Norendoxifen

Norendoxifen, also known as N,N-didesmethyl-4-hydroxytamoxifen, 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 (K_i = 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]

Norendoxifen

Clinical data
Other names	N,N-Didesmethyl-4-hydroxytamoxifen
Identifiers
IUPAC name 4-[(Z)-1-[4-(2-Aminoethoxy)phenyl]-2-phenylbut-1-enyl]phenol
CAS Number	1217237-98-3
PubChem CID	68037237
DrugBank	DBMET00963
ChemSpider	32817000
ChEMBL	ChEMBL2386284
Chemical and physical data
Formula	C24H25NO2
Molar mass	359.469 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CCC(=C(c1ccc(cc1)O)c2ccc(cc2)OCCN)c3ccccc3
InChI 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

See also

• Afimoxifene (4-hydroxytamoxifen)
• Endoxifen (N-desmethyl-4-hydroxytamoxifen)

References

1. 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.