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	EU EMA: by INN; US DailyMed: Raloxifene; US FDA: Evista;
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: WARNINGRx-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 ;
	(verify)

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.^[5] For osteoporosis it is less preferred than bisphosphonates.^[5] It is also used to reduce the risk of breast cancer in those at high risk.^[5] It is taken by mouth.^[5]

Common side effects include hot flashes, leg cramps, swelling, and joint pain.^[5] Severe side effects may include blood clots and stroke.^[5] Use during pregnancy may harm the baby.^[5] The medication may worsen menstrual symptoms.^[6] Raloxifene is a selective estrogen receptor modulator (SERM) and therefore a mixed agonist–antagonist of the estrogen receptor (ER).^[5] It has estrogenic effects in bone and antiestrogenic effects in the breasts and uterus.^[5]

Raloxifene was approved for medical use in the United States in 1997.^[5] It is available as a generic medication.^[5]^[7] In 2020, it was the 292nd most commonly prescribed medication in the United States, with more than 1 million prescriptions.^[8]^[9]

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
^ ^a ^b ^c ^d ^e ^f Cite error: The named reference MorelloWurz2003 was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e ^f Cite error: The named reference pmid10428318 was invoked but never defined (see the help page).
^ Jeong EJ, Liu Y, Lin H, Hu M (June 2005). "Species- and disposition model-dependent metabolism of raloxifene in gut and liver: role of UGT1A10". Drug Metabolism and Disposition. 33 (6). ASPET: 785–794. doi:10.1124/dmd.104.001883. PMID 15769887. S2CID 24273998.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k "Raloxifene Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 22 March 2019.
^ Yang ZD, Yu J, Zhang Q (August 2013). "Effects of raloxifene on cognition, mental health, sleep and sexual function in menopausal women: a systematic review of randomized controlled trials". Maturitas. 75 (4): 341–348. doi:10.1016/j.maturitas.2013.05.010. PMID 23764354.
^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 736–737. ISBN 9780857113382.
^ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
^ "Raloxifene - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

[MorelloWurz2003-2] ^ ^a ^b ^c ^d ^e ^f Cite error: The named reference MorelloWurz2003 was invoked but never defined (see the help page).

[pmid10428318-3] ^ ^a ^b ^c ^d ^e ^f Cite error: The named reference pmid10428318 was invoked but never defined (see the help page).

[Jeong-4] Jeong EJ, Liu Y, Lin H, Hu M (June 2005). "Species- and disposition model-dependent metabolism of raloxifene in gut and liver: role of UGT1A10". Drug Metabolism and Disposition. 33 (6). ASPET: 785–794. doi:10.1124/dmd.104.001883. PMID 15769887. S2CID 24273998.

[AHFS2019-5] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k "Raloxifene Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 22 March 2019.

[6] Yang ZD, Yu J, Zhang Q (August 2013). "Effects of raloxifene on cognition, mental health, sleep and sexual function in menopausal women: a systematic review of randomized controlled trials". Maturitas. 75 (4): 341–348. doi:10.1016/j.maturitas.2013.05.010. PMID 23764354.

[BNF76-7] British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 736–737. ISBN 9780857113382.

[8] "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.

[9] "Raloxifene - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.

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