词条 | Flumedroxone acetate |
释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = [(6S,8R,9S,10R,13S,14S,17R)-17-acetyl-10,13-dimethyl-3-oxo-6-(trifluoromethyl)-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate | image = Flumedroxone acetate.svg | width = 225px | tradename = Demigran, Leomigran | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = By mouth[1] | class = Progestin; Progestogen; Progestogen ester | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 987-18-8 | CAS_supplemental = | ATC_prefix = N02 | ATC_suffix = CB01 | ATC_supplemental = | PubChem = 192154 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 166814 | UNII = S0S93EK936 | KEGG = | ChEBI = | ChEMBL = | synonyms = WG-537; 6α-(Trifluoromethyl)-17α-acetoxyprogesterone; 6α-(Trifluoromethyl)-17α-acetoxypregn-4-ene-3,20-dione | C=24 | H=31 | F=3 | O=4 | molecular_weight = 440.503 g/mol | SMILES = CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@@H](C4=CC(=O)CC[C@]34C)C(F)(F)F)C)OC(=O)C | StdInChI_Ref = | StdInChI = 1S/C24H31F3O4/c1-13(28)23(31-14(2)29)10-7-18-16-12-20(24(25,26)27)19-11-15(30)5-8-21(19,3)17(16)6-9-22(18,23)4/h11,16-18,20H,5-10,12H2,1-4H3/t16-,17+,18+,20+,21-,22+,23+/m1/s1 | StdInChIKey_Ref = | StdInChIKey = MXZYUFNILISKBC-WXLIAARGSA-N }}Flumedroxone acetate, sold under the brand names Demigran and Leomigran, is a progestogen medication which is or has been used as an antimigraine agent.[1][2][3] It is taken by mouth.[1] Medical usesFlumedroxone acetate has been assessed in over 1,000 patients for the treatment of migraine, with effectiveness ranging from excellent to less than that of the reference antimigraine drug methysergide.[6] Other progestogens including medroxyprogesterone acetate, lynestrenol, allylestrenol, dydrogesterone, and normethandrone have also been found to be effective for migraine in a high percentage of women.[6] Side effectsIn accordance with its progestogenic activity, flumedroxone acetate produces menstrual irregularities, namely polymenorrhea, and breast tension as side effects in women.[6][4][5] PharmacologyPharmacodynamicsFlumedroxone acetate is said to have weak or slight progestogenic activity without other hormonal activity, including no estrogenic, antiestrogenic, androgenic, anabolic, or glucocorticoid activity.[6][7] Chemistry{{See also|List of progestogens|Progestogen ester|List of progestogen esters}}Flumedroxone acetate, also known as 6α-(trifluoromethyl)-17α-acetoxyprogesterone or as 6α-(trifluoromethyl)-17α-acetoxypregn-4-ene-3,20-dione, is a synthetic pregnane steroid and a derivative of progesterone and 17α-hydroxyprogesterone.[1] It is specifically a derivative of 17α-hydroxyprogesterone with a trifluoromethyl group at the C6α position and an acetate ester attached to the C17α hydroxyl group.[2] The medication is the C17α acetate ester of flumedroxone (6α-(trifluoromethyl)-17α-hydroxyprogesterone) and the C6α trifluoromethyl derivative of hydroxyprogesterone acetate (17α-acetoxyprogesterone).[1] HistoryFlumedroxone acetate was introduced for medical use in the 1960s.[3] Society and cultureGeneric namesFlumedroxone is the {{abbrlink|INN|International Nonproprietary Name}} and {{abbrlink|BAN|British Approved Name}} of the free alcohol form of the drug, flumedroxone.[1] Flumedroxone acetate is also known by its developmental code name WG-537.[1]Brand namesFlumedroxone acetate is or has been marketed under the brand names Demigran and Leomigran.[1][3] AvailabilityFlumedroxone acetate is or has been marketed in Europe.[3] References1. ^1 2 3 4 5 {{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA560|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=560–}} {{Antimigraine preparations}}{{Progestogens and antiprogestogens}}{{Progesterone receptor modulators}}2. ^1 {{cite book|author1=Jean-Pierre Bégué|author2=Daniele Bonnet-Delpon|title=Bioorganic and Medicinal Chemistry of Fluorine|url=https://books.google.com/books?id=QMVSvZ-R7I0C&pg=PA329|date=2 June 2008|publisher=John Wiley & Sons|isbn=978-0-470-28187-1|pages=329–}} 3. ^1 2 3 {{cite journal | vauthors = Hudgson P, Foster JB, Newell DJ | title = Controlled trial of demigran in the prophylaxis of migraine | journal = Br Med J | volume = 2 | issue = 5544 | pages = 91–3 | year = 1967 | pmid = 6020856 | pmc = 1841258 | doi = | url = }} 4. ^{{cite journal | vauthors = Bradley WG, Hudgson P, Foster JB, Newell DJ | title = Double-blind controlled trial of a micronized preparation of flumedroxone (Demigran) in prophylaxis of migraine | journal = Br Med J | volume = 3 | issue = 5617 | pages = 531–3 | year = 1968 | pmid = 4877801 | pmc = 1986487 | doi = | url = }} 5. ^{{cite journal | vauthors = Lundberg PO | title = Prophylactic treatment of migraine with flumedroxone | journal = Acta Neurol. Scand. | volume = 45 | issue = 3 | pages = 309–26 | year = 1969 | pmid = 5817457 | doi = | url = }} 6. ^1 2 3 {{cite book|author1=Volker Pfaffenrath|author2=Per-Olov Lundberg|author3=Ottar Sjaastad|title=Updating in Headache|url=https://books.google.com/books?id=czSSBgAAQBAJ&pg=PA229|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-88581-5|pages=229–}} 7. ^1 2 {{cite book|author=Hartwig Heyck|title=Headache and facial pain: differential diagnosis, pathogenesis, treatment|url=https://books.google.com/books?id=B69pAAAAMAAJ|year=1981|publisher=Year Book Medical|isbn=978-3-13-589501-7|quote=Lundberg (1969) recommended the oral application of a steroid (flumedroxone) which has only a weak progesterone effect and does not display any other gonadotropic effects.}} 10 : Abandoned drugs|Acetate esters|Alcohols|Antimigraine drugs|Diketones|Fluoroarenes|Pregnanes|Progestogen esters|Progestogens|Trifluoromethyl compounds |
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