Chemical compound
Pharmaceutical compound
Flumedroxone acetate Clinical data Trade names Demigran, Leomigran Other names WG-537; 6α-(Trifluoromethyl)-17α-acetoxyprogesterone; 6α-(Trifluoromethyl)-17α-acetoxypregn-4-ene-3,20-dione Routes of By mouth [ 1] Drug class Progestogen ;Progestin ;Progestogen ester ATC code Identifiers [(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
CAS Number PubChem CID ChemSpider UNII CompTox Dashboard (EPA) ECHA InfoCard 100.012.343 Chemical and physical data Formula C 24 H 31 F 3 O 4 Molar mass −1 3D model (JSmol ) InChI=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
Key:MXZYUFNILISKBC-WXLIAARGSA-N
Flumedroxone acetate , sold under the brand namesDemigran andLeomigran , is aprogestin medication which is or has been used as anantimigraine agent .[ 2] [ 3] [ 4] by mouth .[ 1]
Flumedroxone acetate has been assessed in over 1,000 patients for the treatment ofmigraine , with effectiveness ranging from excellent to less than that of the reference antimigraine drugmethysergide .[ 5] progestogens includingmedroxyprogesterone acetate ,lynestrenol ,allylestrenol ,dydrogesterone , andnormethandrone have also been found to be effective for migraine in a high percentage of women.[ 5]
In accordance with itsprogestogenic activity, flumedroxone acetate producesmenstrual irregularities , namelypolymenorrhea , andbreast tension asside effects in women.[ 5] [ 6] [ 7]
Flumedroxone acetate is said to have weak or slightprogestogenic activity without otherhormonal activity, including noestrogenic ,antiestrogenic ,androgenic ,anabolic , orglucocorticoid activity.[ 5] [ 1]
Flumedroxone acetate, also known as 6α-(trifluoromethyl)-17α-acetoxyprogesterone or as 6α-(trifluoromethyl)-17α-acetoxypregn-4-ene-3,20-dione, is asynthetic pregnane steroid and aderivative ofprogesterone and17α-hydroxyprogesterone .[ 2] trifluoromethyl group at the C6α position and anacetate ester attached to the C17αhydroxyl group .[ 3] flumedroxone (6α-(trifluoromethyl)-17α-hydroxyprogesterone) and the C6αtrifluoromethyl derivative ofhydroxyprogesterone acetate (17α-acetoxyprogesterone).[ 2]
Flumedroxone acetate was introduced for medical use in the 1960s.[ 4]
Society and culture [ edit ] Flumedroxone is theINN Tooltip International Nonproprietary Name andBAN Tooltip British Approved Name of the freealcohol form of the drug,flumedroxone .[ 2] WG-537 .[ 2]
Flumedroxone acetate is or has been marketed under the brand names Demigran and Leomigran.[ 2] [ 4]
Flumedroxone acetate is or has been marketed inEurope .[ 4]
^a b c Heyck H (1981).Headache and facial pain: differential diagnosis, pathogenesis, treatment ISBN 978-3-13-589501-7 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. ^a b c d e f Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies ISBN 978-1-4757-2085-3 ^a b Bégué JP, Bonnet-Delpon D (2 June 2008)."Drugs for Endocrine and Metabolic Disorders" .Bioorganic and Medicinal Chemistry of Fluorine . John Wiley & Sons. pp. 329–.ISBN 978-0-470-28187-1 ^a b c d Hudgson P, Foster JB, Newell DJ (April 1967)."Controlled trial of demigran in the prophylaxis of migraine" .British Medical Journal .2 (5544):91– 93.doi :10.1136/bmj.2.5544.91 .PMC 1841258 PMID 6020856 . ^a b c d Lundberg PO (6 December 2012)."Endocrinology of Headache: A Review" . In Pfaffenrath V, Lundberg PO, Sjaastad O (eds.).Updating in Headache . Springer Science & Business Media. pp. 229–.ISBN 978-3-642-88581-5 ^ Bradley WG, Hudgson P, Foster JB, Newell DJ (August 1968)."Double-blind controlled trial of a micronized preparation of flumedroxone (Demigran) in prophylaxis of migraine" .British Medical Journal .3 (5617):531– 533.doi :10.1136/bmj.3.5617.531 .PMC 1986487 PMID 4877801 . ^ Lundberg PO (1969)."Prophylactic treatment of migraine with flumedroxone" .Acta Neurologica Scandinavica .45 (3):309– 326.doi :10.1111/j.1600-0404.1969.tb01243.x PMID 5817457 .S2CID 9835328 .
PR Tooltip Progesterone receptor
Agonists Testosterone derivatives: Progestins:6,6-Difluoronorethisterone 6,6-Difluoronorethisterone acetate 17α-Allyl-19-nortestosterone Allylestrenol Altrenogest Chloroethynylnorgestrel Cingestol Danazol Desogestrel Dienogest Ethinylandrostenediol Ethisterone Ethynerone Etonogestrel Etynodiol Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel esters (e.g.,levonorgestrel butanoate )Lynestrenol Lynestrenol phenylpropionate Metynodiol Metynodiol diacetate Norelgestromin Norethisterone (norethindrone) Norethisterone esters (e.g.,norethisterone acetate ,norethisterone enanthate )Noretynodrel Norgesterone Norgestimate Norgestrel Norgestrienone Norvinisterone Oxendolone Quingestanol Quingestanol acetate Tibolone Tigestol Tosagestin ; Anabolic–androgenic steroids:11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosterone dodecylcarbonate 19-Nor-5-androstenediol 19-Nor-5-androstenedione 19-Nordehydroepiandrosterone Bolandiol Bolandiol dipropionate Bolandione Dimethisterone Dienedione Dienolone Dimethandrolone Dimethandrolone buciclate Dimethandrolone dodecylcarbonate Dimethandrolone undecanoate Dimethyldienolone Dimethyltrienolone Ethyldienolone Ethylestrenol (ethylnandrol) Methyldienolone Metribolone (R-1881) Methoxydienone (methoxygonadiene) Mibolerone Nandrolone Nandrolone esters (e.g.,nandrolone decanoate ,nandrolone phenylpropionate )Norethandrolone Normethandrone (methylestrenolone, normethandrolone, normethisterone) RU-2309 Tetrahydrogestrinone Trenbolone (trienolone) Trenbolone esters (e.g.,trenbolone acetate ,trenbolone enanthate )Trendione Trestolone Trestolone acetate MixedSPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor PAQR Tooltip Progestin and adipoQ receptor )
