Bisdehydrodoisynolic acid (BDDA), as the (Z)-isomer ((Z)-BDDA), is a
synthetic,
nonsteroidalestrogen related to
doisynolic acid that was never marketed.[1] It is one of the most potent estrogens known,[2][3] although it has more recently been characterized as a
selective estrogen receptor modulator (SERM).[3][4] BDDA and other doisynolic acid derivatives display relatively low
affinity accompanied by disproportionately high estrogenic
potencyin vivo,[5] which was eventually determined to be due to transformation into
metabolites with greater estrogenic activity.[4] The drug was discovered in 1947 as a degradation product of the reaction of
equilenin or
dihydroequilenin with
potassium hydroxide.[6] It is the seco-analogue of equilenin, while doisynolic acid is the seco-analogue of
estrone.[7] These compounds, along with
diethylstilbestrol, can be considered to be open-ring analogues of
estradiol.[8] The
methylether of BDDA,
doisynoestrol, is also an estrogen, and in contrast to BDDA, has been marketed.[2][9]
^
abJohnson WS, Graber RP (1950). "The Stobbe Condensation with 6-Methoxy-2-propionylnaphthalene. A Synthesis of Bisdehydrodoisynolic Acid1". Journal of the American Chemical Society. 72 (2): 925–935.
doi:
10.1021/ja01158a075.
ISSN0002-7863.
^Banz WJ, Winters TA, Hou Y, Adler S, Meyers CY (December 1998). "Comparative effects of the selective estrogen receptor modulators (-)-, (+)- and (+/-)-Z bisdehydrodoisynolic acids on metabolic and reproductive parameters in male and female rats". Hormone and Metabolic Research. 30 (12): 730–736.
doi:
10.1055/s-2007-978968.
PMID9930631.
^Elks J (14 November 2014).
"Doisynoestrol". The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 465–.
ISBN978-1-4757-2085-3.