Identification

Name
Rivaroxaban
Accession Number
DB06228
Description

Rivaroxaban is an anticoagulant and the first orally active direct factor Xa inhibitor. Unlike warfarin, routine lab monitoring of INR is not necessary. However there is no antidote available in the event of a major bleed. Only the 10 mg tablet can be taken without regard to food. The 15 mg and 20 mg tablet should be taken with food. FDA approved on July 1, 2011.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 435.881
Monoisotopic: 435.065569098
Chemical Formula
C19H18ClN3O5S
Synonyms
  • Rivaroxaban
External IDs
  • BAY 59-7939
  • BAY-59-7939
  • JNJ-39039039
  • JNJ39039039

Pharmacology

Indication

Rivaroxaban is indicated for the prevention of venous thromboembolic events (VTE) in patients who have undergone total hips replacements and total knee replacement surgery; prevention of stroke and systemic embolism in patients with nonvalvular atrial fibrillation; treatment of deep vein thrombosis (DVT) and pulmonary embolism (PE); to reduce risk of recurrent DVT and/or PE. Rivaroxaban is also indicated, in combination with aspirin, for reducing the risk of major cardiovascular events in patients with chronic coronary artery disease or peripheral artery disease. Due to a lack of safety studies, it is not recommended for use in those under 18 years old. Its use is also not recommended in those with severe renal impairment (<30mL/min).

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Rivaroxaban is an anticoagulant which binds directly to factor Xa. Thereafter, it effectively blocks the amplification of the coagulation cascade, preventing the formation of thrombus. Rivaroxaban is a unqiue anticoagulant for two reasons. First of all, it is does not involve antithrombin III (ATIII) to exert its anticoagulant effects. Secondly, it is an oral agent whereas the widely used unfractionated heparin and low molecular weight heparins are for parenteral use only. Although the activated partial thromboplastin time (aPTT) and HepTest (a test developed to assay low molecular weight heparins) are prolonged in a dose-dependant manner, neither test is recommended for the assessment of the pharmacodynamic effects of rivaroxaban. Anti-Xa activity and inhibition of anti-Xa activity monitoring is also not recommended despite being influenced by rivaroxaban.

Mechanism of action

Rivaroxaban competitively inhibits free and clot bound factor Xa. Factor Xa is needed to activate prothrombin (factor II) to thrombin (factor IIa). Thrombin is a serine protease that is required to activate fibrinogen to fibrin, which is the loose meshwork that completes the clotting process. Since one molecule of factor Xa can generate more than 1000 molecules of thrombin, selective inhibitors of factor Xa are profoundly useful in terminating the amplification of thrombin generation. The action of rivaroxaban is irreversible.

TargetActionsOrganism
ACoagulation factor X
antagonist
Humans
Absorption

Following oral administration, rivaroxaban is rapidly absorbed and reaches peak plasma concentration in 2-4 hours. Bioavailability of the 10 mg dose is >80%. However, the 15-20 mg dose have a lower bioavailability if taken in the fasted state and consequently should be taken with food.

Volume of distribution

The steady state Vd is 50 L

Protein binding

Plasma protein binding is about 92% to 95%

Metabolism

Approximately two-thirds of the dose is metabolized. It is metabolized by CYP3A4, CYP3A5, CYP2J2 and CYP-independant mechanisms

Route of elimination

Approximately two-thirds of rivaroxaban is excreted into urine (via active tubular secretion in which approximately 36% as unchanged drug and 30% as inactive metabolism). The remaining third of the administered dose is excreted via feces in which 7% is in the form of unchanged drug and 21% as inactive metabolites.

Half-life

The terminal half life is 5-9 hours in adults and 11-13 hours in the elderly.

Clearance

Systemic clearance is approximately 10 L/h, so rivaroxaban is considered a drug with low clearance. Renal clearance is ~3-4 L/h.

Adverse Effects
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Toxicity

Excessive bleeding. Overdosages should be treated using activated charcoal and supportive measures such as mechanical compression and hemodynamic support. If bleeding is not controlled, the following procoagulants can be administered: activated prothrombin complex concentrate, prothrombin complex concentrate and recombinant factor VIIa. There is also a higher chance of post procedural hemorrhage compared to enoxaparin (1.55% vs. 1.39% respectively).

