Home Other Building Blocks 2-Naphthalenol, 5,6,7,8-tetrahydro-6-phenyl-5-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-, (5R,6S)-

2-Naphthalenol, 5,6,7,8-tetrahydro-6-phenyl-5-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-, (5R,6S)-

CAS No.:
180916-16-9
Catalog Number:
AG0022GL
Molecular Formula:
C28H31NO2
Molecular Weight:
413.5512
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$194
- +
5mg
≥98%
1 week
United States
$469
- +
10mg
≥98%
1 week
United States
$814
- +
25mg
≥98%
1 week
United States
$1432
- +
Product Description
Catalog Number:
AG0022GL
Chemical Name:
2-Naphthalenol, 5,6,7,8-tetrahydro-6-phenyl-5-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-, (5R,6S)-
CAS Number:
180916-16-9
Molecular Formula:
C28H31NO2
Molecular Weight:
413.5512
MDL Number:
MFCD09475650
IUPAC Name:
(5R,6S)-6-phenyl-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5,6,7,8-tetrahydronaphthalen-2-ol
InChI:
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
InChI Key:
GXESHMAMLJKROZ-IAPPQJPRSA-N
SMILES:
Oc1ccc2c(c1)CC[C@@H]([C@@H]2c1ccc(cc1)OCCN1CCCC1)c1ccccc1
UNII:
337G83N988
Properties
Complexity:
533  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
0
Exact Mass:
413.235g/mol
Formal Charge:
0
Heavy Atom Count:
31  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
413.561g/mol
Monoisotopic Mass:
413.235g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
32.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
6.1  
Literature
Title Journal
The molecular mechanisms underlying the pharmacological actions of estrogens, SERMs and oxysterols: implications for the treatment and prevention of osteoporosis. Bone 20130301
Targeted therapy for breast cancer prevention. Frontiers in oncology 20130101
The evolution of selective estrogen receptor modulators in osteoporosis therapy. Climacteric : the journal of the International Menopause Society 20121201
Preventive therapy for breast cancer. Current oncology reports 20121201
Denosumab--a powerful RANKL inhibitor to stop lytic metastases and other bone loss actions by osteoclasts. Pathology oncology research : POR 20121001
Selective estrogen receptor modulator (SERM) lasofoxifene forms reactive quinones similar to estradiol. Chemical research in toxicology 20120716
Effects of 3 years of lasofoxifene treatment on bone turnover markers in women with postmenopausal osteoporosis. Bone 20120501
An update on selective estrogen receptor modulators for the prevention and treatment of osteoporosis. Maturitas 20120301
Extraskeletal benefits and risks of calcium, vitamin D and anti-osteoporosis medications. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20120201
Management of vulvovaginal atrophy-related sexual dysfunction in postmenopausal women: an up-to-date review. Menopause (New York, N.Y.) 20120101
Incorporating bazedoxifene/conjugated estrogens into the current paradigm of menopausal therapy. International journal of women's health 20120101
Tissue-Specific Effects of Loss of Estrogen during Menopause and Aging. Frontiers in endocrinology 20120101
Bioactive dietary supplements reactivate ER expression in ER-negative breast cancer cells by active chromatin modifications. PloS one 20120101
Progress in endocrine approaches to the treatment and prevention of breast cancer. Maturitas 20111201
Effects of antiresorptive treatment on nonvertebral fracture outcomes. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20111001
The St. Gallen Prize Lecture 2011: evolution of long-term adjuvant anti-hormone therapy: consequences and opportunities. Breast (Edinburgh, Scotland) 20111001
Adverse reactions and drug-drug interactions in the management of women with postmenopausal osteoporosis. Calcified tissue international 20110801
Selective estrogen receptor modulators: the future in menopausal treatment. Minerva ginecologica 20110601
Preventive therapy for breast cancer: a consensus statement. The Lancet. Oncology 20110501
Lasofoxifene: selective estrogen receptor modulator for the prevention and treatment of postmenopausal osteoporosis. The Annals of pharmacotherapy 20110401
New and emerging antiresorptive treatments in osteoporosis. Current drug safety 20110401
Lasofoxifene, from the preclinical drug discovery to the treatment of postmenopausal osteoporosis. Expert opinion on drug discovery 20110201
Postmenopausal Evaluation and Risk Reduction With Lasofoxifene (PEARL) trial: 5-year gynecological outcomes. Menopause (New York, N.Y.) 20110101
The gynecologic effects of lasofoxifene, an estrogen agonist/antagonist, in postmenopausal women. Menopause (New York, N.Y.) 20110101
Prevention of breast cancer by newer SERMs in the future. Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer 20110101
Chemoprevention of hormone receptor-negative breast cancer: new approaches needed. Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer 20110101
