C3D

(5R,6S)-6-PHENYL-5-[4-(2-PYRROLIDIN-1-YLETHOXY)PHENYL]-5,6,7,8-TETRAHYDRONAPHTHALEN-2-OL


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Chemical Component Summary

Name(5R,6S)-6-PHENYL-5-[4-(2-PYRROLIDIN-1-YLETHOXY)PHENYL]-5,6,7,8-TETRAHYDRONAPHTHALEN-2-OL
SynonymsLasofoxifene
Identifiers(5R,6S)-6-phenyl-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5,6,7,8-tetrahydronaphthalen-2-ol
FormulaC28 H31 N O2
Molecular Weight413.551
TypeNON-POLYMER
Isomeric SMILESc1ccc(cc1)[C@H]2CCc3cc(ccc3[C@H]2c4ccc(cc4)OCCN5CCCC5)O
InChIInChI=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
InChIKeyGXESHMAMLJKROZ-IAPPQJPRSA-N

Chemical Details

Formal Charge0
Atom Count62
Chiral Atom Count2
Bond Count66
Aromatic Bond Count18

Drug Info: DrugBank

DrugBank IDDB06202 
NameLasofoxifene
Groups
  • investigational
  • approved
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.
Synonyms
  • (-)-cis-5,6,7,8-Tetrahydro-6-phenyl-5-(p-(2-(1-pyrrolidinyl)ethoxy)phenyl)-2-naphthol
  • Lasofoxifene tartrate
  • Lasofoxifene hydrochloride
  • Lasofoxifene
Brand NamesFablyn
IndicationInvestigated for use/treatment in postmenopausal osteoporosis to reduce the risk of both vertebral and novertebral fractures, as well as address other postmenopausal conditions, including reduction in risk of breast cancer and treatment of vulvar and vaginal atrophy (VVA)
Categories
  • Genito Urinary System and Sex Hormones
  • Naphthalenes
  • Selective Estrogen Receptor Modulators
  • Sex Hormones and Modulators of the Genital System
ATC-CodeG03XC03
CAS number180916-16-9

Drug Targets

NameTarget SequencePharmacological ActionActions
Estrogen receptor alphaMTMTLHTKASGMALLHQIQGNELEPLNRPQLKIPLERPLGEVYLDSSKPA...unknownantagonist,agonist,negative modulator
Estrogen receptor betaMDIKNSPSSLNSPSSYNCSQSILPLEHGSIYIPSSYVDSHHEYPAMTFYS...unknownagonist
Cannabinoid receptor 2MEECWVTEIANGSKDGLDSNPMKDYMILSGPQKTAVAVLCTLLGLLSALE...unknowninverse agonist
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL328190
PubChem 216416
ChEMBL CHEMBL328190
CCDC/CSD GIQRED