Flumedroxone acetate, sold under the brand names Demigran and Leomigran, is a
progestin
A progestogen, also referred to as a progestagen, gestagen, or gestogen, is a type of medication which produces effects similar to those of the natural product, natural female sex hormone progesterone in the body. A progestin is a ''synthetic co ...
medication which is or has been used as an
antimigraine agent
Antimigraine drugs are medications intended to reduce the effects or intensity of migraine headache. They include drugs for the treatment of acute migraine symptoms as well as drugs for the prevention of migraine attacks.
Treatment of acute symp ...
.
It is taken
by mouth.
Medical uses
Flumedroxone acetate has been assessed in over 1,000 patients for the treatment of
migraine
Migraine (, ) is a common neurological disorder characterized by recurrent headaches. Typically, the associated headache affects one side of the head, is pulsating in nature, may be moderate to severe in intensity, and could last from a few hou ...
, with effectiveness ranging from excellent to less than that of the reference antimigraine drug
methysergide
Methysergide, sold under the brand names Deseril and Sansert, is a monoaminergic medication of the ergoline and lysergamide groups which is used in the prophylaxis and treatment of migraine and cluster headaches. It has been withdrawn from the ma ...
.
Other
progestogen
Progestogens, also sometimes written progestagens or gestagens, are a class of natural or synthetic steroid hormones that bind to and activate the progesterone receptors (PR). Progesterone is the major and most important progestogen in the body. ...
s including
medroxyprogesterone acetate
Medroxyprogesterone acetate (MPA), also known as depot medroxyprogesterone acetate (DMPA) in injectable form and sold under the brand name Depo-Provera among others, is a hormonal medication of the progestin type. It is used as a method of bi ...
,
lynestrenol
Lynestrenol, sold under the brand names Exluton and Ministat among others, is a progestin medication which is used in birth control pills and in the treatment of gynecological disorders. The medication is available both alone and in combination w ...
,
allylestrenol
Allylestrenol, sold under the brand names Gestanin and Turinal among others, is a progestin medication which is used to treat habitual abortion, recurrent and miscarriage, threatened miscarriage and to prevent premature labor in pregnancy, pregna ...
,
dydrogesterone, and
normethandrone
Normethandrone, also known as methylestrenolone or methylnortestosterone and sold under the brand name Metalutin among others, is a progestin and androgen/anabolic steroid (AAS) medication which is used in combination with an estrogen in the tre ...
have also been found to be effective for migraine in a high percentage of women.
Side effects
In accordance with its
progestogen
Progestogens, also sometimes written progestagens or gestagens, are a class of natural or synthetic steroid hormones that bind to and activate the progesterone receptors (PR). Progesterone is the major and most important progestogen in the body. ...
ic activity, flumedroxone acetate produces
menstrual irregularities
Irregular menstruation is a menstrual disorder whose manifestations include irregular cycle lengths as well as metrorrhagia (vaginal bleeding between expected periods). The possible causes of irregular menstruation may vary. The common factors of ...
, namely
polymenorrhea
Polymenorrhea, also known as frequent periods, frequent menstruation, or frequent menstrual bleeding, is a menstrual disorder in which menstrual cycles are shorter than 21days in length and hence where menstruation occurs more frequently than us ...
, and
breast tension
Breast tension is a constellation of symptoms involving the breasts including:
* Breast pain
* Breast engorgement
Breast engorgement occurs in the mammary glands due to expansion and pressure exerted by the synthesis and storage of breast m ...
as
side effects in women.
Pharmacology
Pharmacodynamics
Flumedroxone acetate is said to have weak or slight
progestogen
Progestogens, also sometimes written progestagens or gestagens, are a class of natural or synthetic steroid hormones that bind to and activate the progesterone receptors (PR). Progesterone is the major and most important progestogen in the body. ...
ic activity without other
hormonal activity, including no
estrogen
Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal acti ...
ic,
antiestrogenic,
androgenic,
anabolic
Anabolism () is the set of metabolic pathways that construct molecules from smaller units. These reactions require energy, known also as an endergonic process. Anabolism is the building-up aspect of metabolism, whereas catabolism is the breaking-do ...
