It is also the only newer-generation progestin with reduced androgenic activity that is used in such formulations. In addition to hormonal contraception, desogestrel has been used in combination with estrogens such as estradiol as a component of menopausal hormone therapy. The medication has also been used in the treatment of endometriosis. Available forms
Desogestrel is available alone in the form of 75 μg oral tablets and at a dose of 150 μg in combination with 20 or 30 μg ethinylestradiol in oral tablets. These formulations are all indicated specifically for contraceptive purposes. Contraindications
Contraindications of desogestrel include:
Allergy to desogestrel or any other ingredients
Active thrombosis (deep vein thrombosis or pulmonary embolism)
Jaundice or severe liver disease
Hormone-sensitive cancers (e.g., breast cancer)
Unexplained vaginal bleedingDesogestrel is not indicated for use in pregnancy. It is not contraindicated during lactation and breastfeeding. Side effects
Common side effects of desogestrel may include menstrual irregularities, amenorrhea, headaches, nausea, breast tenderness, and mood changes (e.g., depression), as well as weight gain, acne, and hirsutism. However, it has also been reported to not adversely affect weight. In addition, acne and hirsutism are negligible when combined with ethinylestradiol, and this combination can actually be used to treat such symptoms. Desogestrel can also cause changes in total, LDL, and HDL cholesterol. Uncommon side effects of desogestrel may include vaginal infection, contact lens intolerance, vomiting, hair loss, dysmenorrhea, ovarian cysts, and fatigue, while rare side effects include rash, urticaria, and erythema nodosum. Breast discharge, ectopic pregnancies, and aggravation of angioedema may also occur with desogestrel.
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.