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]

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
administrationBy mouth

Drug classAngiogenesis inhibitor; Progestogen; Progestogen ester; Progestin; Glucocorticoid

CAS Number

171611-77-1^Y

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Fluoromedroxyprogesterone acetate

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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^Y
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