17α-Methylprogesterone (17α-MP), or 17α-methylpregn-4-ene-3,20-dione, is a

steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...

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 female sex hormone progesterone in the body. A progestin is a '' synthetic'' progestogen. ...

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 ma ...

that was synthesized and characterized in 1949 but was never marketed. Along with

ethisterone Ethisterone, also known as ethinyltestosterone, pregneninolone, and anhydrohydroxyprogesterone and formerly sold under the brand names Proluton C and Pranone among others, is a progestin medication which was used in the treatment of gynecologica ...

(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 progestins, 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 progestoge ...

ic activity. Similarly to progesterone and derivatives like 17α-hydroxyprogesterone and 19-norprogesterone, 17α-MP was found to possess poor (though not negligible)

oral The word oral may refer to: Relating to the mouth * Relating to the mouth, the first portion of the alimentary canal that primarily receives food and liquid **Oral administration of medicines ** Oral examination (also known as an oral exam or ora ...

bioavailability In pharmacology, bioavailability is a subcategory of absorption and is the fraction (%) of an administered drug that reaches the systemic circulation. By definition, when a medication is administered intravenously, its bioavailability is 100%. H ...

, but showed improved progestogenic activity relative to progesterone when administered via other routes (e.g., subcutaneous or

vaginal In mammals and other animals, the vagina (: vaginas or vaginae) is the elastic, muscular reproductive organ of the female genital tract. In humans, it extends from the vulval vestibule to the cervix (neck of the uterus). The vaginal introit ...

). In addition to its activity as a progestogen, 17α-MP has also been found to possess some

antiglucocorticoid Antiglucocorticoid drugs are a class of medications that act to reduce the effects of glucocorticoids, primarily cortisol, in the body. They include direct glucocorticoid receptor antagonists such as mifepristone and synthesis inhibitors such as ...

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 and

hydroxyprogesterone caproate Hydroxyprogesterone caproate, sold under the brand name Delalutin among others, is a medication used to reduce the risk of preterm birth in women pregnant with one baby who have a history of spontaneous preterm birth. In March 2023, the manuf ...

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 ...

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 Medrogestone, sold under the brand name Colprone among others, is a progestin medication which has been used in menopausal hormone therapy and in the treatment of gynecological disorders. It is available both alone and in combination with an est ...

(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.: It is taken by mouth. Demegestone is a progestin, or a synthetic progestogen, a ...

(1974),

promegestone Promegestone, sold under the brand name Surgestone, is a progestin medication which is used in menopausal hormone therapy and in the treatment of gynecological disorders. It is taken by mouth. Side effects of promegestone include menstrual irr ...

(1983), and

trimegestone Trimegestone, sold under the brand names Ondeva and Totelle among others, is a progestin medication which is used in menopausal hormone therapy and in the prevention of postmenopausal osteoporosis. It was also under development for use in birth c ...

(2001), have been marketed.

Chemistry

References

{{DEFAULTSORT:Methylprogesterone, 17α- Antiglucocorticoids Diketones Pregnanes Progestogens

Chemistry

See also

References