Lasofoxifene

Catalog No: 24053

CAS Number: 180916-16-9

Purity: 98% Min.

Lasofoxifene, also known as CP 336156, is a non-steroidal selective estrogen receptor modulator (SERM) for the prevention and treatment of osteoporosis and for the treatment of vaginal atrophy. Lasofoxifene selectively binds to both ERα and ERβ with high affinity. Its IC50 for ERα (1.5 nM) is similar to that of estradiol (4.8 nM) and is at least 10-fold higher than those of tamoxifen and raloxifene.

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Chemical Information

Name	Lasofoxifene
Iupac Chemical Name	(5R,6S)-6-phenyl-5-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-5,6,7,8-tetrahydronaphthalen-2-ol.
Synonyms	CP 336156; CP336156; CP-336156; CP 336,156; CP336,156; CP-33,6156; Lasofoxifene; trade name Fably; Oporia.
Molecular Formula	C28H31NO2
Molecular Weight	413.55
Smile	OC1=CC=C2[C@@H](C3=CC=C(OCCN4CCCC4)C=C3)[C@@H](C5=CC=CC=C5)CCC2=C1
InChiKey	GXESHMAMLJKROZ-IAPPQJPRSA-N
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
CAS Number	180916-16-9
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Formulation	Off-white solid
Purity	98% Min.
Storage	Dry, dark and at 0 - 4℃ for short term (days to weeks) or -20℃ for long term (months to years).
Solubility	Soluble in DMSO
Handling	Refer to MSDS
Shipping Condition	Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
HS Code	2934200090

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1: Kumar P, Song ZH. CB2 cannabinoid receptor is a novel target for third-generation selective estrogen receptor modulators bazedoxifene and lasofoxifene. Biochem Biophys Res Commun. 2014 Jan 3;443(1):144-9. doi: 10.1016/j.bbrc.2013.11.071. Epub 2013 Nov 23. PubMed PMID: 24275139.

2: Michalsen BT, Gherezghiher TB, Choi J, Chandrasena RE, Qin Z, Thatcher GR, Bolton JL. Selective estrogen receptor modulator (SERM) lasofoxifene forms reactive quinones similar to estradiol. Chem Res Toxicol. 2012 Jul 16;25(7):1472-83. doi: 10.1021/tx300142h. Epub 2012 Jun 14. PubMed PMID: 22642258; PubMed Central PMCID: PMC3398215.

3: Eastell R, Reid DM, Vukicevic S, Ensrud KE, LaCroix AZ, Thompson JR, Thompson DD, Cummings SR. Effects of 3 years of lasofoxifene treatment on bone turnover markers in women with postmenopausal osteoporosis. Bone. 2012 May;50(5):1135-40. doi: 10.1016/j.bone.2012.02.004. Epub 2012 Feb 12. PubMed PMID: 22348983.

4: Peterson GM, Naunton M, Tichelaar LK, Gennari L. Lasofoxifene: selective estrogen receptor modulator for the prevention and treatment of postmenopausal osteoporosis. Ann Pharmacother. 2011 Apr;45(4):499-509. doi: 10.1345/aph.1P604. Epub 2011 Apr 5. Review. PubMed PMID: 21467260.

5: Gennari L, Merlotti D, Stolakis K, Nuti R. Lasofoxifene, from the preclinical drug discovery to the treatment of postmenopausal osteoporosis. Expert Opin Drug Discov. 2011 Feb;6(2):205-17. doi: 10.1517/17460441.2011.547188. PubMed PMID: 22647137.

6: Archer DF. The gynecologic effects of lasofoxifene, an estrogen agonist/antagonist, in postmenopausal women. Menopause. 2011 Jan;18(1):6-7. doi: 10.1097/gme.0b013e318203a46b. PubMed PMID: 21173718.

7: Swan VJ, Hamilton CJ, Jamal SA. Lasofoxifene in osteoporosis and its place in therapy. Adv Ther. 2010 Dec;27(12):917-32. doi: 10.1007/s12325-010-0081-y. Epub 2010 Nov 10. Review. PubMed PMID: 21080249.

