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.
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2D Structure
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Physico-chemical Properties
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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
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1992), EMA (1998))
Is prodrug? Yes
Active form etonogestrel
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
4384 desogestrel
Synonyms Click here for help
Database Links Click here for help
CAS Registry No. 54024-22-5
ChEMBL Ligand CHEMBL1533
DrugBank Ligand DB00304
DrugCentral Ligand 818
GtoPdb PubChem SID 178103644
PubChem CID 40973
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Wikipedia Desogestrel