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Chemical compound
Flumedroxone acetate
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
[(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
ECHA InfoCard
100.012.343
Formula C 24 H 31 F 3 O 4
Molar mass 440.503 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
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
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
Pharmacodynamics
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
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
Flumedroxone acetate was introduced for medical use in the 1960s.
[4]
Society and culture
Generic names
Flumedroxone is the
INN Tooltip International Nonproprietary Name and
BAN Tooltip 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
Flumedroxone acetate is or has been marketed under the brand names Demigran and Leomigran.
[2]
[4]
Availability
Flumedroxone acetate is or has been marketed in
Europe .
[4]
See also
References
^
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 .
PR Tooltip Progesterone receptor
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RU-2309
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