Chemistry:D-15414
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| Formula | C17H17NO2 |
| Molar mass | 267.328 g·mol−1 |
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D-15414 is a nonsteroidal weak estrogen of the 2-phenylindole group which was never marketed.[1][2] It is the major metabolite of the selective estrogen receptor modulator (SERM) zindoxifene (D-16726).[3] D-15414 has high affinity for the estrogen receptor (ER) and inhibits the growth of ER-positive MCF-7 breast cancer cells in vitro.[3] 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.[1][2] The reason for the discrepancy between the findings is unclear, though may be due to methodology.[2] The unexpected estrogenic activity of D-15414 may be responsible for the failure of zindoxifene in clinical trials as a treatment for breast cancer.[1][4]
References
- ↑ 1.0 1.1 1.2 "Antiestrogen therapy for breast cancer: current strategies and future prospects". Cancer Treatment and Research 39: 97–110. 1988. doi:10.1007/978-1-4613-1731-9_7. ISBN 978-1-4612-8974-6. PMID 2908611.
- ↑ 2.0 2.1 2.2 "In vitro estrogenic actions in rat and human cells of hydroxylated derivatives of D16726 (zindoxifene), an agent with known antimammary cancer activity in vivo". Cancer Research 48 (4): 784–787. February 1988. PMID 3338076.
- ↑ 3.0 3.1 "The inhibitory effect of 5-acetoxy-2-(4-acetoxyphenyl)-1-ethyl-3-methylindole (D 16726) on estrogen-dependent mammary tumors". European Journal of Cancer & Clinical Oncology 21 (4): 531–537. April 1985. doi:10.1016/0277-5379(85)90048-3. PMID 3924626.
- ↑ Tamoxifen: Pioneering Medicine in Breast Cancer. Springer Science & Business Media. 23 July 2013. pp. 170–. ISBN 978-3-0348-0664-0. https://books.google.com/books?id=p-W5BAAAQBAJ&pg=PA170.
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