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180916-16-9,MFCD09475650
Catalog No.:AA0022DT

180916-16-9 | 2-Naphthalenol, 5,6,7,8-tetrahydro-6-phenyl-5-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-, (5R,6S)-

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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0022DT
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
SMILES:
Oc1ccc2c(c1)CC[C@@H]([C@@H]2c1ccc(cc1)OCCN1CCCC1)c1ccccc1
Properties
Properties
 
Form:
Solid  
MP:
110 - 113°C  
Storage:
2-8℃;  

Computed Properties
 
Complexity:
533  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
31  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
6  
XLogP3:
6.1  

Literature

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Title: The evolution of selective estrogen receptor modulators in osteoporosis therapy.

Journal: Climacteric : the journal of the International Menopause Society 20121201

Title: Preventive therapy for breast cancer.

Journal: Current oncology reports 20121201

Title: Denosumab--a powerful RANKL inhibitor to stop lytic metastases and other bone loss actions by osteoclasts.

Journal: Pathology oncology research : POR 20121001

Title: Selective estrogen receptor modulator (SERM) lasofoxifene forms reactive quinones similar to estradiol.

Journal: Chemical research in toxicology 20120716

Title: Effects of 3 years of lasofoxifene treatment on bone turnover markers in women with postmenopausal osteoporosis.

Journal: Bone 20120501

Title: An update on selective estrogen receptor modulators for the prevention and treatment of osteoporosis.

Journal: Maturitas 20120301

Title: Extraskeletal benefits and risks of calcium, vitamin D and anti-osteoporosis medications.

Journal: Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20120201

Title: Management of vulvovaginal atrophy-related sexual dysfunction in postmenopausal women: an up-to-date review.

Journal: Menopause (New York, N.Y.) 20120101

Title: Incorporating bazedoxifene/conjugated estrogens into the current paradigm of menopausal therapy.

Journal: International journal of women's health 20120101

Title: Tissue-Specific Effects of Loss of Estrogen during Menopause and Aging.

Journal: Frontiers in endocrinology 20120101

Title: Bioactive dietary supplements reactivate ER expression in ER-negative breast cancer cells by active chromatin modifications.

Journal: PloS one 20120101

Title: Progress in endocrine approaches to the treatment and prevention of breast cancer.

Journal: Maturitas 20111201

Title: Effects of antiresorptive treatment on nonvertebral fracture outcomes.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20111001

Title: The St. Gallen Prize Lecture 2011: evolution of long-term adjuvant anti-hormone therapy: consequences and opportunities.

Journal: Breast (Edinburgh, Scotland) 20111001

Title: Adverse reactions and drug-drug interactions in the management of women with postmenopausal osteoporosis.

Journal: Calcified tissue international 20110801

Title: Selective estrogen receptor modulators: the future in menopausal treatment.

Journal: Minerva ginecologica 20110601

Title: Preventive therapy for breast cancer: a consensus statement.

Journal: The Lancet. Oncology 20110501

Title: Lasofoxifene: selective estrogen receptor modulator for the prevention and treatment of postmenopausal osteoporosis.

Journal: The Annals of pharmacotherapy 20110401

Title: New and emerging antiresorptive treatments in osteoporosis.

Journal: Current drug safety 20110401

Title: Lasofoxifene, from the preclinical drug discovery to the treatment of postmenopausal osteoporosis.

Journal: Expert opinion on drug discovery 20110201

Title: Postmenopausal Evaluation and Risk Reduction With Lasofoxifene (PEARL) trial: 5-year gynecological outcomes.

Journal: Menopause (New York, N.Y.) 20110101

Title: The gynecologic effects of lasofoxifene, an estrogen agonist/antagonist, in postmenopausal women.

Journal: Menopause (New York, N.Y.) 20110101

Title: Prevention of breast cancer by newer SERMs in the future.

Journal: Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer 20110101

Title: Chemoprevention of hormone receptor-negative breast cancer: new approaches needed.

Journal: Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer 20110101

Title: Combined treatment with dexamethasone and raloxifene totally abrogates osteoporosis and joint destruction in experimental postmenopausal arthritis.

Journal: Arthritis research & therapy 20110101

Title: Efficacy and safety of bazedoxifene for postmenopausal osteoporosis.

Journal: Clinical interventions in aging 20110101

Title: Lasofoxifene in osteoporosis and its place in therapy.

Journal: Advances in therapy 20101201

Title: Breast cancer incidence in the randomized PEARL trial of lasofoxifene in postmenopausal osteoporotic women.

Journal: Journal of the National Cancer Institute 20101117

Title: Tipping the balance for the primary prevention of breast cancer.

Journal: Journal of the National Cancer Institute 20101117

Title: Third-generation SERMs may face uphill battle.

