Doisynolic acid explained

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. 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. 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

• Allenolic acid
• Diethylstilbestrol
• Stilbestrol
• Chlorotrianisene
• Triphenylethylene

Notes and References

1. Book: Hill RA, Makin HL, Kirk DN, Murphy GM . Dictionary of Steroids. 23 May 1991. CRC Press. 978-0-412-27060-4. 422–.
2. Book: Leclerc G . Estrogens, Antiestrogens, and Other Estrane Compounds . Blickenstaff RT . Antitumor Steroids. https://books.google.com/books?id=sxMBCIoDS1MC&pg=PA11 . 2 December 2012. Academic Press. 978-0-323-13916-8. 11–12.
3. Book: Hilf R, Wittliff JL . Mechanisms of Action of Estrogens . Sartorelli AC, Johns DG . Antineoplastic and Immunosuppressive Agents. https://books.google.com/books?id=aU_oCAAAQBAJ&pg=PA106. 27 November 2013. Springer Science & Business Media. 978-3-642-65806-8. 106–.
4. Book: Pearlman WH . The Chemistry and Metabolism of the Estrogens . Pincus G, Thimann KV . The Hormones V1: Physiology, Chemistry and Applications. https://books.google.com/books?id=Thtz7On_lhEC&pg=PA364. 2 December 2012. Elsevier. 978-0-323-14206-9. 364–366.
5. Book: Blickenstaff RT, Ghosh AC, Wolf GC . Chapter 3.4: 18,19-Norprogesterone and 19-Norpreganes . Total Synthesis of Steroids: Organic Chemistry: A Series of Monographs. https://books.google.com/books?id=Vpb-BAAAQBAJ&pg=PA65. 22 October 2013. Elsevier Science. 978-1-4832-1642-3. 65–.
6. Book: Brueggemeir RW, Miller DD, Dalton JT . Estrogen, Progestins, and Androgens . Williams DA, Foye WO, Lemke TL . Foye's Principles of Medicinal Chemistry. https://books.google.com/books?id=qLJ6Bs1Qml4C&pg=PA692 . January 2002. Lippincott Williams & Wilkins. 978-0-683-30737-5. 692–.
7. Dodds C . Synthetic oestrogens . British Medical Bulletin . 11 . 2 . 131–134 . May 1955 . 14378564 . 10.1093/oxfordjournals.bmb.a069465 . free .
8. Book: Frieden E . Estrogens . Chemical Endocrinology. https://books.google.com/books?id=CRQ-KO0qsT0C&pg=PA53. 2 December 2012. Elsevier Science. 978-0-323-15906-7. 53–.
9. Book: Kirk RE, Othmer DF . Encyclopedia of chemical technology. 1980. Wiley. 978-0-471-02065-3. 670,672.
10. Book: Elks J . The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014. Springer. 978-1-4757-2085-3. 465–.