ARGATROBAN

Search structure
Trade Names:
Synonyms:
Status: Approved (2000)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: B01AE03
UNII: OCY3U280Y3

Structure
InChI Key KXNPVXPOPUZYGB-IOVMHBDKSA-N
Smile CC1CNc2c(cccc2S(=O)(=O)N[C@@H](CCCNC(=N)N)C(=O)N2CC[C@@H](C)C[C@@H]2C(=O)O)C1
InChI
InChI=1S/C23H36N6O5S/c1-14-8-10-29(18(12-14)22(31)32)21(30)17(6-4-9-26-23(24)25)28-35(33,34)19-7-3-5-16-11-15(2)13-27-20(16)19/h3,5,7,14-15,17-18,27-28H,4,6,8-13H2,1-2H3,(H,31,32)(H4,24,25,26)/t14-,15?,17+,18-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H36N6O5S
Molecular Weight 508.65
AlogP 0.91
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 6.0
Number of Rotational Bond 9.0
Polar Surface Area 177.71
Molecular species ZWITTERION
Aromatic Rings 1.0
Heavy Atoms 35.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Thrombin inhibitor DailyMed
Primary Target
coagulation factor II, thrombin
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Serine protease Serine protease PA clan Serine protease S1A subfamily
- 4-1580 2 4-40 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Ischemic Stroke 3 D000083242 ClinicalTrials
Angina, Unstable 2 D000789 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Vascular disorders Thrombosis 19.6
Cardiac disorders Chest pain 15.2
Infections and infestations Pneumonia 15.0
Vascular disorders Thrombophlebitis 15.0
Vascular disorders Thrombosis 15.0
Infections and infestations Sepsis 14.0
Musculoskeletal and connective tissue disorders Back pain 13.7
Respiratory, thoracic and mediastinal disorders Pulmonary embolism 13.0
Infections and infestations Sepsis 12.4
Renal and urinary disorders Haematuria 11.6
Gastrointestinal disorders Nausea 11.5
Cardiac disorders Atrial fibrillation 11.4
Gastrointestinal disorders Diarrhoea 11.0
Vascular disorders Hypotension 10.7
Vascular disorders Hypotension 10.3
Vascular disorders Thrombosis 9.54
Cardiac disorders Chest pain 9.3
Infections and infestations Pneumonia 9.3
Investigations Body temperature increased 9.0
Cardiac disorders Cardiac arrest 9.0
Vascular disorders Hypotension 9.0
General disorders and administration site conditions Pain 9.0
Infections and infestations Sepsis 9.0
Cardiac disorders Dyspnoea 8.8
Cardiac disorders Dyspnoea 8.1
Respiratory, thoracic and mediastinal disorders Apnoea 8.0
Musculoskeletal and connective tissue disorders Back pain 8.0
Investigations Body temperature increased 8.0
Cardiac disorders Cardiac arrest 8.0
Gastrointestinal disorders Constipation 8.0
Vascular disorders Hypotension 8.0
Vascular disorders Peripheral ischaemia 8.0
Infections and infestations Sepsis 8.0
Infections and infestations Urinary tract infection 8.0
Vascular disorders Hypotension 7.2
Gastrointestinal disorders Nausea 7.1
Respiratory, thoracic and mediastinal disorders Apnoea 7.0
Skin and subcutaneous tissue disorders Dermatitis 7.0
Gastrointestinal disorders Diarrhoea 7.0
Vascular disorders Hypotension 7.0
Infections and infestations Infection 7.0
Vascular disorders Peripheral ischaemia 7.0
Respiratory, thoracic and mediastinal disorders Pulmonary embolism 7.0
Skin and subcutaneous tissue disorders Rash 7.0
Renal failure acute 7.0
Cardiac disorders Tachycardia 7.0
Vascular disorders Thrombophlebitis 7.0
Investigations Body temperature increased 6.9
Gastrointestinal disorders Vomiting 6.8
Investigations Haemoglobin 6.7
Vascular disorders Haemorrhage 6.7