Combined treatment with dexamethasone and raloxifene totally abrogates osteoporosis and joint destruction in experimental postmenopausal arthritis. Arthritis research & therapy 20110101
Efficacy and safety of bazedoxifene for postmenopausal osteoporosis. Clinical interventions in aging 20110101
Lasofoxifene in osteoporosis and its place in therapy. Advances in therapy 20101201
Breast cancer incidence in the randomized PEARL trial of lasofoxifene in postmenopausal osteoporotic women. Journal of the National Cancer Institute 20101117
Tipping the balance for the primary prevention of breast cancer. Journal of the National Cancer Institute 20101117
Third-generation SERMs may face uphill battle. Journal of the National Cancer Institute 20101117
What is the best balance of benefits and risks among anti-resorptive therapies for postmenopausal osteoporosis? Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20101101
Lasofoxifene and cardiovascular events in postmenopausal women with osteoporosis: Five-year results from the Postmenopausal Evaluation and Risk Reduction with Lasofoxifene (PEARL) trial. Circulation 20101026
Evidence-based guidelines for the pharmacological treatment of postmenopausal osteoporosis: a consensus document by the Belgian Bone Club. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20101001
New selective estrogen receptor modulators (SERMs) in development. Current osteoporosis reports 20100901
Therapeutics. Lasofoxifene reduced vertebral fractures in postmenopausal women with osteoporosis. Annals of internal medicine 20100720
Interest of lasofoxifene in the treatment of osteoporosis. Evaluation of 'Lasofoxifene in postmenopausal women with osteoporosis'. N Engl J Med 2010;362:686-96. Expert opinion on pharmacotherapy 20100701
Lasofoxifene for postmenopausal women with osteoporosis. The New England journal of medicine 20100610
Lasofoxifene for postmenopausal women with osteoporosis. The New England journal of medicine 20100610
Lasofoxifene for postmenopausal women with osteoporosis. The New England journal of medicine 20100610
An innovative method to classify SERMs based on the dynamics of estrogen receptor transcriptional activity in living animals. Molecular endocrinology (Baltimore, Md.) 20100401
SERMs in the prevention and treatment of postmenopausal osteoporosis: an update. Arquivos brasileiros de endocrinologia e metabologia 20100301
Lasofoxifene in postmenopausal women with osteoporosis. The New England journal of medicine 20100225
Another selective estrogen-receptor modulator for osteoporosis. The New England journal of medicine 20100225
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. The Journal of steroid biochemistry and molecular biology 20100101
Endometrial safety: a key hurdle for selective estrogen receptor modulators in development. Menopause (New York, N.Y.) 20100101
Selective estrogen receptor modulator (SERM) for the treatment of osteoporosis in postmenopausal women: focus on lasofoxifene. Clinical interventions in aging 20100101
Safety of bazedoxifene in a randomized, double-blind, placebo- and active-controlled Phase 3 study of postmenopausal women with osteoporosis. BMC musculoskeletal disorders 20100101
Modulators of androgen and estrogen receptor activity. Critical reviews in eukaryotic gene expression 20100101
A randomised, double-blinded, placebo-controlled, trial to determine the individual response in bone turnover markers to lasofoxifene therapy. Bone 20091201
Lasofoxifene: new drug. Osteoporosis: no better than raloxifene. Prescrire international 20091201
Current and emerging pharmacologic therapies for the management of postmenopausal osteoporosis. Journal of women's health (2002) 20091001
Lasofoxifene, a new selective estrogen receptor modulator for the treatment of osteoporosis and vaginal atrophy. Expert opinion on pharmacotherapy 20090901
Thresholds for therapies: highlights of the St Gallen International Expert Consensus on the primary therapy of early breast cancer 2009. Annals of oncology : official journal of the European Society for Medical Oncology 20090801
New selective estrogen and androgen receptor modulators. Current opinion in rheumatology 20090701
Effects of various selective estrogen receptor modulators with or without conjugated estrogens on mouse mammary gland. Endocrinology 20090401
Designing the ideal selective estrogen receptor modulator--an achievable goal? Menopause (New York, N.Y.) 20090101
Docking study of triphenylphosphonium cations as estrogen receptor alpha modulators. Bioinformation 20090101
Treatment of osteoporosis with annual iv zoledronic acid: effects on hip fracture. Therapeutics and clinical risk management 20090101
