Doisynolic acid

Doisynolic acid
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 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)
SMILES
  • CCC1C2CCC3=C(C2CCC1(C)C(=O)O)C=CC(=C3)O
InChI
  • 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 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.[7]

Doisynolic acid is the parent compound of a group of synthetic, nonsteroidal estrogens with high oral activity.[8] The synthetic, nonsteroidal estrogens methallenestril, fenestrel, and carbestrol were all derived from doisynolic acid and are seco-analogues of the compound.[9] Doisynoestrol, also known as fenocycline, is cis-bisdehydrdoisynolic acid methyl ether, and is another estrogenic derivative.[10]

See also

References

  1. ↑ R.A. Hill; H.L.J. Makin; D.N. Kirk; G.M. Murphy (23 May 1991). Dictionary of Steroids. CRC Press. pp. 422–. ISBN 978-0-412-27060-4.
  2. ↑ R T Blickenstaff (2 December 2012). Antitumor Steroids. Academic Press. pp. 11–12. ISBN 978-0-323-13916-8.
  3. ↑ Alan C. Sartorelli; David G. Johns (27 November 2013). Antineoplastic and Immunosuppressive Agents. Springer Science & Business Media. pp. 106–. ISBN 978-3-642-65806-8.
  4. 1 2 3 Gregory Pincus; Thimann Kenneth Vivian Pincus Gregory (2 December 2012). The Hormones V1: Physiology, Chemistry and Applications. Elsevier. pp. 364–366. ISBN 978-0-323-14206-9.
  5. ↑ Robert T. Blickenstaff; Anil C. Ghosh; Gordon C. Wolf (22 October 2013). Total Synthesis of Steroids: Organic Chemistry: A Series of Monographs. Elsevier Science. pp. 65–. ISBN 978-1-4832-1642-3.
  6. ↑ David A. Williams; William O. Foye; Thomas L. Lemke (January 2002). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 692–. ISBN 978-0-683-30737-5.
  7. ↑ Dodds C (May 1955). "Synthetic oestrogens". British Medical Bulletin. 11 (2): 131–4. doi:10.1093/oxfordjournals.bmb.a069465. PMID 14378564.
  8. ↑ Edward Frieden (2 December 2012). Chemical Endocrinology. Elsevier Science. pp. 53–. ISBN 978-0-323-15906-7.
  9. ↑ Raymond Eller Kirk; Donald Frederick Othmer (1980). Encyclopedia of chemical technology. Wiley. p. 670,672. ISBN 978-0-471-02065-3.
  10. ↑ J. Elks (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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