Zindoxifene

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]

Zindoxifene
Clinical data
Other namesD-16726; NSC-341952
Identifiers
IUPAC name
  • [4-(5-Acetyloxy-1-ethyl-3-methylindol-2-yl)phenyl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H21NO4
Molar mass351.402 g·mol−1
3D model (JSmol)
SMILES
  • CCN1C2=C(C=C(C=C2)OC(=O)C)C(=C1C3=CC=C(C=C3)OC(=O)C)C
InChI
  • InChI=1S/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
  • Key:KSZGVNZSUJHOJA-UHFFFAOYSA-N

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". In Litwack G (ed.). 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.



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