Details of the Drug

General Information of Drug (ID: DMECRX1)

Drug Name
Bivalirudin
Synonyms
128270-60-0; Angiomax; Hirulog; bivalirudinum; bivalirudina; Bivalirudin Trifluoroacetate; BG-8967; UNII-TN9BEX005G; BG8967; Bivalirudin Trifluoacetate; TN9BEX005G; D-Phenylalanyl-L-prolyl-L-arginyl-L-prolylglycylglycylglycylglycyl-L-asparaginylglycyl-L-alpha-aspartyl-L-phenylalanyl-L-alpha-glutamyl-L-alpha-glutamyl-L-isoleucyl-L-prolyl-L-alpha-glutamyl-L-alpha-glutamyl-L-tyrosyl-L-leucine; CHEBI:59173; Hirulog-1; Angiox; Bivalirudina; Bivalirudine; Bivalirudinum; The Medicines Company brand of bivalirudin; BG 8967; Angiomax (TN); HS-2004; Bivalirudin [USAN:BAN:INN]; Phe-Pro-Arg-Pro-(Gly)4 desulfato-Tyr63'-hirugen; Phe-Pro-Arg-Pro-(Gly)4-desulfohirudin-(53-64); Phe-Pro-Arg-Pro-(Gly)4-Asn-Gly-Asp-Phe-Glu-Glu-Ile-Pro-Glu-Glu-Tyr-Leu
Indication
Disease Entry ICD 11 Status REF
Thrombocytopenia 3B64 Approved [1], [2]
Therapeutic Class
Antithrombotic Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 5 Molecular Weight (mw) 2180.3
Topological Polar Surface Area (xlogp) -7.1
Rotatable Bond Count (rotbonds) 67
Hydrogen Bond Donor Count (hbonddonor) 28
Hydrogen Bond Acceptor Count (hbondacc) 35
ADMET Property
Clearance
The drug present in the plasma can be removed from the body at the rate of 8.1 mL/min/kg [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 25 minutes [3]
Unbound Fraction
The unbound fraction of drug in plasma is 1% [3]
Vd
The volume of distribution (Vd) of drug is 0.2 L/kg [4]
Chemical Identifiers
Formula
C98H138N24O33
IUPAC Name
(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-4-amino-2-[[2-[[2-[[2-[[2-[[(2S)-1-[(2S)-2-[[(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidine-2-carbonyl]amino]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]acetyl]amino]acetyl]amino]acetyl]amino]-4-oxobutanoyl]amino]acetyl]amino]-3-carboxypropanoyl]amino]-3-phenylpropanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoic acid
Canonical SMILES
CC[C@H](C)[C@@H](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](CC2=CC=C(C=C2)O)C(=O)N[C@@H](CC(C)C)C(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC3=CC=CC=C3)NC(=O)[C@H](CC(=O)O)NC(=O)CNC(=O)[C@H](CC(=O)N)NC(=O)CNC(=O)CNC(=O)CNC(=O)CNC(=O)[C@@H]4CCCN4C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]5CCCN5C(=O)[C@@H](CC6=CC=CC=C6)N
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
InChIKey
OIRCOABEOLEUMC-GEJPAHFPSA-N
Cross-matching ID
PubChem CID
16129704
ChEBI ID
CHEBI:59173
CAS Number
128270-60-0
DrugBank ID
DB00006
TTD ID
D09HVL

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Coagulation factor IIa (F2) TT6L509 THRB_HUMAN Inhibitor [5], [6], [7]
Trypanosoma Trypanothione reductase (Trypano TPR) TTRTKPV TYTR_TRYBB Inhibitor [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Bivalirudin
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Caplacizumab DMPUKA7 Major Increased risk of bleeding by the combination of Bivalirudin and Caplacizumab. Thrombocytopenia [3B64] [24]
Coadministration of a Drug Treating the Disease Different from Bivalirudin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Abciximab DMJO6GV Moderate Increased risk of bleeding by the combination of Bivalirudin and Abciximab. Angina pectoris [BA40] [25]
Eptifibatide DMQXTJS Moderate Increased risk of bleeding by the combination of Bivalirudin and Eptifibatide. Angina pectoris [BA40] [25]
Cilostazol DMZMSCT Major Increased risk of bleeding by the combination of Bivalirudin and Cilostazol. Arterial occlusive disease [BD40] [26]
Vitamin E DMZC90K Moderate Increased risk of bleeding by the combination of Bivalirudin and Vitamin E. Cardiovascular disease [BA00-BE2Z] [27]
Drotrecogin alfa DM59JCN Major Increased risk of bleeding by the combination of Bivalirudin and Drotrecogin alfa. Cerebral ischaemia [8B1Z] [28]
Pentosan polysulfate DM2HRKE Moderate Increased risk of bleeding by the combination of Bivalirudin and Pentosan polysulfate. Chronic pain [MG30] [29]
