desogestrel   Click here for help

GtoPdb Ligand ID: 7065

Synonyms: ORG-2969
Approved drug
desogestrel is an approved drug (FDA (1992), EMA (1998))
Compound class: Synthetic organic
Comment: Desogestrel is a progestin (synthetic progesterone-like agent) widely used in third-generation hormonal contraceptives. Desogestrel is converted to etonogestrel (3-ketodesogestrel) in vivo. There has been controversy surrounding reports that third-generation oral contraceptives containing desogestrel pose a risk of dangerous blood clots compared to older second-generation oral contraceptives.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: desogestrel

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 20.23
Molecular weight 310.23
XLogP 5.49
No. Lipinski's rules broken 1
Click here for help
Isomeric SMILES CC[C@]12CC(=C)[C@H]3[C@H]([C@@H]1CC[C@@]2(O)C#C)CCC1=CCCC[C@H]31
InChI 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
No information available.
Summary of Clinical Use Click here for help
Used as a component of combined oral contraceptive formulations. The 1992 US FDA approval for this compound is in combination with ethinyl estradiol. The Electronic Medicines Compendium (eMC) has records for the single component drug with marketing authorisation granted in 2012.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Desogestrel is an agonist of the progesterone receptor. Artificial maintainence of high levels of circulating progesterone feeds back to reduce the frequency of gonadotrophin-releasing hormone (GnRH) pulses which blunts the pre-ovulatory lutenising hormone (LH) surge, and the ovaries cease cyclic ovulation.
External links Click here for help