U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C28H31NO2
Molecular Weight 413.5512
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LASOFOXIFENE

SMILES

OC1=CC=C2[C@H]([C@H](CCC2=C1)C3=CC=CC=C3)C4=CC=C(OCCN5CCCC5)C=C4

InChI

InChIKey=GXESHMAMLJKROZ-IAPPQJPRSA-N
InChI=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

HIDE SMILES / InChI

Molecular Formula C28H31NO2
Molecular Weight 413.5512
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Lasofoxifene is an active component of Fablyn. Fablyn is used for the treatment of osteoporosis in postmenopausal women. Lasofoxifene is a nonsteroidal selective estrogen receptor modulator. Lasofoxifene has no effect on CYP2E1- or CYP2D6-mediated drug metabolism and should not affect drugs metabolized by other cytochrome P450 isoenzymes. Common adverse reactions considered to be related to Fablyn therapy were muscle spasms, hot flush and vaginal discharge. Lasofoxifene approved in the EU in 2009 is now withdrawn from use in the European Union.

Originator

Curator's Comment: # Ligand Pharmaceuticals; Pfizer

Approval Year

PubMed

PubMed

TitleDatePubMed
Lasofoxifene (CP-336,156) protects against the age-related changes in bone mass, bone strength, and total serum cholesterol in intact aged male rats.
2001 Apr
Chemical and biochemical issues related to X-ray crystallography of the ligand-binding domain of estrogen receptor alpha.
2001 May-Jun
Estrogen receptor ligands. Part 11: Synthesis and activity of isochromans and isothiochromans.
2005 Feb 1
[Next generation selective estrogen receptor modulators].
2006 Jan
Update on bazedoxifene: a novel selective estrogen receptor modulator.
2007
Effect of estrogens on skin aging and the potential role of SERMs.
2007
Selective estrogen receptor modulators for postmenopausal osteoporosis: current state of development.
2007
Validation of a dissolution method with HPLC analysis for lasofoxifene tartrate low dose tablets.
2007 Sep 3
Bazedoxifene for the prevention of postmenopausal osteoporosis.
2008 Dec
Hormone-dependent aging problems in women.
2008 Jun 30
Effects of selective oestrogen receptor modulators on proliferation in tissue cultures of pre- and postmenopausal human endometrium.
2008 Nov
Lasofoxifene for the prevention and treatment of postmenopausal osteoporosis.
2009
Clinical issues regarding cardiovascular disease and selective estrogen receptor modulators in postmenopausal women.
2009
Treatment of osteoporosis with annual iv zoledronic acid: effects on hip fracture.
2009 Apr
Thresholds for therapies: highlights of the St Gallen International Expert Consensus on the primary therapy of early breast cancer 2009.
2009 Aug
A randomised, double-blinded, placebo-controlled, trial to determine the individual response in bone turnover markers to lasofoxifene therapy.
2009 Dec
New selective estrogen and androgen receptor modulators.
2009 Jul
Selective estrogen receptor modulator (SERM) for the treatment of osteoporosis in postmenopausal women: focus on lasofoxifene.
2010 Feb 2
Interest of lasofoxifene in the treatment of osteoporosis. Evaluation of "Lasofoxifene in postmenopausal women with osteoporosis". N Engl J Med 2010;362:686-96.
2010 Jul
Therapeutics. Lasofoxifene reduced vertebral fractures in postmenopausal women with osteoporosis.
2010 Jul 20
SERMs in the prevention and treatment of postmenopausal osteoporosis: an update.
2010 Mar
Endometrial safety: a key hurdle for selective estrogen receptor modulators in development.
2010 May-Jun
What is the best balance of benefits and risks among anti-resorptive therapies for postmenopausal osteoporosis?
2010 Nov
Tipping the balance for the primary prevention of breast cancer.
2010 Nov 17
Patents

