Nafoxidine

Nafoxidine

Nafoxidine
Systematic (IUPAC) name
1-[2-[4-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl]pyrrolidine
Clinical data
Legal status
?
Identifiers
CAS number
ATC code None
PubChem
ChemSpider
UNII  YesY
ChEMBL
Chemical data
Formula C29H31NO2 
Mol. mass 425.562 g/mol

Nafoxidine (U-11,000A) is a non-steroidal antiestrogenic drug that has been investigated to treat advanced breast cancer.[1] It is structurally related to tamoxifen.

The drug is one of a series of similar structures invented at Upjohn. An earlier compound known as U-11,555 is related to Nafoxidine was found to cause photosensitivity in human volunteers.[2][3]

U-11,555

Synthesis

The synthesis depicted is more modern, but also see Lasofoxifene for an earlier synthesis.

Cameron, C. O.; Dasilva Jardine, P. A.; Rosati, R. L.; 1996, U.S. Patent 5,552,412.

References

  1. ^ Steinbaum, F. L.; De Jager, R.; Krakoff, I. (1978). "Clinical trial of nafoxidine in advanced breast cancer". Medical and Pediatric Oncology 4 (2): 123–126.  
  2. ^ http://www.sciencebase.com/serendipity_and_science.html
  3. ^ Lednicer,, D.; Babcock, J.C.; Marlatt, P.E.; Lyster, S.C.; Duncan, G.W. (1965). "Mammalian Antifertility Agents. I. Derivatives of 2,3-Diphenylindenes". J. Med. Chem. 8 (1): 52–57.