ChEMBL logo

ChEMBL

spacer
ChEMBL Statistics
  Loading Statistics...
spacer

Compound Report Card

Compound Name and Classification

Compound ID CHEMBL198362
CHEMBL198362
Compound Name RIVAROXABAN
ChEMBL Synonyms RIVAROXABAN | XARELTO | BAY 59-7939
Max Phase 4 (Approved)
Trade Names XARELTO
Molecular Formula C19H18ClN3O5S

Additional synonyms for CHEMBL198362 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Clc1ccc(s1)C(=O)NC[C@H]2CN(C(=O)O2)c3ccc(cc3)N4CCOCC4=O
Standard InChI InChI=1S/C19H18ClN3O5S/c20-16-6-5-15(29-16)18(25)21-9-14-10- ...
Download InChI
Standard InChI Key KGFYHTZWPPHNLQ-AWEZNQCLSA-N

Sources

  • AstraZeneca Deposited Data
  • BindingDB Database
  • British National Formulary
  • Orange Book
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL198362

Molecule Features

CHEMBL198362 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:Y Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Coagulation factor X inhibitor Coagulation factor X DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Diabetes Mellitus, Type 2D003924EFO:0001360type II diabetes mellitus3ClinicalTrials
ThrombosisD013927HP:0004419Recurrent thrombophlebitis4ATC
Acute Coronary SyndromeD054058EFO:0005672acute coronary syndrome2ClinicalTrials
Anemia, Sickle CellD000755Orphanet:232Sickle cell anemia2ClinicalTrials
Coronary Artery DiseaseD003324EFO:0000378coronary artery disease2ClinicalTrials
Heart DiseasesD006331EFO:0003777heart disease2ClinicalTrials
Peripheral Arterial DiseaseD058729EFO:0004265peripheral arterial disease3ClinicalTrials
Renal Insufficiency, ChronicD051436EFO:0003884chronic kidney disease1ClinicalTrials
ThrombocytopeniaD0139213ClinicalTrials
Venous ThromboembolismD054556EFO:0004286venous thromboembolism3ClinicalTrials
Antiphospholipid SyndromeD016736EFO:0002689antiphospholipid syndrome3ClinicalTrials
IschemiaD007511EFO:0000556ischemia2ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma2ClinicalTrials
Pulmonary EmbolismD011655EFO:0003827pulmonary embolism4ClinicalTrials
DailyMed
DailyMed
Renal InsufficiencyD0514373ClinicalTrials
Atrial FibrillationD001281EFO:0000275atrial fibrillation4ClinicalTrials
DailyMed
DailyMed
Liver CirrhosisD008103EFO:0001422cirrhosis of liver3ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm3ClinicalTrials
Rheumatic Heart DiseaseD012214EFO:1001161rheumatic heart disease3ClinicalTrials
HemorrhageD006470MP:0001914hemorrhage2ClinicalTrials
StrokeD020521EFO:0000712stroke3ClinicalTrials
Venous ThrombosisD020246EFO:0003907deep vein thrombosis4ClinicalTrials
DailyMed
DailyMed
Venous ThrombosisD020246HP:0004936Venous thrombosis4ClinicalTrials

Clinical Data

ClinicalTrials.gov RIVAROXABAN
The Cochrane Collaboration RIVAROXABAN

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL198362. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL5062 Coagulation factor X Oryctolagus cuniculus 1.000
CHEMBL244 Coagulation factor X Homo sapiens 1.000

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL5062 Coagulation factor X Oryctolagus cuniculus 1.000
CHEMBL244 Coagulation factor X Homo sapiens 1.000

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
435.9 435.0656 2.52 5 88.18 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
6 1 0 8 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
13.36 1.01 1.71 1.71 2 29 0.78

Structural Alerts

There are no structural alerts for CHEMBL198362

Compound Cross References

ATC B - BLOOD AND BLOOD FORMING ORGANS
B01 - ANTITHROMBOTIC AGENTS
B01A - ANTITHROMBOTIC AGENTS
B01AF - Direct factor Xa inhibitors
B01AF01 - rivaroxaban

ChemSpider ChemSpider:KGFYHTZWPPHNLQ-AWEZNQCLSA-N
DailyMed rivaroxaban
Wikipedia Rivaroxaban

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL198362



ACToR 366789-02-8
BindingDB 7840
Brenda 85908 4737
ChEBI 68579
ChemicalBook CB91176772
DrugBank DB06228
DrugCentral 4182
eMolecules 27523812
FDA SRS 9NDF7JZ4M3
Guide to Pharmacology 6388
IBM Patent System 45B6912085012BF0D3D9936D8235985B
LINCS LSM-5499
MolPort MolPort-003-850-195
Nikkaji J2.395.184C
PDBe RIV
PubChem 9875401
PubChem: Drugs of the Future 22395270
PubChem: Thomson Pharma 14856850 15279667
SureChEMBL SCHEMBL3914
ZINC ZINC000003964126

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/KGFYHTZWPPHNLQ-AWEZNQCLSA-N spacer
spacer