Phenylbutazone DMAYL0T Moderate Increased risk of bleeding by the combination of Bivalirudin and Phenylbutazone. Chronic pain [MG30] [25]
Ketoprofen DMRKXPT Moderate Increased risk of bleeding by the combination of Bivalirudin and Ketoprofen. Chronic pain [MG30] [25]
Levomilnacipran DMV26S8 Moderate Increased risk of bleeding by the combination of Bivalirudin and Levomilnacipran. Chronic pain [MG30] [30]
Anisindione DM2C48U Major Increased risk of bleeding by the combination of Bivalirudin and Anisindione. Coagulation defect [3B10] [25]
Regorafenib DMHSY1I Major Increased risk of bleeding by the combination of Bivalirudin and Regorafenib. Colorectal cancer [2B91] [31]
Intedanib DMSTA36 Moderate Increased risk of bleeding by the combination of Bivalirudin and Intedanib. Colorectal cancer [2B91] [32]
Ardeparin DMYRX8B Major Increased risk of bleeding by the combination of Bivalirudin and Ardeparin. Coronary thrombosis [BA43] [33]
Danaparoid DM6CLBN Major Increased risk of bleeding by the combination of Bivalirudin and Danaparoid. Deep vein thrombosis [BD71] [33]
Rivaroxaban DMQMBZ1 Major Increased risk of bleeding by the combination of Bivalirudin and Rivaroxaban. Deep vein thrombosis [BD71] [34]
Sertraline DM0FB1J Moderate Increased risk of bleeding by the combination of Bivalirudin and Sertraline. Depression [6A70-6A7Z] [30]
Fluoxetine DM3PD2C Moderate Increased risk of bleeding by the combination of Bivalirudin and Fluoxetine. Depression [6A70-6A7Z] [30]
Vilazodone DM4LECQ Moderate Increased risk of bleeding by the combination of Bivalirudin and Vilazodone. Depression [6A70-6A7Z] [30]
Paroxetine DM5PVQE Moderate Increased risk of bleeding by the combination of Bivalirudin and Paroxetine. Depression [6A70-6A7Z] [30]
Vortioxetine DM6F1PU Moderate Increased risk of bleeding by the combination of Bivalirudin and Vortioxetine. Depression [6A70-6A7Z] [30]
Duloxetine DM9BI7M Moderate Increased risk of bleeding by the combination of Bivalirudin and Duloxetine. Depression [6A70-6A7Z] [30]
Milnacipran DMBFE74 Moderate Increased risk of bleeding by the combination of Bivalirudin and Milnacipran. Depression [6A70-6A7Z] [30]
Escitalopram DMFK9HG Moderate Increased risk of bleeding by the combination of Bivalirudin and Escitalopram. Depression [6A70-6A7Z] [30]
Desvenlafaxine DMHD4PE Moderate Increased risk of bleeding by the combination of Bivalirudin and Desvenlafaxine. Depression [6A70-6A7Z] [30]
Clomipramine DMINRKW Moderate Increased risk of bleeding by the combination of Bivalirudin and Clomipramine. Depression [6A70-6A7Z] [30]
Fluvoxamine DMQTJSX Moderate Increased risk of bleeding by the combination of Bivalirudin and Fluvoxamine. Depression [6A70-6A7Z] [30]
Venlafaxine DMR6QH0 Moderate Increased risk of bleeding by the combination of Bivalirudin and Venlafaxine. Depression [6A70-6A7Z] [30]
Heme DMGC287 Moderate Increased risk of bleeding by the combination of Bivalirudin and Heme. Discovery agent [N.A.] [35]
Apigenin DMI3491 Minor Increased risk of bleeding by the combination of Bivalirudin and Apigenin. Discovery agent [N.A.] [36]
Citalopram derivative 1 DMITX1G Moderate Increased risk of bleeding by the combination of Bivalirudin and Citalopram derivative 1. Discovery agent [N.A.] [30]
PMID28870136-Compound-49 DMTUC9E Moderate Increased risk of bleeding by the combination of Bivalirudin and PMID28870136-Compound-49. Discovery agent [N.A.] [37]
Fenfluramine DM0762O Moderate Increased risk of bleeding by the combination of Bivalirudin and Fenfluramine. Epilepsy/seizure [8A61-8A6Z] [30]
Suprofen DMKXJZ7 Moderate Increased risk of bleeding by the combination of Bivalirudin and Suprofen. Eye anterior segment structural developmental anomaly [LA11] [38]
Mefenamic acid DMK7HFI Moderate Increased risk of bleeding by the combination of Bivalirudin and Mefenamic acid. Female pelvic pain [GA34] [25]
Avapritinib DMK2GZX Major Increased risk of bleeding by the combination of Bivalirudin and Avapritinib. Gastrointestinal stromal tumour [2B5B] [31]
