BIVALIRUDIN

Search structure
Trade Names:
Synonyms:
Status: Approved (2000)
Entry Type: Protein
Molecule Category: UNKNOWN
ATC: B01AE06
UNII: TN9BEX005G

Structure
InChI Key OIRCOABEOLEUMC-GEJPAHFPSA-N
Smile CC[C@H](C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(=O)O)NC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)CNC(=O)CNC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](N)Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CC(C)C)C(=O)O
InChI
InChI=1S/C98H138N24O33/c1-5-52(4)82(96(153)122-39-15-23-70(122)92(149)114-60(30-34-79(134)135)85(142)111-59(29-33-78(132)133)86(143)116-64(43-55-24-26-56(123)27-25-55)89(146)118-67(97(154)155)40-51(2)3)119-87(144)61(31-35-80(136)137)112-84(141)58(28-32-77(130)131)113-88(145)63(42-54-18-10-7-11-19-54)117-90(147)66(45-81(138)139)110-76(129)50-107-83(140)65(44-71(100)124)109-75(128)49-106-73(126)47-104-72(125)46-105-74(127)48-108-91(148)68-21-13-38-121(68)95(152)62(20-12-36-103-98(101)102)115-93(150)69-22-14-37-120(69)94(151)57(99)41-53-16-8-6-9-17-53/h6-11,16-19,24-27,51-52,57-70,82,123H,5,12-15,20-23,28-50,99H2,1-4H3,(H2,100,124)(H,104,125)(H,105,127)(H,106,126)(H,107,140)(H,108,148)(H,109,128)(H,110,129)(H,111,142)(H,112,141)(H,113,145)(H,114,149)(H,115,150)(H,116,143)(H,117,147)(H,118,146)(H,119,144)(H,130,131)(H,132,133)(H,134,135)(H,136,137)(H,138,139)(H,154,155)(H4,101,102,103)/t52-,57+,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,82-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C98H138N24O33
Molecular Weight 2180.32
AlogP None
Hydrogen Bond Acceptor None
Hydrogen Bond Donor None
Number of Rotational Bond None
Polar Surface Area None
Molecular species None
Aromatic Rings None
Heavy Atoms None

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Thrombin inhibitor DailyMed
Primary Target
coagulation factor II, thrombin

