Bivalirudin
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Bivalirudin
structure -
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CAS No:
128270-60-0
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Formula:
C98H138N24O33
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Chemical Name:
Bivalirudin
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CAS No:
Description
Bivalirudin Trifluoroacetate is a synthetic 20 residue peptide which reversibly inhibits thrombin.IC50 Value:Target: thrombinin vitro: Eptifibatide (8 mg/mL) added together with a low (70 ng/mL) concentration of bivalirudin (a direct thrombin inhibitor) effectively (approximately 90%) reduced platelet aggregation induced by thrombin (0.2 U/mL) [1]. In thrombin generation assay (TGA), bivalirudin had no effect on these parameters up to 10 μmol/l [2]. Bivalirudin-facilitated binding of MPO
Bivalirudin is a synthetic peptide of 20 amino acids, comprising D-Phe, Pro, Arg, Pro, Gly, Gly, Gly, Gly, Asn, Gly, Asp, Phe, Glu, Glu, Ile, Pro, Glu, Glu, Tyr, and Leu in sequence. A congener of hirudin (a naturally occurring drug found in the saliva of the medicinal leech), it a specific and reversible inhibitor of thrombin, and is used as an anticoagulant. It has a role as an anticoagulant and an EC 3.4.21.5 (thrombin) inhibitor.|Bivalirudin is a synthetic 20 residue peptide (thrombin inhibitor) which reversibly inhibits thrombin. Once bound to the active site, thrombin cannot activate fibrinogen into fibrin, the crucial step in the formation of thrombus. It is administered intravenously. Because it can cause blood stagnation, it is important to monitor changes in hematocrit, activated partial thromboplastin time, international normalized ratio and blood pressure.|Bivalirudin is an Anti-coagulant and Direct Thrombin Inhibitor. The mechanism of action of bivalirudin is as a Thrombin Inhibitor.|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.
Bivalirudin Basic Attributes
218029
2179.989
DTXSID00155847
C47415
B01AE06|B - Blood and blood forming organs
2942000000
Toxicity
Based on a study by Gleason et al., the no-observed-adverse-effect level (NOAEL) for bivalirudin, administered to rats via intravenous infusion over a 24-hour period, was 2000 mg/kg/24 h.
Other than thrombin and red blood cells, bivalirudin does not bind to plasma proteins.
Drug Information
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.|Treatment of atherosclerosis, Treatment of thrombosis
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.
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.)
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.|Bivalirudin is cleared from plasma by a combination of renal mechanisms (20%) and proteolytic cleavage.|0.2L/kg|3.4 mL/min/kg [Normal renal function]
80% proteolytic cleavage
Normal renal function: 25 min (in normal conditions)
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.
Angiomax
Bivalirudin Use and Manufacturing
Bivalirudin (Angiomax or Angiox, manufactured by The Medicines Company) is a specific and reversible direct thrombin inhibitor (DTI).Chemically, it is a synthetic congener of the naturally occurring drug hirudin (found in the saliva of the medicinal leech Hirudo medicinalis).Bivalirudin is a DTI that overcomes many limitations seen with indirect thrombin inhibitors, such as heparin. Bivalirudin is a short, synthetic peptide that is potent, highly specific, and a reversible inhibitor of thrombin. It inhibits both circulating and clot-bound thrombin, while also inhibiting thrombin-mediated platelet activation and aggregation. Bivalirudin has a quick onset of action and a short half-life. It does not bind to plasma proteins (other than thrombin) or to red blood cells. Therefore, it has a predictable antithrombotic response. There is no risk for Heparin Induced Thrombocytopenia/Heparin Induced Thrombosis-Thrombocytopenia Syndrome (HIT/HITTS). It does not require a binding cofactor such as antithrombin and does not activate platelets. These characteristics make bivalirudin an ideal alternative to heparin.Bivalirudin clinical studies demonstrated consistent positive outcomes in patients with stable angina, unstable angina (UA), non-ST segment elevation myocardial infarction (NSTEMI), and ST-segment elevation myocardial infarction (STEMI) undergoing PCI in 7 major randomized trials. Patients receiving bivalirudin had fewer adverse events compared to patients that received heparin.
Human drugs -> Angiox -> EMA Drug Category|Antithrombotic agents -> Human pharmacotherapeutic group|Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Computed Properties
Molecular Weight:2180.3
XLogP3:-7.1
Hydrogen Bond Donor Count:28
Hydrogen Bond Acceptor Count:35
Rotatable Bond Count:67
Exact Mass:2179.9891678
Monoisotopic Mass:2178.9858129
Topological Polar Surface Area:902
Heavy Atom Count:155
Complexity:4950
Defined Atom Stereocenter Count:16
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Pharmacological effects of bivalirudin for injection
Registered Holders
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Bachem AG
Active
Switzerland
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DR. REDDYS LABORATORIES LTD.
Active
Philippines
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TAPI NL B.V.
Active
France
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