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| | {{Short description|Synthetic progestin}} |
| {{Drugbox | | {{Drugbox |
| | Verifiedfields = | | | Verifiedfields = changed |
| | Watchedfields =
| | | verifiedrevid = 477002123 |
| | verifiedrevid = | | | IUPAC_name = (8S,9S,10R,13S,14S,17S)-17-acetyl-9-fluoro-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one |
| | drug_name =
| |
| | IUPAC_name = [(6''S'',8''S'',9''R'',10''S'',13''S'',14''S'',17''R'')-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 | |
| | image = Fluoromedroxyprogesterone acetate.svg | | | image = Fluoromedroxyprogesterone acetate.svg |
| | width = 225px | | | width = 200px |
| | | | CAS_number = 2642-88-2 |
| <!--Clinical data-->
| | | ATC_prefix = none |
| | tradename =
| | | PubChem = 200550 |
| | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| | | ChemSpiderID = 173611 |
| | pregnancy_US = <!-- A / B / C / D / X -->
| | | UNII = 3X7Q2F3K0F |
| | pregnancy_category =
| | | ChEMBL = 2104120 |
| | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| | | C=24 |
| | legal_CA =
| | | H=31 |
| | legal_UK =
| | | F=1 |
| | legal_US =
| | | O=4 |
| | legal_status =
| | | smiles = CC(=O)C1(CCC2C1(CCC3C2C(=O)CC4C3(CCC(C4)F)C)C)C |
| | routes_of_administration = [[Oral administration|By mouth]]
| | | StdInChI = 1S/C24H31FO4/c1-14(26)24(13)8-6-18-17-5-4-15-12-16(25)7-9-21(15,2)23(17)19(27)10-11-22(18,24)3/h12,17-18H,4-11,13H2,1-3H3/t17-,18-,21-,22-,23-,24-/m0/s1 |
| | class = [[Angiogenesis inhibitor]]; [[Progestogen]]; [[Progestogen ester]]; [[Progestin]]; [[Glucocorticoid]]
| | | StdInChIKey = ZQXKQXUSKJQZKX-OBKQYJSNSA-N |
| | | }} |
| <!--Pharmacokinetic data-->
| |
| | bioavailability =
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| | protein_bound =
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| | metabolism =
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| | elimination_half-life =
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| | excretion =
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| <!-- Identifiers -->
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| | CAS_number_Ref =
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| | CAS_number = 171611-77-1 | |
| | CAS_supplemental =
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| | ATC_prefix = | |
| | ATC_suffix = | |
| | ATC_supplemental = | |
| | PubChem = 9865941 | |
| | IUPHAR_ligand = | |
| | DrugBank_Ref = | |
| | DrugBank = | |
| | ChemSpiderID_Ref = | |
| | ChemSpiderID = 8041632 | |
| | UNII = | |
| | KEGG =
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| | ChEBI =
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| | ChEMBL =
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| | synonyms = FMPA; 9α-Fluoromedroxy<wbr />progesterone 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 | |
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|
| <!--Chemical data-->
| | '''Fluoromedroxyprogesterone acetate''' (FMPA) is a [[synthetic progestin]], a type of [[progestogen]] that is used in [[hormonal contraception]] and [[hormone replacement therapy]]. It is a derivative of [[medroxyprogesterone acetate]] (MPA), with a fluorine atom added to its chemical structure, which enhances its biological activity. |
| | C=24 | H=33 | F=1 | O=4
| |
| | molecular_weight = 404.522 g/mol
| |
| | 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
| |
| | StdInChI_Ref =
| |
| | StdInChI = 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
| |
| | StdInChIKey_Ref =
| |
| | StdInChIKey = OITYTGLRWMEVSQ-XDBMOVBSSA-N
| |
| }}
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| '''Fluoromedroxyprogesterone acetate''' ('''FMPA''', '''9α-fluoromedroxyprogesterone acetate''', or '''9α-FMPA''') is a [[synthetic compound|synthetic]] [[steroid]] medication which was under development by Meiji Dairies Corporation in the 1990s and 2000s for the potential treatment of [[cancer]]s but was never marketed.