U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C35H49N11O9S2
Molecular Weight 831.9654
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPTIFIBATIDE

SMILES

c1ccc2c(c1)c(C[C@@]3([H])C(=O)N4CCC[C@@]4([H])C(=N[C@@]([H])(CSSCCC(=N[C@@]([H])(CCCCNC(=N)N)C(=NCC(=N[C@@]([H])(CC(=O)O)C(=N3)O)O)O)O)C(=N)O)O)c[nH]2

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

HIDE SMILES / InChI

Description
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

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

Targets

Primary TargetPharmacologyConditionPotency
8.7 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Sources: www.accessdata.fda.gov/drugsatfda_docs/label/2011/020718s034lbl.pdf
Primary
INTEGRILIN

Approved Use

Eptifibatide

Launch Date

9.2871361E11
PubMed

PubMed

TitleDatePubMed
[Optimal thrombolysis].
2001 Aug
Platelet glycoprotein IIb/IIIa-receptor inhibitors in patients with acute coronary syndromes or undergoing percutaneous coronary interventions: a review.
2001 Aug
Comparison of eptifibatide and abciximab with decision analysis.
2001 Aug 1
Association of eptifibatide and acute profound thrombocytopenia.
2001 Aug 15
GP IIb/IIIa inhibitors in coronary artery disease management: what the latest trials tell us.
2001 Dec
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
Platelet inhibition after glycoprotein IIb/IIIa inhibitor therapy.
2001 Dec 18
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
Glycoprotein IIb/IIIa receptor blockers in acute coronary syndromes.
2001 Dec 8
Administration of abciximab to patients receiving tirofiban or eptifibatide: effect on platelet function.
2001 Mar 1
Short-term comparative outcomes associated with the use of GP IIb/IIIa antagonists in patients undergoing coronary intervention.
2001 May
Novel dosing regimen of eptifibatide in planned coronary stent implantation (ESPRIT): a randomized placebo-controlled study.
2001 May-Jun
[Indications for intravenous GPIIb/IIIa receptor inhibitors in acute coronary syndrome without prolonged ST syndrome].
2001 Nov
Small peptide GP IIb/IIIa receptor inhibitors as upstream therapy in non-ST-segment elevation acute coronary syndromes: results of the PURSUIT, PRISM, PRISM-PLUS, TACTICS, and PARAGON trials.
2001 Nov
ESPRIT in context: pharmacology matters!
2001 Nov
Effect of eptifibatide on angiographic complications during percutaneous coronary intervention in the IMPACT--(Integrilin to Minimize Platelet Aggregation and Coronary Thrombosis) II Trial.
2001 Nov 1
Clinical pharmacology of higher dose eptifibatide in percutaneous coronary intervention (the PRIDE study).
2001 Nov 15
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
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
Eptifibatide and abciximab exhibit equivalent antiplatelet efficacy in an experimental model of stenting in both healthy volunteers and patients with coronary artery disease.
2001 Oct
Bleeding in a patient receiving platelet aggregation inhibitors.
2001 Oct
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
[Platelet glycoprotein IIb/IIIa blockade with eptifibatide in angioplasty followed by stent implantation at 6 month in the ESPRIT study].
2001 Sep
Severe thrombocytopenia possibly related to readministration of eptifibatide.
2001 Sep
Effect of glycoprotein IIb/IIIa receptor inhibition on angiographic complications during percutaneous coronary intervention in the ESPRIT trial.
2001 Sep
Differential inhibition of adenosine diphosphate- versus thrombin receptor-activating peptide-stimulated platelet fibrinogen binding by abciximab due to different glycoprotein IIb/IIIa activation kinetics.
2001 Sep 1
Oral glycoprotein IIb/IIa antagonists for unstable angina--is there still a chance for the oral substances?
2001 Sep 30
The role of glycoprotein IIb/IIIa inhibition in the management of acute coronary syndromes.
2001 Sep-Oct
Pharmacodynamic profile of the direct thrombin antagonist bivalirudin given in combination with the glycoprotein IIb/IIIa antagonist eptifibatide.
2002 Apr
Indications for appropriate platelet glycoprotein IIb/IIIa inhibitor therapy.
2002 Apr
Reversible thrombocytopenia associated with eptifibatide.
2002 Apr
The role of alpha(v)beta3 integrins in vascular healing.
2002 Feb