Gastrointestinal disorders Vomiting 6.3
Gastrointestinal disorders Diarrhoea 6.2
Respiratory, thoracic and mediastinal disorders Apnoea 6.0
Investigations Body temperature increased 6.0
Cardiac disorders Chest pain 6.0
Nervous system disorders Confusional state 6.0
General disorders and administration site conditions Feeling abnormal 6.0
Gastrointestinal disorders Nausea 6.0
Vascular disorders Peripheral ischaemia 6.0
Metabolism and nutrition disorders Respiratory failure 6.0
Infections and infestations Sepsis 6.0
Vascular disorders Thrombophlebitis 6.0
Gastrointestinal disorders Vomiting 6.0
Cardiac disorders Cardiac arrest 5.8
Vascular disorders Thrombosis 5.61
Nervous system disorders Headache 5.5
Nervous system disorders Headache 5.4
Investigations Haemoglobin 5.3
Vascular disorders Haemorrhage 5.3
Infections and infestations Urinary tract infection 5.2
Respiratory, thoracic and mediastinal disorders Apnoea 5.0
Cardiac disorders Cardiac failure 5.0
Cardiac disorders Dizziness 5.0
Infections and infestations Gangrene 5.0
Vascular disorders Hypotension 5.0
Respiratory, thoracic and mediastinal disorders Pleural effusion 5.0
Infections and infestations Pneumonia 5.0
Renal failure acute 5.0
Cardiac disorders Tachycardia 5.0
Gastrointestinal disorders Vomiting 5.0
Gastrointestinal disorders Nausea 4.8
Cardiac disorders Ventricular tachycardia 4.8
Renal and urinary disorders Renal impairment 4.7
General disorders and administration site conditions Pain 4.6
Infections and infestations Urinary tract infection 4.6
Cardiac disorders Bradycardia 4.5
Gastrointestinal disorders Vomiting 4.2
Vascular disorders Cerebrovascular disorder 4.1
Investigations Body temperature increased 4.0
Skin and subcutaneous tissue disorders Dermatitis 4.0
Gastrointestinal disorders Diarrhoea 4.0
Infections and infestations Gangrene 4.0
Infections and infestations Infection 4.0
Gastrointestinal disorders Nausea 4.0
General disorders and administration site conditions Pain 4.0
Respiratory, thoracic and mediastinal disorders Pleural effusion 4.0
Respiratory, thoracic and mediastinal disorders Pulmonary embolism 4.0
Skin and subcutaneous tissue disorders Rash 4.0
Cardiac disorders Tachycardia 4.0
Vascular disorders Thrombophlebitis 4.0
Infections and infestations Urinary tract infection 4.0
Infections and infestations Infection 3.7
Gastrointestinal disorders Abdominal pain 3.6
Cardiac disorders Acute coronary syndrome 3.6
Investigations Body temperature increased 3.6
Gastrointestinal disorders Gastrointestinal pain 3.6
Vascular disorders Haematoma 3.6
Investigations Haemoglobin 3.6
Vascular disorders Haemorrhage 3.6
Infections and infestations Infection 3.6
Cardiac disorders Myocardial infarction 3.6
Cardiac disorders Acute coronary syndrome 3.57
Cardiac disorders Myocardial infarction 3.57
Cardiac disorders Bradycardia 3.5
Infections and infestations Pneumonia 3.3
Cardiac disorders Cardiac arrest 3.1
General disorders and administration site conditions Pain 3.1
Cardiac disorders Ventricular tachycardia 3.1
Cardiac disorders Atrial fibrillation 3.0
Vascular disorders Hypotension 3.0
Gastrointestinal disorders Nausea 3.0
General disorders and administration site conditions Pain 3.0
Respiratory, thoracic and mediastinal disorders Pleural effusion 3.0
Renal failure acute 3.0
Infections and infestations Sepsis 3.0
Cardiac disorders Tachycardia 3.0
Gastrointestinal disorders Vomiting 3.0
