Gestronol

This article is about a non-clinically used progestin compound. For the pharmaceutical medication, see Gestonorone caproate.
Gestronol
Clinical data
Other namesGestonorone; 17α-Hydroxy-19-norprogesterone; 17α-Hydroxy-19-norpregn-4-ene-3,20-dione
Identifiers
  • (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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.016.708 Edit this at Wikidata
Chemical and physical data
FormulaC20H28O3
Molar mass316.441 g·mol−1
3D model (JSmol)
  • 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=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 (BANTooltip British Approved Name), 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 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]

  1. ^ a b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 595–. ISBN 978-1-4757-2085-3.
  2. ^ a b Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 132–. ISBN 978-94-011-4439-1.
  3. ^ a b Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1357–. ISBN 978-3-88763-075-1.
  4. ^ a b 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". Journal of Endocrinological Investigation. 13 (11): 905–910. doi:10.1007/BF03349652. PMID 2090671. S2CID 37429648.