Zindoxifene
Iupac name[4-(5-Acetyloxy-1-ethyl-3-methylindol-2-yl)phenyl] acetate
Width250
Cas number86111-26-4
Pubchem65645
Chemspiderid59082
Unii1IRS95M8DN
KeggC14745
Chebi35052
Chembl32227
C21
H21
N1
O4
SmilesCCN1C2=C(C=C(C=C2)OC(=O)C)C(=C1C3=CC=C(C=C3)OC(=O)C)C
Stdinchi1S/C21H21NO4/c1-5-22-20-11-10-18(26-15(4)24)12-19(20)13(2)21(22)16-6-8-17(9-7-16)25-14(3)23/h6-12H,5H2,1-4H3
StdinchikeyKSZGVNZSUJHOJA-UHFFFAOYSA-N
SynonymsD-16726; NSC-341952

Zindoxifene (INN; former developmental code names D-16726, NSC-341952) 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.[1] It showed estrogenic-like activity in preclinical studies and failed to demonstrate effectiveness as a treatment for breast cancer in clinical trials.[2][3] Zindoxifene was the lead compound of the distinct 2-phenylindole class of SERMs,[4][5] and the marketed SERM bazedoxifene was derived from the major active metabolite of zindoxifene, D-15414.[2][3] Zindoxifene was first described in 1984.[1]

References

  1. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1300–. ISBN 978-1-4757-2085-3.
  2. ^ Maximov PY, McDaniel RE, Jordan VC (23 July 2013). "The Legacy of Tamoxifen". Tamoxifen: Pioneering Medicine in Breast Cancer. Springer Science & Business Media. pp. 170–. ISBN 978-3-0348-0664-0.
  3. ^ McDaniel R, Maximov PY, Jordan VC (25 June 2013). "The Legacy of Tamoxifen". Hormones and Breast Cancer. Elsevier. pp. 32–. ISBN 978-0-12-416676-9.
  4. ^ Oettel M, Schillinger E (6 December 2012). Estrogens and Antiestrogens I: Physiology and Mechanisms of Action of Estrogens and Antiestrogens. Springer Science & Business Media. pp. 68–69. ISBN 978-3-642-58616-3.
  5. ^ Maggi A, Paoletti R (2002). "The Pharmacological Modulations of Estrogen Receptor Activity". International position paper on women's health and menopause : a comprehensive approach. DIANE Publishing. pp. 111–. ISBN 978-1-4289-0521-4.