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Doisynolic acid

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, orally active, nonsteroidal 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, whose levorotatory isomer 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. ^ 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). "Mechanisms 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. ^ a b c 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. ^ Dodds C (May 1955). "Synthetic oestrogens". British Medical Bulletin. 11 (2): 131–134. doi:10.1093/oxfordjournals.bmb.a069465. PMID 14378564.
  8. ^ Frieden E (2 December 2012). "Estrogens". Chemical Endocrinology. Elsevier Science. pp. 53–. ISBN 978-0-323-15906-7.
  9. ^ Kirk RE, Othmer DF (1980). Encyclopedia of chemical technology. Wiley. p. 670,672. ISBN 978-0-471-02065-3.
  10. ^ 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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