Sample Use Guides

500 ug daily. The tablet may be taken any time of day without regard to food and beverage intake.
Route of Administration: Oral
In Vitro Use Guide
Lasofoxifene was determined to be an extremely potent antagonist to the growth of estrogen-dependent MCF-7 breast cancer cell line (IC50 =0.05 nM).
Substance Class Chemical
Created
by admin
on Fri Dec 16 19:07:23 UTC 2022
Edited
by admin
on Fri Dec 16 19:07:23 UTC 2022
Record UNII
337G83N988
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LASOFOXIFENE
EMA EPAR   INN   MART.   MI   WHO-DD  
INN  
Official Name English
Lasofoxifene [WHO-DD]
Common Name English
LASOFOXIFENE [MI]
Common Name English
LASOFOXIFENE [MART.]
Common Name English
LASOFOXIFENE [EMA EPAR]
Common Name English
(-)-CIS-5,6,7,8-TETRAHYDRO-6-PHENYL-5-(P-(2-(1-PYRROLIDINYL)ETHOXY)PHENYL)-2-NAPHTHOL
Common Name English
lasofoxifene [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QG03XC03
Created by admin on Fri Dec 16 19:07:23 UTC 2022 , Edited by admin on Fri Dec 16 19:07:23 UTC 2022
NCI_THESAURUS C1821
Created by admin on Fri Dec 16 19:07:23 UTC 2022 , Edited by admin on Fri Dec 16 19:07:23 UTC 2022
WHO-ATC G03XC03
Created by admin on Fri Dec 16 19:07:23 UTC 2022 , Edited by admin on Fri Dec 16 19:07:23 UTC 2022
Code System Code Type Description
CHEBI
135938
Created by admin on Fri Dec 16 19:07:23 UTC 2022 , Edited by admin on Fri Dec 16 19:07:23 UTC 2022
PRIMARY
PUBCHEM
216416
Created by admin on Fri Dec 16 19:07:23 UTC 2022 , Edited by admin on Fri Dec 16 19:07:23 UTC 2022
PRIMARY
DRUG CENTRAL
4308
Created by admin on Fri Dec 16 19:07:23 UTC 2022 , Edited by admin on Fri Dec 16 19:07:23 UTC 2022
PRIMARY
EPA CompTox
DTXSID50171037
Created by admin on Fri Dec 16 19:07:23 UTC 2022 , Edited by admin on Fri Dec 16 19:07:23 UTC 2022
PRIMARY
DRUG BANK
DB06202
Created by admin on Fri Dec 16 19:07:23 UTC 2022 , Edited by admin on Fri Dec 16 19:07:23 UTC 2022
PRIMARY
CAS
180916-16-9
Created by admin on Fri Dec 16 19:07:23 UTC 2022 , Edited by admin on Fri Dec 16 19:07:23 UTC 2022
PRIMARY
NCI_THESAURUS
C80679
Created by admin on Fri Dec 16 19:07:23 UTC 2022 , Edited by admin on Fri Dec 16 19:07:23 UTC 2022
PRIMARY
FDA UNII
337G83N988
Created by admin on Fri Dec 16 19:07:23 UTC 2022 , Edited by admin on Fri Dec 16 19:07:23 UTC 2022
PRIMARY
MERCK INDEX
M6700
Created by admin on Fri Dec 16 19:07:23 UTC 2022 , Edited by admin on Fri Dec 16 19:07:23 UTC 2022
PRIMARY Merck Index
WIKIPEDIA
Lasofoxifene
Created by admin on Fri Dec 16 19:07:23 UTC 2022 , Edited by admin on Fri Dec 16 19:07:23 UTC 2022
PRIMARY
EVMPD
SUB27754
Created by admin on Fri Dec 16 19:07:23 UTC 2022 , Edited by admin on Fri Dec 16 19:07:23 UTC 2022
PRIMARY
INN
7875
Created by admin on Fri Dec 16 19:07:23 UTC 2022 , Edited by admin on Fri Dec 16 19:07:23 UTC 2022
PRIMARY
ChEMBL
CHEMBL328190
Created by admin on Fri Dec 16 19:07:23 UTC 2022 , Edited by admin on Fri Dec 16 19:07:23 UTC 2022
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
EXCRETED UNCHANGED
FECAL
METABOLIC ENZYME -> SUBSTRATE
TARGET -> AGONIST
METABOLIC ENZYME -> SUBSTRATE
EXCRETED UNCHANGED
URINE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
ACTIVE MOIETY