Lasofoxifene

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Lasofoxifene
Clinical data
ATC code	G03XC03 (WHO) ;
Identifiers
	IUPAC name (5R,6S)-6-phenyl-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5,6,7,8-tetrahydronaphthalen-2-ol;
CAS Number	180916-16-9 ;
PubChem CID	216416;
ChemSpider	187585 ;
UNII	337G83N988;
ChEMBL	ChEMBL328190 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C28H31NO2
Molar mass	413.55 g/mol; 563.64 g/mol (tartrate)
3D model (JSmol)	Interactive image;
	SMILES O(c1ccc(cc1)[C@@H]4c2ccc(O)cc2CC[C@@H]4c3ccccc3)CCN5CCCC5;
	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 ; Key:GXESHMAMLJKROZ-IAPPQJPRSA-N ;
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Lasofoxifene (INN) (proposed tradename Fablyn) is a non-steroidal selective estrogen receptor modulator (SERM) which is under development by Pfizer for the prevention and treatment of osteoporosis and for the treatment of vaginal atrophy,^[1] and the result of an exclusive research collaboration with Ligand Pharmaceuticals (LGND). It also appears to have had a statistically significant effect of reducing breast cancer in women according to a study published online November 4 in The Journal of the National Cancer Institute.

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.

On January 2008, Ligand Pharmaceuticals, through its marketing partner, Pfizer, submitted a New Drug Application for lasofoxifene, which is expected to be marketed under the tradename Fablyn. Lasofoxifene was approved in the EU under the brand name Fablyn by the EMEA in March 2009.^[2]

Lasofoxifene is a desmethyl dihydro analog of nafoxidine.^[3]

Treatment

In postmenopausal women with osteoporosis, lasofoxifene at a dose of 0.5 mg per day was associated with reduced risks of nonvertebral and vertebral fractures, ER-positive breast cancer, coronary heart disease, and stroke but an increased risk of venous thromboembolic events.^[4]^[5]

References

↑ Gennari L, Merlotti D, Martini G, Nuti R (2006). "Lasofoxifene: a third-generation selective estrogen receptor modulator for the prevention and treatment of osteoporosis". Expert Opin Investig Drugs. 15 (9): 1091&ndash, 103. doi:10.1517/13543784.15.9.1091. PMID 16916275.
↑ Fablyn - lasofoxifene
↑ Lednicer D, Emmert DE, Lyster SC, Duncan GW (September 1969). "Mammalian antifertility agents. VI. A novel sequence for the preparation of 1,2-disubstituted 3,4-dihydronaphthalenes". J. Med. Chem. 12 (5): 881–5. doi:10.1021/jm00305a038. PMID 5812203.
↑ Gennari L, Merlotti D, Nuti R (2010). "Selective estrogen receptor modulator (SERM) for the treatment of osteoporosis in postmenopausal women: focus on lasofoxifene". Clin Interv Aging. 5: 19–29. doi:10.2147/cia.s6083. PMC 2817938. PMID 20169039.
↑ 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 R, Zanchetta J, Kendler D, Neven P, Eastell R, the PEARL Study Investigators (2010). "Lasofoxifene in Postmenopausal Women with Osteoporosis". N Engl J Med. 362 (8): 686–696. doi:10.1056/NEJMoa0808692. PMID 20181970.

External links

"Reference site for lasofoxifene information". Anakena Internet Services SL. Retrieved 2008-03-18.

[pmid16916275-1] Gennari L, Merlotti D, Martini G, Nuti R (2006). "Lasofoxifene: a third-generation selective estrogen receptor modulator for the prevention and treatment of osteoporosis". Expert Opin Investig Drugs. 15 (9): 1091&ndash, 103. doi:10.1517/13543784.15.9.1091. PMID 16916275.

[2] Fablyn - lasofoxifene

[pmid5812203-3] Lednicer D, Emmert DE, Lyster SC, Duncan GW (September 1969). "Mammalian antifertility agents. VI. A novel sequence for the preparation of 1,2-disubstituted 3,4-dihydronaphthalenes". J. Med. Chem. 12 (5): 881–5. doi:10.1021/jm00305a038. PMID 5812203.

[pmid20169039-4] Gennari L, Merlotti D, Nuti R (2010). "Selective estrogen receptor modulator (SERM) for the treatment of osteoporosis in postmenopausal women: focus on lasofoxifene". Clin Interv Aging. 5: 19–29. doi:10.2147/cia.s6083. PMC 2817938. PMID 20169039.

[Cummings_2010-5] 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 R, Zanchetta J, Kendler D, Neven P, Eastell R, the PEARL Study Investigators (2010). "Lasofoxifene in Postmenopausal Women with Osteoporosis". N Engl J Med. 362 (8): 686–696. doi:10.1056/NEJMoa0808692. PMID 20181970.

[1]

[2]

[3]

[4]

[5]

Clinical data

ATC code	G03XC03 (WHO)
Identifiers
IUPAC name (5R,6S)-6-phenyl-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5,6,7,8-tetrahydronaphthalen-2-ol
CAS Number	180916-16-9^N
PubChem CID	216416
ChemSpider	187585^Y
UNII	337G83N988
ChEMBL	ChEMBL328190^Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₂₈H₃₁NO₂
Molar mass	413.55 g/mol 563.64 g/mol (tartrate)
3D model (JSmol)	Interactive image
SMILES O(c1ccc(cc1)[C@@H]4c2ccc(O)cc2CC[C@@H]4c3ccccc3)CCN5CCCC5
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^Y Key:GXESHMAMLJKROZ-IAPPQJPRSA-N^Y
^NY (what is this?) (verify)

Lasofoxifene

Overview

Treatment

References

External links

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