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Desogestrel, sold under the brand names Azalia, Cerazette, Marvelon, Mircette, Mercilon, and Novynette among others, is a progestin that is used in hormonal contraceptives. Most combined oral contraceptive pills (COCPs, or simply OCs) on the market today contain both an estrogen (usually ethinylestradiol) plus a progestin (a synthetic progesterone-like agent) such as desogestrel. Desogestrel-containing birth control pills are sometimes referred to as "third generation" oral contraceptives. In contrast, birth control pills that are considered "second generation" (Tri-Levlen, for example) contain an estrogen and a progestin, but the progestin is different, such as levonorgestrel.

Desogestrel
Desogestrel.svg
Clinical data
Trade names Azalia, Cerazette, Marvelon, Mircette, Mercilon, Novynette, others
Synonyms 3-Deketo-11-methylene-17α-ethynyl-18-methyl-19-nortestosterone; 3-Deketo-11-methylene-17α-ethynyl-18-methylestr-4-en-17β-ol-3-one
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a601050
Pregnancy
category
  • US: X (Contraindicated)
Routes of
administration
Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding 98.3%
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.053.555
Chemical and physical data
Formula C22H30O
Molar mass 310.473 g/mol
3D model (JSmol)
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Contents

Medical usesEdit

Desogestrel is used both alone and in combination with an estrogen such as ethinylestradiol in hormonal contraceptives.

Third-generation oral contraceptives like those containing desogestrel are suitable for use in patients with diabetes or lipid disorders because they have minimal impact on blood glucose levels and the lipid profile. Their synthetic estrogen dosage is lower than second-generation oral contraceptives, reducing the likelihood of weight gain, breast tenderness and migraine.

PharmacologyEdit

Desogestrel is a progestogen. It behaves as a prodrug to etonogestrel (3-ketodesogestrel).[1] It has low androgenic activity.[1]

ChemistryEdit

Desogestrel, also known as 3-deketo-11-methylene-17α-ethynyl-18-methyl-19-nortestosterone or as 3-deketo-11-methylene-17α-ethynyl-18-methylestr-4-en-17β-ol-3-one, is a synthetic estrane steroid and a derivative of testosterone.[2][3] It is more specifically a derivative of norethisterone (17α-ethynyl-19-nortestosterone) and is a member of the gonane (18-methylestrane) subgroup of the 19-nortestosterone family of progestins.[4][5] Desogestrel is the C3 deketo and C11 methylene analogue of levonorgestrel.[6]

SynthesisEdit

Synthesis:[7]

HistoryEdit

Desogestrel was introduced in 1981.[8]

Society and cultureEdit

Generic nameEdit

Desogestrel is the generic name of the drug and its INN, USAN, BAN, DCF, DCIT, and JAN.[2][3][9]

Brand namesEdit

Desogestrel is marketed under a variety of brand names throughout the world including Alenvona, Apri, Azalia, Azurette, Caziant, Cerazette, Cerelle, Cesia, Cyclessa, Denise, Desogen, Desirett, Diamilla, Emoquette, Feanolla, Gedarel, Gracial, Kariva, Laurina, Linessa, Marvelon, Mercilon, Mircette, Mirvala, Novynette, Ortho-Cept, Reclipsen, Regulon, Solia, Velivet, and Viorele among others.[3][9]

ControversyEdit

In February 2007, the consumer advocacy group Public Citizen released a petition requesting that the FDA ban oral contraceptives containing desogestrel, citing studies going as far back as 1995 that suggest the risk of dangerous blood clots is doubled for women on such pills in comparison to other oral contraceptives.[10] In 2009, Public Citizen released a list of recommendations that included numerous alternative, second-generation birth control pills that women could take in place of oral contraceptives containing desogestrel. Most of those second-generation medications have been on the market longer and have been shown to be as effective in preventing unwanted pregnancy, but with a lower risk of blood clots.[11]

Drugs cited specifically in the petition include Apri-28, Cyclessa, Desogen, Kariva, Mircette, Ortho-Cept, Reclipsen, Velivet, and some generic pills.[10]

Drugs containing desogestrel as the only active ingredient (as opposed to being used in conjunction with estrogen, like in combined oral contraceptives) do not show an increased thrombosis risk and are therefore safer than second-generation birth-control pills in regards to thrombosis.[12]

ReferencesEdit

  1. ^ a b Thomas L. Lemke; David A. Williams (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1316–. ISBN 978-0-7817-6879-5. 
  2. ^ a b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 364–. ISBN 978-1-4757-2085-3. 
  3. ^ a b c Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 305–. ISBN 978-3-88763-075-1. 
  4. ^ KD Tripathi (30 September 2013). Essentials of Medical Pharmacology. JP Medical Ltd. pp. 316–. ISBN 978-93-5025-937-5. 
  5. ^ Gretchen M. Lentz (2012). Comprehensive Gynecology. Elsevier Health Sciences. pp. 223–. ISBN 0-323-06986-X. 
  6. ^ Sven O. Skouby (15 July 1997). Clinical Perspectives on a New Gestodene Oral Contraceptive Containing 20μg of Ethinylestradiol. CRC Press. pp. 11–. ISBN 978-1-85070-786-8. 
  7. ^ Van Den Broek, A. J.; Van Bokhoven, C.; Hobbelen, P. M. J.; Leemhuis, J. (2010). "11-Alkylidene steroids in the 19-nor series". Recueil des Travaux Chimiques des Pays-Bas. 94 (2): 35. doi:10.1002/recl.19750940203. 
  8. ^ Benno Clemens Runnebaum; Thomas Rabe; Ludwig Kiesel (6 December 2012). Female Contraception: Update and Trends. Springer Science & Business Media. pp. 13–. ISBN 978-3-642-73790-9. 
  9. ^ a b https://www.drugs.com/international/desogestrel.html
  10. ^ a b Public Citizen's Health Research Group: Petition to the U.S. Food and Drug Administration to Ban Third Generation Oral Contraceptives Containing Desogestrel due to Increased Risk of Venous Thrombosis HRG Publication #1799, 2007
  11. ^ Public Citizen Think Twice About Third-Generation Oral Contraceptives and YASMIN Worst Pills, Best Pills, December, 2009
  12. ^ Lidegaard, Øjvind; Nielsen, Lars Hougaard; Skovlund, Charlotte Wessel; Skjeldestad, Finn Egil; Løkkegaard, Ellen (2011-10-25). "Risk of venous thromboembolism from use of oral contraceptives containing different progestogens and oestrogen doses: Danish cohort study, 2001-9". BMJ. 343: d6423. ISSN 0959-8138. PMC 3202015 . PMID 22027398. doi:10.1136/bmj.d6423. Progestogen only products conferred no increased risk of venous thromboembolism, whether taken as low dose norethisterone pills, as desogestrel only pills, or in the form of hormone releasing intrauterine devices.