nafoxidine (CHEM042807)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 10:16:32 UTC
Update Date2016-11-09 01:22:48 UTC
Accession NumberCHEM042807
Identification
Common Namenafoxidine
ClassSmall Molecule
DescriptionNafoxidine (INN; developmental code names U-11,000A, NSC-70735) or nafoxidine hydrochloride (USAN) 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.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Hydrochloride, nafoxidineMeSH
Nafoxidine hydrochlorideMeSH
U-11000aChEMBL
Chemical FormulaC29H31NO2
Average Molecular Mass425.572 g/mol
Monoisotopic Mass425.235 g/mol
CAS Registry Number1845-11-0
IUPAC Name1-{2-[4-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine
Traditional Namenafoxidine
SMILESCOC1=CC=C2C(CCC(C3=CC=CC=C3)=C2C2=CC=C(OCCN3CCCC3)C=C2)=C1
InChI IdentifierInChI=1S/C29H31NO2/c1-31-26-14-16-28-24(21-26)11-15-27(22-7-3-2-4-8-22)29(28)23-9-12-25(13-10-23)32-20-19-30-17-5-6-18-30/h2-4,7-10,12-14,16,21H,5-6,11,15,17-20H2,1H3
InChI KeyJEYWNNAZDLFBFF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassPhenylnaphthalenes
Direct ParentPhenylnaphthalenes
Alternative Parents
Substituents
  • Phenylnaphthalene
  • Stilbene
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00053 g/LALOGPS
logP6.36ALOGPS
logP6.2ChemAxon
logS-5.9ALOGPS
pKa (Strongest Basic)8.95ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area21.7 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity141.07 m³·mol⁻¹ChemAxon
Polarizability50.19 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-003r-9005100000-bf42a00371c7c92f6d61Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2103900000-20d62335a037a2cecbb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9323100000-41f3b5ce93ea16447ea1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9212000000-56de5f6b718fb9c79afdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0002900000-f87c247d1b57adee23b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-3029600000-2a34647b9a72227ebc9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0201-5069000000-d8cb7647eeef6cefb87aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNafoxidine
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID4416
Kegg Compound IDC14212
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available