Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C35H49N11O9S2 |
Molecular Weight | 831.962 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CCCN1C(=O)[C@H](CC3=CNC4=CC=CC=C34)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)CCSSC[C@H](NC2=O)C(N)=O
InChI
InChIKey=CZKPOZZJODAYPZ-LROMGURASA-N
InChI=1S/C35H49N11O9S2/c36-30(51)25-18-57-56-13-10-27(47)42-22(8-3-4-11-39-35(37)38)31(52)41-17-28(48)43-23(15-29(49)50)32(53)44-24(14-19-16-40-21-7-2-1-6-20(19)21)34(55)46-12-5-9-26(46)33(54)45-25/h1-2,6-7,16,22-26,40H,3-5,8-15,17-18H2,(H2,36,51)(H,41,52)(H,42,47)(H,43,48)(H,44,53)(H,45,54)(H,49,50)(H4,37,38,39)/t22-,23-,24-,25-,26-/m0/s1
DescriptionSources: www.accessdata.fda.gov/drugsatfda_docs/label/2011/020718s034lbl.pdfCurator's Comment: Description was created using several sources including:
http://www.ncbi.nlm.nih.gov/pubmed/10577440; http://www.drugbank.ca/drugs/DB00063
Sources: www.accessdata.fda.gov/drugsatfda_docs/label/2011/020718s034lbl.pdf
Curator's Comment: Description was created using several sources including:
http://www.ncbi.nlm.nih.gov/pubmed/10577440; http://www.drugbank.ca/drugs/DB00063
Eptifibatide is a platelet aggregation inhibitor - an anti-coagulant that selectively blocks the platelet glycoprotein IIb/IIIa receptor. It is a cyclic heptapeptide derived from a protein found in the venom of the southeastern pygmy rattlesnake. It belongs to the class of the so called arginin-glycin-aspartat-mimetics and reversibly binds to platelets. Eptifibatide inhibits platelet aggregation by reversibly binding to the platelet receptor glycoprotein (GP) IIb/IIIa of human platelets, thus preventing the binding of fibrinogen, von Willebrand factor, and other adhesive ligands. Inhibition of platelet aggregation occurs in a dose- and concentration-dependent manner. It is used for treatment of myocardial infarction and acute coronary syndrome.
Originator
Sources: http://www.ncbi.nlm.nih.gov/pubmed/10577440
Curator's Comment: Integrilin (Eptifibatide) was invented by Robert M. Scarborough and David Phillips, at COR Therapeutics, Inc.The company was acquired by Millennium Pharmaceuticals, Inc. , MA in 2001.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093869 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10577440 |
8.7 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: www.accessdata.fda.gov/drugsatfda_docs/label/2011/020718s034lbl.pdf |
Primary | INTEGRILIN Approved UseEptifibatide Launch Date1999 |
PubMed
Title | Date | PubMed |
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Platelet glycoprotein IIb-IIIa antagonists as prototypical integrin blockers: novel parenteral and potential oral antithrombotic agents. | 2000 Sep 21 |
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[Pathophysiology of platelet activation and pharmacology of GPIIb/IIIa inhibitors]. | 2001 Apr |
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Comparative efficacy of fibrinogen and platelet supplementation on the in vitro reversibility of competitive glycoprotein IIb/IIIa (alphaIIb/beta3) receptor-directed platelet inhibition. | 2001 Aug |
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Comparison of eptifibatide and abciximab with decision analysis. | 2001 Aug 1 |
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There is synergism between high-intensity, low-frequency ultrasound and streptokinase but not with eptifibatide, heparin, and aspirin. Differential effects on fresh and aged blood clots. An in vitro study. | 2001 Aug 15 |
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Association of eptifibatide and acute profound thrombocytopenia. | 2001 Aug 15 |
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GP IIb/IIIa inhibitors in coronary artery disease management: what the latest trials tell us. | 2001 Dec |
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A risk stratification scheme for selection of a glycoprotein IIb/IIIa inhibitor during percutaneous coronary intervention based on clinical and angiographic criteria. | 2001 Dec 1 |
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Platelet inhibition after glycoprotein IIb/IIIa inhibitor therapy. | 2001 Dec 18 |
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Attenuation of rebound ischemia after discontinuation of heparin therapy by glycoprotein IIb/IIIa inhibition with eptifibatide in patients with acute coronary syndromes: observations from the platelet IIb/IIIa in unstable angina: receptor suppression using integrilin therapy (PURSUIT) trial. | 2001 Dec 4 |
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Glycoprotein IIb/IIIa receptor blockers in acute coronary syndromes. | 2001 Dec 8 |
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[Integrin-ligands binding reaction upregulates the antioxidant activity of rabbit bronchial epithelial cells]. | 2001 Feb |
