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]

• Therapeutic Class: Antithrombotic Agents
• Affected Organisms: Humans and other mammals
• ATC Code:
  B01AE06: Bivalirudin
  B01AE: Direct thrombin inhibitors
  B01A: ANTITHROMBOTIC AGENTS
  B01: ANTITHROMBOTIC AGENTS
  B: BLOOD AND BLOOD FORMING ORGANS
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 5:
  Molecular Weight (mw); 2180.3
  Logarithm of the Partition Coefficient (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 [2]
  Half-life: The concentration or amount of drug in body reduced by one-half in 25 minutes [2]
  Unbound Fraction: The unbound fraction of drug in plasma is 1% [2]
  Vd: The volume of distribution (Vd) of drug is 0.2 L/kg []
• 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
  UNII: TN9BEX005G
  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	[3]
Trypanosoma Trypanothione reductase (Trypano TPR)	TTRTKPV	TYTR_TRYBB	Inhibitor	[4]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
C-reactive protein (CRP)	OT0RFT8F	CRP_HUMAN	Gene/Protein Processing	[5]
Myeloperoxidase (MPO)	OTOOXLIN	PERM_HUMAN	Gene/Protein Processing	[6]
Proteinase-activated receptor 1 (F2R)	OT4WVWBO	PAR1_HUMAN	Gene/Protein Processing	[7]
Proteinase-activated receptor 4 (F2RL3)	OTUNAKDB	PAR4_HUMAN	Gene/Protein Processing	[7]

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]	[8]

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]	[9]
Eptifibatide	DMQXTJS	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Eptifibatide.	Angina pectoris [BA40]	[9]
Cilostazol	DMZMSCT	Major	Increased risk of bleeding by the combination of Bivalirudin and Cilostazol.	Arterial occlusive disease [BD40]	[10]
Vitamin E	DMZC90K	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Vitamin E.	Cardiovascular disease [BA00-BE2Z]	[11]
Drotrecogin alfa	DM59JCN	Major	Increased risk of bleeding by the combination of Bivalirudin and Drotrecogin alfa.	Cerebral ischaemia [8B1Z]	[12]
Pentosan polysulfate	DM2HRKE	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Pentosan polysulfate.	Chronic pain [MG30]	[13]
Phenylbutazone	DMAYL0T	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Phenylbutazone.	Chronic pain [MG30]	[9]
Ketoprofen	DMRKXPT	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Ketoprofen.	Chronic pain [MG30]	[9]
Levomilnacipran	DMV26S8	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Levomilnacipran.	Chronic pain [MG30]	[14]
Anisindione	DM2C48U	Major	Increased risk of bleeding by the combination of Bivalirudin and Anisindione.	Coagulation defect [3B10]	[9]
Regorafenib	DMHSY1I	Major	Increased risk of bleeding by the combination of Bivalirudin and Regorafenib.	Colorectal cancer [2B91]	[15]
Intedanib	DMSTA36	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Intedanib.	Colorectal cancer [2B91]	[16]
Ardeparin	DMYRX8B	Major	Increased risk of bleeding by the combination of Bivalirudin and Ardeparin.	Coronary thrombosis [BA43]	[17]
Danaparoid	DM6CLBN	Major	Increased risk of bleeding by the combination of Bivalirudin and Danaparoid.	Deep vein thrombosis [BD71]	[17]
Rivaroxaban	DMQMBZ1	Major	Increased risk of bleeding by the combination of Bivalirudin and Rivaroxaban.	Deep vein thrombosis [BD71]	[18]
Sertraline	DM0FB1J	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Sertraline.	Depression [6A70-6A7Z]	[14]
Fluoxetine	DM3PD2C	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Fluoxetine.	Depression [6A70-6A7Z]	[14]
Vilazodone	DM4LECQ	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Vilazodone.	Depression [6A70-6A7Z]	[14]
Paroxetine	DM5PVQE	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Paroxetine.	Depression [6A70-6A7Z]	[14]
Vortioxetine	DM6F1PU	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Vortioxetine.	Depression [6A70-6A7Z]	[14]
Duloxetine	DM9BI7M	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Duloxetine.	Depression [6A70-6A7Z]	[14]
Milnacipran	DMBFE74	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Milnacipran.	Depression [6A70-6A7Z]	[14]
Escitalopram	DMFK9HG	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Escitalopram.	Depression [6A70-6A7Z]	[14]
Desvenlafaxine	DMHD4PE	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Desvenlafaxine.	Depression [6A70-6A7Z]	[14]
