Desogestrel

Desogestrel
Clinical data
Trade namesCerazette, Lovima, Hana, others
Other namesDSG; ORG-2969; 3-Deketo-11-methylene-17α-ethynyl-18-methyl-19-nortestosterone; 11-Methylene-17α-ethynyl-18-methylestr-4-en-17β-ol
AHFS/Drugs.comMultum Consumer Information
MedlinePlusa601050
License data
Routes of
administration		By mouth[1]
Drug classProgestogen
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability76% (range 40–100%)[11][12]
Protein bindingDesogestrel: 99%:[13]
• Albumin: 99%
Etonogestrel: 95–98%:[1][14]
• Albumin: 65–66%
• SHBGTooltip sex hormone-binding globulin: 30–32%
• Free: 2–5%
MetabolismLiver, intestines (5α- and 5β-reductase, cytochrome P450 enzymes, others)[14]
Metabolites• Etonogestrel[14][1][11]
• Others[13][14][11]
Elimination half-lifeDesogestrel: 1.5 hours[13]
Etonogestrel: 21–38 hrs[13][15]
ExcretionUrine: 50%[13]
Feces: 35%[13]
Identifiers
  • (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.053.555 Edit this at Wikidata
Chemical and physical data
FormulaC22H30O
Molar mass310.481 g·mol−1
3D model (JSmol)
Melting point109 to 110 °C (228 to 230 °F)
  • CC[C@]12CC(=C)[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CCCC[C@H]34
  • InChI=1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1 checkY
  • Key:RPLCPCMSCLEKRS-BPIQYHPVSA-N checkY
  (verify)

Desogestrel is a progestin medication which is used in birth control pills.[1][14] It is also used in the treatment of menopausal symptoms in women.[1] The medication is available and used alone or in combination with an estrogen.[1][14] It is taken by mouth.[1]

Side effects of desogestrel include menstrual irregularities, headaches, nausea, breast tenderness, mood changes, acne, increased hair growth, and others.[1] Desogestrel is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[1][14] It has very weak androgenic and glucocorticoid activity and no other important hormonal activity.[14] The medication is a prodrug of etonogestrel (3-ketodesogestrel) in the body.[1][14]

Desogestrel was discovered in 1972 and was introduced for medical use in Europe in 1981.[16][13][17] It became available in the United States in 1992.[18][19][20] Desogestrel is sometimes referred to as a "third-generation" progestin.[21] Likenorethisterone and Norgestrel, Desogestrel is widely available as a progestogen-only "mini pill" for birth control.[22][23][24] Desogestrel is marketed widely throughout the world.[25] It is available as a generic medication.[26] In 2020, the version with ethinylestradiol was the 120th most commonly prescribed medication in the United States, with more than 5 million prescriptions.[27][28]

  1. ^ a b c d e f g h i j Stone SC (December 1995). "Desogestrel". Clinical Obstetrics and Gynecology. 38 (4): 821–828. doi:10.1097/00003081-199538040-00017. PMID 8616978.
  2. ^ "Marvelon Tablets - Summary of Product Characteristics (SmPC)". (emc). 11 March 2021. Archived from the original on 10 July 2021. Retrieved 9 July 2021.
  3. ^ "Mercilon Tablets - Summary of Product Characteristics (SmPC)". (emc). 11 March 2021. Archived from the original on 10 July 2021. Retrieved 9 July 2021.
  4. ^ "Cerazette 75 microgram film-coated tablet - Summary of Product Characteristics (SmPC)". (emc). 20 November 2020. Archived from the original on 10 July 2021. Retrieved 9 July 2021.
  5. ^ Cite error: The named reference Hana SmPC was invoked but never defined (see the help page).
  6. ^ "Lovima 75 microgram film-coated tablets - Summary of Product Characteristics (SmPC)". (emc). 9 July 2021. Archived from the original on 6 July 2022. Retrieved 6 July 2022.
  7. ^ "Apri 28 Day- desogestrel and ethinyl estradiol kit". DailyMed. Archived from the original on 10 July 2021. Retrieved 9 July 2021.
  8. ^ "Mircette- desogestrel/ethinyl estradiol and ethinyl estradiol kit". DailyMed. Archived from the original on 10 July 2021. Retrieved 9 July 2021.
  9. ^ "Kariva- desogestrel/ethinyl estradiol and ethinyl estradiol kit". DailyMed. Archived from the original on 10 July 2021. Retrieved 9 July 2021.
  10. ^ "Velivet Triphasic Regimen- desogestrel and ethinyl estradiol kit". DailyMed. Archived from the original on 10 July 2021. Retrieved 9 July 2021.
  11. ^ a b c Cite error: The named reference pmid8447355 was invoked but never defined (see the help page).
  12. ^ Fotherby K (August 1996). "Bioavailability of orally administered sex steroids used in oral contraception and hormone replacement therapy". Contraception. 54 (2): 59–69. doi:10.1016/0010-7824(96)00136-9. PMID 8842581.
  13. ^ a b c d e f g Cite error: The named reference RunnebaumRabe2012 was invoked but never defined (see the help page).
  14. ^ a b c d e f g h i Kuhl H (February 1996). "Comparative pharmacology of newer progestogens". Drugs. 51 (2): 188–215. doi:10.2165/00003495-199651020-00002. PMID 8808163. S2CID 1019532.
  15. ^ Cite error: The named reference Mosby2001 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference Kuhl2011 was invoked but never defined (see the help page).
  17. ^ Cite error: The named reference Holtsclaw2007 was invoked but never defined (see the help page).
  18. ^ Cite error: The named reference pmid8520092 was invoked but never defined (see the help page).
  19. ^ Cite error: The named reference KornsteinClayton2004 was invoked but never defined (see the help page).
  20. ^ Cite error: The named reference pmid8178905 was invoked but never defined (see the help page).
  21. ^ Carp HJ (9 April 2015). Progestogens in Obstetrics and Gynecology. Springer. pp. 112, 136. ISBN 978-3-319-14385-9.
  22. ^ Grimes DA, Lopez LM, O'Brien PA, Raymond EG (November 2013). "Progestin-only pills for contraception". The Cochrane Database of Systematic Reviews (11): CD007541. doi:10.1002/14651858.CD007541.pub3. PMID 24226383.
  23. ^ Hussain SF (February 2004). "Progestogen-only pills and high blood pressure: is there an association? A literature review". Contraception. 69 (2): 89–97. doi:10.1016/j.contraception.2003.09.002. PMID 14759612.
  24. ^ "Opill: Package Insert / Prescribing Information". Drugs.com. Retrieved 30 September 2024.
  25. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  26. ^ "Generic Desogen Availability". Archived from the original on 6 January 2018. Retrieved 6 January 2018.
  27. ^ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  28. ^ "Desogestrel; Ethinyl Estradiol - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.