Following further metabolism of etonogestrel, which occurs mainly by reduction of the Δ4-3-keto group (by 5α- and 5β-reductases) and hydroxylation (by monooxygenases), the major metabolite of desogestrel is 3α,5α-tetrahydroetonogestrel. Desogestrel has a very short terminal half-life of about 1.5 hours while etonogestrel has a relatively long elimination half-life of about 21 to 38 hours, reflecting the nature of desogestrel as a prodrug. Desogestrel and etonogestrel are eliminated exclusively as metabolites 50% in urine and 35% in feces. Chemistry
Desogestrel, also known as 3-deketo-11-methylene-17α-ethynyl-18-methyl-19-nortestosterone or as 11-methylene-17α-ethynyl-18-methylestr-4-en-17β-ol, is a synthetic estrane steroid and a derivative of testosterone. It is more specifically a derivative of norethisterone (17α-ethynyl-19-nortestosterone) and is a member of the gonane (13β-ethylgonane or 18-methylestrane) subgroup of the 19-nortestosterone family of progestins. Desogestrel is the C3 deketo analogue of etonogestrel and the C3 deketo and C11 methylene analogue of levonorgestrel. Synthesis
A chemical synthesis of desogestrel has been published. History
Desogestrel was synthesized in 1972 by Organon International in the Netherlands and was first described in the literature in 1975. It was developed following the discovery that C11 substitutions enhance the biological activity of norethisterone. Desogestrel was introduced for medical use in 1981 under the brand names Marvelon and Desogen in the Netherlands. Along with gestodene and norgestimate, it is sometimes referred to as a "third-generation" progestin based on the time of its introduction to the market. It was the first of the three "third-generation" progestins to be introduced.
Desogestrel is a progestin medication which is used in birth control pills for women. It is also used in the treatment of menopausal symptoms in women. The medication is available and used alone or in combination with an estrogen. It is taken by mouth.Side effects of desogestrel include menstrual irregularities, headaches, nausea, breast tenderness, mood changes, acne, increased hair growth, and others. Desogestrel is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has very weak androgenic and glucocorticoid activity and no other important hormonal activity. The medication is a prodrug of etonogestrel (3-ketodesogestrel) in the body.Desogestrel was discovered in 1972 and was introduced for medical use in Europe in 1981. It became available in the United States in 1992. Desogestrel is sometimes referred to as a "third-generation" progestin. Along with norethisterone, it is one of the only progestins that is widely available as a progestogen-only "mini pill" for birth control. Desogestrel is marketed widely throughout the world. It is available as a generic medication. In 2019, the version with ethinylestradiol was the 128th most commonly prescribed medication in the United States, with more than 5 million prescriptions. Medical uses
Desogestrel is used in hormonal contraception in women, specifically in birth control pills. It is used alone in progestogen-only pills ("mini pills") and in combination with the estrogen ethinylestradiol in combined oral contraceptive pills. Desogestrel and norethisterone are the only progestins that are widely used as a progestogen-only "mini pill".