Nitromifene

Nitromifene (INN; also as the citrate salt nitromifene citrate (USAN), 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.[1] It is a mixture of (E)- and (Z)-isomers that possess similar antiestrogenic activity.[2] The drug was described in 1966.[1] Along with tamoxifen, nafoxidine, and clomifene, it was one of the earliest SERMs.[3]

Nitromifene
Clinical data
Other namesCI-628; CN-5518; CN-55945
Identifiers
IUPAC name
  • 1-[2-[4-[1-(4-Methoxyphenyl)-2-nitro-2-phenylethenyl]phenoxy]ethyl]pyrrolidine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC27H28N2O4
Molar mass444.531 g·mol−1
3D model (JSmol)
SMILES
  • COC1=CC=C(C=C1)C(=C(C2=CC=CC=C2)[N+](=O)[O-])C3=CC=C(C=C3)OCCN4CCCC4
InChI
  • InChI=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
  • Key:MFKMXUFMHOCZHP-UHFFFAOYSA-N

Nitromifene has been found to dissociate from the estrogen receptor 250-fold faster than estradiol.[4] This may be involved in its antagonistic activity at the estrogen receptor.[4]

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 880–. ISBN 978-1-4757-2085-3.
  2. Raymond Eller Kirk; Donald Frederick Othmer (1980). Encyclopedia of chemical technology. Wiley. p. 676. ISBN 978-0-471-02065-3.
  3. Jordan VC, Morrow M (1999). "Tamoxifen, raloxifene, and the prevention of breast cancer". Endocr. Rev. 20 (3): 253–78. doi:10.1210/edrv.20.3.0368. PMID 10368771.
  4. De Boer W, Notides AC, Katzenellenbogen BS, Hayes JR, Katzenellenbogen JA (January 1981). "The capacity of the antiestrogen CI-628 to activate the estrogen receptor in vitro". Endocrinology. 108 (1): 206–12. doi:10.1210/endo-108-1-206. PMID 7007019.



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