Journal: Journal of the National Cancer Institute 20101117

Title: What is the best balance of benefits and risks among anti-resorptive therapies for postmenopausal osteoporosis?

Journal: Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20101101

Title: Lasofoxifene and cardiovascular events in postmenopausal women with osteoporosis: Five-year results from the Postmenopausal Evaluation and Risk Reduction with Lasofoxifene (PEARL) trial.

Journal: Circulation 20101026

Title: Evidence-based guidelines for the pharmacological treatment of postmenopausal osteoporosis: a consensus document by the Belgian Bone Club.

Journal: Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20101001

Title: New selective estrogen receptor modulators (SERMs) in development.

Journal: Current osteoporosis reports 20100901

Title: Therapeutics. Lasofoxifene reduced vertebral fractures in postmenopausal women with osteoporosis.

Journal: Annals of internal medicine 20100720

Title: Interest of lasofoxifene in the treatment of osteoporosis. Evaluation of 'Lasofoxifene in postmenopausal women with osteoporosis'. N Engl J Med 2010;362:686-96.

Journal: Expert opinion on pharmacotherapy 20100701

Title: Lasofoxifene for postmenopausal women with osteoporosis.

Journal: The New England journal of medicine 20100610

Title: Lasofoxifene for postmenopausal women with osteoporosis.

Journal: The New England journal of medicine 20100610

Title: Lasofoxifene for postmenopausal women with osteoporosis.

Journal: The New England journal of medicine 20100610

Title: An innovative method to classify SERMs based on the dynamics of estrogen receptor transcriptional activity in living animals.

Journal: Molecular endocrinology (Baltimore, Md.) 20100401

Title: SERMs in the prevention and treatment of postmenopausal osteoporosis: an update.

Journal: Arquivos brasileiros de endocrinologia e metabologia 20100301

Title: Lasofoxifene in postmenopausal women with osteoporosis.

Journal: The New England journal of medicine 20100225

Title: Another selective estrogen-receptor modulator for osteoporosis.

Journal: The New England journal of medicine 20100225

Title: 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.

Journal: The Journal of steroid biochemistry and molecular biology 20100101

Title: Endometrial safety: a key hurdle for selective estrogen receptor modulators in development.

Journal: Menopause (New York, N.Y.) 20100101

Title: Selective estrogen receptor modulator (SERM) for the treatment of osteoporosis in postmenopausal women: focus on lasofoxifene.

Journal: Clinical interventions in aging 20100101

Title: Safety of bazedoxifene in a randomized, double-blind, placebo- and active-controlled Phase 3 study of postmenopausal women with osteoporosis.

Journal: BMC musculoskeletal disorders 20100101

Title: Modulators of androgen and estrogen receptor activity.

Journal: Critical reviews in eukaryotic gene expression 20100101

Title: A randomised, double-blinded, placebo-controlled, trial to determine the individual response in bone turnover markers to lasofoxifene therapy.

Journal: Bone 20091201

Title: Lasofoxifene: new drug. Osteoporosis: no better than raloxifene.

Journal: Prescrire international 20091201

Title: Current and emerging pharmacologic therapies for the management of postmenopausal osteoporosis.

Journal: Journal of women's health (2002) 20091001

Title: Lasofoxifene, a new selective estrogen receptor modulator for the treatment of osteoporosis and vaginal atrophy.

Journal: Expert opinion on pharmacotherapy 20090901

Title: Thresholds for therapies: highlights of the St Gallen International Expert Consensus on the primary therapy of early breast cancer 2009.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20090801

Title: New selective estrogen and androgen receptor modulators.

Journal: Current opinion in rheumatology 20090701

Title: Effects of various selective estrogen receptor modulators with or without conjugated estrogens on mouse mammary gland.

Journal: Endocrinology 20090401

Title: Designing the ideal selective estrogen receptor modulator--an achievable goal?

Journal: Menopause (New York, N.Y.) 20090101

Title: Docking study of triphenylphosphonium cations as estrogen receptor alpha modulators.

Journal: Bioinformation 20090101

Title: Treatment of osteoporosis with annual iv zoledronic acid: effects on hip fracture.

Journal: Therapeutics and clinical risk management 20090101

Title: Clinical issues regarding cardiovascular disease and selective estrogen receptor modulators in postmenopausal women.

Journal: Climacteric : the journal of the International Menopause Society 20090101

Title: Progress in osteoporosis and fracture prevention: focus on postmenopausal women.

Journal: Arthritis research & therapy 20090101

Title: Lasofoxifene for the prevention and treatment of postmenopausal osteoporosis.

Journal: Therapeutics and clinical risk management 20090101

Title: Lasofoxifene: Evidence of its therapeutic value in osteoporosis.

Journal: Core evidence 20090101

Title: Recent advances in managing osteoporosis.

Journal: F1000 medicine reports 20090101

Title: Long-term safety and efficacy of raloxifene in the prevention and treatment of postmenopausal osteoporosis: an update.