[Eptifibatide blocks the increase in C-reactive protein concentration after coronary angioplasty].
2002 Feb
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
Eptifibatide and 7E3, but not tirofiban, inhibit alpha(v)beta3 integrin-mediated binding of smooth muscle cells to thrombospondin and prothrombin.
2002 Feb 12
Minor myocardial damage and prognosis: are spontaneous and percutaneous coronary intervention-related events different?
2002 Feb 5
Long-term efficacy of platelet glycoprotein IIb/IIIa integrin blockade with eptifibatide in coronary stent intervention.
2002 Feb 6
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
Platelet glycoprotein IIb/IIIa inhibitor effect examined in 2 studies.
2002 Jan 22
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
Platelet aggregation inhibitors for use in peripheral vascular interventions: what can we learn from the experience in the coronary arteries?
2002 Mar
Using a peptide inhibitor of the glycoprotein IIb/IIIa platelet receptor: initial experience in patients with acute peripheral arterial occlusions.
2002 Mar
A structural and dynamic investigation of the facilitating effect of glycoprotein IIb/IIIa inhibitors in dissolving platelet-rich clots.
2002 Mar 8
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
Name Type Language
EPTIFIBATIDE
EMA EPAR   INN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
EPTIFIBATIDE [MART.]
Common Name English
N(SUP 6)-AMIDINO-N(SUP 2)-(3-MERCAPTOPROPIONYL)-L-LYSYLGLYCYL-L-ALPHA-ASPARTYL-L-TRYPTOPHYL-L-PROLYL-L-CYSTEINAMIDE, CYCLIC(1-6)-DISULPHIDE
Common Name English
INTEGRELIN
Brand Name English
EPTIFIBATIDE [MI]
Common Name English
EPTIFIBATIDE [EMA EPAR]
Common Name English
EPTIFIBATIDE [INN]
Common Name English
EPTIFIBATIDE [VANDF]
Common Name English
EPTIFIBATIDE [WHO-DD]
Common Name English
N(SUP 6)-AMIDINO-N(SUP 2)-(3-MERCAPTOPROPIONYL)-L-LYSYLGLYCYL-L-ALPHA-ASPARTYL-L-TRYPTOPHYL-L-PROLYL-L-CYSTEINAMIDE, CYCLIC(1-6)-DISULFIDE
Common Name English
EPTIFIBATIDE [ORANGE BOOK]
Common Name English
INTEGRILIN
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C1327
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
NDF-RT N0000008832
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
WHO-ATC B01AC16
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
NDF-RT N0000175578
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
EMA ASSESSMENT REPORTS INTEGRILIN (AUTHORIZED: ANGINA, UNSTABLE)
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
WHO-VATC QB01AC16
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
FDA ORPHAN DRUG 364012
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
EMA ASSESSMENT REPORTS INTEGRILIN (AUTHORIZED: MYOCARDIAL INFARCTION)
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
NDF-RT N0000008832
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
Code System Code Type Description
EVMPD
SUB12498MIG
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
PRIMARY
CAS
148031-34-9
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
SUPERSEDED
MESH
C086648
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
PRIMARY
EPA CompTox
188627-80-7
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
PRIMARY
MERCK INDEX
M4968
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB00063
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
PRIMARY
RXCUI
75635
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
PRIMARY RxNorm
LACTMED
Eptifibatide
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
PRIMARY
CHEMBL
CHEMBL1174
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
PRIMARY
IUPHAR
6585
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
PRIMARY
CAS
188627-80-7
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
PRIMARY
HSDB
8313
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
PRIMARY
DRUG CENTRAL
1040
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
PRIMARY
WIKIPEDIA
EPTIFIBATIDE
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
PRIMARY
PUBCHEM
448812
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
PRIMARY
NCI_THESAURUS
C47516
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
PRIMARY
FDA UNII
NA8320J834
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
PRIMARY
INN
7717
Created by admin on Sat Jun 26 14:33:59 UTC 2021 , Edited by admin on Sat Jun 26 14:33:59 UTC 2021
PRIMARY