthren-17-yl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC24H33FO4
Molar mass404.522 g·mol
3D model (JSmol)
SMILES
  • C1C23CC(3(CC2(4(C1=CC(=O)CC4)C)F)C)(C(=O)C)OC(=O)C
InChI
  • 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. 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. FMPA showed about the same affinities for the progesterone and glucocorticoid receptors as MPA. It reached the preclinical phase of research prior to the discontinuation of its development.

See also

References

  1. ^ "FMPA - AdisInsight".
  2. ^ 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 )". 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. ^ 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. ^ 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 dimethylbenzanthracene 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

Progesterone receptor modulators
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens
Glucocorticoid receptor modulators
GRTooltip Glucocorticoid receptor
Agonists
Mixed
(SEGRMsTooltip Selective glucocorticoid receptor agonists)
Antagonists
Others
See also
Receptor/signaling modulators
Glucocorticoids and antiglucocorticoids
Mineralocorticoid receptor modulators
List of corticosteroids


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