, or
glucocorticoid
Glucocorticoids (or, less commonly, glucocorticosteroids) are a class of corticosteroids, which are a class of steroid hormones. Glucocorticoids are corticosteroids that bind to the glucocorticoid receptor that is present in almost every vertebr ...
activity.
Chemistry
Flumedroxone acetate, also known as 6α-(trifluoromethyl)-17α-acetoxyprogesterone or as 6α-(trifluoromethyl)-17α-acetoxypregn-4-ene-3,20-dione, is a
synthetic Synthetic things are composed of multiple parts, often with the implication that they are artificial. In particular, 'synthetic' may refer to:
Science
* Synthetic chemical or compound, produced by the process of chemical synthesis
* Synthetic o ...
pregnane steroid
A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and a ...
and a
derivative
In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. F ...
of
progesterone
Progesterone (P4) is an endogenous steroid and progestogen sex hormone involved in the menstrual cycle, pregnancy, and embryogenesis of humans and other species. It belongs to a group of steroid hormones called the progestogens and is the m ...
and
17α-hydroxyprogesterone
17α-Hydroxyprogesterone (17α-OHP), also known as 17-OH progesterone (17-OHP), or hydroxyprogesterone (OHP), is an endogenous progestogen steroid hormone related to progesterone. It is also a chemical intermediate in the biosynthesis of many ot ...
.
It is specifically a derivative of 17α-hydroxyprogesterone with a
trifluoromethyl group
The trifluoromethyl group is a functional group that has the formula -CF3. The naming of is group is derived from the methyl group (which has the formula -CH3), by replacing each hydrogen atom by a fluorine atom. Some common examples are trifluorom ...
at the C6α position and an
acetate
An acetate is a salt (chemistry), salt formed by the combination of acetic acid with a base (e.g. Alkali metal, alkaline, Alkaline earth metal, earthy, Transition metal, metallic, nonmetallic or radical Radical (chemistry), base). "Acetate" als ...
ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...
attached to the C17α
hydroxyl group
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy g ...
.
The medication is the C17α acetate ester of
flumedroxone (6α-(trifluoromethyl)-17α-hydroxyprogesterone) and the C6α
trifluoromethyl derivative of
hydroxyprogesterone acetate
Hydroxyprogesterone acetate (OHPA), sold under the brand name Prodox, is an orally active progestin related to hydroxyprogesterone caproate (OHPC) which has been used in clinical and veterinary medicine. It has reportedly also been used in bi ...
(17α-acetoxyprogesterone).
History
Flumedroxone acetate was introduced for medical use in the 1960s.
Society and culture
Generic names
''Flumedroxone'' is the and of the free
alcohol
Alcohol most commonly refers to:
* Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom
* Alcohol (drug), an intoxicant found in alcoholic drinks
Alcohol may also refer to:
Chemicals
* Ethanol, one of sev ...
form of the drug,
flumedroxone.
Flumedroxone acetate is also known by its developmental code name ''WG-537''.
Brand names
Flumedroxone acetate is or has been marketed under the brand names Demigran and Leomigran.
Availability
Flumedroxone acetate is or has been marketed in
Europe
Europe is a large peninsula conventionally considered a continent in its own right because of its great physical size and the weight of its history and traditions. Europe is also considered a Continent#Subcontinents, subcontinent of Eurasia ...
.
See also
*
Fluorometholone acetate
Fluorometholone acetate, also known as oxylone acetate and sold under the brand names Flarex, Florate, and Omnitrol, is a synthetic glucocorticoid corticosteroid and a corticosteroid ester, as well as a progestogen and progestogen ester. It is t ...
*
Mometasone furoate
Mometasone, also known as mometasone y 3 s, is a glucocorticoid, steroid medication used to treat certain skin conditions, hay fever, and asthma. Specifically it is used to prevent rather than treat asthma attacks. It can be applied to the skin, ...
References
{{Progesterone receptor modulators
Abandoned drugs
Acetate esters
Antimigraine drugs
Diketones
Fluoroarenes
Pregnanes
Progestogen esters
Progestogens
Trifluoromethyl compounds