Flumedroxone acetate
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| 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 administration | By mouth[1] |
| Drug class | Progestogen; Progestin; Progestogen ester |
| ATC code | |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| ChemSpider | |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.012.343 |
| Chemical and physical data | |
| Formula | C24H31F3O4 |
| Molar mass | 440.503 g·mol−1 |
| 3D model (JSmol) | |
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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 tension as side 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]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.[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 INN and BAN 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]- ^ 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.