Raloxifene

Raloxifene

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
Pregnancy category	AU: X (High risk) US: X (Contraindicated)
Legal status	℞ (Prescription only)
Routes of administration	Oral
Pharmacokinetic data
Bioavailability	2%
Protein binding	95%
Metabolism	Gut glucuronidation CYP system not involved
Biological half-life	27.7 hours
Excretion	Fecal
Identifiers
CAS Number	84449-90-1 Y
ATC code	G03XC01 (WHO)
PubChem	CID: 5035
IUPHAR/BPS	2820
DrugBank	DB00481 Y
ChemSpider	4859 Y
UNII	YX9162EO3I Y
ChEBI	CHEBI:8772 Y
ChEMBL	CHEMBL81 Y
PDB ligand ID	RAL (PDBe, RCSB PDB)
Chemical data
Formula	C28H27NO4S
Molecular mass	473.584 g/mol
SMILES O=C(c1c3ccc(O)cc3sc1c2ccc(O)cc2)c5ccc(OCCN4CCCCC4)cc5
InChI InChI=1S/C28H27NO4S/c30-21-8-4-20(5-9-21)28-26(24-13-10-22(31)18-25(24)34-28)27(32)19-6-11-23(12-7-19)33-17-16-29-14-2-1-3-15-29/h4-13,18,30-31H,1-3,14-17H2 Y Key:GZUITABIAKMVPG-UHFFFAOYSA-N Y
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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.

Medical use

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. 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

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

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.

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.

Contradications and precautions

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.

Pharmacology

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

Bottle of Raloxifene

Physical and chemical properties

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.

Society and culture

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

See also

• Ethamoxytriphetol

External links

• STAR: a head-to-head comparison of tamoxifen and raloxifene as breast-cancer preventatives
• Full Prescribing Information
• Position paper of the National Women's Health Network