Details
Stereochemistry | ACHIRAL |
Molecular Formula | C27H28N2O4 |
Molecular Weight | 444.5222 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(C=C1)C(=C(C2=CC=CC=C2)[N+]([O-])=O)C3=CC=C(OCCN4CCCC4)C=C3
InChI
InChIKey=MFKMXUFMHOCZHP-RQZHXJHFSA-N
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/b27-26-
Nitromiphene (NIT; CI 628) is a triarylethylene antiestrogen shown to be effective in treatment of experimental breast cancer. Nitromiphene is one of the earliest nonsteroidal selective estrogen receptor modulators (SERMs). It is an anti-estrogen capable to translocate the estrogen receptor to the nucleus and to induce the replenishment of the cytosol receptor. Nitromiphene inhibited the uptake of [3H]-estradiol in rat whole homogenates and isolated cell nuclei tissues and the pituitary, and inhibited estradiol-induced female sexual behavior. Nitromiphene has thus been shown to suppress the growth of chemically induced and ransplantedmammary tumors in rodents. Also, Nitromiphene was shown to have potent, prolonged antiuterotropic effects in immature rats. Nitromiphene has been shown to undergo conversion to demethyl Nitromiphene (CI628M), a phenolic metabolite which had greater affinity for estrogen receptors and greater biological potency in vitro than did Nitromiphene. However, the in vivo antiestrogenic effects of Nitromiphene and demethyl Nitromiphene were similar, possibly due to facile O-demethylation of the former compound after administration.
Approval Year
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/856418
Rats: Nitromiphene was injected intraperitoneally 2 h prior to an intravenous injection of [3H]estradiol, and the animals were killed 2 h after the estradiol.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6391811
Curator's Comment: CI-628 citrate (1.5 ug/ml) significantly inhibited the transformation of rabbit morulae to blastocysts. https://www.ncbi.nlm.nih.gov/pubmed/6230443
Nitromiphene (CI-628) on the morphology and 17 beta-hydroxysteroid dehydrogenase (17 beta-HSD) activity of mouse blastocysts were compared in culture. When Day 4 mouse blastocysts were cultured in Eagle's medium containing 214 ng 3H-estradiol (E2) and CI-628 at 0, 1.5, 3, 6, 12 and 18 ug/ml, shedding of the zona pellucida was prevented by CI-628. The effect of CI-628 on the morphology was dose-dependent: little effects were seen at 1.5 and 3 ug/ml during the first 2 days, but the blastocysts became small, dense and eventually collapsed inside the zona. At 6 ug/ml and higher, the effect was quite pronounced. The earliest change was seen at 10 hours in 12 and 18 ug/ml CI-628 medium when 1/3 of the embryos became dense and smaller.
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NCI_THESAURUS |
C481
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C90720
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Nitromifene
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100000084122
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DTXSID50883143
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10448-84-7
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SUB09327MIG
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5FS1NJ6Q8N
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CHEMBL2105203
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3773
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22150
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)