Desogestrel

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Desogestrel
File:Desogestrel.svg
Systematic (IUPAC) name
13-ethyl-17-ethynyl- 11-methylidene- 1,2,3,6,7,8,9,10,12,13,14,15, 16,17- tetradecahydrocyclopenta[a] phenanthren-17-ol
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a601050
Pregnancy
category
  • US: X (Contraindicated)
Legal status
Routes of
administration		 oral
Pharmacokinetic data
Protein binding 98.3%
Identifiers
CAS Number 54024-22-5 YesY
ATC code G03AC09 (WHO)
PubChem CID: 40973
IUPHAR/BPS 7065
DrugBank DB00304 YesY
ChemSpider 37400 YesY
UNII 81K9V7M3A3 YesY
KEGG D02367 YesY
ChEBI CHEBI:4453 YesY
ChEMBL CHEMBL1533 YesY
Chemical data
Formula C22H30O
Molecular mass 310.473 g/mol
  • C#C[C@@]4(O)[C@@]2([C@H]([C@@H]3CC/C1=C/CCC[C@@H]1[C@H]3C(=C)\C2)CC4)CC
  • 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 YesY
  • Key:RPLCPCMSCLEKRS-BPIQYHPVSA-N YesY
  (verify)

Desogestrel (INN, USAN, BAN) is a progestin used in hormonal contraceptives. Most combined oral contraceptive pills (COCPs, or simply OCs) on the market today contain both an estrogen (ethinyl estradiol is common) 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 behaves as a prodrug to etonogestrel (3-ketodesogestrel).[1] It has low androgenic activity.[1]

Benefits

Third-generation oral contraceptives 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.

Controversy

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.[2] 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.[3]

Drugs cited specifically in the petition include Apri-28, Cyclessa, Desogen, Kariva, Mircette, Ortho-Cept, Reclipsen, Velivet and some generic pills.[2]

References

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External links


  1. ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ 2.0 2.1 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
  3. ↑ Public Citizen Think Twice About Third-Generation Oral Contraceptives and YASMIN Worst Pills, Best Pills, December, 2009
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