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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H18ClN3O5S
Molecular Weight 435.881
Optical Activity ( - )
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

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

Primary TargetPharmacologyConditionPotency
0.4 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
XARELTO

Cmax

ValueDoseCo-administeredAnalytePopulation
138.4 μg/L
10 mg single, oral
RIVAROXABAN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1.114 μg × h/L
10 mg single, oral
RIVAROXABAN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
10.77 h
10 mg single, oral
RIVAROXABAN plasma
Homo sapiens
9 h
20 mg 1 times / day unknown, oral
RIVAROXABAN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
20 mg 1 times / day unknown, oral
RIVAROXABAN plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

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.