Journal: International journal of women's health 20090101

Title: Bazedoxifene for the prevention of postmenopausal osteoporosis.

Journal: Therapeutics and clinical risk management 20081201

Title: Effects of selective oestrogen receptor modulators on proliferation in tissue cultures of pre- and postmenopausal human endometrium.

Journal: The Journal of steroid biochemistry and molecular biology 20081101

Title: Metabolism, distribution, and excretion of a next generation selective estrogen receptor modulator, lasofoxifene, in rats and monkeys.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20080901

Title: Effects of lasofoxifene on the uterus, vagina, and breast in ovariectomized cynomolgus monkeys (Macaca fascicularis).

Journal: American journal of obstetrics and gynecology 20080801

Title: Disposition of lasofoxifene, a next-generation selective estrogen receptor modulator, in healthy male subjects.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20080701

Title: Hormone-dependent aging problems in women.

Journal: Yonsei medical journal 20080630

Title: Activity of three selective estrogen receptor modulators on hormone-dependent responses in the mouse uterus and mammary gland.

Journal: Molecular and cellular endocrinology 20080611

Title: Selective estrogen receptor modulators: an update on recent clinical findings.

Journal: Obstetrical & gynecological survey 20080301

Title: Bazedoxifene: bazedoxifene acetate, TSE 424, TSE-424, WAY 140424.

Journal: Drugs in R&D 20080101

Title: [Status of novel bone-targeting SERMs in development].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20071128

Title: In silico elucidation of the molecular mechanism defining the adverse effect of selective estrogen receptor modulators.

Journal: PLoS computational biology 20071101

Title: Validation of a dissolution method with HPLC analysis for lasofoxifene tartrate low dose tablets.

Journal: Journal of pharmaceutical and biomedical analysis 20070903

Title: Effect of estrogens on skin aging and the potential role of SERMs.

Journal: Clinical interventions in aging 20070901

Title: Update on bazedoxifene: a novel selective estrogen receptor modulator.

Journal: Clinical interventions in aging 20070901

Title: The 2.0 A crystal structure of the ERalpha ligand-binding domain complexed with lasofoxifene.

Journal: Protein science : a publication of the Protein Society 20070501

Title: The future of the new selective estrogen receptor modulators.

Journal: Menopause international 20070301

Title: Effects of three cytochrome P450 inhibitors, ketoconazole, fluconazole, and paroxetine, on the pharmacokinetics of lasofoxifene.

Journal: British journal of clinical pharmacology 20070101

Title: Effects of lasofoxifene on bone in surgically postmenopausal cynomolgus monkeys.

Journal: Menopause (New York, N.Y.) 20070101

Title: Selective estrogen receptor modulators for postmenopausal osteoporosis: current state of development.

Journal: Drugs & aging 20070101

Title: Lasofoxifene: a third-generation selective estrogen receptor modulator for the prevention and treatment of osteoporosis.

Journal: Expert opinion on investigational drugs 20060901

Title: Management of age-related osteoporosis and prevention of associated fractures.

Journal: Therapeutics and clinical risk management 20060901

Title: Developments in the pharmacotherapeutic management of osteoporosis.

Journal: Expert opinion on pharmacotherapy 20060801

Title: Clinical pharmacology of lasofoxifene in Japanese and white postmenopausal women.

Journal: Journal of clinical pharmacology 20060601

Title: Effects of lasofoxifene on the pharmacokinetics and pharmacodynamics of single-dose warfarin.

Journal: British journal of clinical pharmacology 20060601

Title: Lasofoxifene: a new type of selective estrogen receptor modulator for the treatment of osteoporosis.

Journal: Drugs of today (Barcelona, Spain : 1998) 20060601

Title: Effects of steady-state lasofoxifene on CYP2D6- and CYP2E1-mediated metabolism.

Journal: The Annals of pharmacotherapy 20060101

Title: A single-dose pharmacokinetic study of lasofoxifene in healthy volunteers and subjects with mild and moderate hepatic impairment.

Journal: Journal of clinical pharmacology 20060101

Title: Clinical pharmacology of multiple doses of lasofoxifene in postmenopausal women.

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Title: [Next generation selective estrogen receptor modulators].

Journal: Clinical calcium 20060101

Title: Emerging selective estrogen receptor modulators: special focus on effects on coronary heart disease in postmenopausal women.

Journal: Drugs 20060101

Title: Estrogen receptors as therapeutic targets in breast cancer.

Journal: Current topics in medicinal chemistry 20060101

Title: Not all SERMs are created equal.

Journal: Menopause (New York, N.Y.) 20060101

Title: Prevention of bone loss in postmenopausal women treated with lasofoxifene compared with raloxifene.

