From Wikipedia, the free encyclopedia
Jump to: navigation, search
Raloxifene Chemical Structure V.1.svg
Systematic (IUPAC) name
[6-hydroxy-2-(4-hydroxyphenyl)- benzothiophen-3-yl]- [4-[2-(1-piperidyl)ethoxy]phenyl] -methanone
Clinical data
Trade names Evista
AHFS/Drugs.com monograph
MedlinePlus a698007
Licence data EMA:Link, US FDA:link
  • AU: X (High risk)
  • US: X (Contraindicated)
Legal status
  • (Prescription only)
Routes of
Pharmacokinetic data
Bioavailability 2%
Protein binding 95%
Metabolism Gut glucuronidation[1]
CYP system not involved
Biological half-life 27.7 hours
Excretion Fecal
CAS Number 84449-90-1 YesY
ATC code G03XC01
PubChem CID 5035
DrugBank DB00481 YesY
ChemSpider 4859 YesY
Chemical data
Formula C28H27NO4S
Molar mass 473.584 g/mol

Raloxifene (marketed as Evista by Eli Lilly and Company) is an oral selective estrogen receptor modulator (SERM) that has estrogenic actions on bone and anti-estrogenic actions on the uterus and breast. It is used in the prevention of osteoporosis in postmenopausal women and to reduce the risk of invasive breast cancer in postmenopausal women with osteoporosis and in postmenopausal women at high risk for invasive breast cancer.[2]

Medical use[edit]

Raloxifene is indicated for the treatment and prevention of osteoporosis in postmenopausal women. It is also used for reduction of risk and treatment of invasive breast cancer, and it also reduces breast density.[3] For either osteoporosis treatment or prevention, supplemental calcium and/or vitamin D should be added to the diet if daily intake is inadequate.

Adverse reactions[edit]

Common adverse events considered to be drug-related were hot flashes and leg cramps.[4]

Raloxifene may infrequently cause serious blood clots to form in the legs, lungs, or eyes. Other reactions experienced include leg swelling/pain, trouble breathing, chest pain, vision changes. Raloxifene is a teratogenic drug, i.e., can cause developmental abnormalities such as birth defects.

Black box warnings were added to the label of raloxifene in 2007 warning of increased risk of death due to stroke for postmenopausal women with documented coronary heart disease or at increased risk for major coronary events, as well as increased risks for deep vein thrombosis and pulmonary embolism.[4]

A report in September 2009 from Health and Human Services' Agency for Healthcare Research and Quality suggests that tamoxifen and raloxifene, used to treat breast cancer, significantly reduce invasive breast cancer in midlife and older women, but also increase the risk of adverse side effects.[5]

Contradications and precautions[edit]

Raloxifene is contraindicated in lactating women or women who are or may become pregnant, in women with active or past history of venous thromboembolic events, including deep vein thrombosis, pulmonary embolism, and retinal vein thrombosis and in women known to be hypersensitive to raloxifene.[4]


SERMs mimic estrogen in some tissues and have anti-estrogen activity in others.[4]

Bottle of Raloxifene

Physical and chemical properties[edit]

Raloxifene hydrochloride (HCl) has the empirical formula C28H27NO4S•HCl, which corresponds to a molecular weight of 510.05 g/mol. Raloxifene HCl is an off-white to pale-yellow solid that is slightly soluble in water.[4]

Society and culture[edit]

An editorial in Lancet Oncology criticized the way that information about the drug was released.[6]

See also[edit]


  1. ^ Jeong, Eun Ju; Liu, Yong; Lin, Huimin; Hu, Ming (2005-03-15). "Species- and Disposition Model-Dependent Metabolism of Raloxifene in Gut and Liver: Role of UGT1A10". Drug Metabolism and Disposition ( ASPET) 33 (6): 785–794. doi:10.1124/dmd.104.001883. PMID 15769887. Retrieved 2010-10-20. 
  2. ^ "FDA Approves New Uses for Evista" (Press release). U.S. Food and Drug Administration. 2007-09-14. Retrieved 2007-09-15. 
  3. ^ Jeon-Hor, Chen; et al. (September 15, 2003). "Reduction of Breast Density Following Tamoxifen Treatment Evaluated by 3-D MRI: Preliminary Study". Magn Reson Imaging. doi:10.1016/j.mri.2010.07.009. Retrieved March 30, 2013. 
  4. ^ a b c d e Raloxifene label Last updated 09/2007]
  5. ^ Agency for Healthcare Research and Quality, Rockville, MD. (September 2009). "Medications Effective in Reducing Risk of Breast Cancer But Increase Risk of Adverse Effects". Retrieved 2009-09-14. 
  6. ^ Thelancetoncology, (2006). "A STARring role for raloxifene?". Lancet Oncol 7 (6): 443. doi:10.1016/S1470-2045(06)70701-X. PMID 16750489. 

External links[edit]