8: LaCroix AZ, Powles T, Osborne CK, Wolter K, Thompson JR, Thompson DD, Allred DC, Armstrong R, Cummings SR, Eastell R, Ensrud KE, Goss P, Lee A, Neven P, Reid DM, Curto M, Vukicevic S; PEARL Investigators. Breast cancer incidence in the randomized PEARL trial of lasofoxifene in postmenopausal osteoporotic women. J Natl Cancer Inst. 2010 Nov 17;102(22):1706-15. doi: 10.1093/jnci/djq415. Epub 2010 Nov 4. PubMed PMID: 21051656.

9: Ensrud K, LaCroix A, Thompson JR, Thompson DD, Eastell R, Reid DM, Vukicevic S, Cauley J, Barrett-Connor E, Armstrong R, Welty F, Cummings S. Lasofoxifene and cardiovascular events in postmenopausal women with osteoporosis: Five-year results from the Postmenopausal Evaluation and Risk Reduction with Lasofoxifene (PEARL) trial. Circulation. 2010 Oct 26;122(17):1716-24. doi: 10.1161/CIRCULATIONAHA.109.924571. Epub 2010 Oct 11. PubMed PMID: 20937977.

10: Gennari L, Merlotti D, De Paola V, Nuti R. Lasofoxifene: Evidence of its therapeutic value in osteoporosis. Core Evid. 2010 Jun 15;4:113-29. PubMed PMID: 20694069; PubMed Central PMCID: PMC2899785.

11: Goldstein SR, Neven P, Cummings S, Colgan T, Runowicz CD, Krpan D, Proulx J, Johnson M, Thompson D, Thompson J, Sriram U. Postmenopausal Evaluation and Risk Reduction With Lasofoxifene (PEARL) trial: 5-year gynecological outcomes. Menopause. 2011 Jan;18(1):17-22. doi: 10.1097/gme.0b013e3181e84bb4. PubMed PMID: 20689465.

12: Crandall CJ. Therapeutics. Lasofoxifene reduced vertebral fractures in postmenopausal women with osteoporosis. Ann Intern Med. 2010 Jul 20;153(2):JC1-11. doi: 10.7326/0003-4819-153-2-201007200-02011. PubMed PMID: 20643977.

13: Silva-FernÃ¡ndez L, Andreu JL. Lasofoxifene for postmenopausal women with osteoporosis. N Engl J Med. 2010 Jun 10;362(23):2228; author reply 2228-9. PubMed PMID: 20568310.

14: Katzeff BS. Lasofoxifene for postmenopausal women with osteoporosis. N Engl J Med. 2010 Jun 10;362(23):2227-8; author reply 2228-9. PubMed PMID: 20568309.

15: Malozowski S. Lasofoxifene for postmenopausal women with osteoporosis. N Engl J Med. 2010 Jun 10;362(23):2227; author reply 2228-9. doi: 10.1056/NEJMc1003454. PubMed PMID: 20558377.

16: Reginster JY. 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 Opin Pharmacother. 2010 Jul;11(10):1773-5. doi: 10.1517/14656561003785755. PubMed PMID: 20446861.

17: Cummings SR, Ensrud K, Delmas PD, LaCroix AZ, Vukicevic S, Reid DM, Goldstein S, Sriram U, Lee A, Thompson J, Armstrong RA, Thompson DD, Powles T, Zanchetta J, Kendler D, Neven P, Eastell R; PEARL Study Investigators. Lasofoxifene in postmenopausal women with osteoporosis. N Engl J Med. 2010 Feb 25;362(8):686-96. doi: 10.1056/NEJMoa0808692. Erratum in: N Engl J Med. 2011 Jan 20;364(3):290. Kucu kdeveci A [corrected to Kucukdeveci, A]. PubMed PMID: 20181970.

18: Gennari L, Merlotti D, Nuti R. Selective estrogen receptor modulator (SERM) for the treatment of osteoporosis in postmenopausal women: focus on lasofoxifene. Clin Interv Aging. 2010 Feb 2;5:19-29. Review. PubMed PMID: 20169039; PubMed Central PMCID: PMC2817938.

19: Lasofoxifene: new drug. Osteoporosis: no better than raloxifene. Prescrire Int. 2009 Dec;18(104):247. PubMed PMID: 20020572.

20: Lewiecki EM. Lasofoxifene for the prevention and treatment of postmenopausal osteoporosis. Ther Clin Risk Manag. 2009;5:817-27. Epub 2009 Nov 2. PubMed PMID: 19898646; PubMed Central PMCID: PMC2773750.

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Lasofoxifene

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