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    Also known as: 128270-60-0, Angiomax, Bivalirudin trifluoroacetate, Bg-8967, Bg8967, Hirulog
    Molecular Formula
    C98H138N24O33
    Molecular Weight
    2180.3  g/mol
    InChI Key
    OIRCOABEOLEUMC-GEJPAHFPSA-N
    Bivalirudin
    Bivalirudin is a 20 amino acid long synthetic peptide with thrombin-specific anticoagulant properties. Bivalirudin reversibly binds thrombin, free as well as clot bound, at the catalytic site and the anion-binding exosite, thereby preventing the formation and activation of fibrin, factor XIIIa, and other coagulation factors. This drug is primarily used during coronary angioplasty procedures, in combination with aspirin, in patients with unstable angina.
    1 2D Structure

    Bivalirudin

    2 Identification
    2.1 Computed Descriptors
    2.1.1 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
    2.1.2 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
    2.1.3 InChI Key
    OIRCOABEOLEUMC-GEJPAHFPSA-N
    2.1.4 Canonical SMILES
    CCC(C)C(C(=O)N1CCCC1C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)O)C(=O)NC(CC2=CC=C(C=C2)O)C(=O)NC(CC(C)C)C(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(CC3=CC=CC=C3)NC(=O)C(CC(=O)O)NC(=O)CNC(=O)C(CC(=O)N)NC(=O)CNC(=O)CNC(=O)CNC(=O)CNC(=O)C4CCCN4C(=O)C(CCCNC(=N)N)NC(=O)C5CCCN5C(=O)C(CC6=CC=CC=C6)N
    2.1.5 Isomeric 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
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Angiomax

    2. Angiomax Rtu

    3. Bg 8967

    4. Bg-8967

    5. Bg8967

    6. Bivalirudin Trifluoroacetate

    7. Ctb-001

    8. Hirulog

    9. Hirulog-1

    10. L-leucine, 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-

    11. Phe-pro-arg-pro-(gly)4 Desulfato-tyr63'-hirugen

    12. Phe-pro-arg-pro-(gly)4-asn-gly-asp-phe-glu-glu-ile-pro-glu-glu-tyr-leu

    13. Phe-pro-arg-pro-(gly)4-desulfohirudin-(53-64)

    2.2.2 Depositor-Supplied Synonyms

    1. 128270-60-0

    2. Angiomax

    3. Bivalirudin Trifluoroacetate

    4. Bg-8967

    5. Bg8967

    6. Hirulog

    7. Chebi:59173

    8. Hirulog-1

    9. 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

    10. L-leucine, 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-

    11. Angiox

    12. Bivalirudina

    13. Bivalirudine

    14. Bivalirudinum

    15. Bg 8967

    16. Unii-tn9bex005g

    17. Bivalirudin [usan:inn:ban]

    18. Bivalirudin Tfa

    19. 1191386-55-6

    20. Hs-2004

    21. Tn9bex005g

    22. Schembl25739

    23. Gtpl6470

    24. Bivalirudin Trifluoroacetate Salt

    25. Chembl2103749

    26. Dtxsid00155847

    27. Bivalirudin;0.9% Sodium Chloride

    28. Ex-a5843

    29. Bdbm50248103

    30. Mfcd08692016

    31. Akos015994644

    32. Db00006

    33. 70b600

    34. 270b600

    35. J-005587

    36. Q4919218

    37. Bivalirudin Trifluoroacetate (h-dl-phe-dl-pro-dl-arg-dl-pro-gly-gly-gly-gly-dl-asn-gly-dl-asp-dl-phe-dl-glu-dl-glu-xiile-dl-pro-dl-glu-dl-glu-dl-tyr-dl-leu-oh.tfa)

    2.3 Create Date
    2007-07-03
    3 Chemical and Physical Properties
    Molecular Weight 2180.3 g/mol
    Molecular Formula C98H138N24O33
    XLogP3-7.1
    Hydrogen Bond Donor Count28
    Hydrogen Bond Acceptor Count35
    Rotatable Bond Count67
    Exact Mass2179.9891678 g/mol
    Monoisotopic Mass2178.9858129 g/mol
    Topological Polar Surface Area902 Ų
    Heavy Atom Count155
    Formal Charge0
    Complexity4950
    Isotope Atom Count0
    Defined Atom Stereocenter Count16
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameAngiomax
    PubMed HealthBivalirudin (Injection)
    Drug ClassesAnticoagulant
    Drug LabelAngiomax is a specific and reversible direct thrombin inhibitor. The active substance is a synthetic, 20amino acid peptide. The chemical name is D-phenylalanyl-L-prolyl-L-arginyl-L-prolyl-glycyl-glycyl-glycyl-glycyl-L-asparagyl-glycyl-L-aspartyl-L-...
    Active IngredientBivalirudin
    Dosage FormInjectable
    RouteIntravenous
    Strength250mg/vial
    Market StatusPrescription
    CompanyMedicines

    2 of 4  
    Drug NameBivalirudin
    PubMed HealthBivalirudin (Injection)
    Drug ClassesAnticoagulant
    Drug LabelAngiomax is a specific and reversible direct thrombin inhibitor. The active substance is a synthetic, 20amino acid peptide. The chemical name is D-phenylalanyl-L-prolyl-L-arginyl-L-prolyl-glycyl-glycyl-glycyl-glycyl-L-asparagyl-glycyl-L-aspartyl-L-...
    Active IngredientBivalirudin
    Dosage FormInjectable
    Routeinjection
    Strength250mg
    Market StatusTentative Approval
    CompanyHospira

