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Contents

   



(Top)
  


1 Medical uses  




2 Side effects  




3 Pharmacology  


3.1  Pharmacodynamics  






4 Chemistry  




5 History  




6 Society and culture  


6.1  Generic names  




6.2  Brand names  




6.3  Availability  






7 See also  




8 References  













Flumedroxone acetate






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From Wikipedia, the free encyclopedia
  

Flumedroxone acetate
Clinical data
Trade namesDemigran, Leomigran
Other namesWG-537; 6α-(Trifluoromethyl)-17α-acetoxyprogesterone; 6α-(Trifluoromethyl)-17α-acetoxypregn-4-ene-3,20-dione
Routes of
administration		By mouth[1]
Drug classProgestogen; 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 InfoCard100.012.343 Edit this at Wikidata
Chemical and physical data
FormulaC24H31F3O4
Molar mass440.503 g·mol−1
3D model (JSmol)

  • 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

  • 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 names Demigran and Leomigran, is a progestin medication which is or has been used as an antimigraine agent.[2][3][4] It is taken by mouth.[1]

Medical uses[edit]

Flumedroxone 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.[5] 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.[5]

Side effects[edit]

In accordance with its progestogenic activity, flumedroxone acetate produces menstrual irregularities, namely polymenorrhea, and breast tensionasside effects in women.[5][6][7]

Pharmacology[edit]

Pharmacodynamics[edit]

Flumedroxone acetate is said to have weak or slight progestogenic activity without other hormonal activity, including no estrogenic, antiestrogenic, androgenic, anabolic, or glucocorticoid activity.[5][1]

Chemistry[edit]

See also: List of progestogens, Progestogen ester, and 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 derivativeofprogesterone and 17α-hydroxyprogesterone.[2] 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.[3] The medication is the C17α acetate ester of flumedroxone (6α-(trifluoromethyl)-17α-hydroxyprogesterone) and the C6α trifluoromethyl derivative of hydroxyprogesterone acetate (17α-acetoxyprogesterone).[2]

History[edit]

Flumedroxone acetate was introduced for medical use in the 1960s.[4]

Society and culture[edit]

Generic names[edit]

Flumedroxone is the INNTooltip International Nonproprietary Name and BANTooltip British Approved Name of the free alcohol form of the drug, flumedroxone.[2] Flumedroxone acetate is also known by its developmental code name WG-537.[2]

Brand names[edit]

Flumedroxone acetate is or has been marketed under the brand names Demigran and Leomigran.[2][4]

Availability[edit]

Flumedroxone acetate is or has been marketed in Europe.[4]

See also[edit]

References[edit]

  1. ^ a b c Heyck H (1981). Headache and facial pain: differential diagnosis, pathogenesis, treatment. Year Book Medical. p. 97. 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. Springer. pp. 560–. 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.

    • Retrieved from "https://en.wikipedia.org/w/index.php?title=Flumedroxone_acetate&oldid=1188722604"
    Categories: 
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     ●Trifluoromethyl compounds
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