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Compound Detail

CHEMBL198362

RIVAROXABAN
💊 Approved Drug
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💊 Approved Drug
O=C(NC[C@H]1CN(c2ccc(N3CCOCC3=O)cc2)C(=O)O1)c1ccc(Cl)s1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL198362
Name RIVAROXABAN
Phase Approved
Structure Type MOL
InChI Key KGFYHTZWPPHNLQ-AWEZNQCLSA-N
Therapeutic ✓ Yes

Known Names

BAY 59-7939 BAY-59-7939 JNJ-39039039 JNJ39039039 Rivaroxaban Rivaroxaban accord Rivaroxaban viatris (previously rivaroxaban mylan) Xarelto
5
Targets
27
Activities
3
Assay Types
30
PK Parameters
20
Publications
8
Known Names
20
Indications
1
Mechanisms

Molecular Properties

435.9
MW (Da)
2.52
ALogP
6
HBA
1
HBD
88.2
PSA (Ų)
0.78
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2008
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product First in Class
USAN Stem -xaban
USAN Year 2006

Extended Properties

Molecular Formula C19H18ClN3O5S
MW 435.89
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness -1.79

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Coagulation factor X inhibitor INHIBITOR Coagulation factor X ✓ ✓

Indications

Acute Coronary Syndrome Arthroplasty, Replacement Atrial Fibrillation Coronary Artery Disease Peripheral Arterial Disease Pulmonary Embolism Stroke Thrombosis Thrombosis Venous Thromboembolism Venous Thrombosis Venous Thrombosis Angina, Unstable Aortic Valve Stenosis Diabetes Mellitus, Type 2 Hematoma Hip Fractures Ischemic Stroke Liver Cirrhosis Myocardial Infarction

ATC Classification

B01AF01
rivaroxaban
Level 1: BLOOD AND BLOOD FORMING ORGANS
Level 2: ANTITHROMBOTIC AGENTS

