For research use only. Not for therapeutic 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. In September 2005, Pfizer received a non-approvable letter from the U.S. Food and Drug Administration regarding lasofoxifene (trade name Oporia), a selective estrogen receptor modulator for the prevention of osteoporosis. Lasofoxifene was approved in the EU under the brand name Fablyn by the EMEA in March 2009. Lasofoxifene is a desmethyl dihydro analog of nafoxidine. (source: http://en.wikipedia.org/wiki/Lasofoxifene).
| Catalog Number | R010608 |
| CAS Number | 180916-16-9 |
| Synonyms | (5R,6S)-5,6,7,8-Tetrahydro-6-phenyl-5-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-2-naphthalenol; (5R-cis)-5,6,7,8-Tetrahydro-6-phenyl-5-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-?2-naphthalenol; |
| Molecular Formula | C28H31NO2 |
| Purity | ≥95% |
| Target | Estrogen Receptor/ERR |
| Storage | -20°C |
| 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 |
| InChIKey | GXESHMAMLJKROZ-IAPPQJPRSA-N |
| SMILES | C1CCN(C1)CCOC2=CC=C(C=C2)C3C(CCC4=C3C=CC(=C4)O)C5=CC=CC=C5 |
| Reference | </br>1:Selective oestrogen receptor modulators lasofoxifene and bazedoxifene inhibit joint inflammation and osteoporosis in ovariectomised mice with collagen-induced arthritis. Andersson A, Bernardi AI, Stubelius A, Nurkkala-Karlsson M, Ohlsson C, Carlsten H, Islander U.Rheumatology (Oxford). 2016 Mar;55(3):553-63. doi: 10.1093/rheumatology/kev355. Epub 2015 Sep 30. PMID: 26424839 Free PMC Article</br>2:Effects of lasofoxifene and bazedoxifene on B cell development and function. Bernardi AI, Andersson A, Grahnemo L, Nurkkala-Karlsson M, Ohlsson C, Carlsten H, Islander U.Immun Inflamm Dis. 2014 Dec;2(4):214-25. doi: 10.1002/iid3.37. Epub 2014 Dec 2. PMID: 25866629 Free PMC Article</br>3:CB2 cannabinoid receptor is a novel target for third-generation selective estrogen receptor modulators bazedoxifene and lasofoxifene. Kumar P, Song ZH.Biochem Biophys Res Commun. 2014 Jan 3;443(1):144-9. doi: 10.1016/j.bbrc.2013.11.071. Epub 2013 Nov 23. PMID: 24275139 Free PMC Article</br>4:Selective estrogen receptor modulator (SERM) lasofoxifene forms reactive quinones similar to estradiol. Michalsen BT, Gherezghiher TB, Choi J, Chandrasena RE, Qin Z, Thatcher GR, Bolton JL.Chem Res Toxicol. 2012 Jul 16;25(7):1472-83. doi: 10.1021/tx300142h. Epub 2012 Jun 14. PMID: 22642258 Free PMC Article</br>5:Effects of 3 years of lasofoxifene treatment on bone turnover markers in women with postmenopausal osteoporosis. Eastell R, Reid DM, Vukicevic S, Ensrud KE, LaCroix AZ, Thompson JR, Thompson DD, Cummings SR.Bone. 2012 May;50(5):1135-40. doi: 10.1016/j.bone.2012.02.004. Epub 2012 Feb 12. PMID: 22348983 </br>6:Lasofoxifene: selective estrogen receptor modulator for the prevention and treatment of postmenopausal osteoporosis. Peterson GM, Naunton M, Tichelaar LK, Gennari L.Ann Pharmacother. 2011 Apr;45(4):499-509. doi: 10.1345/aph.1P604. Epub 2011 Apr 5. Review. PMID: 21467260 </br>7:Lasofoxifene, from the preclinical drug discovery to the treatment of postmenopausal osteoporosis. Gennari L, Merlotti D, Stolakis K, Nuti R.Expert Opin Drug Discov. 2011 Feb;6(2):205-17. doi: 10.1517/17460441.2011.547188. PMID: 22647137 </br>8:The gynecologic effects of lasofoxifene, an estrogen agonist/antagonist, in postmenopausal women. Archer DF.Menopause. 2011 Jan;18(1):6-7. doi: 10.1097/gme.0b013e318203a46b. No abstract available. PMID: 21173718 </br>9:Lasofoxifene in osteoporosis and its place in therapy. Swan VJ, Hamilton CJ, Jamal SA.Adv Ther. 2010 Dec;27(12):917-32. doi: 10.1007/s12325-010-0081-y. Epub 2010 Nov 10. Review. PMID: 21080249 </br>10:Breast cancer incidence in the randomized PEARL trial of lasofoxifene in postmenopausal osteoporotic women. 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..J Natl Cancer Inst. 2010 Nov 17;102(22):1706-15. doi: 10.1093/jnci/djq415. Epub 2010 Nov 4. PMID: 21051656 |
