lasofoxifene (CHEM043963)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:29:24 UTC
Update Date2016-11-09 01:23:01 UTC
Accession NumberCHEM043963
Identification
Common Namelasofoxifene
ClassSmall Molecule
DescriptionLasofoxifene is a non-steroidal 3rd generation selective estrogen receptor modulator (SERM) that selectively binds to both ERα and ERβ with high affinity. It is a naphthalene derivative marketed for prevention and treatment of osteoporosis and for the treatment of vaginal atrophy. It was initially developed as Oporia by Pfizer as a treatment for postmenopausal osteoporosis and vaginal atrophy, in which were both rejected for approval by FDA. Later Fablyn was developed as a result of a research collaboration between Pfizer and Ligand Pharmaceuticals with a newly submitted New Drug Application in 2008. It gained approval by European Commission in March 2009. Ligand Pharmaceuticals signed a license agreement with Sermonix Pharmaceuticals for the development and commercialization of oral lasofoxifene in the USA.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Lasofoxifene hydrochlorideMeSH
(-)-cis-5,6,7,8-tetrahydro-6-Phenyl-5-(P-(2-(1-pyrrolidinyl)ethoxy)phenyl)-2-naphtholMeSH
cis-1R-(4'-Pyrrolidinoethoxyphenyl)-2S-phenyl-6-hydroxy-1,2,3,4-tetrahydronaphthalene, tartrate saltMeSH
LAS estrogen receptor modulatorMeSH
Chemical FormulaC28H31NO2
Average Molecular Mass413.551 g/mol
Monoisotopic Mass413.235 g/mol
CAS Registry Number180916-16-9
IUPAC Name(5R,6S)-6-phenyl-5-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}-5,6,7,8-tetrahydronaphthalen-2-ol
Traditional Namelasofoxifene
SMILES[H][C@@]1(CCC2=CC(O)=CC=C2[C@@]1([H])C1=CC=C(OCCN2CCCC2)C=C1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C28H31NO2/c30-24-11-15-27-23(20-24)10-14-26(21-6-2-1-3-7-21)28(27)22-8-12-25(13-9-22)31-19-18-29-16-4-5-17-29/h1-3,6-9,11-13,15,20,26,28,30H,4-5,10,14,16-19H2/t26-,28+/m1/s1
InChI KeyGXESHMAMLJKROZ-IAPPQJPRSA-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
  • Tetralin
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • 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 Solubility0.0004 g/LALOGPS
logP6.36ALOGPS
logP5.97ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)10.21ChemAxon
pKa (Strongest Basic)8.98ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.7 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity126.83 m³·mol⁻¹ChemAxon
Polarizability47.58 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2021900000-fa2afd3a45e77e79caffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9142100000-aa9a530d9148928aca60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0592-9121000000-aa9348b7693d712742d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1002900000-e9d0c9bba98fa211160cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-3029400000-c4994f82dc45badd2774Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01b9-8089000000-27271370f02794cae069Spectrum
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 IDDB06202
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 LinkLasofoxifene
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID216416
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available