Nitromifene - Misplaced Pages

Chemical compound Pharmaceutical compound

Nitromifene
Clinical data

Other names	CI-628; CN-5518; CN-55945
Identifiers
IUPAC name 1-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
3D model (JSmol)	Interactive image
SMILES COC1=CC=C(C=C1)C(=C(C2=CC=CC=C2)(=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 (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. It is a mixture of (E)- and (Z)-isomers that possess similar antiestrogenic activity. The drug was described in 1966. Along with tamoxifen, nafoxidine, and clomifene, it was one of the earliest SERMs.

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

References

^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 880–. ISBN 978-1-4757-2085-3.
Kirk RE, Othmer DF (1980). Encyclopedia of chemical technology. Wiley. p. 676. ISBN 978-0-471-02065-3.
Jordan VC, Morrow M (June 1999). "Tamoxifen, raloxifene, and the prevention of breast cancer". Endocrine Reviews. 20 (3): 253–278. doi:10.1210/edrv.20.3.0368. PMID 10368771.
^ 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): 206–212. doi:10.1210/endo-108-1-206. PMID 7007019.

Estrogen receptor modulators

ERTooltip Estrogen receptor

Agonists

Unknown/unsorted: ERB-26
ERA-45
ERB-79
ZK-283197

Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole)
Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone)
Coumestans (e.g., coumestrol, psoralidin)
Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, penduletin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin)
Lavender oil
Lignans (e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol))
Metalloestrogens (e.g., cadmium)
Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, HPTE, methiocarb, methoxychlor, triclocarban, triclosan)
Phytosteroids (e.g., digitoxin (digitalis), diosgenin, guggulsterone)
Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol)
Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol))
Steroid-like (e.g., deoxymiroestrol, miroestrol)
Stilbenoids (e.g., resveratrol, rhaponticin)
Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs)
Others (e.g., agnuside, rotundifuran)

Mixed
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

Coregulator-binding modulators: ERX-11

Noncompetitive inhibitors: Trilostane

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

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