<ref name="AdisInsight">https://adisinsight.springer.com/drugs/800011224</ref><ref name="pmid9118456">{{cite journal | vauthors = Sugino E, Fujimori S, Hibino S, Choshi T, Ichihara Y, Sato Y, Yamaji T, Tsuboi H, Murata N, Uchida M, Shimamura M, Oikawa T | title = Synthesis of a new potent anti-angiogenic agent, 17 alpha-acetoxy-9 alpha-fluoro-6 alpha-methylprogesterone (9 alpha-fluoromedroxyprogesterone acetate [FMPA]) | journal = Chem. Pharm. Bull. | volume = 45 | issue = 2 | pages = 421–3 | date = February 1997 | pmid = 9118456 | doi = 10.1002/chin.199737217 | url = }}</ref><ref name="pmid10701698">{{cite journal | vauthors = Kozutsumi D, Kawashima A, Sugimoto T, Kotohda Y, Fujimori S, Takami M, Kohno T, Oikawa T, Sugino E, Choshi T, Hibino S | title = Pharmacokinetics of 9alpha-fluoromedroxyprogesterone acetate in rats: comparison with medroxyprogesterone acetate | journal = Biopharm Drug Dispos | volume = 20 | issue = 6 | pages = 277–84 | date = September 1999 | pmid = 10701698 | doi = 10.1002/(SICI)1099-081X(199909)20:6<277::AID-BDD186>3.0.CO;2-T | url = }}</ref><ref name="pmid10530777">{{cite journal | vauthors = Yamaji T, Tsuboi H, Murata N, Uchida M, Kohno T, Sugino E, Hibino S, Shimamura M, Oikawa T | title = Anti-angiogenic activity of a novel synthetic agent, 9alpha-fluoromedroxyprogesterone acetate | journal = Cancer Lett. | volume = 145 | issue = 1-2 | pages = 107–14 | date = October 1999 | pmid = 10530777 | doi = 10.1016/S0304-3835(99)00239-6 | url = }}</ref><ref name="pmid10799740">{{cite journal | vauthors = Uchida M, Tsuboi H, Yamaji T, Murata N, Kohno T, Sugino E, Hibino S, Shimamura M, Oikawa T | title = 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) | journal = Cancer Lett. | volume = 154 | issue = 1 | pages = 63–9 | date = June 2000 | pmid = 10799740 | doi = 10.1016/S0304-3835(00)00375-X | url = }}</ref><ref name="pmid17077554">{{cite journal | vauthors = 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 | title = Synthesis and anti-tumor activity of a fluorinated analog of medroxyprogesterone acetate (MPA), 9alpha-fluoromedroxyprogesterone acetate (FMPA) | journal = Chem. Pharm. Bull. | volume = 54 | issue = 11 | pages = 1567–70 | date = November 2006 | pmid = 17077554 | doi = 10.1248/cpb.54.1567 | url = }}</ref><ref name="pmid17142973">{{cite journal | vauthors = Murata N, Yamaji T, Uchida M, Tsuboi H, Suzuki H, Yamada M, Oikawa T, Nobuhiro J, Choshi T, Hibino S | title = Suppression of laser-induced choroidal neovascularization by subconjunctival injection of 9alpha-fluoromedroxyprogesterone acetate (FMPA), an anti-angiogenic agent, in rats | journal = Biol. Pharm. Bull. | volume = 29 | issue = 12 | pages = 2410–4 | date = December 2006 | pmid = 17142973 | doi = 10.1248/bpb.29.2410 | url = }}</ref> It is described as an [[angiogenesis inhibitor|antiangiogenic agent]], with about two orders of magnitude greater [[potency (pharmacology)|potency]] for inhibition of [[angiogenesis]] than its [[parent compound]] [[medroxyprogesterone acetate]].<ref name="pmid9118456" /><ref name="pmid10530777" /><ref name="pmid10799740" /> FMPA showed about the same [[affinity (pharmacology)|affinities]] for the [[progesterone receptor|progesterone]] and [[glucocorticoid receptor]]s as MPA.<ref name="pmid10530777" /> It reached the [[preclinical research|preclinical]] phase of research prior to the discontinuation of its development.<ref name="AdisInsight" />
| | ==Chemical Structure and Properties== |
| | Fluoromedroxyprogesterone acetate is a fluorinated derivative of [[medroxyprogesterone acetate]], a well-known progestin. The addition of a fluorine atom at the 9α position of the steroid nucleus increases its potency and alters its pharmacokinetic properties. The chemical formula of FMPA is C<sub>24</sub>H<sub>31</sub>FO<sub>4</sub>, and it has a molecular weight of 402.50 g/mol. |
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| ==See also== | | ==Mechanism of Action== |
| * [[Anecortave acetate]]
| | As a progestin, FMPA works by binding to the [[progesterone receptor]] in target tissues. This binding mimics the effects of natural [[progesterone]], leading to changes in the [[endometrium]] that prevent [[ovulation]] and alter the cervical mucus, making it more difficult for [[sperm]] to enter the [[uterus]]. These actions make FMPA effective as a contraceptive agent. |
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| ==References== | | ==Pharmacokinetics== |
| {{Reflist}}
| | Fluoromedroxyprogesterone acetate is administered via injection, allowing for a slow release and prolonged duration of action. The fluorination of the molecule increases its lipophilicity, enhancing its ability to cross cell membranes and increasing its half-life in the body. This results in sustained levels of the drug, which is beneficial for long-term contraceptive use. |
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| ==External links== | | ==Clinical Uses== |
| * [https://adisinsight.springer.com/drugs/800011224 Fluoromedroxyprogesterone acetate (FMPA) - AdisInsight]
