17α-Methylprogesterone (17α-MP), or 17α-methylpregn-4-ene-3,20-dione, is a
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 ...
al
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 ...
related to
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 ...
that was
synthesized and characterized in 1949 but was never marketed.
[Plattner, Pl A., H. Heusser, and P. Th Herzig. "* UBER STEROIDE UND SEXUALHORMONE. 159. DIE SYNTHESE VON 17-METHYL-PROGESTERON." HELVETICA CHIMICA ACTA 32.1 (1949): 270-275.] Along with
ethisterone (1938) and
19-norprogesterone (1951), 17α-MP was one of the earliest derivatives of progesterone to be identified as possessing
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.
Similarly to progesterone and derivatives like
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 ...
and 19-norprogesterone, 17α-MP was found to possess poor (though not negligible)
oral bioavailability,
but showed improved progestogenic activity relative to progesterone when administered via other routes (e.g.,
subcutaneous Subcutaneous may refer to:
* Subcutaneous injection
* Subcutaneous tissue
The subcutaneous tissue (), also called the hypodermis, hypoderm (), subcutis, superficial fascia, is the lowermost layer of the integumentary system in vertebrates. The ...
or
vaginal
In mammals, the vagina is the elastic, muscular part of the female genital tract. In humans, it extends from the vestibule to the cervix. The outer vaginal opening is normally partly covered by a thin layer of mucosal tissue called the hyme ...
).
In addition to its activity as a progestogen, 17α-MP has also been found to possess some
antiglucocorticoid
An antiglucocorticoid is a drug which reduces glucocorticoid activity in the body. They include direct glucocorticoid receptor antagonists such as mifepristone and synthesis inhibitors such as metyrapone, ketoconazole, and aminoglutethimide. ...
activity.
The observation of two-fold improved potency of 17α-MP relative to progesterone led to renewed interest in 17α-substituted derivatives of progesterone.
Subsequently,
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 ...
and
hydroxyprogesterone caproate were synthesized in 1953 and introduced in 1956 and 1957, respectively, and
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 ...
was discovered in 1957 and introduced in 1959.
In addition, though 17α-MP itself was never introduced for medical use, progestogen derivatives of the compound, including
medrogestone (1966) and the 19-norprogesterone derivatives
demegestone
Demegestone, sold under the brand name Lutionex, is a progestin medication which was previously used to treat luteal insufficiency but is now no longer marketed.http://www.micromedexsolutions.com/micromedex2/ It is taken oral administration, by m ...
(1974),
promegestone (1983), and
trimegestone (2001), have been marketed.
Chemistry
See also
*
17α-Bromoprogesterone
17α-Bromoprogesterone (17α-BP) is a progestin which was first described in 1957 and was never marketed. It is about twice as potent as progesterone in terms of progestogenic activity in animal bioassays. 17α-BP is a parent compound of hal ...
*
Ethinylestradiol
*
Methylestradiol
Methylestradiol, sold under the brand names Ginecosid, Ginecoside, Mediol, and Renodiol, is an estrogen medication which is used in the treatment of menopausal symptoms. It is formulated in combination with normethandrone, a progestin and andr ...
*
Methyltestosterone
Methyltestosterone, sold under the brand names Android, Metandren, and Testred among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, at low ...
References
{{DEFAULTSORT:Methylprogesterone, 17α-
Antiglucocorticoids
Diketones
Pregnanes
Progestogens