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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H31NO2.C4H6O6
Molecular Weight 563.6381
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LASOFOXIFENE TARTRATE

SMILES

O[C@@H]([C@H](O)C(O)=O)C(O)=O.OC1=CC2=C(C=C1)[C@H]([C@H](CC2)C3=CC=CC=C3)C4=CC=C(OCCN5CCCC5)C=C4

InChI

InChIKey=INEHJXCWEVNEDZ-LUDNRVPPSA-N
InChI=1S/C28H31NO2.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h1-3,6-9,11-13,15,20,26,28,30H,4-5,10,14,16-19H2;1-2,5-6H,(H,7,8)(H,9,10)/t26-,28+;1-,2-/m10/s1

HIDE SMILES / InChI
Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED
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

Description

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 Lasofoxifene approved in the EU in 2009 is now withdrawn from use in the European Union.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

Ligand Pharmaceuticals|Pfizer
3
Curator's Comment: # Ligand Pharmaceuticals; Pfizer

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
828
 15.0 nM [IC50]
Modulator
828
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Withdrawn
Fablyn

Approved Use

Treatment of osteoporosis in postmenopausal women at increased risk of fracture

Launch Date

2009
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Update on endocrine aspects of breast cancer: report from the 23rd San Antonio Breast Cancer Symposium, San Antonio, Texas, USA, 6-9 December 2000.
2001
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
SERMs: current status and future trends.
2002 Jul
Long-term treatment of lasofoxifene preserves bone mass and bone strength and does not adversely affect the uterus in ovariectomized rats.
2004 Apr
Embryo/fetal toxicity assessment of lasofoxifene, a selective estrogen receptor modulator (SERM), in rats and rabbits.
2004 Jun
[Lasofoxifene, a next generation estrogen receptor modulator: preclinical studies].
2004 Oct
Endocrinology and hormone therapy in breast cancer: selective oestrogen receptor modulators and downregulators for breast cancer - have they lost their way?
2005
Lasofoxifene: CP 336156, CP-336156.
2005
Estrogen receptor ligands. Part 11: Synthesis and activity of isochromans and isothiochromans.
2005 Feb 1
Lasofoxifene (Pfizer).
2005 Oct
Urogenital effects of selective estrogen receptor modulators: a systematic review.
2005 Sep
Not all selective estrogen response modulators are created equal: update on lasofoxifene.
2006
Emerging selective estrogen receptor modulators: special focus on effects on coronary heart disease in postmenopausal women.
2006
Prevention of bone loss in postmenopausal women treated with lasofoxifene compared with raloxifene.
2006 May-Jun
Management of age-related osteoporosis and prevention of associated fractures.
2006 Sep
Update on bazedoxifene: a novel selective estrogen receptor modulator.
2007
Effects of lasofoxifene on bone in surgically postmenopausal cynomolgus monkeys.
2007 Jan-Feb
The future of the new selective estrogen receptor modulators.
2007 Mar
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
Docking study of triphenylphosphonium cations as estrogen receptor alpha modulators.
2009
Effects of various selective estrogen receptor modulators with or without conjugated estrogens on mouse mammary gland.
2009 Apr
Lasofoxifene: new drug. Osteoporosis: no better than raloxifene.
2009 Dec
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
Designing the ideal selective estrogen receptor modulator--an achievable goal?
2009 May-Jun
Current and emerging pharmacologic therapies for the management of postmenopausal osteoporosis.
2009 Oct
Lasofoxifene in osteoporosis and its place in therapy.
2010 Dec
Gene expression profiling studies of three SERMs and their conjugated estrogen combinations in human breast cancer cells: insights into the unique antagonistic effects of bazedoxifene on conjugated estrogens.
2010 Jan
Safety of bazedoxifene in a randomized, double-blind, placebo- and active-controlled Phase 3 study of postmenopausal women with osteoporosis.
2010 Jun 22
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
New selective estrogen receptor modulators (SERMs) in development.
2010 Sep
Patents