Clinical issues regarding cardiovascular disease and selective estrogen receptor modulators in postmenopausal women. Climacteric : the journal of the International Menopause Society 20090101
Progress in osteoporosis and fracture prevention: focus on postmenopausal women. Arthritis research & therapy 20090101
Lasofoxifene for the prevention and treatment of postmenopausal osteoporosis. Therapeutics and clinical risk management 20090101
Lasofoxifene: Evidence of its therapeutic value in osteoporosis. Core evidence 20090101
Recent advances in managing osteoporosis. F1000 medicine reports 20090101
Long-term safety and efficacy of raloxifene in the prevention and treatment of postmenopausal osteoporosis: an update. International journal of women's health 20090101
Bazedoxifene for the prevention of postmenopausal osteoporosis. Therapeutics and clinical risk management 20081201
Effects of selective oestrogen receptor modulators on proliferation in tissue cultures of pre- and postmenopausal human endometrium. The Journal of steroid biochemistry and molecular biology 20081101
Metabolism, distribution, and excretion of a next generation selective estrogen receptor modulator, lasofoxifene, in rats and monkeys. Drug metabolism and disposition: the biological fate of chemicals 20080901
Effects of lasofoxifene on the uterus, vagina, and breast in ovariectomized cynomolgus monkeys (Macaca fascicularis). American journal of obstetrics and gynecology 20080801
Disposition of lasofoxifene, a next-generation selective estrogen receptor modulator, in healthy male subjects. Drug metabolism and disposition: the biological fate of chemicals 20080701
Hormone-dependent aging problems in women. Yonsei medical journal 20080630
Activity of three selective estrogen receptor modulators on hormone-dependent responses in the mouse uterus and mammary gland. Molecular and cellular endocrinology 20080611
Selective estrogen receptor modulators: an update on recent clinical findings. Obstetrical & gynecological survey 20080301
Bazedoxifene: bazedoxifene acetate, TSE 424, TSE-424, WAY 140424. Drugs in R&D 20080101
[Status of novel bone-targeting SERMs in development]. Nihon rinsho. Japanese journal of clinical medicine 20071128
In silico elucidation of the molecular mechanism defining the adverse effect of selective estrogen receptor modulators. PLoS computational biology 20071101
Validation of a dissolution method with HPLC analysis for lasofoxifene tartrate low dose tablets. Journal of pharmaceutical and biomedical analysis 20070903
Effect of estrogens on skin aging and the potential role of SERMs. Clinical interventions in aging 20070901
Update on bazedoxifene: a novel selective estrogen receptor modulator. Clinical interventions in aging 20070901
The 2.0 A crystal structure of the ERalpha ligand-binding domain complexed with lasofoxifene. Protein science : a publication of the Protein Society 20070501
The future of the new selective estrogen receptor modulators. Menopause international 20070301
Effects of three cytochrome P450 inhibitors, ketoconazole, fluconazole, and paroxetine, on the pharmacokinetics of lasofoxifene. British journal of clinical pharmacology 20070101
Effects of lasofoxifene on bone in surgically postmenopausal cynomolgus monkeys. Menopause (New York, N.Y.) 20070101
Selective estrogen receptor modulators for postmenopausal osteoporosis: current state of development. Drugs & aging 20070101
Lasofoxifene: a third-generation selective estrogen receptor modulator for the prevention and treatment of osteoporosis. Expert opinion on investigational drugs 20060901
Management of age-related osteoporosis and prevention of associated fractures. Therapeutics and clinical risk management 20060901
Developments in the pharmacotherapeutic management of osteoporosis. Expert opinion on pharmacotherapy 20060801
Clinical pharmacology of lasofoxifene in Japanese and white postmenopausal women. Journal of clinical pharmacology 20060601
Effects of lasofoxifene on the pharmacokinetics and pharmacodynamics of single-dose warfarin. British journal of clinical pharmacology 20060601
Lasofoxifene: a new type of selective estrogen receptor modulator for the treatment of osteoporosis. Drugs of today (Barcelona, Spain : 1998) 20060601
Effects of steady-state lasofoxifene on CYP2D6- and CYP2E1-mediated metabolism. The Annals of pharmacotherapy 20060101
A single-dose pharmacokinetic study of lasofoxifene in healthy volunteers and subjects with mild and moderate hepatic impairment. Journal of clinical pharmacology 20060101
Clinical pharmacology of multiple doses of lasofoxifene in postmenopausal women. Journal of clinical pharmacology 20060101
[Next generation selective estrogen receptor modulators]. Clinical calcium 20060101
Emerging selective estrogen receptor modulators: special focus on effects on coronary heart disease in postmenopausal women. Drugs 20060101
