U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H18ClN3O5S
Molecular Weight 435.881
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIVAROXABAN

SMILES

ClC1=CC=C(S1)C(=O)NC[C@H]2CN(C(=O)O2)C3=CC=C(C=C3)N4CCOCC4=O

InChI

InChIKey=KGFYHTZWPPHNLQ-AWEZNQCLSA-N
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

HIDE SMILES / InChI

Molecular Formula C19H18ClN3O5S
Molecular Weight 435.881
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Rivaroxaban (trade name Xarelto) is an oral anticoagulant. It is the first available orally active direct factor Xa inhibitor. Upon oral administration, rivaroxaban selectively binds to both free factor Xa and factor Xa bound in the prothrombinase complex. This interferes with the conversion of prothrombin (factor II) to thrombin and eventually prevents the formation of cross-linked fibrin clots. Rivaroxaban does not affect existing thrombin levels. Activation of factor X to factor Xa (FXa) via the intrinsic and extrinsic pathways plays a central role in the cascade of blood coagulation. Xarelto is indicated to reduce the risk of stroke and systemic embolism in patients with nonvalvular atrial fibrillation, treatment and prophylaxis of deep vein thrombosis (DVT) which may lead to PE in patients undergoing knee or hip replacement surgery, pulmonary embolism (PE) and for the reduction in the risk of recurrence of deep vein thrombosis and of pulmonary embolism following initial 6 months treatment for DVT and/or PE.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.4 nM [Ki]
Conditions
PubMed

PubMed

TitleDatePubMed
New issues in oral anticoagulants.
2008
New compounds in the management of venous thromboembolism after orthopedic surgery: focus on rivaroxaban.
2008
Brave new world: the current and future use of novel anticoagulants.
2008
The top 4 advances in antithrombotic care in the last year.
2008
Gateways to clinical trials.
2008 Apr
Potent anticoagulants are associated with a higher all-cause mortality rate after hip and knee arthroplasty.
2008 Aug
Rivaroxaban: an oral direct inhibitor of factor Xa.
2008 Aug 15
[Summary and perspectives. Rivaroxaban].
2008 Dec
[Rivaroxaban (Xarelto): efficacy and safety].
2008 Dec
[Perioperative venous thromboembolism prophylaxis: short review and recommendations].
2008 Dec
[Rivaroxaban: clinical pharmacology].
2008 Dec
[Rivaroxaban: a decisive step forward in the management of postoperative thromboembolic disease?].
2008 Dec
[Pharmacology of heparins and direct anticoagulants].
2008 Dec
The laboratory diagnosis and clinical management of patients with heparin-induced thrombocytopenia: an update.
2008 Feb
Current and future prospects for anticoagulant therapy: inhibitors of factor Xa and factor IIa.
2008 Feb
Gateways to clinical trials.
2008 Jan-Feb
Selective factor Xa inhibition for thromboprophylaxis.
2008 Jul 5
Extended duration rivaroxaban versus short-term enoxaparin for the prevention of venous thromboembolism after total hip arthroplasty: a double-blind, randomised controlled trial.
2008 Jul 5
Gateways to clinical trials.
2008 Jun
Rivaroxaban, an oral direct factor Xa inhibitor.
2008 Jun
New anticoagulants--the path from discovery to clinical practice.
2008 Jun 26
Rivaroxaban versus enoxaparin for thromboprophylaxis after total knee arthroplasty.
2008 Jun 26
Rivaroxaban versus enoxaparin for thromboprophylaxis after hip arthroplasty.
2008 Jun 26
Preventing venous thromboembolism through risk assessment approaches.
2008 Jun 26-Jul 9
[New oral anticoagulants: molecular characteristics, mechanisms of action, pharmacokinetics and pharmacodynamics].
2008 Nov
[Anaesthesia and thromboembolic disease].
2008 Nov
[Thromboembolic disease in orthopedic surgery].
2008 Nov
[Rivaroxaban. The first factor Xa inhibitor].
2008 Nov
Controversies in the antiphospholipid syndrome: can we ever stop warfarin?
2008 Nov 11
Rivaroxaban for thromboprophylaxis.
2008 Nov 13
Rivaroxaban for thromboprophylaxis.
2008 Nov 13
Rivaroxaban for thromboprophylaxis.
2008 Nov 13
Rivaroxaban for thromboprophylaxis.
2008 Nov 13
Thromboprophylaxis with rivaroxaban or enoxaparin did not differ for major bleeding in knee arthroplasty.
2008 Nov-Dec
Thromboprophylaxis with rivaroxaban or enoxaparin did not differ for major bleeding or other safety outcomes in hip arthroplasty.
2008 Nov-Dec
Orally administered factor xa inhibitor, rivaroxaban: a novel thromboembolic prophylaxis agent.
2008 Oct
[Always more amputations in Germany?].
2008 Oct
More effective, simpler-to-use clot-buster is on the way. Clot-prevention drug could save lives after joint replacement.
2008 Oct
Rivaroxaban: future in anticoagulation practice?
2008 Oct
[Prophylaxis of venous thromboembolism].
2008 Oct
[Anticoagulation in atrial fibrillation].
2008 Oct
Dose-escalation study of the pharmacokinetics and pharmacodynamics of rivaroxaban in healthy elderly subjects.
2008 Oct
Differences in urinary prothrombin fragment 1 + 2 levels after total hip replacement in relation to venous thromboembolism and bleeding events.
2008 Oct
Rivaroxaban--an oral, direct Factor Xa inhibitor--has potential for the management of patients with heparin-induced thrombocytopenia.
2008 Oct
Polyphosphate as a general procoagulant agent.
2008 Oct
New developments in anticoagulation for atrial fibrillation.
2008 Sep
Determination of rivaroxaban--a novel, oral, direct Factor Xa inhibitor--in human plasma by high-performance liquid chromatography-tandem mass spectrometry.
2008 Sep 1
A dose-ranging study evaluating once-daily oral administration of the factor Xa inhibitor rivaroxaban in the treatment of patients with acute symptomatic deep vein thrombosis: the Einstein-DVT Dose-Ranging Study.
2008 Sep 15
Comparative pharmacodynamics and pharmacokinetics of oral direct thrombin and factor xa inhibitors in development.
2009
Rivaroxaban: a novel, oral, direct factor Xa inhibitor.
2009 Feb
Patents