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[Economic evaluation of eptifibatide]. | 2001 Feb |
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Anti-GPIIb/IIIa drugs: current strategies and future directions. | 2001 Jul |
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Assembly of a fibronectin matrix by adherent platelets stimulated by lysophosphatidic acid and other agonists. | 2001 Jul 1 |
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Pharmacodynamics and pharmacokinetics of eptifibatide in patients with acute coronary syndromes: prospective analysis from PURSUIT. | 2001 Jul 24 |
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Initial experience with a newer generation coronary stent. | 2001 Mar |
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Variation in patient management and outcomes for acute coronary syndromes in Latin America and North America: results from the Platelet IIb/IIIa in Unstable Angina: Receptor Suppression Using Integrilin Therapy (PURSUIT) trial. | 2001 Mar |
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Prognostic importance of concomitant heparin with eptifibatide in acute coronary syndromes. PURSUIT Investigators. Platelet Glycoprotein IIb/IIIa in Unstable Angina: Receptor Suppression Using Integrilin Therapy. | 2001 Mar 1 |
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New approaches to diagnosis and management of unstable angina and non-ST-segment elevation myocardial infarction. | 2001 Mar 12 |
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Short-term comparative outcomes associated with the use of GP IIb/IIIa antagonists in patients undergoing coronary intervention. | 2001 May |
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Drug-company sponsorship and the Declaration of Helsinki. | 2001 May 5 |
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Stabilization of eptifibatide by cosolvents. | 2001 May 7 |
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Novel dosing regimen of eptifibatide in planned coronary stent implantation (ESPRIT): a randomized placebo-controlled study. | 2001 May-Jun |
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[Indications for intravenous GPIIb/IIIa receptor inhibitors in acute coronary syndrome without prolonged ST syndrome]. | 2001 Nov |
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Intravenous glycoprotein IIb/IIIa inhibition in non-ST segment elevation acute coronary syndromes. | 2001 Nov-Dec |
|
Comparison of GP IIB/IIIA inhibitors and their activity as measured by aggregometry, flow cytometry, single platelet counting, and the rapid platelet function analyzer. | 2001 Oct |
|
Differential effects of citrate versus PPACK anticoagulation on measured platelet inhibition by abciximab, eptifibatide and tirofiban. | 2001 Oct |
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Increased reperfusion by glycoprotein IIb/IIIa receptor antagonist administration in case of unsuccessful and failed thrombolysis in patients with acute myocardial infarction: a pilot study. | 2001 Oct |
|
Bleeding in a patient receiving platelet aggregation inhibitors. | 2001 Oct |
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Modulation of platelet aggregation in baboons: implications for mixed chimerism in xenotransplantation. I. The roles of individual components of a transplantation conditioning regimen and of pig peripheral blood progenitor cells. | 2001 Oct 15 |
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Effect of glycoprotein IIb/IIIa receptor inhibition on angiographic complications during percutaneous coronary intervention in the ESPRIT trial. | 2001 Sep |
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Oral glycoprotein IIb/IIa antagonists for unstable angina--is there still a chance for the oral substances? | 2001 Sep 30 |
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Pharmacodynamic profile of the direct thrombin antagonist bivalirudin given in combination with the glycoprotein IIb/IIIa antagonist eptifibatide. | 2002 Apr |
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Indications for appropriate platelet glycoprotein IIb/IIIa inhibitor therapy. | 2002 Apr |
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Reversible thrombocytopenia associated with eptifibatide. | 2002 Apr |
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The role of alpha(v)beta3 integrins in vascular healing. | 2002 Feb |
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Patients with acute coronary syndromes without persistent ST elevation undergoing percutaneous coronary intervention benefit most from early intervention with protection by a glycoprotein IIb/IIIa receptor blocker. | 2002 Feb |
|
