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Rivaroxaban

Rivaroxaban
Clinical data
Trade namesXarelto, others
Other namesBAY 59-7939
AHFS/Drugs.comMonograph
MedlinePlusa611049
License data
Pregnancy
category
Routes of
administration
By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability80–100%; Cmax = 2–4 hours (10 mg oral)[4]
MetabolismCYP3A4, CYP2J2 and CYP-independent mechanisms[4]
Elimination half-life5–9 hours in healthy subjects aged 20 to 45[4][7]
Excretion2/3 metabolized in liver and 1/3 eliminated unchanged[4]
Identifiers
  • (S)-5-chloro-N-{[2-oxo-3-[4-(3-oxomorpholin-4-yl)
    phenyl]oxazolidin-5-yl]methyl} thiophene-2-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.210.589 Edit this at Wikidata
Chemical and physical data
FormulaC19H18ClN3O5S
Molar mass435.88 g·mol−1
3D model (JSmol)
  • O=C1COCCN1c2ccc(cc2)N3C[C@@H](OC3=O)CNC(=O)c4ccc(s4)Cl
  • InChI=1S/C19H18ClN3O5S/c20-16-6-5-15(29-16)18(25)21-9-14-10-23(19(26)28-14)13-3-1-12(2-4-13)22-7-8-27-11-17(22)24/h1-6,14H,7-11H2,(H,21,25)/t14-/m0/s1 checkY
  • Key:KGFYHTZWPPHNLQ-AWEZNQCLSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Rivaroxaban, sold under the brand name Xarelto among others, is an anticoagulant medication (blood thinner) used to treat and prevent blood clots.[8] Specifically it is used to treat deep vein thrombosis and pulmonary emboli and prevent blood clots in atrial fibrillation and following hip or knee surgery.[8] It is taken by mouth.[8]

Common side effects include bleeding.[8] Other serious side effects may include spinal hematoma and anaphylaxis.[8] It is unclear if use in pregnancy and breastfeeding is safe.[1] Compared to warfarin it has fewer interactions with other medications.[9] It works by blocking the activity of the clotting protein factor Xa.[8]

Rivaroxaban was patented in 2007 and approved for medical use in the United States in 2011.[10] In the United States, it will not be available as a generic medication until 2024.[11][12] It is on the World Health Organization's List of Essential Medicines.[13] In 2022, it was the 90th most commonly prescribed medication in the United States, with more than 7 million prescriptions.[14][15]

  1. ^ a b "Rivaroxaban Use During Pregnancy". Drugs.com. Retrieved March 3, 2019.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved October 22, 2023.
  3. ^ Xarelto (Bayer Australia Ltd)
  4. ^ a b c d e "Xarelto 2.5 mg film-coated tablets - Summary of Product Characteristics (SmPC)". (emc). August 9, 2022. Retrieved November 9, 2022.
  5. ^ Cite error: The named reference Xarelto FDA label was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Xarelto EPAR was invoked but never defined (see the help page).
  7. ^ Abdulsattar Y, Bhambri R, Nogid A (May 2009). "Rivaroxaban (xarelto) for the prevention of thromboembolic disease: an inside look at the oral direct factor xa inhibitor". P & T. 34 (5): 238–44. PMC 2697099. PMID 19561868.
  8. ^ a b c d e f "Rivaroxaban Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved March 3, 2019.
  9. ^ Kiser K (2017). Oral Anticoagulation Therapy: Cases and Clinical Correlation. Springer. p. 11. ISBN 9783319546438.
  10. ^ "Generic Xarelto Availability". Drugs.com. Retrieved May 9, 2017.
  11. ^ "Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations". www.accessdata.fda.gov. Retrieved April 24, 2019.
  12. ^ "Bayer, J&J Win Ruling That Upholds Patent for Xarelto Drug". April 22, 2019. Retrieved April 24, 2019.
  13. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  14. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on August 30, 2024. Retrieved August 30, 2024.
  15. ^ "Rivaroxaban Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved August 30, 2024.

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