2,8-Dihydroxyhexahydrochrysene

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2,8-Dihydroxyhexahydrochrysene
2,8-Dihydroxyhexahydrochrysene.svg
Clinical data
ATC code
  • None
Chemical and physical data
Formula C18H18O2
Molar mass 266.340 g·mol−1

2,8-Dihydroxyhexahydrochrysene (2,8-DHHHC) is a synthetic, nonsteroidal weak estrogen with approximately 1/2,000th the estrogenic potency of the structurally-related estrogen diethylstilbestrol. [1] [2] [3] It is said to be intermediate in structure between estradiol and hexestrol, but conversely to both of them, it is drastically less potent in comparison. [3]

See also

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18
H
12
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<span class="mw-page-title-main">Dianol</span> Chemical compound

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<span class="mw-page-title-main">Triphenylchloroethylene</span> Synthetic form of estrogen

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<span class="mw-page-title-main">Zindoxifene</span> Chemical compound

Zindoxifene is a nonsteroidal selective estrogen receptor modulator (SERM) that was under development in the 1980s and early 1990s for the treatment of breast cancer but was not marketed. It showed estrogenic-like activity in preclinical studies and failed to demonstrate effectiveness as a treatment for breast cancer in clinical trials. Zindoxifene was the lead compound of the distinct 2-phenylindole class of SERMs, and the marketed SERM bazedoxifene was derived from the major active metabolite of zindoxifene, D-15414. Zindoxifene was first described in 1984.

<span class="mw-page-title-main">D-15414</span> Chemical compound

D-15414 is a nonsteroidal weak estrogen of the 2-phenylindole group which was never marketed. It is the major metabolite of the selective estrogen receptor modulator (SERM) zindoxifene (D-16726). D-15414 has high affinity for the estrogen receptor (ER) and inhibits the growth of ER-positive MCF-7 breast cancer cells in vitro. However, contradictorily, subsequent research found that the drug produced fully estrogenic effects in vitro similarly to but less actively than estradiol, with no antiestrogenic activity observed. The reason for the discrepancy between the findings is unclear, though may be due to methodology. The unexpected estrogenic activity of D-15414 may be responsible for the failure of zindoxifene in clinical trials as a treatment for breast cancer.

References

  1. Maximov PY, McDaniel RE, Jordan VC (23 July 2013). Tamoxifen: Pioneering Medicine in Breast Cancer. Springer Science & Business Media. pp. 4–. ISBN   978-3-0348-0664-0.
  2. Jordan VC (1986). Estrogen/antiestrogen Action and Breast Cancer Therapy. Univ of Wisconsin Press. pp. 22–. ISBN   978-0-299-10480-1.
  3. 1 2 Wilds AL, Sutton RE (1951). "Cyclic Analogs of Hexestrol in the Chrysene Series". The Journal of Organic Chemistry. 16 (9): 1371–1379. doi:10.1021/jo50003a006. ISSN   0022-3263.