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| Other names | U-11,000A; NSC-70735 |
| Routes of administration | By mouth |
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| ECHA InfoCard | 100.222.756 |
| Chemical and physical data | |
| Formula | C29H31NO2 |
| Molar mass | 425.572 g·mol−1 |
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Nafoxidine (INNTooltip International Nonproprietary Name; developmental code namesU-11,000A) ornafoxidine hydrochloride (USANTooltip United States Adopted Name) is anonsteroidalselective estrogen receptor modulator (SERM) orpartialantiestrogen of thetriphenylethylene group that was developed for the treatment ofadvancedbreast cancer byUpjohn in the 1970s but was never marketed.[1][2][3] It was developed at around the same time astamoxifen andclomifene, which are also triphenylethylene derivatives.[2] The drug was originally synthesized by the fertility control program at Upjohn as apostcoital 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 producedside effects includingichthyosis, partialhair loss, andphototoxicity of the skin in almost all patients,[5] and this resulted in the discontinuation of its development.[4][7]
Nafoxidine is a long-actingestrogen receptorligand, with anuclear retention in the range of 24 to 48 hours or more.[8]
| Antiestrogen | Dosage | Year(s) | Response rate | Adverse effects |
|---|---|---|---|---|
| Ethamoxytriphetol | 500–4,500 mg/day | 1960 | 25% | Acute psychotic episodes |
| Clomifene | 100–300 mg/day | 1964–1974 | 34% | Risks ofcataracts |
| Nafoxidine | 180–240 mg/day | 1976 | 31% | Cataracts,ichthyosis,photophobia |
| Tamoxifen | 20–40 mg/day | 1971–1973 | 31% | Transientthrombocytopeniaa |
| Footnotes:a = "The particular advantage of this drug is the low incidence of troublesome side effects (25)." "Side effects were usually trivial (26)."Sources:[9][10] | ||||