Cardiac disorders Haemoptysis 2.9
Respiratory, thoracic and mediastinal disorders Cough 2.8
Renal and urinary disorders Renal impairment 2.8
Gastrointestinal disorders Abdominal pain 2.6
Gastrointestinal disorders Gastrointestinal pain 2.6
Gastrointestinal disorders Haematemesis 2.6
Vascular disorders Hypotension 2.6
Vascular disorders Cerebrovascular disorder 2.3
Gastrointestinal disorders Abdominal pain 2.2
Gastrointestinal disorders Gastrointestinal pain 2.2
Investigations Body temperature increased 2.1
Investigations Body temperature increased 2.0
Cardiac disorders Chest pain 2.0
Gastrointestinal disorders Constipation 2.0
Skin and subcutaneous tissue disorders Dermatitis 2.0
Gastrointestinal disorders Diarrhoea 2.0
Cardiac disorders Dizziness 2.0
Gastrointestinal disorders Nausea 2.0
Infections and infestations Pneumonia 2.0
Skin and subcutaneous tissue disorders Rash 2.0
Vascular disorders Thrombophlebitis 2.0
Renal and urinary disorders Haematuria 1.8
Cardiac disorders Angina pectoris 1.79
Cardiac disorders Coronary artery occlusion 1.79
Cardiac disorders Coronary artery thrombosis 1.79
Cardiac disorders Myocardial ischaemia 1.79
Gastrointestinal disorders Abdominal pain 1.6
Respiratory, thoracic and mediastinal disorders Cough 1.6
Gastrointestinal disorders Diarrhoea 1.6
Gastrointestinal disorders Gastrointestinal pain 1.6
Nervous system disorders Confusional state 1.0
Gastrointestinal disorders Constipation 1.0
General disorders and administration site conditions Feeling abnormal 1.0
Infections and infestations Gangrene 1.0
Investigations Haemoglobin 1.0
Vascular disorders Haemorrhage 1.0
Metabolism and nutrition disorders Respiratory failure 1.0
Renal and urinary disorders Haematuria 0.9
Cardiac disorders Haemoptysis 0.9
Vascular disorders Angiopathy 0.893
Cardiac disorders Aortic valve stenosis 0.893
Vascular disorders Arterial thrombosis 0.893
Investigations Body temperature increased 0.893
Vascular disorders Cerebrovascular disorder 0.893
Cardiac disorders Chest pain 0.893
Gastrointestinal disorders Gastrointestinal disorder 0.893
Gastrointestinal disorders Gastrointestinal haemorrhage 0.893
Gastrointestinal disorders Gastrooesophageal reflux disease 0.893
Cardiac disorders Pulmonary oedema 0.893
Gastrointestinal disorders Retroperitoneal haemorrhage 0.893
Renal and urinary disorders Haematuria 0.8
Cardiac disorders Haemoptysis 0.8
Investigations Body temperature increased 0.5
Renal and urinary disorders Haematuria 0.5
Investigations Haemoglobin 0.5
Vascular disorders Haemorrhage 0.5
Nervous system disorders Haemorrhage intracranial 0.5
Gastrointestinal disorders Nausea 0.5

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Vascular disorders
29.01
Blood and lymphatic system disorders
7.88
Nervous system disorders
7.6
General disorders and administration site conditions
7.32
Respiratory, thoracic and mediastinal disorders
7.15
Injury, poisoning and procedural complications
6.99
Investigations
6.6
Hepatobiliary disorders
5.93
Cardiac disorders
3.91
Gastrointestinal disorders
3.19
Skin and subcutaneous tissue disorders
2.91
Metabolism and nutrition disorders
2.79
Infections and infestations
2.35

Cross References

Resources Reference
CAS NUMBER 74863-84-6
ChEBI 94385
ChEMBL CHEMBL1166
DrugBank DB00278
DrugCentral 239
FDA SRS OCY3U280Y3
Guide to Pharmacology 6385
PubChem 92721
SureChEMBL SCHEMBL20567702
ZINC ZINC12466745
CONTENTS