Estrogen receptors as therapeutic targets in breast cancer. Current topics in medicinal chemistry 20060101
Not all SERMs are created equal. Menopause (New York, N.Y.) 20060101
Prevention of bone loss in postmenopausal women treated with lasofoxifene compared with raloxifene. Menopause (New York, N.Y.) 20060101
Lasofoxifene enhances vaginal mucus formation without causing hypertrophy and increases estrogen receptor beta and androgen receptor in rats. Menopause (New York, N.Y.) 20060101
Not all selective estrogen response modulators are created equal: update on lasofoxifene. International journal of gynecological cancer : official journal of the International Gynecological Cancer Society 20060101
Prevention of breast cancer using selective oestrogen receptor modulators (SERMs). Breast cancer research : BCR 20060101
Estrogen receptor ligands. Part 14: application of novel antagonist side chains to existing platforms. Bioorganic & medicinal chemistry letters 20051201
Effect of lasofoxifene on the pharmacokinetics of digoxin in healthy postmenopausal women. Journal of clinical pharmacology 20051201
A new selective estrogen receptor modulator, CHF 4227.01, preserves bone mass and microarchitecture in ovariectomized rats. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20051201
Lasofoxifene (Pfizer). Current opinion in investigational drugs (London, England : 2000) 20051001
Urogenital effects of selective estrogen receptor modulators: a systematic review. Climacteric : the journal of the International Menopause Society 20050901
Differential effects of estrogen and raloxifene on messenger RNA and matrix metalloproteinase 2 activity in the rat uterus. Biology of reproduction 20050401
Estrogen receptor ligands. Part 11: Synthesis and activity of isochromans and isothiochromans. Bioorganic & medicinal chemistry letters 20050201
Selective estrogen receptor modulators with conformationally restricted side chains. Synthesis and structure-activity relationship of ERalpha-selective tetrahydroisoquinoline ligands. Journal of medicinal chemistry 20050127
Lasofoxifene: CP 336156, CP-336156. Drugs in R&D 20050101
Endocrinology and hormone therapy in breast cancer: selective oestrogen receptor modulators and downregulators for breast cancer - have they lost their way? Breast cancer research : BCR 20050101
Selective estrogen receptor modulators protect hippocampal neurons from kainic acid excitotoxicity: differences with the effect of estradiol. Journal of neurobiology 20041101
[Lasofoxifene, a next generation estrogen receptor modulator: preclinical studies]. Clinical calcium 20041001
Reproductive toxicity assessment of lasofoxifene, a selective estrogen receptor modulator (SERM), in male rats. Birth defects research. Part B, Developmental and reproductive toxicology 20040601
Reproductive toxicity assessment of lasofoxifene, a selective estrogen receptor modulator (SERM), in female rats. Birth defects research. Part B, Developmental and reproductive toxicology 20040601
Embryo/fetal toxicity assessment of lasofoxifene, a selective estrogen receptor modulator (SERM), in rats and rabbits. Birth defects research. Part B, Developmental and reproductive toxicology 20040601
Pre- and postnatal development studies of lasofoxifene, a selective estrogen receptor modulator (SERM), in Sprague-Dawley rats. Birth defects research. Part B, Developmental and reproductive toxicology 20040601
Long-term treatment of lasofoxifene preserves bone mass and bone strength and does not adversely affect the uterus in ovariectomized rats. Endocrinology 20040401
Target specificity of selective estrogen receptor modulators within human endometrial cancer cells. The Journal of steroid biochemistry and molecular biology 20030701
Novel therapies for osteoporosis. Expert opinion on investigational drugs 20030401
SERMs: current status and future trends. Critical reviews in oncology/hematology 20020701
Selective estrogen receptor modulators as a new therapeutic drug group: concept to reality in a decade. Clinical breast cancer 20020101
LAS, a novel selective estrogen receptor modulator with chemopreventive and therapeutic activity in the N-nitroso-N-methylurea-induced rat mammary tumor model. Cancer research 20011215
Lasofoxifene (CP-336,156) protects against the age-related changes in bone mass, bone strength, and total serum cholesterol in intact aged male rats. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20010401
Update on endocrine aspects of breast cancer: report from the 23rd San Antonio Breast Cancer Symposium, San Antonio, Texas, USA, 6-9 December 2000. Breast cancer research : BCR 20010101
Chemical and biochemical issues related to X-ray crystallography of the ligand-binding domain of estrogen receptor alpha. Bioconjugate chemistry 20010101
Properties