Journal: Menopause (New York, N.Y.) 20060101

Title: Lasofoxifene enhances vaginal mucus formation without causing hypertrophy and increases estrogen receptor beta and androgen receptor in rats.

Journal: Menopause (New York, N.Y.) 20060101

Title: Not all selective estrogen response modulators are created equal: update on lasofoxifene.

Journal: International journal of gynecological cancer : official journal of the International Gynecological Cancer Society 20060101

Title: Prevention of breast cancer using selective oestrogen receptor modulators (SERMs).

Journal: Breast cancer research : BCR 20060101

Title: Estrogen receptor ligands. Part 14: application of novel antagonist side chains to existing platforms.

Journal: Bioorganic & medicinal chemistry letters 20051201

Title: Effect of lasofoxifene on the pharmacokinetics of digoxin in healthy postmenopausal women.

Journal: Journal of clinical pharmacology 20051201

Title: A new selective estrogen receptor modulator, CHF 4227.01, preserves bone mass and microarchitecture in ovariectomized rats.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20051201

Title: Lasofoxifene (Pfizer).

Journal: Current opinion in investigational drugs (London, England : 2000) 20051001

Title: Urogenital effects of selective estrogen receptor modulators: a systematic review.

Journal: Climacteric : the journal of the International Menopause Society 20050901

Title: Differential effects of estrogen and raloxifene on messenger RNA and matrix metalloproteinase 2 activity in the rat uterus.

Journal: Biology of reproduction 20050401

Title: Estrogen receptor ligands. Part 11: Synthesis and activity of isochromans and isothiochromans.

Journal: Bioorganic & medicinal chemistry letters 20050201

Title: Selective estrogen receptor modulators with conformationally restricted side chains. Synthesis and structure-activity relationship of ERalpha-selective tetrahydroisoquinoline ligands.

Journal: Journal of medicinal chemistry 20050127

Title: Lasofoxifene: CP 336156, CP-336156.

Journal: Drugs in R&D 20050101

Title: Endocrinology and hormone therapy in breast cancer: selective oestrogen receptor modulators and downregulators for breast cancer - have they lost their way?

Journal: Breast cancer research : BCR 20050101

Title: Selective estrogen receptor modulators protect hippocampal neurons from kainic acid excitotoxicity: differences with the effect of estradiol.

Journal: Journal of neurobiology 20041101

Title: [Lasofoxifene, a next generation estrogen receptor modulator: preclinical studies].

Journal: Clinical calcium 20041001

Title: Reproductive toxicity assessment of lasofoxifene, a selective estrogen receptor modulator (SERM), in male rats.

Journal: Birth defects research. Part B, Developmental and reproductive toxicology 20040601

Title: Reproductive toxicity assessment of lasofoxifene, a selective estrogen receptor modulator (SERM), in female rats.

Journal: Birth defects research. Part B, Developmental and reproductive toxicology 20040601

Title: Embryo/fetal toxicity assessment of lasofoxifene, a selective estrogen receptor modulator (SERM), in rats and rabbits.

Journal: Birth defects research. Part B, Developmental and reproductive toxicology 20040601

Title: Pre- and postnatal development studies of lasofoxifene, a selective estrogen receptor modulator (SERM), in Sprague-Dawley rats.

Journal: Birth defects research. Part B, Developmental and reproductive toxicology 20040601

Title: Long-term treatment of lasofoxifene preserves bone mass and bone strength and does not adversely affect the uterus in ovariectomized rats.

Journal: Endocrinology 20040401

Title: Target specificity of selective estrogen receptor modulators within human endometrial cancer cells.

Journal: The Journal of steroid biochemistry and molecular biology 20030701

Title: Novel therapies for osteoporosis.

Journal: Expert opinion on investigational drugs 20030401

Title: SERMs: current status and future trends.

Journal: Critical reviews in oncology/hematology 20020701

Title: Selective estrogen receptor modulators as a new therapeutic drug group: concept to reality in a decade.

Journal: Clinical breast cancer 20020101

Title: LAS, a novel selective estrogen receptor modulator with chemopreventive and therapeutic activity in the N-nitroso-N-methylurea-induced rat mammary tumor model.

Journal: Cancer research 20011215

Title: 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: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20010401

Title: Update on endocrine aspects of breast cancer: report from the 23rd San Antonio Breast Cancer Symposium, San Antonio, Texas, USA, 6-9 December 2000.

Journal: Breast cancer research : BCR 20010101

Title: Chemical and biochemical issues related to X-ray crystallography of the ligand-binding domain of estrogen receptor alpha.

Journal: Bioconjugate chemistry 20010101

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Tags:180916-16-9 Molecular Formula|180916-16-9 MDL|180916-16-9 SMILES|180916-16-9 2-Naphthalenol, 5,6,7,8-tetrahydro-6-phenyl-5-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-, (5R,6S)-