Sample Use Guides

In Vivo Use Guide
15 mg and 20 mg tablets with food; take 10 mg tablets with or without food. For patients with CrCl >50 mL/min 20 mg orally, once daily and for patients with CrCl 15 - 50 mL/min 15 mg orally, once daily with the evening meal.
Route of Administration: Oral
In Vitro Use Guide
To evaluate the influence of prothrombin complex concentrate (PCC) on the anticoagulant effects of rivaroxaban as measured by prothrombin time (PT) and thrombin generation tests plasma and whole blood samples from healthy volunteers were spiked with Rivaroxaban (up to 800 ug/L) and prothrombin complex concentrate (PCC) was added to these samples in concentration ranges as used clinically to reverse the effects of vitamin K antagonists. Prothrombin complex concentrate does not neutralize the lengthening effect on PT and TGT lag time/T-Lag of rivaroxaban anticoagulated blood in vitro; however, total thrombin potential could be normalized.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:01:00 UTC 2019
Edited
by admin
on Tue Oct 22 00:01:00 UTC 2019
Record UNII
9NDF7JZ4M3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RIVAROXABAN
DASH   EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
RIVAROXABAN [EMA EPAR]
Common Name English
JNJ-39039039
Code English
RIVAROXABAN [ORANGE BOOK]
Common Name English
RIVAROXABAN [MI]
Common Name English
RIVAROXABAN [INN]
Common Name English
RIVAROXABAN [WHO-DD]
Common Name English
RIVAROXABAN [MART.]
Common Name English
2-THIOPHENECARBOXAMIDE, 5-CHLORO-N-(((5S)-2-OXO-3-(4-(3-OXO-4-MORPHOLINYL)PHENYL)-5-OXAZOLIDINYL)METHYL)-
Systematic Name English
RIVAROXABAN [VANDF]
Common Name English
JNJ39039039
Code English
RIVAROXABAN [JAN]
Common Name English
BAY 59-7939
Code English
RIVAROXABAN [USAN]
Common Name English
XARELTO
Brand Name English
5-CHLORO-N-(((5S)-2-OXO-3-(4-(3-OXOMORPHOLIN-4-YL)PHENYL)-1,3-OXAZOLIDIN-5-YL)METHYL)THIOPHENE-2-CARBOXAMIDE
Systematic Name English
BAY-59-7939
Code English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS XARELTO (AUTHORIZED: ARTHROPLASTY, REPLACEMENT)
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
NCI_THESAURUS C263
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
WHO-ATC B01AF01
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
NDF-RT N0000175637
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
EMA ASSESSMENT REPORTS XARELTO (AUTHORIZED: VENOUS THROMBOEMBOLISM)
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
WHO-ATC B01AX06
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
WHO-VATC QB01AF01
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
LIVERTOX 855
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
Code System Code Type Description
EPA CompTox
366789-02-8
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
PRIMARY
NCI_THESAURUS
C77995
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
PRIMARY
DRUG BANK
DB06228
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
PRIMARY
MERCK INDEX
M9638
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
PRIMARY Merck Index
WIKIPEDIA
RIVAROXABAN
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
PRIMARY
LactMed
366789-02-8
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
PRIMARY
INN
8428
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
PRIMARY
IUPHAR
6388
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
PRIMARY
ChEMBL
CHEMBL198362
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
PRIMARY
RXCUI
1114195
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
PRIMARY RxNorm
CAS
366789-02-8
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
PRIMARY
MESH
C503223
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
PRIMARY
PUBCHEM
9875401
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
PRIMARY
HSDB
366789-02-8
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
PRIMARY
EVMPD
SUB29263
Created by admin on Tue Oct 22 00:01:00 UTC 2019 , Edited by admin on Tue Oct 22 00:01:00 UTC 2019
PRIMARY
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Name Property Type Amount Referenced Substance Defining Parameters References
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