    3 of 4  
    Drug NameAngiomax
    PubMed HealthBivalirudin (Injection)
    Drug ClassesAnticoagulant
    Drug LabelAngiomax is a specific and reversible direct thrombin inhibitor. The active substance is a synthetic, 20amino acid peptide. The chemical name is D-phenylalanyl-L-prolyl-L-arginyl-L-prolyl-glycyl-glycyl-glycyl-glycyl-L-asparagyl-glycyl-L-aspartyl-L-...
    Active IngredientBivalirudin
    Dosage FormInjectable
    RouteIntravenous
    Strength250mg/vial
    Market StatusPrescription
    CompanyMedicines

    4 of 4  
    Drug NameBivalirudin
    PubMed HealthBivalirudin (Injection)
    Drug ClassesAnticoagulant
    Drug LabelAngiomax is a specific and reversible direct thrombin inhibitor. The active substance is a synthetic, 20amino acid peptide. The chemical name is D-phenylalanyl-L-prolyl-L-arginyl-L-prolyl-glycyl-glycyl-glycyl-glycyl-L-asparagyl-glycyl-L-aspartyl-L-...
    Active IngredientBivalirudin
    Dosage FormInjectable
    Routeinjection
    Strength250mg
    Market StatusTentative Approval
    CompanyHospira

    4.2 Drug Indication

    For treatment of heparin-induced thrombocytopenia and for the prevention of thrombosis. Bivalirudin is indicated for use in patients undergoing percutaneous coronary intervention (PCI), in patients at moderate to high risk acute coronary syndromes due to unstable angina or non-ST segment elevation in whom a PCI is planned.

    FDA Label

    Angiox is indicated as an anticoagulant in adult patients undergoing percutaneous coronary intervention (PCI), including patients with ST-segment-elevation myocardial infarction (STEMI) undergoing primary PCI.

    Angiox is also indicated for the treatment of adult patients with unstable angina / non-ST-segment-elevation myocardial infarction (UA / NSTEMI) planned for urgent or early intervention.

    Angiox should be administered with aspirin and clopidogrel.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Bivalirudin mediates an inhibitory action on thrombin by directly and specifically binding to both the catalytic site and anion-binding exosite of circulating and clot-bound thrombin. The action of bivalirudin is reversible because thrombin will slowly cleave the thrombin-bivalirudin bond which recovers the active site of thrombin.

    5.2 MeSH Pharmacological Classification

    Antithrombins

    Endogenous factors and drugs that directly inhibit the action of THROMBIN, usually by blocking its enzymatic activity. They are distinguished from INDIRECT THROMBIN INHIBITORS, such as HEPARIN, which act by enhancing the inhibitory effects of antithrombins. (See all compounds classified as Antithrombins.)

    5.3 FDA Pharmacological Classification
    5.3.1 Pharmacological Classes
    Direct Thrombin Inhibitor [EPC]; Thrombin Inhibitors [MoA]; Anti-coagulant [EPC]
    5.4 ATC Code

    B01AE06

    B - Blood and blood forming organs

    B01 - Antithrombotic agents

    B01A - Antithrombotic agents

    B01AE - Direct thrombin inhibitors

    B01AE06 - Bivalirudin

    5.5 Absorption, Distribution and Excretion

    Absorption

    Following intravenous administration, bivalirudin exhibits linear pharmacokinetics. The mean steady state concentration is 12.3 +/- 1.7mcg/mL after administration of an intravenous bolus of 1mg/kg followd by a 2.5mg/kg/hr intravenous infusion given over 4 hours.

    Route of Elimination

    Bivalirudin is cleared from plasma by a combination of renal mechanisms (20%) and proteolytic cleavage.

    Volume of Distribution

    0.2L/kg

    Clearance

    3.4 mL/min/kg [Normal renal function]

    3.4 mL/min/kg [mild renal function]

    2.7 mL/min/kg [moderate renal function]

    2.8 mL/min/kg [severe renal function]

    1 mL/min/kg [Dialysis-dependent patients]

    5.6 Metabolism/Metabolites

    80% proteolytic cleavage

    5.7 Biological Half-Life

    Normal renal function: 25 min (in normal conditions)

    Creatinine clearance 10-29mL/min: 57min

    Dialysis-dependant patients: 3.5h

    5.8 Mechanism of Action

    Inhibits the action of thrombin by binding both to its catalytic site and to its anion-binding exosite. Thrombin is a serine proteinase that plays a central role in the thrombotic process, acting to cleave fibrinogen into fibrin monomers and to activate Factor XIII to Factor XIIIa, allowing fibrin to develop a covalently cross-linked framework which stabilizes the thrombus; thrombin also activates Factors V and VIII, promoting further thrombin generation, and activates platelets, stimulating aggregation and granule release.

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    12-Feb-2021
    19-Aug-2024
    KGS
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    Average Price (USD/KGS)

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    DOSAGE - SOLUTION;INTRAVENOUS - 250MG/50ML (5...DOSAGE - SOLUTION;INTRAVENOUS - 250MG/50ML (5MG/ML)

    USFDA APPLICATION NUMBER - 208374

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    DOSAGE - SOLUTION;INTRAVENOUS - 500MG/100ML (...DOSAGE - SOLUTION;INTRAVENOUS - 500MG/100ML (5MG/ML)

    USFDA APPLICATION NUMBER - 208374

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    DOSAGE - INJECTABLE;INTRAVENOUS - 250MG/VIAL

    USFDA APPLICATION NUMBER - 20873

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