Fluoromedroxyprogesterone acetate

Fluoromedroxyprogesterone acetate
Clinical data
Other names	FMPA; 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 class	Angiogenesis inhibitor; Progestogen; Progestogen ester; Progestin; Glucocorticoid
Identifiers
	IUPAC 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] acetate;
CAS Number	171611-77-1 ;
PubChem CID	9865941;
ChemSpider	8041632;
UNII	8Q7RBX3VSU;
Chemical and physical data
Formula	C24H33FO4
Molar mass	404.522 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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]

References

^ ^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<277::AID-BDD186>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

Fluoromedroxyprogesterone acetate (FMPA) - AdisInsight

This article about a steroid is a stub. You can help Wikipedia by expanding it.

This antineoplastic or immunomodulatory drug article is a stub. You can help Wikipedia by expanding it.

[AdisInsight-1] "FMPA - AdisInsight".

[pmid9118456-2] 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 [FMPA])". Chem. Pharm. Bull. 45 (2): 421–3. doi:10.1002/chin.199737217. PMID 9118456.

[pmid10701698-3] 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.

[pmid10530777-4] 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.

[pmid10799740-5] 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 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.

[pmid17077554-6] 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.

[pmid17142973-7] 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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

See also

References

External links