Patents

06153622
3
07553500
3

Sample Use Guides

In Vivo Use Guide
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 15 15:47:27 GMT 2023
Edited
by admin
on Fri Dec 15 15:47:27 GMT 2023
Record UNII
85X09V2GSO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LASOFOXIFENE TARTRATE
DASH   JAN   MART.   MI   USAN  
USAN  
Official Name English
LASOFOXIFENE D-TARTRATE
Common Name English
CP-336156-CB
Code English
CP-336156
Code English
CB-336156EB
Code English
2-Naphthalenol, 5,6,7,8-tetrahydro-6-phenyl-5-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-, (5R,6S)-, (2S,3S)-2,3-dihydroxybutanedioate (1:1)
Systematic Name English
LASOFOXIFENE TARTRATE [JAN]
Common Name English
CP-336,156-CB
Code English
FABLYN
Brand Name English
(-)-CIS-5,6,7,8-TETRAHYDRO-6-PHENYL-5-(P-(2-(1-PYRROLIDINYL)ETHOXY)PHENYL))-2-NAPHTHOL D-TARTRATE (1:1)
Common Name English
LASOFOXIFENE TARTRATE [USAN]
Common Name English
Lasofoxifene tartrate [WHO-DD]
Common Name English
OPORIA
Brand Name English
LASOFOXIFENE TARTRATE [MI]
Common Name English
LASOFOXIFENE TARTRATE [MART.]
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS FABLYN (WITHDRAWN: OSTEOPOROSIS, POSTMENOPAUSAL)
Created by admin on Fri Dec 15 15:47:27 GMT 2023 , Edited by admin on Fri Dec 15 15:47:27 GMT 2023
NCI_THESAURUS C1821
Created by admin on Fri Dec 15 15:47:27 GMT 2023 , Edited by admin on Fri Dec 15 15:47:27 GMT 2023
Code System Code Type Description
FDA UNII
85X09V2GSO
Created by admin on Fri Dec 15 15:47:27 GMT 2023 , Edited by admin on Fri Dec 15 15:47:27 GMT 2023
PRIMARY
DRUG BANK
DBSALT001953
Created by admin on Fri Dec 15 15:47:27 GMT 2023 , Edited by admin on Fri Dec 15 15:47:27 GMT 2023
PRIMARY
PUBCHEM
3081919
Created by admin on Fri Dec 15 15:47:27 GMT 2023 , Edited by admin on Fri Dec 15 15:47:27 GMT 2023
PRIMARY
CAS
190791-29-8
Created by admin on Fri Dec 15 15:47:27 GMT 2023 , Edited by admin on Fri Dec 15 15:47:27 GMT 2023
PRIMARY
SMS_ID
100000092749
Created by admin on Fri Dec 15 15:47:27 GMT 2023 , Edited by admin on Fri Dec 15 15:47:27 GMT 2023
PRIMARY
USAN
KK-66
Created by admin on Fri Dec 15 15:47:27 GMT 2023 , Edited by admin on Fri Dec 15 15:47:27 GMT 2023
PRIMARY
EVMPD
SUB30307
Created by admin on Fri Dec 15 15:47:27 GMT 2023 , Edited by admin on Fri Dec 15 15:47:27 GMT 2023
PRIMARY
NCI_THESAURUS
C80680
Created by admin on Fri Dec 15 15:47:27 GMT 2023 , Edited by admin on Fri Dec 15 15:47:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID60940655
Created by admin on Fri Dec 15 15:47:27 GMT 2023 , Edited by admin on Fri Dec 15 15:47:27 GMT 2023
PRIMARY
MERCK INDEX
m6700
Created by admin on Fri Dec 15 15:47:27 GMT 2023 , Edited by admin on Fri Dec 15 15:47:27 GMT 2023
PRIMARY Merck Index
CHEBI
135938
Created by admin on Fri Dec 15 15:47:27 GMT 2023 , Edited by admin on Fri Dec 15 15:47:27 GMT 2023
PRIMARY
Related Record Type Details
Structure of TARTARIC ACID
PARENT -> SALT/SOLVATE
Structure of LASOFOXIFENE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of LASOFOXIFENE
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