Clomipramine	DMINRKW	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Clomipramine.	Depression [6A70-6A7Z]	[14]
Fluvoxamine	DMQTJSX	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Fluvoxamine.	Depression [6A70-6A7Z]	[14]
Venlafaxine	DMR6QH0	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Venlafaxine.	Depression [6A70-6A7Z]	[14]
Heme	DMGC287	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Heme.	Discovery agent [N.A.]	[19]
Apigenin	DMI3491	Minor	Increased risk of bleeding by the combination of Bivalirudin and Apigenin.	Discovery agent [N.A.]	[20]
Citalopram derivative 1	DMITX1G	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Citalopram derivative 1.	Discovery agent [N.A.]	[14]
PMID28870136-Compound-49	DMTUC9E	Moderate	Increased risk of bleeding by the combination of Bivalirudin and PMID28870136-Compound-49.	Discovery agent [N.A.]	[21]
Fenfluramine	DM0762O	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Fenfluramine.	Epilepsy/seizure [8A61-8A6Z]	[14]
Suprofen	DMKXJZ7	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Suprofen.	Eye anterior segment structural developmental anomaly [LA11]	[22]
Mefenamic acid	DMK7HFI	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Mefenamic acid.	Female pelvic pain [GA34]	[9]
Avapritinib	DMK2GZX	Major	Increased risk of bleeding by the combination of Bivalirudin and Avapritinib.	Gastrointestinal stromal tumour [2B5B]	[15]
Sulfinpyrazone	DMEV954	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Sulfinpyrazone.	Gout [FA25]	[9]
Tipranavir	DM8HJX6	Major	Increased risk of bleeding by the combination of Bivalirudin and Tipranavir.	Human immunodeficiency virus disease [1C60-1C62]	[23]
Dipyridamole	DMXY30O	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Dipyridamole.	Hypertension [BA00-BA04]	[9]
Meclofenamic acid	DM05FXR	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Meclofenamic acid.	Inflammatory spondyloarthritis [FA92]	[9]
Ticlopidine	DMO946V	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Ticlopidine.	Ischaemic/haemorrhagic stroke [8B20]	[9]
Tositumomab	DMMYZ3D	Major	Increased risk of bleeding by the combination of Bivalirudin and Tositumomab.	Malignant haematopoietic neoplasm [2B33]	[24]
Acalabrutinib	DM7GCVW	Major	Increased risk of bleeding by the combination of Bivalirudin and Acalabrutinib.	Mature B-cell lymphoma [2A85]	[25]
Ibrutinib	DMHZCPO	Major	Increased risk of bleeding by the combination of Bivalirudin and Ibrutinib.	Mature B-cell lymphoma [2A85]	[26]
Ponatinib	DMYGJQO	Major	Increased risk of bleeding by the combination of Bivalirudin and Ponatinib.	Mature B-cell lymphoma [2A85]	[27]
Panobinostat	DM58WKG	Major	Increased risk of bleeding by the combination of Bivalirudin and Panobinostat.	Multiple myeloma [2A83]	[8]
Fedratinib	DM4ZBK6	Major	Increased risk of bleeding by the combination of Bivalirudin and Fedratinib.	Myeloproliferative neoplasm [2A20]	[10]
Dasatinib	DMJV2EK	Major	Increased risk of bleeding by the combination of Bivalirudin and Dasatinib.	Myeloproliferative neoplasm [2A20]	[28]
Omacetaxine mepesuccinate	DMPU2WX	Major	Increased risk of bleeding by the combination of Bivalirudin and Omacetaxine mepesuccinate.	Myeloproliferative neoplasm [2A20]	[13]
Urokinase	DM0GOUD	Major	Increased risk of bleeding by the combination of Bivalirudin and Urokinase.	Myocardial infarction [BA41-BA43]	[10]
Anistreplase	DM6Q4B0	Major	Increased risk of bleeding by the combination of Bivalirudin and Anistreplase.	Myocardial infarction [BA41-BA43]	[10]
Prasugrel	DM7MT6E	Major	Increased risk of bleeding by the combination of Bivalirudin and Prasugrel.	Myocardial infarction [BA41-BA43]	[15]
Vorapaxar	DMA16BR	Major	Increased risk of bleeding by the combination of Bivalirudin and Vorapaxar.	Myocardial infarction [BA41-BA43]	[29]
Tenecteplase	DMJYN25	Major	Increased risk of bleeding by the combination of Bivalirudin and Tenecteplase.	Myocardial infarction [BA41-BA43]	[10]
Reteplase	DML0D1P	Major	Increased risk of bleeding by the combination of Bivalirudin and Reteplase.	Myocardial infarction [BA41-BA43]	[10]
Tirofiban	DMQG17S	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Tirofiban.	Myocardial infarction [BA41-BA43]	[9]
Sibutramine	DMFJTDI	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Sibutramine.	Obesity [5B80-5B81]	[14]
