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
E number{{#property:P628}}
CompTox Dashboard (EPA)
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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

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