| | FMPA is primarily used in [[hormonal contraception]] as a long-acting injectable. It is also used in [[hormone replacement therapy]] for the management of [[menopausal symptoms]] and in the treatment of certain [[gynecological disorders]] such as [[endometriosis]]. |
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| | ==Side Effects== |
| | Common side effects of FMPA include changes in [[menstrual bleeding patterns]], weight gain, and mood changes. Long-term use may be associated with a decrease in [[bone mineral density]], similar to other progestin-only contraceptives. Patients are advised to discuss potential risks and benefits with their healthcare provider. |
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| {{Progesterone receptor modulators}}
| | ==Related Pages== |
| {{Glucocorticoid receptor modulators}}
| | * [[Progestin]] |
| | * [[Medroxyprogesterone acetate]] |
| | * [[Hormonal contraception]] |
| | * [[Hormone replacement therapy]] |
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| [[Category:Abandoned drugs]]
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| [[Category:Acetate esters]]
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| [[Category:Angiogenesis inhibitors]]
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| [[Category:Drugs with unknown mechanisms of action]]
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| [[Category:Experimental cancer drugs]]
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| [[Category:Glucocorticoids]]
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| [[Category:Pregnanes]]
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| [[Category:Progestogen esters]]
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| [[Category:Progestogens]] | | [[Category:Progestogens]] |
| | | [[Category:Contraceptives]] |
| | | [[Category:Steroids]] |
| {{Steroid-stub}}
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| {{Antineoplastic-drug-stub}}
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| {{dictionary-stub1}}
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| <gallery>
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| File:Fluoromedroxyprogesterone_acetate.svg|Fluoromedroxyprogesterone acetate
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| </gallery>
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Synthetic progestin
Fluoromedroxyprogesterone acetate (FMPA) is a synthetic progestin, a type of progestogen that is used in hormonal contraception and hormone replacement therapy. It is a derivative of medroxyprogesterone acetate (MPA), with a fluorine atom added to its chemical structure, which enhances its biological activity.
Chemical Structure and Properties[edit]
Fluoromedroxyprogesterone acetate is a fluorinated derivative of medroxyprogesterone acetate, a well-known progestin. The addition of a fluorine atom at the 9α position of the steroid nucleus increases its potency and alters its pharmacokinetic properties. The chemical formula of FMPA is C24H31FO4, and it has a molecular weight of 402.50 g/mol.
Mechanism of Action[edit]
As a progestin, FMPA works by binding to the progesterone receptor in target tissues. This binding mimics the effects of natural progesterone, leading to changes in the endometrium that prevent ovulation and alter the cervical mucus, making it more difficult for sperm to enter the uterus. These actions make FMPA effective as a contraceptive agent.
Pharmacokinetics[edit]
Fluoromedroxyprogesterone acetate is administered via injection, allowing for a slow release and prolonged duration of action. The fluorination of the molecule increases its lipophilicity, enhancing its ability to cross cell membranes and increasing its half-life in the body. This results in sustained levels of the drug, which is beneficial for long-term contraceptive use.
Clinical Uses[edit]
FMPA is primarily used in hormonal contraception as a long-acting injectable. It is also used in hormone replacement therapy for the management of menopausal symptoms and in the treatment of certain gynecological disorders such as endometriosis.
Side Effects[edit]
Common side effects of FMPA include changes in menstrual bleeding patterns, weight gain, and mood changes. Long-term use may be associated with a decrease in bone mineral density, similar to other progestin-only contraceptives. Patients are advised to discuss potential risks and benefits with their healthcare provider.
Related Pages[edit]
