Lasofoxifene| CAS#180916-16-9 | SERM

MedKoo Cat#: 201720 | Name: Lasofoxifene

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Lasofoxifene

CAS#180916-16-9 (free base)

Theoretical Analysis

MedKoo Cat#: 201720

Name: Lasofoxifene

CAS#: 180916-16-9 (free base)

Chemical Formula: C28H31NO2

Exact Mass: 413.2355

Molecular Weight: 413.56

Elemental Analysis: C, 81.32; H, 7.56; N, 3.39; O, 7.74

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 450.00	2 Weeks
5mg	USD 950.00	2 Weeks

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Related CAS #

180916-16-9 (free base) 190791-29-8 (tartrate)

Synonym

CP 336156; CP336156; CP-336156; CP 336,156; CP336,156; CP-33,6156; Lasofoxifene; trade name Fably; Oporia.

IUPAC/Chemical Name

(5R,6S)-6-phenyl-5-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-5,6,7,8-tetrahydronaphthalen-2-ol.

InChi Key

GXESHMAMLJKROZ-IAPPQJPRSA-N

InChi Code

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

SMILES Code

OC1=CC=C2[C@@H](C3=CC=C(OCCN4CCCC4)C=C3)[C@@H](C5=CC=CC=C5)CCC2=C1

Appearance

white solid powder

Purity

>98% (or refer to the Certificate of Analysis)

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.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

In Jan 2009, Pfizer Inc said it has received a complete response letter from the U.S. Food and Drug Administration (FDA) asking for additional information on the company's application for lasofoxifene. The investigational compound is currently under review for the treatment of osteoporosis in postmenopausal women at increased risk of fracture. Pfizer submitted the current application for lasofoxifene on December 18, 2007. On September 8, 2008, an FDA scientific advisory panel voted 9-3 (with one abstention) that there is a population of postmenopausal women with osteoporosis in which the benefits of lasofoxifene likely outweigh the risks. FDA is not required to follow the advice of the panel. From: http://www.medicalnewstoday.com/articles/135923.php .

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C24M04C17

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Lasofoxifene (CP-336156) is an orally active and selective estrogen receptor modulator (SERM).

In vitro activity:

TBD

In vivo activity:

Lasofoxifene inhibited joint inflammation and enhanced BMD in SKG mice, a model of SpA. Laso also affected the composition and biodiversity of gut microbiota. Reference: Sci Rep. 2021 Jun 7;11(1):11923. https://pubmed.ncbi.nlm.nih.gov/34099783/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	48.36
	DMSO	20.0	48.36
	DMSO:PBS (pH 7.2) (1:1)	0.5	1.21
	Ethanol	1.5	3.63

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 413.56 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Jeong H, Kim IY, Bae EK, Jeon CH, Ahn KS, Cha HS. Selective estrogen receptor modulator lasofoxifene suppresses spondyloarthritis manifestation and affects characteristics of gut microbiota in zymosan-induced SKG mice. Sci Rep. 2021 Jun 7;11(1):11923. doi: 10.1038/s41598-021-91320-1. PMID: 34099783; PMCID: PMC8184804. 2. Lainé M, Fanning SW, Chang YF, Green B, Greene ME, Komm B, Kurleto JD, Phung L, Greene GL. Lasofoxifene as a potential treatment for therapy-resistant ER-positive metastatic breast cancer. Breast Cancer Res. 2021 May 12;23(1):54. doi: 10.1186/s13058-021-01431-w. PMID: 33980285; PMCID: PMC8117302.

In vitro protocol:

TBD

In vivo protocol:

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.