NITROMIFENE CITRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C27H28N2O4.C6H8O7
Molecular Weight	636.6457
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=LHAPNDAERSFWSC-JGUILPGDSA-N

InChI=1S/C27H28N2O4.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h2-4,7-16H,5-6,17-20H2,1H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b27-26+;

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3536077 | https://www.ncbi.nlm.nih.gov/pubmed/171186 | https://www.ncbi.nlm.nih.gov/pubmed/856418

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

PubMed

Title	Date	PubMed
Effect of subcutaneous vs intraperitoneal administration of an anti-estrogen, CI-628, estradiol-and estradiol benzoate-stimulated lordosis in the ovariectomized rat.	1976 Oct	1005494
Anti-oestrogen action: uterine nuclear retention of the CI-628 anti-oestrogen receptor complex in vitro.	1977 Feb	576349
Biological potency and uterine estrogen receptor interactions of the metabolites of the antiestrogens CI628 and U23,469.	1981 Jan	7007017
Formation of benzophenone and alpha, alpha-diarylacetophenone metabolites of the antiestrogen nitromiphene (CI628) in the presence of rat cecal contents.	1983 Sep 12	6412010

Patents

Sample Use Guides

In Vivo Use Guide

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

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.

Name

Type

Language

NITROMIFENE CITRATE

Official Name

English

CI 628

Code

English

NITROMIFENE CITRATE [USAN]

Common Name

English

CN 55945-27

Code

English

PYRROLIDINE, 1-(2-(4-(1-(4-METHOXYPHENYL)-2-NITRO-2-PHENYLETHENYL)PHENOXY)ETHYL)-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)

Systematic Name

English

NSC-110407

Code

English

1-(2-(P-(.ALPHA.-(P-METHOXYPHENYL)-.BETA.-NITROSTYRYL)PHENOXY)ETHYL)PYRROLIDINE CITRATE (1:1)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C481