Norendoxifen

Norendoxifen
Clinical data
Other names4-Hydroxy-N,N-didesmethyltamoxifen
Identifiers
  • 4-[(Z)-1-[4-(2-Aminoethoxy)phenyl]-2-phenylbut-1-enyl]phenol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H25NO2
Molar mass359.469 g·mol−1
3D model (JSmol)
  • CCC(=C(c1ccc(cc1)O)c2ccc(cc2)OCCN)c3ccccc3
  • InChI=1S/C24H25NO2/c1-2-23(18-6-4-3-5-7-18)24(19-8-12-21(26)13-9-19)20-10-14-22(15-11-20)27-17-16-25/h3-15,26H,2,16-17,25H2,1H3
  • Key:YCQBLTPGQSYLHD-UHFFFAOYSA-N

Norendoxifen, also known as 4-hydroxy-N,N-didesmethyltamoxifen, is a nonsteroidal aromatase inhibitor (AI) of the triphenylethylene group that was never marketed.[1]

It is an active metabolite of the selective estrogen receptor modulator (SERM) tamoxifen.[1] Unlike tamoxifen, norendoxifen is not a SERM, and instead has been found to act as a potent and selective competitive inhibitor of aromatase (Ki = 35 nM).[1] Drugs with dual SERM and AI activity, such as 4'-hydroxynorendoxifen, have been developed from norendoxifen, and may have therapeutic potential as antiestrogens in the treatment of estrogen receptor-positive breast cancer.[2]

See also

References

  1. ^ a b c Lu WJ, Xu C, Pei Z, Mayhoub AS, Cushman M, Flockhart DA (May 2012). "The tamoxifen metabolite norendoxifen is a potent and selective inhibitor of aromatase (CYP19) and a potential lead compound for novel therapeutic agents". Breast Cancer Research and Treatment. 133 (1): 99–109. doi:10.1007/s10549-011-1699-4. PMID 21814747. S2CID 22096941.
  2. ^ Lv W, Liu J, Skaar TC, Flockhart DA, Cushman M (March 2015). "Design and synthesis of norendoxifen analogues with dual aromatase inhibitory and estrogen receptor modulatory activities". Journal of Medicinal Chemistry. 58 (6): 2623–48. doi:10.1021/jm501218e. PMC 4687028. PMID 25751283.
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