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Rivaroxaban information


Rivaroxaban
Clinical data
Trade namesXarelto, others
Other namesBAY 59-7939
AHFS/Drugs.comMonograph
MedlinePlusa611049
License data
  • US DailyMed: Rivaroxaban
Pregnancy
category
  • AU: C[1]
Routes of
administration
By mouth
ATC code
  • B01AF01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)[3]
  • CA: ℞-only
  • UK: POM (Prescription only)[4]
  • US: WARNING[2]Rx-only[5]
  • EU: Rx-only[6]
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
IUPAC name
  • (S)-5-chloro-N-{[2-oxo-3-[4-(3-oxomorpholin-4-yl)
    phenyl]oxazolidin-5-yl]methyl} thiophene-2-carboxamide
CAS Number
  • 366789-02-8 checkY
PubChem CID
  • 6433119
IUPHAR/BPS
  • 6388
DrugBank
  • DB06228 checkY
ChemSpider
  • 8051086 checkY
UNII
  • 9NDF7JZ4M3
KEGG
  • D07086 ☒N
ChEBI
  • CHEBI:68579
ChEMBL
  • ChEMBL198362 checkY
PDB ligand
  • RIV (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID3057723 Edit this at Wikidata
ECHA InfoCard100.210.589 Edit this at Wikidata
Chemical and physical data
FormulaC19H18ClN3O5S
Molar mass435.88 g·mol−1
3D model (JSmol)
  • Interactive image
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 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 2021, it was the 86th most commonly prescribed medication in the United States, with more than 8 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 2021". ClinCalc. Archived from the original on January 15, 2024. Retrieved January 14, 2024.
  15. ^ "Rivaroxaban - Drug Usage Statistics". ClinCalc. Retrieved January 14, 2024.

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brand name Andexxa among others, is an antidote for the medications rivaroxaban and apixaban, when reversal of anticoagulation is needed due to uncontrolled...

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Bayer

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gross revenue. In 2019, identified "key growth" products were Xarelto (rivaroxaban), Eylea (aflibercept), Stivarga (regorafenib), Xofigo (radium-223), and...

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Anticoagulant

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include direct thrombin inhibitor (dabigatran) and factor Xa inhibitor (rivaroxaban, apixaban, betrixaban and edoxaban), and they have been shown to be as...

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Dabigatran

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hemorrhage, and all-cause mortality compared with dabigatran, edoxaban, and rivaroxaban. Dabigatran is contraindicated in patients who have active pathological...

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anticoagulant (anti-blood clotting) drugs, including factor Xa inhibitors (rivaroxaban, apixaban and edoxaban), dabigatran, and heparins (including fondaparinux...

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Apixaban

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failure. Apixaban and other anticoagulants (dabigatran, edoxaban and rivaroxaban) appear equally effective as warfarin in preventing non-hemorrhagic stroke...

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ATC code B01

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B01AE07 Dabigatran etexilate B01AF01 Rivaroxaban B01AF02 Apixaban B01AF03 Edoxaban B01AF04 Betrixaban B01AF51 Rivaroxaban and acetylsalicylic acid B01AX01...

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Direct factor Xa inhibitors

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people with atrial fibrillation (AF). Direct factor Xa inhibitors include rivaroxaban, apixaban and edoxaban, and are types of direct oral anticoagulant (DOAC)...

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Pulmonary embolism

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vitamin K antagonists by American professional guidelines. Two of these (rivaroxaban and apixaban) do not require initial heparin or fondaparinux treatment...

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Deep vein thrombosis

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blood thinners is the standard treatment. Typical medications include rivaroxaban, apixaban, and warfarin. Beginning warfarin treatment requires an additional...

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Alexion Pharmaceuticals

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life threatening or uncontrollable bleeding in people who are taking rivaroxaban or apixaban. With costs that can reach as much as $2 million per year...

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coagulation factors (the directly acting oral anticoagulants: dabigatran, rivaroxaban, apixaban, and edoxaban). Theories on the coagulation of blood have existed...

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WHO Model List of Essential Medicines

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quality-assured biosimilars are alternatives Apixaban, edoxaban, and rivaroxaban are alternatives Alternatives are dalteparin and nadroparin, including...

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Natco Pharma

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Grindeks

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Edoxaban

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antidote for edoxaban overdose, but has only been approved for reversing rivaroxaban and apixaban effects by the FDA and the EMA as of 2019. Edoxaban is a...

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Atrial fibrillation

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achieved through several means including warfarin, heparin, dabigatran, rivaroxaban, edoxaban, and apixaban. Many issues should be considered related to...

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Barbiturates phenobarbital, secobarbital -xaban Direct Xa inhibitor apixaban, rivaroxaban -afil Inhibitor of PDE5 with vasodilator action sildenafil, tadalafil...

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Activated carbon

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the direct oral anticoagulants (DOACs) such as dabigatran, apixaban, rivaroxaban and edoxaban from blood plasma samples. For this purpose it has been...

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Corvalol

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