nafoxidine
Sign in to saveNafoxidine (; developmental code names U-11,000A) or nafoxidine hydrochloride () is a nonsteroidal selective estrogen receptor modulator (SERM) or partial antiestrogen of the triphenylethylene group that was developed for the treatment of advanced breast cancer by Upjohn in the 1970s but was never marketed. It was developed at around the same time as tamoxifen and clomifene, which are also triphenylethylene derivatives. The drug was originally synthesized by the fertility control program at Upjohn as a postcoital contraceptive, but was subsequently repurposed for the treatment of breast cancer
Research
338 papers- Antiestrogens.Pharmacology & therapeutics · 1981
- [Hormones and lupus].La Revue de medecine interne · 1985
- Therapeutic value of nafoxidine hydrochloride in the treatment of advanced carcinoma of the human breast.Surgery, gynecology & obstetrics · 1976
- Role of protein kinase C-dependent signaling pathways in the antiangiogenic properties of nafoxidine.Anticancer research · 2004
- Raloxifene, tamoxifen, nafoxidine, or estrogen effects on reproductive and nonreproductive tissues in ovariectomized rats.FASEB journal : official publication of the Federation of American Societies for Experimental Biology · 1996
via PubMed
Wikidata facts
- Mass
- 425.235479
Show 3 more facts
- chemical formula
- C₂₉H₃₁NO₂
- canonical SMILES
- COC1=CC2=C(C=C1)C(=C(CC2)C3=CC=CC=C3)C4=CC=C(C=C4)OCCN5CCCC5
- Commons category
- Nafoxidine
Sources (2)
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Article
1 sectionsContents
- References
Nafoxidine (; developmental code names U-11,000A) or nafoxidine hydrochloride () is a nonsteroidal selective estrogen receptor modulator (SERM) or partial antiestrogen of the triphenylethylene group that was developed for the treatment of advanced breast cancer by Upjohn in the 1970s but was never marketed. It was developed at around the same time as tamoxifen and clomifene, which are also triphenylethylene derivatives. The drug was originally synthesized by the fertility control program at Upjohn as a postcoital contraceptive, but was subsequently repurposed for the treatment of breast cancer. Nafoxidine was assessed in clinical trials in the treatment of breast cancer and was found to be effective. However, it produced side effects including ichthyosis, partial hair loss, and phototoxicity of the skin in almost all patients, and this resulted in the discontinuation of its development.
Nafoxidine is a long-acting estrogen receptor ligand, with a nuclear retention in the range of 24 to 48 hours or more.