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Rivaroxaban which could result in a higher serum level.
AbametapirThe serum concentration of Rivaroxaban can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Rivaroxaban can be increased when combined with Abatacept.
AbciximabAbciximab may increase the anticoagulant activities of Rivaroxaban.
AbemaciclibAbemaciclib may decrease the excretion rate of Rivaroxaban which could result in a higher serum level.
AcalabrutinibThe metabolism of Rivaroxaban can be decreased when combined with Acalabrutinib.
AcarboseAcarbose may decrease the excretion rate of Rivaroxaban which could result in a higher serum level.
AceclofenacThe risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Rivaroxaban.
AcemetacinThe risk or severity of bleeding and hemorrhage can be increased when Acemetacin is combined with Rivaroxaban.
AcenocoumarolAcenocoumarol may increase the anticoagulant activities of Rivaroxaban.
Additional Data Available
  • Extended Description
    Extended Description
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
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    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
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    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action
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    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.
  • Avoid St. John's Wort. Co-administration will decrease levels of this medication.
  • Take with food. Rivaroxaban 15-20mg dose should be taken with food as food significantly impacts the bioavailability at that dose.
  • Take with or without food. Rivaroxaban 10mg dose can be taken with or without food as it does not significantly impact the bioavailability at that dose.

Products

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Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Rivaroxaban TabletsTabletOralBayerNot applicableNot applicableCanada flag
Rivaroxaban TabletsTabletOralBayerNot applicableNot applicableCanada flag
Rivaroxaban TabletsTabletOralBayerNot applicableNot applicableCanada flag
Rivaroxaban TabletsTabletOralBayerNot applicableNot applicableCanada flag
XareltoTablet, film coated10 mg/1OralJanssen Pharmaceuticals, Inc.2011-07-01Not applicableUS flag50458 0580 30 nlmimage10 791dbcbd
XareltoTablet, film coated20 mgOralBayer Ag2008-09-30Not applicableEU flag
XareltoTablet, film coated15 mgOralBayer Ag2008-09-30Not applicableEU flag
XareltoTablet, film coated10 mgOralBayer Ag2008-09-30Not applicableEU flag
XareltoTablet, film coated2.5 mgOralBayer Ag2008-09-30Not applicableEU flag
XareltoTablet, film coated20 mgOralBayer Ag2008-09-30Not applicableEU flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
XareltoRivaroxaban (15 mg) + Rivaroxaban (20 mg)Kit; TabletOralBayer2015-11-022018-12-01Canada flag
XareltoRivaroxaban (15 mg/1) + Rivaroxaban (20 mg/1)Kit; TabletOralJanssen Pharmaceuticals, Inc.2014-09-16Not applicableUS flag
XareltoRivaroxaban (15 mg) + Rivaroxaban (20 mg)Kit; TabletOralBayer2015-11-022018-12-01Canada flag
XareltoRivaroxaban (15 mg/1) + Rivaroxaban (20 mg/1)Kit; TabletOralJanssen Pharmaceuticals, Inc.2014-09-16Not applicableUS flag

Categories

ATC Codes
B01AF01 — Rivaroxaban
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Oxazinanes
Sub Class
Morpholines
Direct Parent
Phenylmorpholines
Alternative Parents
Thiophene carboxamides / 2-heteroaryl carboxamides / 2,5-disubstituted thiophenes / Oxazolidinones / Aryl chlorides / Benzene and substituted derivatives / Tertiary carboxylic acid amides / Carbamate esters / Heteroaromatic compounds / Secondary carboxylic acid amides
show 11 more
Substituents
2,5-disubstituted thiophene / 2-heteroaryl carboxamide / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Carbamic acid ester / Carbonic acid derivative / Carbonyl group
show 25 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
monocarboxylic acid amide, organochlorine compound, thiophenes, lactam, aromatic amide, morpholines, oxazolidinone (CHEBI:68579)

Chemical Identifiers

UNII
9NDF7JZ4M3
CAS number
366789-02-8
InChI Key
KGFYHTZWPPHNLQ-AWEZNQCLSA-N
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
IUPAC Name
5-chloro-N-{[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl}thiophene-2-carboxamide
SMILES
ClC1=CC=C(S1)C(=O)NC[[email protected]]1CN(C(=O)O1)C1=CC=C(C=C1)N1CCOCC1=O

References

Synthesis Reference

Prabhudas BODHURI, Gamini Weeratunga, "PROCESSES FOR THE PREPARATION OF RIVAROXABAN AND INTERMEDIATES THEREOF." U.S. Patent US20100273790, issued October 28, 2010.

