Nafoxidine is a non-steroid

Steroid

A steroid is a type of organic compound that contains a characteristic arrangement of four cycloalkane rings that are joined to each other. Examples of steroids include the dietary fat cholesterol, the sex hormones estradiol and testosterone, and the anti-inflammatory drug dexamethasone.The core...

al antiestrogen

Estrogen

Estrogens , oestrogens , or œstrogens, are a group of compounds named for their importance in the estrous cycle of humans and other animals. They are the primary female sex hormones. Natural estrogens are steroid hormones, while some synthetic ones are non-steroidal...

ic drug that has been investigated to treat advanced breast cancer. It is structurally related to tamoxifen

Tamoxifen

Tamoxifen is an antagonist of the estrogen receptor in breast tissue via its active metabolite, hydroxytamoxifen. In other tissues such as the endometrium, it behaves as an agonist, hence tamoxifen may be characterized as a mixed agonist/antagonist...

.

The drug is one of a series of similar structures invented by Dan Lednicer at Upjohn

Upjohn

The Upjohn Company was a pharmaceutical manufacturing firm founded in 1886 in Kalamazoo, Michigan by Dr. William E. Upjohn, an 1875 graduate of the University of Michigan medical school. The company was originally formed to make friable pills, which were specifically designed to be easily digested...

.

An earlier compound known as "U-11,555" is related to Nafoxidine was found to cause photosensitivity in human volunteers(as for example does psoralen

Psoralen

Psoralen is the parent compound in a family of natural products known as furocoumarins. It is structurally related to coumarin by the addition of a fused furan ring, and may be considered as a derivative of umbelliferone...

).

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

Synthesis

The synthesis depicted is more modern, but also see Lasofoxifene

Lasofoxifene

Lasofoxifene is a non-steroidal selective estrogen receptor modulator which is under development by Pfizer for the prevention and treatment of osteoporosis and for the treatment of vaginal atrophy, and the result of an exclusive research collaboration with Ligand Pharmaceuticals .In September...

for an earlier synthesis.
Cameron, C. O.; Dasilva Jardine, P. A.; Rosati, R. L.; 1996, .