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
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
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 Lasofoxifene approved in the EU in 2009 is now withdrawn from use in the European Union.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
Sources: http://adisinsight.springer.com/drugs/800007522
Curator's Comment: # Ligand Pharmaceuticals; Pfizer
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
15.0 nM [IC50] | |||
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Fablyn Approved UseTreatment of osteoporosis in postmenopausal women at increased risk of fracture Launch Date1.23534718E12 |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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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 |
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Chemical and biochemical issues related to X-ray crystallography of the ligand-binding domain of estrogen receptor alpha. | 2001 May-Jun |
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Estrogen receptor ligands. Part 11: Synthesis and activity of isochromans and isothiochromans. | 2005 Feb 1 |
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[Next generation selective estrogen receptor modulators]. | 2006 Jan |
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Update on bazedoxifene: a novel selective estrogen receptor modulator. | 2007 |
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Effect of estrogens on skin aging and the potential role of SERMs. | 2007 |
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Selective estrogen receptor modulators for postmenopausal osteoporosis: current state of development. | 2007 |
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Validation of a dissolution method with HPLC analysis for lasofoxifene tartrate low dose tablets. | 2007 Sep 3 |
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Bazedoxifene for the prevention of postmenopausal osteoporosis. | 2008 Dec |
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Hormone-dependent aging problems in women. | 2008 Jun 30 |
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Effects of selective oestrogen receptor modulators on proliferation in tissue cultures of pre- and postmenopausal human endometrium. | 2008 Nov |
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Lasofoxifene for the prevention and treatment of postmenopausal osteoporosis. | 2009 |
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Clinical issues regarding cardiovascular disease and selective estrogen receptor modulators in postmenopausal women. | 2009 |
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Treatment of osteoporosis with annual iv zoledronic acid: effects on hip fracture. | 2009 Apr |
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Thresholds for therapies: highlights of the St Gallen International Expert Consensus on the primary therapy of early breast cancer 2009. | 2009 Aug |
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A randomised, double-blinded, placebo-controlled, trial to determine the individual response in bone turnover markers to lasofoxifene therapy. | 2009 Dec |
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New selective estrogen and androgen receptor modulators. | 2009 Jul |
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Selective estrogen receptor modulator (SERM) for the treatment of osteoporosis in postmenopausal women: focus on lasofoxifene. | 2010 Feb 2 |
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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 |
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Therapeutics. Lasofoxifene reduced vertebral fractures in postmenopausal women with osteoporosis. | 2010 Jul 20 |
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SERMs in the prevention and treatment of postmenopausal osteoporosis: an update. | 2010 Mar |
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Endometrial safety: a key hurdle for selective estrogen receptor modulators in development. | 2010 May-Jun |
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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 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9685230
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
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admin
on
Edited
Fri Dec 16 19:07:23 UTC 2022
by
admin
on
Fri Dec 16 19:07:23 UTC 2022
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Record UNII |
337G83N988
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QG03XC03
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C1821
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WHO-ATC |
G03XC03
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135938
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C80679
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337G83N988
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M6700
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Lasofoxifene
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SUB27754
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7875
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CHEMBL328190
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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EXCRETED UNCHANGED |
FECAL
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METABOLIC ENZYME -> SUBSTRATE | |||
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TARGET -> AGONIST | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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EXCRETED UNCHANGED |
URINE
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
PLASMA
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Related Record | Type | Details | ||
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ACTIVE MOIETY |