US20100273790
General References
  1. Piccini JP, Patel MR, Mahaffey KW, Fox KA, Califf RM: Rivaroxaban, an oral direct factor Xa inhibitor. Expert Opin Investig Drugs. 2008 Jun;17(6):925-37. doi: 10.1517/13543784.17.6.925 . [PubMed:18491993]
  2. Alban S: Pharmacological strategies for inhibition of thrombin activity. Curr Pharm Des. 2008;14(12):1152-75. [PubMed:18473863]
  3. Stevenson M, Scope A, Holmes M, Rees A, Kaltenthaler E: Rivaroxaban for the prevention of venous thromboembolism: a single technology appraisal. Health Technol Assess. 2009 Oct;13 Suppl 3:43-8. doi: 10.3310/hta13suppl3/07. [PubMed:19846028]
  4. Imberti D, Dall'Asta C, Pierfranceschi MG: Oral factor Xa inhibitors for thromboprophylaxis in major orthopedic surgery: a review. Intern Emerg Med. 2009 Dec;4(6):471-7. doi: 10.1007/s11739-009-0293-9. [PubMed:19696978]
  5. Alexander D, Jeremias A: Rivaroxaban in the contemporary treatment of acute coronary syndromes. Expert Opin Investig Drugs. 2011 Jun;20(6):849-57. doi: 10.1517/13543784.2011.580274. Epub 2011 May 10. [PubMed:21554163]
  6. Cabral KP: Pharmacology of the new target-specific oral anticoagulants. J Thromb Thrombolysis. 2013 Aug;36(2):133-40. doi: 10.1007/s11239-013-0929-5. [PubMed:23645472]
  7. FDA Approved Products: Xarelto (rivaroxaban) oral tablets [Link]
KEGG Drug
D07086
PubChem Compound
9875401
PubChem Substance
175427064
ChemSpider
8051086
BindingDB
7840
RxNav
1114195
ChEBI
68579
ChEMBL
CHEMBL198362
ZINC
ZINC000003964126
PDBe Ligand
RIV
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Rivaroxaban
AHFS Codes
  • 20:12.04.14 — Direct Factor Xa Inhibitors
PDB Entries
2w26 / 5vof
FDA label
Download (537 KB)
MSDS
Download (480 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentAcute Coronary Syndromes (ACS) / Myocardial Infarction / Myocardial Ischemia / Unstable Angina Pectoris1
4CompletedBasic ScienceAcute Coronary Syndromes (ACS) / Atrial Fibrillation (AF)1
4CompletedBasic ScienceAtrial Fibrillation or Pulmonary Embolism / Existent Coronary or Valvular Calcification, or Both and Agatston Score > 50 in at Least One Location / Need of Long Term Oral Anticoagulation Therapy (OAT)1
4CompletedBasic ScienceVenous Thromboembolism1
4CompletedOtherAntiphospholipid Antibody Syndrome1
4CompletedPreventionAtherosclerosis1
4CompletedPreventionAtrial Fibrillation (AF)2
4CompletedPreventionCalcifications, Vascular1
4CompletedPreventionFemur Head Necrosis / Fracture of Neck of Femur / Osteoarthritis in the Hip Joint1
4CompletedPreventionOsteoarthritis of the Knee1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, coatedOral10 mg
Tablet, coatedOral15 mg
Tablet, coatedOral20 mg
TabletOral
Capsule15 mg
Capsule20 mg
Kit; tabletOral
TabletOral10 mg
TabletOral2.5 mg
Tablet, coatedOral2.5 MG
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral10 mg
Tablet, film coatedOral15 mg/1
Tablet, film coatedOral15 mg
Tablet, film coatedOral2.5 mg
Tablet, film coatedOral2.5 mg/1
Tablet, film coatedOral20 mg
Tablet, film coatedOral20 mg/1
TabletOral15 mg
TabletOral20 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2396561No2008-10-142020-12-11Canada flag
CA2547113No2012-01-242024-11-13Canada flag
US7157456No2007-01-022021-02-08US flag
US7585860No2009-09-082020-12-11US flag
US7592339No2009-09-222020-12-11US flag
US9539218No2017-01-102034-02-17US flag
US9415053No2016-08-162024-11-13US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.01 mg/mLALOGPS
logP1.74ALOGPS
logP1.9ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)13.6ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area88.18 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity104.74 m3·mol-1ChemAxon
Polarizability43.41 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9966
Blood Brain Barrier+0.9462
Caco-2 permeable+0.6822