Long-term efficacy of platelet glycoprotein IIb/IIIa integrin blockade with eptifibatide in coronary stent intervention. | 2002 Feb 6 |
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Eptifibatide and low-dose tissue plasminogen activator in acute myocardial infarction: the integrilin and low-dose thrombolysis in acute myocardial infarction (INTRO AMI) trial. | 2002 Feb 6 |
|
Relationship of creatine kinase-myocardial band release to Thrombolysis in Myocardial Infarction perfusion grade after intracoronary stent placement: an ESPRIT substudy. | 2002 Jan |
|
Cost effectiveness of eptifibatide in acute coronary syndromes; an economic analysis of Western European patients enrolled in the PURSUIT trial. The Platelet IIa/IIb in unstable Angina: Receptor Suppression Using Integrilin Therapy. | 2002 Jan |
|
In-hospital costs of coronary stent implantation with and without eptifibatide (the ESPRIT Trial). Enhanced Suppression of the Platelet IIb/IIIa Receptor with Integrilin. | 2002 Jan 1 |
|
Activated monocytes induce smooth muscle cell death: role of macrophage colony-stimulating factor and cell contact. | 2002 Jan 15 |
|
A synthetic polymer matrix for the delayed or pulsatile release of water-soluble peptides. | 2002 Jan 17 |
|
Outcomes of patients with acute coronary syndromes and prior coronary artery bypass grafting: results from the platelet glycoprotein IIb/IIIa in unstable angina: receptor suppression using integrilin therapy (PURSUIT) trial. | 2002 Jan 22 |
|
Using a peptide inhibitor of the glycoprotein IIb/IIIa platelet receptor: initial experience in patients with acute peripheral arterial occlusions. | 2002 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: www.accessdata.fda.gov/drugsatfda_docs/label/2011/020718s034lbl.pdf
Curator's Comment: The recommended adult dosage of eptifibatide in patients with acute coronary syndrome and normal renal function is an intravenous bolus of 180 mcg/kg as soon as possible following diagnosis, followed by a continuous infusion of 2.0 mcg/kg/min until hospital discharge or initiation of CABG surgery, up to 72 hours.
180 ug/kg
Route of Administration:
Intravenous
In Vitro Use Guide
Curator's Comment: Overall, eptifibatide rapidly inhibits in vitro platelet aggregation in blood samples, with an IC50 in the 100 to 600 nmol/L range, depending on the extracellular concentration of ionized calcium; at a low concentration of 40 to 50 μmol/L, the IC50 is approximately 100 nmol/L, whereas at physiologic concentration of approximately 1.1 μmol/L, IC50 is closer to 500 nmol/L
100 - 600 nmol/L
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1327
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NDF-RT |
N0000008832
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WHO-ATC |
B01AC16
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NDF-RT |
N0000175578
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EMA ASSESSMENT REPORTS |
INTEGRILIN (AUTHORIZED: ANGINA, UNSTABLE)
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WHO-VATC |
QB01AC16
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FDA ORPHAN DRUG |
364012
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EMA ASSESSMENT REPORTS |
INTEGRILIN (AUTHORIZED: MYOCARDIAL INFARCTION)
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NDF-RT |
N0000008832
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SUB12498MIG
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100000089288
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148031-34-9
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291902
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C086648
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DTXSID7046673
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m4968
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DB00063
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75635
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Eptifibatide
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1238501
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CHEMBL1174
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6585
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188627-80-7
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8313
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1040
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EPTIFIBATIDE
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448812
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II-61
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C47516
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NA8320J834
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7717
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NA8320J834
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ACTIVE MOIETY