desogestrel   

GtoPdb Ligand ID: 7065

Synonyms: ORG-2969
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
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
SMILES / InChI / InChIKey
Canonical SMILES CCC12CC(=C)C3C(C1CCC2(O)C#C)CCC1=CCCCC31
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
InChI Key RPLCPCMSCLEKRS-BPIQYHPVSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1992), EMA (1998))
Is prodrug? Yes
Active form etonogestrel
IUPAC Name
(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
International Nonproprietary Names
INN number INN
4384 desogestrel
Synonyms
ORG-2969
Database Links
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