RIVAROXABAN

Search structure
Trade Names:
Synonyms:
Status: Approved (2011)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: B01AF01
UNII: 9NDF7JZ4M3

Structure
InChI Key KGFYHTZWPPHNLQ-AWEZNQCLSA-N
Smile O=C(NC[C@H]1CN(c2ccc(N3CCOCC3=O)cc2)C(=O)O1)c1ccc(Cl)s1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H18ClN3O5S
Molecular Weight 435.89
AlogP 2.52
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 88.18
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 29.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Coagulation factor X inhibitor DailyMed
Primary Target
coagulation factor X
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Serine protease Serine protease PA clan Serine protease S1A subfamily
- 1-700 - 0-3 15-55

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Atrial Fibrillation 4 D001281 ClinicalTrials
Thrombosis 4 D013927 ClinicalTrials
Venous Thrombosis 4 D020246 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Diabetes Mellitus, Type 2 3 D003924 ClinicalTrials
Antiphospholipid Syndrome 3 D016736 ClinicalTrials
Venous Thromboembolism 3 D054556 ClinicalTrials
Liver Cirrhosis 3 D008103 ClinicalTrials
Peripheral Arterial Disease 3 D058729 ClinicalTrials
Rheumatic Heart Disease 3 D012214 ClinicalTrials
Myocardial Infarction 3 D009203 ClinicalTrials
Neoplasms 3 D009369 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Hematoma 3 D006406 ClinicalTrials
Renal Insufficiency 3 D051437 ClinicalTrials
Thrombocytopenia 3 D013921 ClinicalTrials
Coronary Disease 3 D003327 ClinicalTrials
Ischemic Stroke 3 D000083242 ClinicalTrials
Neoplasms 3 D009369 ClinicalTrials
Stroke 3 D020521 ClinicalTrials
Acute Coronary Syndrome 2 D054058 ClinicalTrials
Anemia, Sickle Cell 2 D000755 ClinicalTrials
Aortic Valve Disease 2 D000082862 ClinicalTrials
Ischemia 2 D007511 ClinicalTrials
Thromboembolism 2 D013923 ClinicalTrials
Multiple Myeloma 2 D009101 ClinicalTrials
Heart Diseases 2 D006331 ClinicalTrials
Hemorrhage 2 D006470 ClinicalTrials
Renal Insufficiency, Chronic 1 D051436 ClinicalTrials
Obesity, Morbid 1 D009767 ClinicalTrials

