Raloxifene

Raloxifene
Clinical data
Trade namesEvista, Optruma, others
Other namesKeoxifene; Pharoxifene; LY-139481; LY-156758; CCRIS-7129
AHFS/Drugs.comMonograph
MedlinePlusa698007
License data
Pregnancy
category
  • AU: X (High risk)
Routes of
administration		By mouth
Drug classSelective estrogen receptor modulator
ATC code
Legal status
Legal status
  • US: ℞-only
  • EU: Rx-only[1]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability2%[2][3]
Protein binding>95%[2][3]
MetabolismLiver, intestines (glucuro-
nidation);[2][3][4] CYP450 system not involved[2][3]
Elimination half-lifeSingle-dose: 28 hours[2][3]
Multi-dose: 33 hours[2]
ExcretionFeces[3]
Identifiers
IUPAC name
  • [6-hydroxy-2-(4-hydroxyphenyl)-benzothiophen-3-yl]-[4-[2-(1-piperidyl)ethoxy]phenyl]-methanone
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.212.655
Chemical and physical data
FormulaC28H27NO4S
Molar mass473.59 g·mol−1
3D model (JSmol)
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
  (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]

  1. ^ "Optruma EPAR". European Medicines Agency (EMA). 5 August 1998. Retrieved 27 September 2024.
  2. ^ a b c d e f Cite error: The named reference MorelloWurz2003 was invoked but never defined (see the help page).
  3. ^ a b c d e f Cite error: The named reference pmid10428318 was invoked but never defined (see the help page).
  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.
  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.
  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.
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.