Doisynolic acid
Clinical data
ATC code
  • None
Identifiers
  • 1-Ethyl-7-hydroxy-2-methyl-3,4,4a,9,10,10a-hexahydro-1H-phenanthrene-2-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H24O3
Molar mass288.387 g·mol−1
3D model (JSmol)
  • CCC1C2CCC3=C(C2CCC1(C)C(=O)O)C=CC(=C3)O
  • InChI=1S/C18H24O3/c1-3-16-15-6-4-11-10-12(19)5-7-13(11)14(15)8-9-18(16,2)17(20)21/h5,7,10,14-16,19H,3-4,6,8-9H2,1-2H3,(H,20,21)
  • Key:GEGYYIFBFKSCPK-UHFFFAOYSA-N

Doisynolic acid is a synthetic, nonsteroidal, orally active estrogen that was never marketed.[1][2][3] The reaction of estradiol or estrone with potassium hydroxide, a strong base, results in doisynolic acid as a degradation product, which retains high estrogenic activity, and this reaction was how the drug was discovered, in the late 1930s.[4][5][6] The drug is a highly active and potent estrogen by the oral or subcutaneous route.[4] The reaction of equilenin or dihydroequilenin with potassium hydroxide was also found to produce bisdehydrodoisynolic acid, the levorotatory isomer[7] of which is an estrogen with an "astonishingly" high degree of potency, while the dextrorotatory isomer is inactive.[4] Doisynolic acid was named after Edward Adelbert Doisy, a pioneer in the field of estrogen research and one of the discoverers of estrone.[8]

Doisynolic acid is the parent compound of a group of synthetic, nonsteroidal estrogens with high oral activity.[9] The synthetic, nonsteroidal estrogens methallenestril, fenestrel, and carbestrol were all derived from doisynolic acid and are seco-analogues of the compound.[10] Doisynoestrol, also known as fenocycline, is cis-bisdehydrdoisynolic acid methyl ether, and is another estrogenic derivative.[11]

See also

References

  1. ↑ Hill RA, Makin HL, Kirk DN, Murphy GM (23 May 1991). Dictionary of Steroids. CRC Press. pp. 422–. ISBN 978-0-412-27060-4.
  2. ↑ Leclerc G (2 December 2012). "Estrogens, Antiestrogens, and Other Estrane Compounds". In Blickenstaff RT (ed.). Antitumor Steroids. Academic Press. pp. 11–12. ISBN 978-0-323-13916-8.
  3. ↑ Hilf R, Wittliff JL (27 November 2013). "Mechanims of Action of Estrogens". In Sartorelli AC, Johns DG (eds.). Antineoplastic and Immunosuppressive Agents. Springer Science & Business Media. pp. 106–. ISBN 978-3-642-65806-8.
  4. 1 2 3 Pearlman WH (2 December 2012). "The Chemistry and Metabolism of the Estrogens". In Pincus G, Thimann KV (eds.). The Hormones V1: Physiology, Chemistry and Applications. Elsevier. pp. 364–366. ISBN 978-0-323-14206-9.
  5. ↑ Blickenstaff RT, Ghosh AC, Wolf GC (22 October 2013). "Chapter 3.4: 18,19-Norprogesterone and 19-Norpreganes". Total Synthesis of Steroids: Organic Chemistry: A Series of Monographs. Elsevier Science. pp. 65–. ISBN 978-1-4832-1642-3.
  6. ↑ Brueggemeir RW, Miller DD, Dalton JT (January 2002). "Estrogen, Progestins, and Androgens". In Williams DA, Foye WO, Lemke TL (eds.). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 692–. ISBN 978-0-683-30737-5.
  7. ↑ "Doisynolic acid". Miraculous Medicines NFT. #3772. Retrieved 2023-11-02.
  8. ↑ Dodds C (May 1955). "Synthetic oestrogens". British Medical Bulletin. 11 (2): 131–134. doi:10.1093/oxfordjournals.bmb.a069465. PMID 14378564.
  9. ↑ Frieden E (2 December 2012). "Estrogens". Chemical Endocrinology. Elsevier Science. pp. 53–. ISBN 978-0-323-15906-7.
  10. ↑ Kirk RE, Othmer DF (1980). Encyclopedia of chemical technology. Wiley. p. 670,672. ISBN 978-0-471-02065-3.
  11. ↑ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 465–. ISBN 978-1-4757-2085-3.
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