Nafoxidine

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Nafoxidine
File:Nafoxidine.png
Systematic (IUPAC) name
1-[2-[4-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl]pyrrolidine
Identifiers
CAS Number 1845-11-0
ATC code none
PubChem CID 4416
ChemSpider 4263
Chemical data
Formula C28H31NO2
Molar mass 425.562 g/mol[[Script error: No such module "String".]]
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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 by Dan Lednicer at Upjohn.

A drug known as "U-11,555" is more potent than Nafoxidine but also causes photosensitivity (as for example does psoralen).

File:U-11,555 image.png

See: D. Lednicer, J.C. Babcock, P.E. Marlatt, S.C. Lyster, G.W. Duncan, J.Med.Chem., 8, 52(1965). for details.[2]

Synthesis

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

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

References

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Estrogens and progestogens (G03C-D, L02)
Progestogens/
progestins
(progesterone)
Agonist
Other/
ungrouped
Estrogens
Agonist


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  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. doi:10.1002/mpo.2950040207. PMID 661750.  edit
  2. ↑ http://dx.doi.org/10.1021%2Fjm00325a013
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