Related Entries

MCS

Side Effects from Label

Side effects Relative Frequency (%) Labels
Investigations Haemoglobin 28.3
Vascular disorders Haemorrhage 28.3
Investigations Haemoglobin 28.0
Vascular disorders Haemorrhage 28.0
Investigations Haemoglobin 17.4
Vascular disorders Haemorrhage 17.4
Investigations Haemoglobin
Vascular disorders Haemorrhage
Investigations Haemoglobin 8.67
Vascular disorders Haemorrhage 8.67
Investigations Haemoglobin 8.64
Vascular disorders Haemorrhage 8.64
Investigations Haemoglobin 5.82
Vascular disorders Haemorrhage 5.82
Investigations Haemoglobin 5.55
Vascular disorders Haemorrhage 5.55
Investigations Haemoglobin 5.42
Vascular disorders Haemorrhage 5.42
Investigations Haemoglobin 5.35
Vascular disorders Haemorrhage 5.35
Investigations Haemoglobin 4.48
Vascular disorders Haemorrhage 4.48
Investigations Haemoglobin 4.22
Vascular disorders Haemorrhage 4.22
Musculoskeletal and connective tissue disorders Back pain 3.68
Investigations Haemoglobin 3.6
Vascular disorders Haemorrhage 3.6
Investigations Haemoglobin 3.5
Vascular disorders Haemorrhage 3.5
Gastrointestinal disorders Gastrointestinal haemorrhage 3.11
General disorders and administration site conditions Wound secretion 2.79
Investigations Haemoglobin 2.57
Vascular disorders Haemorrhage 2.57
Skin and subcutaneous tissue disorders Pruritus 2.14
Investigations Haemoglobin 2.09
Vascular disorders Haemorrhage 2.09
Gastrointestinal disorders Gastrointestinal haemorrhage 2.0
General disorders and administration site conditions Wound secretion 1.97
Gastrointestinal disorders Gastrointestinal haemorrhage 1.96
Investigations Haemoglobin 1.87
Vascular disorders Haemorrhage 1.87
Investigations Haemoglobin 1.75
Vascular disorders Haemorrhage 1.75
Skin and subcutaneous tissue disorders Pruritus 1.75
Investigations Haemoglobin 1.7
Vascular disorders Haemorrhage 1.7
Gastrointestinal disorders Abdominal pain upper 1.67
Musculoskeletal and connective tissue disorders Osteoarthritis 1.67
Musculoskeletal and connective tissue disorders Pain in extremity 1.65
Skin and subcutaneous tissue disorders Blister 1.4
Skin and subcutaneous tissue disorders Dermatitis bullous 1.4
Gastrointestinal disorders Dyspepsia 1.34
Investigations Haemoglobin 1.34
Vascular disorders Haemorrhage 1.34
Investigations Haemoglobin 1.33
Vascular disorders Haemorrhage 1.33
Investigations Haemoglobin 1.3
Vascular disorders Haemorrhage 1.3
Investigations Haemoglobin 1.28
Vascular disorders Haemorrhage 1.28
Cardiac disorders Dizziness 1.23
Nervous system disorders Loss of consciousness 1.23
Vascular disorders Shock 1.23
Cardiac disorders Syncope 1.23
Musculoskeletal and connective tissue disorders Pain in extremity 1.22
Gastrointestinal disorders Gastrointestinal haemorrhage 1.2
Investigations Haemoglobin 1.2
Vascular disorders Haemorrhage 1.2
Musculoskeletal and connective tissue disorders Back pain
Investigations Haemoglobin
Vascular disorders Haemorrhage
Infections and infestations Sinusitis 1.17
Infections and infestations Urinary tract infection 1.17
Musculoskeletal and connective tissue disorders Muscle spasms 1.16
General disorders and administration site conditions Asthenia 1.0
General disorders and administration site conditions Fatigue 1.0
Gastrointestinal disorders Oropharyngeal pain 1.0
Gastrointestinal disorders Toothache 1.0
Investigations Haemoglobin 0.969
Vascular disorders Haemorrhage 0.969
Investigations Haemoglobin 0.899
Vascular disorders Haemorrhage 0.899
Skin and subcutaneous tissue disorders Blister 0.884
Skin and subcutaneous tissue disorders Dermatitis bullous 0.884
Musculoskeletal and connective tissue disorders Osteoarthritis
Investigations Haemoglobin 0.8
Vascular disorders Haemorrhage 0.8
Investigations Haemoglobin 0.772
Vascular disorders Haemorrhage 0.772
Cardiac disorders Dizziness 0.707
Nervous system disorders Loss of consciousness 0.707
Musculoskeletal and connective tissue disorders Muscle spasms 0.707
Vascular disorders Shock 0.707
Cardiac disorders Syncope 0.707
Investigations Haemoglobin 0.705
Vascular disorders Haemorrhage 0.705
Gastrointestinal disorders Dyspepsia
Investigations Haemoglobin 0.669
Vascular disorders Haemorrhage 0.669
Investigations Haemoglobin 0.654
Vascular disorders Haemorrhage 0.654
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Fatigue
Infections and infestations Sinusitis
Infections and infestations Urinary tract infection
Investigations Haemoglobin 0.5
Vascular disorders Haemorrhage 0.5
Investigations Haemoglobin 0.38
Vascular disorders Haemorrhage 0.38
Gastrointestinal disorders Oropharyngeal pain
Investigations Haemoglobin 0.312
Vascular disorders Haemorrhage 0.312
Investigations Haemoglobin 0.242
Vascular disorders Haemorrhage 0.242
Investigations Haemoglobin 0.2
Vascular disorders Haemorrhage 0.2
Investigations Haemoglobin 0.199
Vascular disorders Haemorrhage 0.199
Investigations Haemoglobin 0.194
Vascular disorders Haemorrhage 0.194
Gastrointestinal disorders Abdominal pain upper
Reproductive system and breast disorders Menorrhagia 0.167
Investigations Haemoglobin 0.156
Vascular disorders Haemorrhage 0.156
Investigations Haemoglobin 0.133
Vascular disorders Haemorrhage 0.133
Investigations Haemoglobin 0.111
Vascular disorders Haemorrhage 0.111
Investigations Haemoglobin 0.0891
Vascular disorders Haemorrhage 0.0891
Investigations Haemoglobin 0.0884
Vascular disorders Haemorrhage 0.0884
Investigations Haemoglobin 0.0726
Vascular disorders Haemorrhage 0.0726
Investigations Haemoglobin 0.0669
Vascular disorders Haemorrhage 0.0669
Investigations Haemoglobin 0.0663
Vascular disorders Haemorrhage 0.0663
Investigations Haemoglobin 0.0446
Vascular disorders Haemorrhage 0.0446
Investigations Haemoglobin 0.0442
Vascular disorders Haemorrhage 0.0442
Investigations Haemoglobin 0.0223
Vascular disorders Haemorrhage 0.0223
Investigations Haemoglobin 0.0221
Vascular disorders Haemorrhage 0.0221

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Vascular disorders
32.4
Gastrointestinal disorders
13.91
Nervous system disorders
8.82
Injury, poisoning and procedural complications
6.71
General disorders and administration site conditions
5.92
Respiratory, thoracic and mediastinal disorders
5.09
Cardiac disorders
3.9
Renal and urinary disorders
2.95
Skin and subcutaneous tissue disorders
2.88
Investigations
2.77
Musculoskeletal and connective tissue disorders
2.49
Reproductive system and breast disorders
2.22
Blood and lymphatic system disorders
2.07

Cross References

Resources Reference
CAS NUMBER 366789-02-8
ChEBI 68579
ChEMBL CHEMBL198362
DrugBank DB06228
DrugCentral 4182
FDA SRS 9NDF7JZ4M3
Guide to Pharmacology 6388
KEGG D07086
PDB RIV
PubChem 9875401
SureChEMBL SCHEMBL3914
ZINC ZINC000003964126
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