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D-15414

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D-15414
Identifiers
  • 1-ethyl-2-(4-hydroxyphenyl)-3-methylindol-5-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H17NO2
Molar mass267.328 g·mol−1
3D model (JSmol)
  • CCN1C2=C(C=C(C=C2)O)C(=C1C3=CC=C(C=C3)O)C
  • InChI=1S/C17H17NO2/c1-3-18-16-9-8-14(20)10-15(16)11(2)17(18)12-4-6-13(19)7-5-12/h4-10,19-20H,3H2,1-2H3
  • Key:BXTNOIWYTWIPEL-UHFFFAOYSA-N

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

[edit]
  1. ^ a b c Jordan VC, Tormey DC (1988). "Antiestrogen Therapy for Breast Cancer". Endocrine Therapies in Breast and Prostate Cancer. Cancer Treatment and Research. Vol. 39. pp. 97–110. doi:10.1007/978-1-4613-1731-9_7. ISBN 978-1-4612-8974-6. PMID 2908611.
  2. ^ a b c Robinson SP, Koch R, Jordan VC (February 1988). "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. PMID 3338076.
  3. ^ a b von Angerer E, Prekajac J, Berger M (April 1985). "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. doi:10.1016/0277-5379(85)90048-3. PMID 3924626.
  4. ^ Maximov PY, McDaniel RE, Jordan VC (23 July 2013). Tamoxifen: Pioneering Medicine in Breast Cancer. Springer Science & Business Media. pp. 170–. ISBN 978-3-0348-0664-0.
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