Compound: Nafoxidine
SMILES: O(c1ccc(C=2c3c(cc(OC)cc3)CCC2c4ccccc4)cc1)CCN5CCCC5
InChIKey: JEYWNNAZDLFBFF-UHFFFAOYSA-N
Synonyms: Nafoxidine, 1845-11-0, Nafoxidina, Nafoxidinum, 1-[2-[4-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl]pyrrolidine, 4RIY10WM82, U-11000A, Pyrrolidine, 1-(2-(4-(3,4-dihydro-6-methoxy-2-phenyl-1-naphthalenyl)phenoxy)ethyl)-, 1-{2-[4-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine, DTXSID7022386, 1-(2-(4-(6-Methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy)ethyl)pyrrolidine, Hydrochloride, Nafoxidine, RefChem:164408, DTXCID602386, U11000A, U 11000A, U11,100A, U 11,100A, Nafoxidine [INN], Nafoxidinum [INN-Latin], Nafoxidina [INN-Spanish], 1-(2-(p-(3,4-Dihydro-6-methoxy-2-phenyl-1-naphthyl)phenoxy)ethyl)pyrrolidine, CHEMBL28211, NSC 70735, Pyrrolidine, 1-(2-(p-(3,4-dihydro-6-methoxy-2-phenyl-1-naphthyl)phenoxy)ethyl)-, Pyrrolidine,1-[2-[4-(3,4-dihydro-6-methoxy-2-phenyl-1-naphthalenyl)phenoxy]ethyl]-, BRN 1440873, UNII-4RIY10WM82, Spectrum5_000222, NAFOXIDINE [WHO-DD], 5-20-01-00210 (Beilstein Handbook Reference), BIDD:ER0063, SCHEMBL153125, 11100A (*Hydrochloride*), GTPL4263, orb1306381, SCHEMBL29494604, CHEBI:34881, U 11100 (*Hydrochloride*), U 11100A (*Hydrochloride*), U-11100A (*Hydrochloride*), GLXC-20942, BDBM50065941, EX-A15027, AKOS040744832, NCGC00188970-01, TS-08148, HY-145716, CS-0379998, NS00005540, Q6958201, 1-(2-(4-(3,4-Dihydro-6-methoxy-2-phenyl-1-naphthalenyl)phenoxy)ethyl)pyrrolidine, 1-(2-[4-(6-Methoxy-2-phenyl-3,4-dihydro-1-naphthalenyl)phenoxy]ethyl)pyrrolidine #, 1-{2-[4-(6-Methoxy-2-phenyl-3,4-dihydro-naphthalen-1-yl)-phenoxy]-ethyl}-pyrrolidine
Theoretical properties:
molecular_formula: C29H31NO2
molecular_weight: 425.6 g/mol
exact_mass: 425.235479232 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 7
heavy_atom_count: 32
topological_polar_surface_area: 21.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Nafoxidine is a member of benzenes, a member of naphthalenes and a ring assembly.
chembl: NAFOXIDINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Nafoxidine (INNTooltip International Nonproprietary Name; developmental code names U-11,000A) or nafoxidine hydrochloride (USANTooltip United States Adopted Name) is a nonsteroidal selective estrogen receptor modulator (SERM) or partial antiestrogen of the triphenylethylene group that was developed for the treatment of advanced breast cancer by Upjohn in the 1970s but was never marketed. It was developed at around the same time as tamoxifen and clomifene, which are also triphenylethylene derivatives. The drug was originally synthesized by the fertility control program at Upjohn as a postcoital contraceptive, but was subsequently repurposed for the treatment of breast cancer. Nafoxidine was assessed in clinical trials in the treatment of breast cancer and was found to be effective. However, it produced side effects including ichthyosis, partial hair loss, and phototoxicity of the skin in almost all patients, and this resulted in the discontinuation of its development.
Nafoxidine is a long-acting estrogen receptor ligand, with a nuclear retention in the range of 24 to 48 hours or more.