Dexfenfluramine	DMJ7YDS	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Dexfenfluramine.	Obesity [5B80-5B81]	[14]
Diclofenac	DMPIHLS	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Diclofenac.	Osteoarthritis [FA00-FA05]	[9]
Nepafenac	DMYK490	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Nepafenac.	Osteoarthritis [FA00-FA05]	[22]
Naproxen	DMZ5RGV	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Naproxen.	Osteoarthritis [FA00-FA05]	[9]
MK-4827	DMLYGH4	Moderate	Increased risk of bleeding by the combination of Bivalirudin and MK-4827.	Ovarian cancer [2C73]	[15]
Etodolac	DM6WJO9	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Etodolac.	Pain [MG30-MG3Z]	[9]
Ibuprofen	DM8VCBE	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Ibuprofen.	Pain [MG30-MG3Z]	[9]
Nabumetone	DMAT2XH	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Nabumetone.	Pain [MG30-MG3Z]	[9]
Piroxicam	DMTK234	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Piroxicam.	Pain [MG30-MG3Z]	[9]
Choline salicylate	DM8P137	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Choline salicylate.	Postoperative inflammation [1A00-CA43]	[30]
Ketorolac	DMI4EL5	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Ketorolac.	Postoperative inflammation [1A00-CA43]	[9]
Bromfenac	DMKB79O	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Bromfenac.	Postoperative inflammation [1A00-CA43]	[9]
Treprostinil	DMTIQF3	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Treprostinil.	Pulmonary hypertension [BB01]	[31]
Epoprostenol	DMUTYR2	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Epoprostenol.	Pulmonary hypertension [BB01]	[31]
Iloprost	DMVPZBE	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Iloprost.	Pulmonary hypertension [BB01]	[31]
Streptokinase	DM5JQ0D	Major	Increased risk of bleeding by the combination of Bivalirudin and Streptokinase.	Pulmonary thromboembolism [BB00]	[10]
Alteplase	DMRJ3YX	Major	Increased risk of bleeding by the combination of Bivalirudin and Alteplase.	Pulmonary thromboembolism [BB00]	[10]
Salsalate	DM13P4C	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Salsalate.	Rheumatoid arthritis [FA20]	[30]
Sulindac	DM2QHZU	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Sulindac.	Rheumatoid arthritis [FA20]	[9]
Oxaprozin	DM9UB0P	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Oxaprozin.	Rheumatoid arthritis [FA20]	[9]
Flurbiprofen	DMGN4BY	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Flurbiprofen.	Rheumatoid arthritis [FA20]	[9]
Fenoprofen	DML5VQ0	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Fenoprofen.	Rheumatoid arthritis [FA20]	[9]
Indomethacin	DMSC4A7	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Indomethacin.	Rheumatoid arthritis [FA20]	[9]
Tolmetin	DMWUIJE	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Tolmetin.	Rheumatoid arthritis [FA20]	[9]
Salicyclic acid	DM2F8XZ	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Salicyclic acid.	Seborrhoeic dermatitis [EA81]	[32]
Curcumin	DMQPH29	Minor	Increased risk of bleeding by the combination of Bivalirudin and Curcumin.	Solid tumour/cancer [2A00-2F9Z]	[33]
Warfarin	DMJYCVW	Major	Increased risk of bleeding by the combination of Bivalirudin and Warfarin.	Supraventricular tachyarrhythmia [BC81]	[9]
Anagrelide	DMSQ8MD	Major	Increased risk of bleeding by the combination of Bivalirudin and Anagrelide.	Thrombocytosis [3B63]	[10]
Apixaban	DM89JLN	Major	Increased risk of bleeding by the combination of Bivalirudin and Apixaban.	Thrombosis [DB61-GB90]	[15]
Brilinta	DMBR01X	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Brilinta.	Thrombosis [DB61-GB90]	[15]
Argatroban	DMFI46A	Major	Increased risk of bleeding by the combination of Bivalirudin and Argatroban.	Thrombosis [DB61-GB90]	[9]
Dicumarol	DMFQCB1	Major	Increased risk of bleeding by the combination of Bivalirudin and Dicumarol.	Thrombosis [DB61-GB90]	[34]
Clopidogrel	DMOL54H	Moderate	Increased risk of bleeding by the combination of Bivalirudin and Clopidogrel.	Thrombosis [DB61-GB90]	[9]
Cabozantinib	DMIYDT4	Major	Increased risk of bleeding by the combination of Bivalirudin and Cabozantinib.	Thyroid cancer [2D10]	[35]
Betrixaban	DM2C4RF	Major	Increased risk of bleeding by the combination of Bivalirudin and Betrixaban.	Venous thromboembolism [BD72]	[36]

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