nitromifene

{{short description|Chemical compound}}

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| IUPAC_name = 1-[2-[4-[1-(4-Methoxyphenyl)-2-nitro-2-phenylethenyl]phenoxy]ethyl]pyrrolidine

| image = Nitromifene.svg

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| CAS_number = 10448-84-7

| CAS_supplemental =
5863-35-4 (citrate)

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| PubChem = 22150

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| ChemSpiderID = 20796

| UNII = 5FS1NJ6Q8N

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| synonyms = CI-628; CN-5518; CN-55945

| C=27 | H=28 | N=2 | O=4

| SMILES = COC1=CC=C(C=C1)C(=C(C2=CC=CC=C2)[N+](=O)[O-])C3=CC=C(C=C3)OCCN4CCCC4

| StdInChI_Ref =

| StdInChI = 1S/C27H28N2O4/c1-32-24-13-9-21(10-14-24)26(27(29(30)31)23-7-3-2-4-8-23)22-11-15-25(16-12-22)33-20-19-28-17-5-6-18-28/h2-4,7-16H,5-6,17-20H2,1H3

| StdInChIKey_Ref =

| StdInChIKey = MFKMXUFMHOCZHP-UHFFFAOYSA-N

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Nitromifene ({{Abbrlink|INN|International Nonproprietary Name}}; also as the citrate salt nitromifene citrate ({{Abbrlink|USAN|United States Adopted Name}}), developmental code names CI-628, CN-5518, CN-55945) is a nonsteroidal selective estrogen receptor modulator (SERM) related to triphenylethylenes like tamoxifen that was never marketed.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA880|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=880–}} It is a mixture of (E)- and (Z)-isomers that possess similar antiestrogenic activity.{{cite book| vauthors = Kirk RE, Othmer DF |title=Encyclopedia of chemical technology|url=https://books.google.com/books?id=yb9TAAAAMAAJ|year=1980|publisher=Wiley|isbn=978-0-471-02065-3|page=676}} The drug was described in 1966. Along with tamoxifen, nafoxidine, and clomifene, it was one of the earliest SERMs.{{cite journal | vauthors = Jordan VC, Morrow M | title = Tamoxifen, raloxifene, and the prevention of breast cancer | journal = Endocrine Reviews | volume = 20 | issue = 3 | pages = 253–278 | date = June 1999 | pmid = 10368771 | doi = 10.1210/edrv.20.3.0368 | doi-access = free }}

Nitromifene has been found to dissociate from the estrogen receptor 250-fold faster than estradiol.{{cite journal | vauthors = De Boer W, Notides AC, Katzenellenbogen BS, Hayes JR, Katzenellenbogen JA | title = The capacity of the antiestrogen CI-628 to activate the estrogen receptor in vitro | journal = Endocrinology | volume = 108 | issue = 1 | pages = 206–212 | date = January 1981 | pmid = 7007019 | doi = 10.1210/endo-108-1-206 }} This may be involved in its antagonistic activity at the estrogen receptor.