Drug Warnings

Black Box Warning
vascular toxicity
Country: United States

Activity Summary

IC50 17 meas. best 9.15
Ki 8 meas. best 9.4
EC50 2 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Coagulation factor X
CHEMBL244
 Ki 9.4 9.2 0.4 7
Coagulation factor X
CHEMBL244
 IC50 9.15 8.4969 0.7 13
Unchecked
CHEMBL612545
 EC50 8.0 8.0 10.0 1
Plasma
CHEMBL613424
 EC50 6.51 6.51 310.0 1
Coagulation factor X
CHEMBL5062
 IC50 6.29 6.18 510.0 2
Suppressor of tumorigenicity 14 protein
CHEMBL3018
 Ki 5.47 5.47 3350.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 9985.0 ng.hr.mL-1 Rattus norvegicus
AUC 2264.0 ng.hr.mL-1 Rattus norvegicus
AUC 1001.6 ng.hr.mL-1 Canis lupus familiaris
AUC 915.7 ng.hr.mL-1 Canis lupus familiaris
AUC 3508.7 ng.hr.mL-1 Rattus norvegicus
AUC 6984.9 ng.hr.mL-1 Rattus norvegicus
CL 6.667 mL.min-1.kg-1 Rattus norvegicus
CL 5.0 mL.min-1.kg-1 Canis lupus familiaris
CL 5.0 mL.min-1.kg-1 Canis lupus familiaris
CL 6.667 mL.min-1.kg-1 Rattus norvegicus
CL 5.05 mL.min-1.kg-1 Rattus norvegicus
CL 10.0 mL.min-1.kg-1 Canis lupus familiaris
CL 0.9 L/hr Rattus norvegicus
CL 1.5 L/hr Rattus norvegicus
Cmax 1950.03 nM Rattus norvegicus
Cmax 763.04 nM Canis lupus familiaris
Cmax 3617.89 nM Rattus norvegicus
F 60.0 % Rattus norvegicus
F 86.0 % Canis lupus familiaris
F 60.0 % Canis lupus familiaris
F 57.0 % Rattus norvegicus
F 21.3 % Rattus norvegicus
F 68.0 % Canis lupus familiaris
F 80.0 % Homo sapiens
F 59.7 % Rattus norvegicus
Fu 0.013 - Rattus norvegicus
Fu 0.104 - Canis lupus familiaris
MRT 6.3 hr Rattus norvegicus
MRT 5.4 hr Rattus norvegicus
T1/2 0.9 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Coagulation factor X Ki = 0.4 nM 9.4 Inhibition of human factor 10a using pefachrome F10a as substrate preincubated f... 29072911
Coagulation factor X Ki = 0.4 nM 9.4 Inhibition of factor-10a (unknown origin) 24175584
Coagulation factor X Ki = 0.4 nM 9.4 Inhibition of factor 10a 20503967
Coagulation factor X Ki = 0.4 nM 9.4 Inhibition of Factor 10a 19297154
Coagulation factor X Ki = 0.66 nM 9.18 Inhibition of F10a (unknown origin) using S-2222 as substrate incubated for 15 m... 23644213
Coagulation factor X IC50 = 0.7 nM 9.15 In vitro inhibition of human coagulation factor Xa after incubation for 10 min a... 16161994
Coagulation factor X IC50 = 0.7 nM 9.15 Inhibition of factor 10a 20503967
Coagulation factor X IC50 = 0.7 nM 9.15 Inhibition of human coagulation factor Xa using Boc-Ile-Glu-Gly-Arg-AMC as fluor... 33089691
Coagulation factor X IC50 = 0.7 nM 9.15 Inhibition of factor Xa (unknown origin) 36634753
Coagulation factor X Ki = 0.7 nM 9.15 Inhibition of factor 10a (unknown origin) -
Coagulation factor X IC50 = 1.4 nM 8.85 Enzyme Inhibition Assay: The enzymatic activity of human factor Xa (FXa) was mea... -
Coagulation factor X IC50 = 1.6 nM 8.8 Inhibition of human F10a using S-2765 as substrate after 45 mins 23124211
Coagulation factor X IC50 = 2.1 nM 8.68 Inhibition of FXa (unknown origin) 38889609
Coagulation factor X IC50 = 2.2 nM 8.66 Inhibition of human F10a using S-2765 as substrate after 45 mins by spectra max ... 25911624
Coagulation factor X Ki = 3.4 nM 8.47 Inhibition of human activated Factor X using S-2765 as substrate incubated for 1... 31563807
Coagulation factor X IC50 = 4.59 nM 8.34 Inhibition of human factor 10a assessed as CBS 31.39 substrate hydrolysis by spe... 21732671
Coagulation factor X IC50 = 6.0 nM 8.22 Inhibition of human factor Xa using S-2765 as chromogenic substrate preincubated... 36462436
Coagulation factor X IC50 = 8.52 nM 8.07 Inhibition of human factor 10a using N-Z-D-Arg-Gly-Arg-pNA, S-2765 chromogenic s... 25179681
Unchecked EC50 = 10.0 nM 8.0 Inhibition of tissue factor induced platelet activation in 76% human blood incub... 36462436
Coagulation factor X IC50 = 14.4 nM 7.84 Inhibition of human F10a using S-2765 as substrate preincubated for 10 mins foll... 26114810

Literature References

PubMed DOI Target Context # Activities
25179681 10.1021/jm501045e Rattus norvegicus 16
31563807 10.1016/j.ejmech.2019.111722 ADMET 12
16161994 10.1021/jm050101d ADMET 10
25179681 10.1021/jm501045e Canis familiaris 9
29072911 10.1021/acs.jmedchem.7b00772 Unchecked 8
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
25911624 10.1016/j.ejmech.2015.04.025 Coagulation factor X 6
31563807 10.1016/j.ejmech.2019.111722 Rattus norvegicus 5
20503967 10.1021/jm100146h Rattus norvegicus 5
20503967 10.1021/jm100146h Canis familiaris 5
20503967 10.1021/jm100146h ADMET 4
37468498 10.1038/s41467-023-40064-9 Bile acid receptor 4
24175584 10.1021/jm4005835 Plasma 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
23124211 10.1016/j.ejmech.2012.10.005 Rattus norvegicus 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 3
16161994 10.1021/jm050101d Rattus norvegicus 3

Data from ChEMBL 36 via Core Engine