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Myocardial Infarction 3 D009203 ClinicalTrials
Coronary Disease 3 D003327 ClinicalTrials
Heart Diseases 3 D006331 ClinicalTrials
Acute Disease 3 D000208 ClinicalTrials
Subarachnoid Hemorrhage 3 D013345 ClinicalTrials
Myocardial Infarction 3 D009203 ClinicalTrials
Hematologic Diseases 3 D006402 ClinicalTrials
Acute Coronary Syndrome 3 D054058 ClinicalTrials
Hemorrhage 3 D006470 ClinicalTrials
Cardiovascular Diseases 3 D002318 ClinicalTrials
Aortic Valve Stenosis 3 D001024 ClinicalTrials
Venous Thrombosis 1 D020246 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Musculoskeletal and connective tissue disorders Back pain 43.9
Musculoskeletal and connective tissue disorders Back pain 42.4
Musculoskeletal and connective tissue disorders Back pain 42.0
Investigations Haemoglobin 28.0
Vascular disorders Haemorrhage 28.0
Investigations Haemoglobin 25.8
Vascular disorders Haemorrhage 25.8
Investigations Haemoglobin 21.7
Vascular disorders Haemorrhage 21.7
Investigations Haemoglobin 21.6
Vascular disorders Haemorrhage 21.6
Investigations Haemoglobin 17.3
Vascular disorders Haemorrhage 17.3
Vascular disorders Hypotension 17.2
General disorders and administration site conditions Pain 16.6
Gastrointestinal disorders Nausea 16.1
General disorders and administration site conditions Pain 15.3
Gastrointestinal disorders Nausea 15.0
General disorders and administration site conditions Pain 15.0
Gastrointestinal disorders Nausea 14.7
Investigations Haemoglobin 13.6
Vascular disorders Haemorrhage 13.6
Investigations Haemoglobin 12.8
Vascular disorders Haemorrhage 12.8
General disorders and administration site conditions Injection site pain 12.7
Nervous system disorders Headache 12.2
Vascular disorders Hypotension 12.1
Nervous system disorders Headache 12.0
Vascular disorders Hypotension 12.0
Nervous system disorders Headache 10.5
Vascular disorders Haemorrhage 9.25
Musculoskeletal and connective tissue disorders Back pain 9.2
Musculoskeletal and connective tissue disorders Back pain 8.8
General disorders and administration site conditions Injection site pain 8.05
Gastrointestinal disorders Pelvic pain 7.86
Gastrointestinal disorders Vomiting 7.86
Cardiac disorders Bradycardia 7.62
Vascular disorders Haematoma 7.5
Vascular disorders Haematoma 7.4
Nervous system disorders Insomnia 6.57
Psychiatric disorders Anxiety 6.51
Nervous system disorders Insomnia 6.46
Investigations Haemoglobin 6.4
Vascular disorders Haemorrhage 6.4
Gastrointestinal disorders Vomiting 6.39
Vascular disorders Hypertension 6.25
Investigations Haemoglobin 6.1
Vascular disorders Haemorrhage 6.1
Gastrointestinal disorders Pelvic pain 6.02
Blood and lymphatic system disorders Ecchymosis 6.0
Psychiatric disorders Anxiety 5.88
Blood and lymphatic system disorders Ecchymosis 5.8
Investigations Haemoglobin 5.7
Vascular disorders Haemorrhage 5.7
Cardiac disorders Bradycardia 5.46
Vascular disorders Hypertension 5.35
Cardiac disorders Angina pectoris 5.3
Investigations Haemoglobin 5.3
Vascular disorders Haemorrhage 5.3
Cardiac disorders Angina pectoris 5.2
Gastrointestinal disorders Dyspepsia 5.16
Investigations Body temperature increased 5.02
Gastrointestinal disorders Abdominal pain 4.83
Gastrointestinal disorders Gastrointestinal pain 4.83
Gastrointestinal disorders Abdominal pain 4.77
Investigations Body temperature increased 4.77
Gastrointestinal disorders Gastrointestinal pain 4.77
Psychiatric disorders Nervousness 4.72
Psychiatric disorders Tension 4.72
Gastrointestinal disorders Dyspepsia 4.63
Renal and urinary disorders Urinary retention 4.56
Vascular disorders Haematoma 4.5
Investigations Haemoglobin 4.2
Vascular disorders Haemorrhage 4.2
Renal and urinary disorders Urinary retention 4.12
Psychiatric disorders Nervousness 4.04
Psychiatric disorders Tension 4.04
Investigations Haemoglobin 4.0
Vascular disorders Haemorrhage 4.0
Vascular disorders Hypotension 4.0
Cardiac disorders Chest pain 3.7
Blood and lymphatic system disorders Ecchymosis 3.7
Investigations Haemoglobin 3.7
Vascular disorders Haemorrhage 3.7
Vascular disorders Haemorrhage 3.66
Cardiac disorders Chest pain 3.4
General disorders and administration site conditions Pain 3.4
Gastrointestinal disorders Nausea 3.2
Nervous system disorders Headache 3.1
Vascular disorders Hypotension 3.1
Investigations Haemoglobin 3.0
Vascular disorders Haemorrhage 3.0
Nervous system disorders Headache 3.0
Gastrointestinal disorders Nausea 3.0
