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)[5]
MetabolismCYP3A4, CYP2J2 and CYP-independent mechanisms[5]
Elimination half-life5–9 hours in healthy subjects aged 20 to 45[5][8]
Excretion2/3 metabolized in liver and 1/3 eliminated unchanged[5]
Identifiers
IUPAC name
  • (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
Chemical and physical data
FormulaC19H18ClN3O5S
Molar mass435.88 g·mol−1
3D model (JSmol)
SMILES
  • O=C1COCCN1c2ccc(cc2)N3C[C@@H](OC3=O)CNC(=O)c4ccc(s4)Cl
InChI
  • 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 Y
  • Key:KGFYHTZWPPHNLQ-AWEZNQCLSA-N Y
 NY (what is this?)  (verify)

Rivaroxaban, sold under the brand name Xarelto among others, is an anticoagulant medication (blood thinner) used to treat and reduce the risk of blood clots.[9] 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.[9] It is taken by mouth.[9]

Common side effects include bleeding.[9] Other serious side effects may include spinal hematoma and anaphylaxis.[9] It is unclear if use in pregnancy and breastfeeding is safe.[1] Compared to warfarin it has fewer interactions with other medications.[10] It works by blocking the activity of the clotting protein factor Xa.[9]

Rivaroxaban was patented in 2007 and approved for medical use in the United States in 2011.[11] It is available as a generic medication.[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. ^ Xarelto (Bayer Australia Ltd)
  3. ^ "Summary Basis of Decision for Xarelto". Drug and Health Products Portal. February 13, 2009. Retrieved March 11, 2025.
  4. ^ "Regulatory Decision Summary for Xarelto". Drug and Health Products Portal. January 12, 2021. Retrieved March 11, 2025.
  5. ^ 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.
  6. ^ Cite error: The named reference Xarelto FDA label was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference Xarelto EPAR was invoked but never defined (see the help page).
  8. ^ 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 : a Peer-reviewed Journal for Formulary Management. 34 (5): 238–244. PMC 2697099. PMID 19561868.
  9. ^ a b c d e f "Rivaroxaban Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved March 3, 2019.
  10. ^ Kiser K (2017). Oral Anticoagulation Therapy: Cases and Clinical Correlation. Springer. p. 11. ISBN 978-3-319-54643-8.
  11. ^ "Generic Xarelto Availability". Drugs.com. Retrieved May 9, 2017.
  12. ^ "FDA Roundup: March 4, 2025". U.S. Food and Drug Administration (Press release). March 4, 2025. Retrieved March 7, 2025.
  13. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  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.