Sulfinpyrazone DMEV954 Moderate Increased risk of bleeding by the combination of Bivalirudin and Sulfinpyrazone. Gout [FA25] [25]
Tipranavir DM8HJX6 Major Increased risk of bleeding by the combination of Bivalirudin and Tipranavir. Human immunodeficiency virus disease [1C60-1C62] [39]
Dipyridamole DMXY30O Moderate Increased risk of bleeding by the combination of Bivalirudin and Dipyridamole. Hypertension [BA00-BA04] [25]
Meclofenamic acid DM05FXR Moderate Increased risk of bleeding by the combination of Bivalirudin and Meclofenamic acid. Inflammatory spondyloarthritis [FA92] [25]
Ticlopidine DMO946V Moderate Increased risk of bleeding by the combination of Bivalirudin and Ticlopidine. Ischaemic/haemorrhagic stroke [8B20] [25]
Tositumomab DMMYZ3D Major Increased risk of bleeding by the combination of Bivalirudin and Tositumomab. Malignant haematopoietic neoplasm [2B33] [40]
Acalabrutinib DM7GCVW Major Increased risk of bleeding by the combination of Bivalirudin and Acalabrutinib. Mature B-cell lymphoma [2A85] [41]
Ibrutinib DMHZCPO Major Increased risk of bleeding by the combination of Bivalirudin and Ibrutinib. Mature B-cell lymphoma [2A85] [42]
Ponatinib DMYGJQO Major Increased risk of bleeding by the combination of Bivalirudin and Ponatinib. Mature B-cell lymphoma [2A85] [43]
Panobinostat DM58WKG Major Increased risk of bleeding by the combination of Bivalirudin and Panobinostat. Multiple myeloma [2A83] [24]
Fedratinib DM4ZBK6 Major Increased risk of bleeding by the combination of Bivalirudin and Fedratinib. Myeloproliferative neoplasm [2A20] [26]
Dasatinib DMJV2EK Major Increased risk of bleeding by the combination of Bivalirudin and Dasatinib. Myeloproliferative neoplasm [2A20] [44]
Omacetaxine mepesuccinate DMPU2WX Major Increased risk of bleeding by the combination of Bivalirudin and Omacetaxine mepesuccinate. Myeloproliferative neoplasm [2A20] [29]
Urokinase DM0GOUD Major Increased risk of bleeding by the combination of Bivalirudin and Urokinase. Myocardial infarction [BA41-BA43] [26]
Anistreplase DM6Q4B0 Major Increased risk of bleeding by the combination of Bivalirudin and Anistreplase. Myocardial infarction [BA41-BA43] [26]
Prasugrel DM7MT6E Major Increased risk of bleeding by the combination of Bivalirudin and Prasugrel. Myocardial infarction [BA41-BA43] [31]
Vorapaxar DMA16BR Major Increased risk of bleeding by the combination of Bivalirudin and Vorapaxar. Myocardial infarction [BA41-BA43] [45]
Tenecteplase DMJYN25 Major Increased risk of bleeding by the combination of Bivalirudin and Tenecteplase. Myocardial infarction [BA41-BA43] [26]
Reteplase DML0D1P Major Increased risk of bleeding by the combination of Bivalirudin and Reteplase. Myocardial infarction [BA41-BA43] [26]
Tirofiban DMQG17S Moderate Increased risk of bleeding by the combination of Bivalirudin and Tirofiban. Myocardial infarction [BA41-BA43] [25]
Sibutramine DMFJTDI Moderate Increased risk of bleeding by the combination of Bivalirudin and Sibutramine. Obesity [5B80-5B81] [30]
Dexfenfluramine DMJ7YDS Moderate Increased risk of bleeding by the combination of Bivalirudin and Dexfenfluramine. Obesity [5B80-5B81] [30]
Diclofenac DMPIHLS Moderate Increased risk of bleeding by the combination of Bivalirudin and Diclofenac. Osteoarthritis [FA00-FA05] [25]
Nepafenac DMYK490 Moderate Increased risk of bleeding by the combination of Bivalirudin and Nepafenac. Osteoarthritis [FA00-FA05] [38]
Naproxen DMZ5RGV Moderate Increased risk of bleeding by the combination of Bivalirudin and Naproxen. Osteoarthritis [FA00-FA05] [25]
MK-4827 DMLYGH4 Moderate Increased risk of bleeding by the combination of Bivalirudin and MK-4827. Ovarian cancer [2C73] [31]
Etodolac DM6WJO9 Moderate Increased risk of bleeding by the combination of Bivalirudin and Etodolac. Pain [MG30-MG3Z] [25]
Ibuprofen DM8VCBE Moderate Increased risk of bleeding by the combination of Bivalirudin and Ibuprofen. Pain [MG30-MG3Z] [25]
