Bisdehydrodoisynolic acid
Chemical compound
From Wikipedia, the free encyclopedia
Bisdehydrodoisynolic acid (BDDA), as the (Z)-isomer ((Z)-BDDA), is a synthetic, nonsteroidal estrogen 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 potency in 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 methyl ether of BDDA, doisynoestrol, is also an estrogen, and in contrast to BDDA, has been marketed.[2][9]
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| Formula | C18H20O3 |
| Molar mass | 284.355 g·mol−1 |
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