Chemistry:Nafoxidine
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| Other names | U-11,000A; NSC-70735 |
| Routes of administration | By mouth |
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| Formula | C29H31NO2 |
| Molar mass | 425.572 g·mol−1 |
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Nafoxidine (INN; developmental code names U-11,000A) or nafoxidine hydrochloride (USAN) 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.[1][2][3] It was developed at around the same time as tamoxifen and clomifene, which are also triphenylethylene derivatives.[2] 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.[4] Nafoxidine was assessed in clinical trials in the treatment of breast cancer and was found to be effective.[5][6] However, it produced side effects including ichthyosis, partial hair loss, and phototoxicity of the skin in almost all patients,[5] and this resulted in the discontinuation of its development.[4][7]
Nafoxidine is a long-acting estrogen receptor ligand, with a nuclear retention in the range of 24 to 48 hours or more.[8]
References
- ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 848–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA848.
- ↑ 2.0 2.1 Hormone Therapy in Breast and Prostate Cancer. Springer Science & Business Media. 5 February 2010. pp. 95–96. ISBN 978-1-59259-152-7. https://books.google.com/books?id=dM0uvBnxiN0C&pg=PA95.
- ↑ Molecular Therapies of Cancer. Springer. 22 July 2015. pp. 361–. ISBN 978-3-319-13278-5. https://books.google.com/books?id=dhs_CgAAQBAJ&pg=PA361.
- ↑ 4.0 4.1 "Estrogen-mediated mechanisms to control the growth and apoptosis of breast cancer cells: a translational research success story". Vitamins and Hormones 93: 1–49. 2013. doi:10.1016/B978-0-12-416673-8.00007-1. PMID 23810002. https://books.google.com/books?id=vBvzF6HQ4-QC&pg=PA32.
- ↑ 5.0 5.1 "The use of high-dose estrogens for the treatment of breast cancer". Maturitas 95: 11–23. January 2017. doi:10.1016/j.maturitas.2016.10.010. PMID 27889048.
- ↑ "Clinical trial of nafoxidine in advanced breast cancer". Medical and Pediatric Oncology 4 (2): 123–126. 1978. doi:10.1002/mpo.2950040207. PMID 661750.
- ↑ Hormones and Vitamins in Cancer Treatment. CRC Press. 24 October 1990. pp. 95–. ISBN 978-0-8493-5973-6. https://books.google.com/books?id=VddUa-2cp-YC&pg=PA95.
- ↑ "Current status of estrogen therapy for the menopause". Fertility and Sterility 37 (1): 5–25. January 1982. doi:10.1016/S0015-0282(16)45970-4. PMID 6277697.
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