P-glycoprotein substrateNon-substrate0.5691
P-glycoprotein inhibitor IInhibitor0.6325
P-glycoprotein inhibitor IIInhibitor0.5601
Renal organic cation transporterNon-inhibitor0.7562
CYP450 2C9 substrateNon-substrate0.7866
CYP450 2D6 substrateNon-substrate0.8761
CYP450 3A4 substrateSubstrate0.5964
CYP450 1A2 substrateNon-inhibitor0.6469
CYP450 2C9 inhibitorNon-inhibitor0.7035
CYP450 2D6 inhibitorNon-inhibitor0.7516
CYP450 2C19 inhibitorInhibitor0.6475
CYP450 3A4 inhibitorNon-inhibitor0.6667
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7463
Ames testNon AMES toxic0.6162
CarcinogenicityNon-carcinogens0.8838
BiodegradationNot ready biodegradable0.9844
Rat acute toxicity2.4353 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8938
hERG inhibition (predictor II)Inhibitor0.6205
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Details
1. Coagulation factor X
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Serine-type endopeptidase activity
Specific Function
Factor Xa is a vitamin K-dependent glycoprotein that converts prothrombin to thrombin in the presence of factor Va, calcium and phospholipid during blood clotting.
Gene Name
F10
Uniprot ID
P00742
Uniprot Name
Coagulation factor X
Molecular Weight
54731.255 Da
References
  1. Melillo SN, Scanlon JV, Exter BP, Steinberg M, Jarvis CI: Rivaroxaban for thromboprophylaxis in patients undergoing major orthopedic surgery. Ann Pharmacother. 2010 Jun;44(6):1061-71. doi: 10.1345/aph.1M681. Epub 2010 Apr 27. [PubMed:20424181]
  2. Ufer M: Comparative efficacy and safety of the novel oral anticoagulants dabigatran, rivaroxaban and apixaban in preclinical and clinical development. Thromb Haemost. 2010 Mar;103(3):572-85. doi: 10.1160/TH09-09-0659. Epub 2010 Feb 2. [PubMed:20135071]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Mismetti P, Laporte S: [Rivaroxaban: clinical pharmacology]. Ann Fr Anesth Reanim. 2008 Dec;27 Suppl 3:S16-21. doi: 10.1016/S0750-7658(08)75142-6. [PubMed:19185782]
  2. Ufer M: Comparative efficacy and safety of the novel oral anticoagulants dabigatran, rivaroxaban and apixaban in preclinical and clinical development. Thromb Haemost. 2010 Mar;103(3):572-85. doi: 10.1160/TH09-09-0659. Epub 2010 Feb 2. [PubMed:20135071]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible f...
Gene Name
CYP2J2
Uniprot ID
P51589
Uniprot Name
Cytochrome P450 2J2
Molecular Weight
57610.165 Da
References
  1. Ufer M: Comparative efficacy and safety of the novel oral anticoagulants dabigatran, rivaroxaban and apixaban in preclinical and clinical development. Thromb Haemost. 2010 Mar;103(3):572-85. doi: 10.1160/TH09-09-0659. Epub 2010 Feb 2. [PubMed:20135071]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Cabral KP: Pharmacology of the new target-specific oral anticoagulants. J Thromb Thrombolysis. 2013 Aug;36(2):133-40. doi: 10.1007/s11239-013-0929-5. [PubMed:23645472]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Walenga JM, Adiguzel C: Drug and dietary interactions of the new and emerging oral anticoagulants. Int J Clin Pract. 2010 Jun;64(7):956-67. doi: 10.1111/j.1742-1241.2009.02286.x. [PubMed:20584229]
  2. Chen T, Lam S: Rivaroxaban: an oral direct factor Xa inhibitor for the prevention of thromboembolism. Cardiol Rev. 2009 Jul-Aug;17(4):192-7. doi: 10.1097/CRD.0b013e3181aa2154. [PubMed:19525681]
  3. Xarelto FDA [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Mueck W, Kubitza D, Becka M: Co-administration of rivaroxaban with drugs that share its elimination pathways: pharmacokinetic effects in healthy subjects. Br J Clin Pharmacol. 2013 Sep;76(3):455-66. doi: 10.1111/bcp.12075. [PubMed:23305158]
  2. Xarelto FDA [File]

Drug created on March 19, 2008 10:18 / Updated on November 29, 2020 03:54

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