Musculoskeletal and connective tissue disorders Back pain 2.9
Musculoskeletal and connective tissue disorders Back pain 2.8
Nervous system disorders Headache 2.8
General disorders and administration site conditions Injection site pain 2.7
Nervous system disorders Headache 2.6
Investigations Haemoglobin 2.4
Vascular disorders Haemorrhage 2.4
Gastrointestinal disorders Nausea 2.4
General disorders and administration site conditions Pain 2.4
Cardiac disorders Chest pain 2.3
Investigations Haemoglobin 2.3
Vascular disorders Haemorrhage 2.3
Vascular disorders Haematoma 2.2
Gastrointestinal disorders Nausea 2.1
Respiratory, thoracic and mediastinal disorders Epistaxis 1.9
Investigations Haemoglobin 1.9
Vascular disorders Haemorrhage 1.9
Investigations Haemoglobin 1.7
Vascular disorders Haemorrhage 1.7
Vascular disorders Hypotension 1.7
Vascular disorders Hypotension 1.6
Gastrointestinal disorders Gingival bleeding 1.5
Nervous system disorders Insomnia 1.5
Respiratory, thoracic and mediastinal disorders Epistaxis 1.4
Nervous system disorders Insomnia 1.4
Cardiac disorders Bradycardia 1.2
Vascular disorders Hypertension 1.2
Cardiac disorders Atrial fibrillation 1.1
Investigations Body temperature increased 1.1
Blood and lymphatic system disorders Thrombocytopenia 1.1
Gastrointestinal disorders Abdominal pain 1.0
Cardiac disorders Atrial fibrillation 1.0
Investigations Body temperature increased 1.0
Gastrointestinal disorders Gastrointestinal pain 1.0
Nervous system disorders Haemorrhage intracranial 1.0
Vascular disorders Hypertension 1.0
Gastrointestinal disorders Retroperitoneal haemorrhage 1.0
Blood and lymphatic system disorders Thrombocytopenia 1.0
Cardiac disorders Ventricular tachycardia 1.0
Gastrointestinal disorders Vomiting 1.0
Investigations Haemoglobin 0.9
Vascular disorders Haemorrhage 0.9
Cardiac disorders Ventricular tachycardia 0.9
Gastrointestinal disorders Abdominal pain 0.8
Gastrointestinal disorders Gastrointestinal pain 0.8
Respiratory, thoracic and mediastinal disorders Epistaxis 0.7
Vascular disorders Haematoma 0.7
Gastrointestinal disorders Retroperitoneal haemorrhage 0.697
Gastrointestinal disorders Gingival bleeding 0.6
Investigations Body temperature increased 0.5
Cardiac disorders Haemoptysis 0.5
Gastrointestinal disorders Nausea 0.5
Gastrointestinal disorders Retroperitoneal haemorrhage 0.5
Cardiac disorders Angina pectoris 0.4
Vascular disorders Hypotension 0.4
Gastrointestinal disorders Melaena 0.4
Gastrointestinal disorders Gingival bleeding 0.3
Cardiac disorders Haemoptysis 0.3
General disorders and administration site conditions Injection site pain 0.3
Gastrointestinal disorders Melaena 0.3
Blood and lymphatic system disorders Thrombocytopenia 0.3
Gastrointestinal disorders Retroperitoneal haemorrhage 0.231
Gastrointestinal disorders Melaena 0.22
Cardiac disorders Angina pectoris 0.2
Nervous system disorders Headache 0.2
Vascular disorders Hypotension 0.2
Gastrointestinal disorders Nausea 0.2
Gastrointestinal disorders Retroperitoneal haemorrhage 0.2
Gastrointestinal disorders Vomiting 0.2
Gastrointestinal disorders Gingival bleeding 0.12
Cardiac disorders Haemoptysis 0.1
Nervous system disorders Haemorrhage intracranial 0.1
General disorders and administration site conditions Injection site pain 0.1
Gastrointestinal disorders Nausea 0.1
Gastrointestinal disorders Vomiting 0.1
Nervous system disorders Haemorrhage intracranial 0.093
Gastrointestinal disorders Retroperitoneal haemorrhage 0.069
Nervous system disorders Haemorrhage intracranial 0.0463
Cardiac disorders Haemoptysis 0.0046
Respiratory, thoracic and mediastinal disorders Epistaxis 0.0012
Investigations Haemoglobin 0.001
Vascular disorders Haemorrhage 0.001
Blood and lymphatic system disorders Ecchymosis 0.0001
Vascular disorders Haematoma 0.0001
Investigations Haemoglobin 0.0001
Vascular disorders Haemorrhage 0.0001

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
24.2
Injury, poisoning and procedural complications
22.33
Eye disorders
14.7
Nervous system disorders
10.73
Skin and subcutaneous tissue disorders
5.47
Gastrointestinal disorders
5.36
Vascular disorders
3.08
Respiratory, thoracic and mediastinal disorders
2.9
Product issues
2.8

Cross References

Resources Reference
CAS NUMBER 128270-60-0
ChEBI 59173
ChEMBL CHEMBL2103749
DrugBank DB00006
DrugCentral 385
EPA CompTox DTXSID00155847
FDA SRS TN9BEX005G
Guide to Pharmacology 6470
PharmGKB PA10032
SureChEMBL SCHEMBL25739
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