Nabumetone DMAT2XH Moderate Increased risk of bleeding by the combination of Bivalirudin and Nabumetone. Pain [MG30-MG3Z] [25]
Piroxicam DMTK234 Moderate Increased risk of bleeding by the combination of Bivalirudin and Piroxicam. Pain [MG30-MG3Z] [25]
Choline salicylate DM8P137 Moderate Increased risk of bleeding by the combination of Bivalirudin and Choline salicylate. Postoperative inflammation [1A00-CA43] [46]
Ketorolac DMI4EL5 Moderate Increased risk of bleeding by the combination of Bivalirudin and Ketorolac. Postoperative inflammation [1A00-CA43] [25]
Bromfenac DMKB79O Moderate Increased risk of bleeding by the combination of Bivalirudin and Bromfenac. Postoperative inflammation [1A00-CA43] [25]
Treprostinil DMTIQF3 Moderate Increased risk of bleeding by the combination of Bivalirudin and Treprostinil. Pulmonary hypertension [BB01] [47]
Epoprostenol DMUTYR2 Moderate Increased risk of bleeding by the combination of Bivalirudin and Epoprostenol. Pulmonary hypertension [BB01] [47]
Iloprost DMVPZBE Moderate Increased risk of bleeding by the combination of Bivalirudin and Iloprost. Pulmonary hypertension [BB01] [47]
Streptokinase DM5JQ0D Major Increased risk of bleeding by the combination of Bivalirudin and Streptokinase. Pulmonary thromboembolism [BB00] [26]
Alteplase DMRJ3YX Major Increased risk of bleeding by the combination of Bivalirudin and Alteplase. Pulmonary thromboembolism [BB00] [26]
Salsalate DM13P4C Moderate Increased risk of bleeding by the combination of Bivalirudin and Salsalate. Rheumatoid arthritis [FA20] [46]
Sulindac DM2QHZU Moderate Increased risk of bleeding by the combination of Bivalirudin and Sulindac. Rheumatoid arthritis [FA20] [25]
Oxaprozin DM9UB0P Moderate Increased risk of bleeding by the combination of Bivalirudin and Oxaprozin. Rheumatoid arthritis [FA20] [25]
Flurbiprofen DMGN4BY Moderate Increased risk of bleeding by the combination of Bivalirudin and Flurbiprofen. Rheumatoid arthritis [FA20] [25]
Fenoprofen DML5VQ0 Moderate Increased risk of bleeding by the combination of Bivalirudin and Fenoprofen. Rheumatoid arthritis [FA20] [25]
Indomethacin DMSC4A7 Moderate Increased risk of bleeding by the combination of Bivalirudin and Indomethacin. Rheumatoid arthritis [FA20] [25]
Tolmetin DMWUIJE Moderate Increased risk of bleeding by the combination of Bivalirudin and Tolmetin. Rheumatoid arthritis [FA20] [25]
Salicyclic acid DM2F8XZ Moderate Increased risk of bleeding by the combination of Bivalirudin and Salicyclic acid. Seborrhoeic dermatitis [EA81] [48]
Curcumin DMQPH29 Minor Increased risk of bleeding by the combination of Bivalirudin and Curcumin. Solid tumour/cancer [2A00-2F9Z] [49]
Warfarin DMJYCVW Major Increased risk of bleeding by the combination of Bivalirudin and Warfarin. Supraventricular tachyarrhythmia [BC81] [25]
Anagrelide DMSQ8MD Major Increased risk of bleeding by the combination of Bivalirudin and Anagrelide. Thrombocytosis [3B63] [26]
Apixaban DM89JLN Major Increased risk of bleeding by the combination of Bivalirudin and Apixaban. Thrombosis [DB61-GB90] [31]
Brilinta DMBR01X Moderate Increased risk of bleeding by the combination of Bivalirudin and Brilinta. Thrombosis [DB61-GB90] [31]
Argatroban DMFI46A Major Increased risk of bleeding by the combination of Bivalirudin and Argatroban. Thrombosis [DB61-GB90] [25]
Dicumarol DMFQCB1 Major Increased risk of bleeding by the combination of Bivalirudin and Dicumarol. Thrombosis [DB61-GB90] [50]
Clopidogrel DMOL54H Moderate Increased risk of bleeding by the combination of Bivalirudin and Clopidogrel. Thrombosis [DB61-GB90] [25]
Cabozantinib DMIYDT4 Major Increased risk of bleeding by the combination of Bivalirudin and Cabozantinib. Thyroid cancer [2D10] [51]
Betrixaban DM2C4RF Major Increased risk of bleeding by the combination of Bivalirudin and Betrixaban. Venous thromboembolism [BD72] [52]
⏷ Show the Full List of 91 DDI Information of This Drug

References

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