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Structure via PubChem · Public domain (PubChem)
gestonorone
Sign in to saveAlso known as 17α-hydroxy-19-norpregn-4-ene-3,20-dione, 17α-hydroxy-19-norprogesterone, gestronol
Gestronol (), also known as gestonorone, as well as 17α-hydroxy-19-norprogesterone or 17α-hydroxy-19-norpregn-4-ene-3,20-dione, is a progestin of the 19-norprogesterone and 17α-hydroxyprogesterone groups which was never marketed. The C17α caproate ester of gestronol, gestonorone caproate (gestronol hexanoate), in contrast, has been marketed.
Chemical data
- Formula
- C20H28O3
- Molecular weight
- 316.4 g/mol
- IUPAC name
- (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
- SMILES
- CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C)O
- InChIKey
- GTFUITFQDGVJSK-XGXHKTLJSA-N
- XLogP
- 2.6
- Polar surface area
- 54.4 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
- Indications
- neoplasm
via ChEMBL · EBI
Wikidata facts
- Mass
- 316.204
Show 5 more facts
- chemical formula
- C₂₀H₂₈O₃
- Commons category
- Gestonorone
- isomeric SMILES
- CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C)O
- canonical SMILES
- CC(=O)C1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C)O
- defined daily dose
- 40
Sources (3)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Gestronol (), also known as gestonorone, as well as 17α-hydroxy-19-norprogesterone or 17α-hydroxy-19-norpregn-4-ene-3,20-dione, is a progestin of the 19-norprogesterone and 17α-hydroxyprogesterone groups which was never marketed. The C17α caproate ester of gestronol, gestonorone caproate (gestronol hexanoate), in contrast, has been marketed.
Gestronol shows relatively low affinity for the progesterone receptor, only about 12.5% of that of progesterone and about 2.5% of that of 19-norprogesterone in one assay. On the other hand, gestronol had far higher affinity than 17α-hydroxyprogesterone, which showed less than 0.1% of the affinity of progesterone for the progesterone receptor.
Excerpted from Wikipedia’s “gestonorone” article, available under the CC BY-SA 4.0 licence.