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{{short description|Chemical compound}}
{{Drugbox
| Verifiedfields =
| Watchedfields =
| verifiedrevid =
| IUPAC_name = 1-[2-[4-(6-Methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl]pyrrolidine
| image = Nafoxidine.svg
| width = 200px


| tradename =
| pregnancy_AU = 
| pregnancy_US = 
| pregnancy_category =
| legal_AU = 
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration = [[Oral administration|By mouth]]


| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =


| CAS_number_Ref =
| CAS_number = 1845-11-0
| CAS_supplemental =
| class =
| ATC_prefix = None
| ATC_suffix =
| ATC_supplemental =
| PubChem = 4416
| IUPHAR_ligand = 4263
| DrugBank_Ref =
| DrugBank =
| ChemSpiderID_Ref =
| ChemSpiderID = 4263
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4RIY10WM82
| KEGG = C14212
| ChEBI = 34881
| ChEMBL = 28211
| synonyms = U-11,000A; NSC-70735


| C=29 | H=31 | N=1 | O=2
| SMILES = COC1=CC2=C(C=C1)C(=C(CC2)C3=CC=CC=C3)C4=CC=C(C=C4)OCCN5CCCC5
| StdInChI_Ref =
| StdInChI = 1S/C29H31NO2/c1-31-26-14-16-28-24(21-26)11-15-27(22-7-3-2-4-8-22)29(28)23-9-12-25(13-10-23)32-20-19-30-17-5-6-18-30/h2-4,7-10,12-14,16,21H,5-6,11,15,17-20H2,1H3
| StdInChIKey_Ref =
| StdInChIKey = JEYWNNAZDLFBFF-UHFFFAOYSA-N
}}

'''Nafoxidine''' ({{Abbrlink|INN|International Nonproprietary Name}}; developmental code names '''U-11,000A''') or '''nafoxidine hydrochloride''' ({{Abbrlink|USAN|United States Adopted Name}}) is a [[nonsteroid]]al [[selective estrogen receptor modulator]] (SERM) or [[partial agonist|partial]] [[antiestrogen]] of the [[triphenylethylene]] group that was developed for the treatment of [[metastatic cancer|advanced]] [[breast cancer]] by [[Upjohn]] in the 1970s but was never marketed.<ref name="Elks2014">{{Cite book |url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA848 |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies |vauthors=Elks J |date=14 November 2014 |publisher=Springer |isbn=978-1-4757-2085-3 |pages=848–}}</ref><ref name="CRAIGFurr2010">{{Cite book |url=https://books.google.com/books?id=dM0uvBnxiN0C&pg=PA95 |title=Hormone Therapy in Breast and Prostate Cancer |vauthors=Craig JV, Furr BJ |date=5 February 2010 |publisher=Springer Science & Business Media |isbn=978-1-59259-152-7 |pages=95–96}}</ref><ref name="Weber2015">{{Cite book |url=https://books.google.com/books?id=dhs_CgAAQBAJ&pg=PA361 |title=Molecular Therapies of Cancer |vauthors=Weber GF |date=22 July 2015 |publisher=Springer |isbn=978-3-319-13278-5 |pages=361–}}</ref> It was developed at around the same time as [[tamoxifen]] and [[clomifene]], which are also triphenylethylene derivatives.<ref name="CRAIGFurr2010" /> The drug was originally synthesized by the fertility control program at Upjohn as a [[emergency contraception|postcoital contraceptive]], but was subsequently repurposed for the treatment of breast cancer.<ref name="Elsevier2013">{{Cite journal |vauthors=McDaniel RE, Maximov PY, Jordan VC |date=2013 |title=Estrogen-mediated mechanisms to control the growth and apoptosis of breast cancer cells: a translational research success story |url=https://books.google.com/books?id=vBvzF6HQ4-QC&pg=PA32 |journal=Vitamins and Hormones |volume=93 |pages=1–49 |doi=10.1016/B978-0-12-416673-8.00007-1 |pmid=23810002}}</ref> Nafoxidine was assessed in clinical trials in the treatment of breast cancer and was found to be effective.<ref name="pmid27889048">{{Cite journal |vauthors=Coelingh Bennink HJ, Verhoeven C, Dutman AE, Thijssen J |date=January 2017 |title=The use of high-dose estrogens for the treatment of breast cancer |journal=Maturitas |volume=95 |pages=11–23 |doi=10.1016/j.maturitas.2016.10.010 |pmid=27889048 |doi-access=free}}</ref><ref name="Steinbaumde Jager1978">{{Cite journal |vauthors=Steinbaum FL, De Jager RL, Krakoff IH |year=1978 |title=Clinical trial of nafoxidine in advanced breast cancer |journal=Medical and Pediatric Oncology |volume=4 |issue=2 |pages=123–126 |doi=10.1002/mpo.2950040207 |pmid=661750}}</ref> However, it produced [[side effect]]s including [[ichthyosis]], partial [[alopecia|hair loss]], and [[phototoxicity]] of the skin in almost all patients,<ref name="pmid27889048" /> and this resulted in the discontinuation of its development.<ref name="Elsevier2013" /><ref name="Lupulescu1990">{{Cite book |url=https://books.google.com/books?id=VddUa-2cp-YC&pg=PA95 |title=Hormones and Vitamins in Cancer Treatment |vauthors=Lupulescu A |date=24 October 1990 |publisher=CRC Press |isbn=978-0-8493-5973-6 |pages=95–}}</ref>

Nafoxidine is a long-acting [[estrogen receptor]] [[ligand (biochemistry)|ligand]], with a [[nuclear retention]] in the range of 24 to 48 hours or more.<ref name="WallachHammond1982">{{Cite journal |vauthors=Hammond CB, Maxson WS |date=January 1982 |title=Current status of estrogen therapy for the menopause |journal=Fertility and Sterility |volume=37 |issue=1 |pages=5–25 |doi=10.1016/S0015-0282(16)45970-4 |pmid=6277697}}</ref>

{{Comparison of early clinical experience with antiestrogens for advanced breast cancer}}

== References ==
{{Reflist}}

{{Estrogen receptor modulators}}

[[Category:Abandoned drugs]]
[[Category:Hormonal antineoplastic drugs]]
[[Category:Phenol ethers]]
[[Category:1-Pyrrolidinyl compounds]]
[[Category:Selective estrogen receptor modulators]]
[[Category:Triphenylethylenes]]

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