Nitromifene

Nitromifene (INNTooltip International Nonproprietary Name; also as the citrate salt nitromifene citrate (USANTooltip 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.^[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]

Other namesCI-628; CN-5518; CN-55945

CAS Number

• 10448-84-7
  5863-35-4 (citrate)

PubChem CID

• 22150

ChemSpider

• 20796

Quick facts Clinical data, Other names ...

Nitromifene

Clinical data
Other names	CI-628; CN-5518; CN-55945
Identifiers
IUPAC name 1-[2-[4-[1-(4-Methoxyphenyl)-2-nitro-2-phenylethenyl]phenoxy]ethyl]pyrrolidine
CAS Number	10448-84-7 5863-35-4 (citrate)
PubChem CID	22150
ChemSpider	20796
UNII	5FS1NJ6Q8N
CompTox Dashboard (EPA)	DTXSID50883143
Chemical and physical data
Formula	C27H28N2O4
Molar mass	444.531 g·mol−1
3D model (JSmol)	Interactive image
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

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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]