Gestronol

Gestronol (BAN), 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.[1][2][3] The C17α caproate ester of gestronol, gestonorone caproate (gestronol hexanoate), in contrast, has been marketed.[1][2][3]

Gestronol

Clinical data
Other names	Gestonorone; 17α-Hydroxy-19-norprogesterone; 17α-Hydroxy-19-norpregn-4-ene-3,20-dione
Identifiers
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
CAS Number	2137-18-0
PubChem CID	102210
ChemSpider	4386807
UNII	H4G605B7VP
CompTox Dashboard (EPA)	DTXSID50175631
ECHA InfoCard	100.016.708
Chemical and physical data
Formula	C20H28O3
Molar mass	316.441 g·mol^−1
3D model (JSmol)	Interactive image
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
InChI InChI=1S/C20H28O3/c1-12(21)20(23)10-8-18-17-5-3-13-11-14(22)4-6-15(13)16(17)7-9-19(18,20)2/h11,15-18,23H,3-10H2,1-2H3/t15-,16+,17+,18-,19-,20-/m0/s1 Key:GTFUITFQDGVJSK-XGXHKTLJSA-N

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.[4] 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.[4]

See also

• 17α-Methyl-19-norprogesterone

References

1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 595–. ISBN 978-1-4757-2085-3.
2. I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 132–. ISBN 978-94-011-4439-1.
3. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1357–. ISBN 978-3-88763-075-1.
4. Botella J, Duc I, Delansorne R, Paris J, Lahlou B (December 1990). "Structure-activity and structure-affinity relationships of 19-nor-progesterone derivatives in rat uterus". J. Endocrinol. Invest. 13 (11): 905–10. doi:10.1007/BF03349652. PMID 2090671. S2CID 37429648.