Raloxifene

Raloxifene
Clinical data
Trade names	Evista, Optruma, others
Other names	Keoxifene; Pharoxifene; LY-139481; LY-156758; CCRIS-7129
AHFS/Drugs.com	Monograph
MedlinePlus	a698007
License data	US DailyMed: Raloxifene;
Pregnancy; category	AU: X (High risk);
Routes of; administration	By mouth
Drug class	Selective estrogen receptor modulator
ATC code	G03XC01 (WHO) ;
Legal status
Legal status	US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	2%
Protein binding	>95%
Metabolism	Liver, intestines (glucuro-; nidation); CYP450 system not involved
Elimination half-life	Single-dose: 28 hours; Multi-dose: 33 hours
Excretion	Feces
Identifiers
	IUPAC name [6-hydroxy-2-(4-hydroxyphenyl)-benzothiophen-3-yl]-[4-[2-(1-piperidyl)ethoxy]phenyl]-methanone;
CAS Number	84449-90-1 ; as HCl: 82640-04-8;
PubChem CID	5035;
IUPHAR/BPS	2820;
DrugBank	DB00481 ;
ChemSpider	4859 ;
UNII	YX9162EO3I; as HCl: 4F86W47BR6;
KEGG	D08465; as HCl: D02217;
ChEBI	CHEBI:8772 ;
ChEMBL	ChEMBL81 ;
PDB ligand	RAL (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID3023550 ;
ECHA InfoCard	100.212.655
Chemical and physical data
Formula	C28H27NO4S
Molar mass	473.59 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:GZUITABIAKMVPG-UHFFFAOYSA-N ;
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Raloxifene, sold under the brand name Evista among others, is a medication used to prevent and treat osteoporosis in postmenopausal women and those on glucocorticoids. For osteoporosis it is less preferred than bisphosphonates. It is also used to reduce the risk of breast cancer in those at high risk. It is taken by mouth.

Common side effects include hot flashes, leg cramps, swelling, and joint pain. Severe side effects may include blood clots and stroke. Use during pregnancy may harm the baby. The medication may worsen menstrual symptoms. Raloxifene is a selective estrogen receptor modulator (SERM) and therefore a mixed agonist–antagonist of the estrogen receptor (ER). It has estrogenic effects in bone and antiestrogenic effects in the breasts and uterus.

Raloxifene was approved for medical use in the United States in 1997. It is available as a generic medication. In 2020, it was the 292nd most commonly prescribed medication in the United States, with more than 1 million prescriptions.