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

Details

Stereochemistry ABSOLUTE
Molecular Formula C35H49N11O9S2
Molecular Weight 831.962
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPTIFIBATIDE

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

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

1999
PubMed

PubMed

TitleDatePubMed
Platelet aggregation inhibition with glycoprotein IIb--IIIa inhibitors.
2001 Apr
[Pathophysiology of platelet activation and pharmacology of GPIIb/IIIa inhibitors].
2001 Apr
Antiplatelet effects of abciximab, tirofiban and eptifibatide in patients undergoing coronary stenting.
2001 Apr
A comparative study of light transmission aggregometry and automated bedside platelet function assays in patients undergoing percutaneous coronary intervention and receiving abciximab, eptifibatide, or tirofiban.
2001 Apr
In vitro dose response to different GPIIb/IIIa-antagonists: inter-laboratory comparison of various platelet function tests.
2001 Apr 1
Antiplatelet agents in tissue factor-induced blood coagulation.
2001 Apr 15
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
GP IIb/IIIa inhibitors in coronary artery disease management: what the latest trials tell us.
2001 Dec
Platelet inhibition after glycoprotein IIb/IIIa inhibitor therapy.
2001 Dec 18
[Economic evaluation of eptifibatide].
2001 Feb
[Update on the treatment with platelet antiaggregation agents].
2001 Jan
[Inhibitors of platelet glycoprotein IIb-IIIa in cardiology].
2001 Jan-Feb
Anti-GPIIb/IIIa drugs: current strategies and future directions.
2001 Jul
Glycoprotein IIb/IIIa inhibitors: more different than alike?
2001 Jul
Pharmacodynamics and pharmacokinetics of higher-dose, double-bolus eptifibatide in percutaneous coronary intervention.
2001 Jul 24
Pharmacodynamics and pharmacokinetics of eptifibatide in patients with acute coronary syndromes: prospective analysis from PURSUIT.
2001 Jul 24
Eptifibatide and 7E3, but not tirofiban, inhibit alpha(v)beta(3) integrin-mediated binding of smooth muscle cells to thrombospondin and prothrombin.
2001 Jul 31
Randomized comparison of ticlopidine and clopidogrel after intracoronary stent implantation in a broad patient population.
2001 Jul 31
Mechanisms of thrombotic microangiopathy following xenogeneic hematopoietic progenitor cell transplantation.
2001 Jun 15
Administration of abciximab to patients receiving tirofiban or eptifibatide: effect on platelet function.
2001 Mar 1
Open-label phase I clinical study to assess the safety of intravenous eptifibatide in patients undergoing internal carotid artery angioplasty and stent placement.
2001 May
Drug-company sponsorship and the Declaration of Helsinki.
2001 May 5
Stabilization of eptifibatide by cosolvents.
2001 May 7
[Indications for intravenous GPIIb/IIIa receptor inhibitors in acute coronary syndrome without prolonged ST syndrome].
2001 Nov
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
Effect of glycoprotein IIb/IIIa receptor inhibition on angiographic complications during percutaneous coronary intervention in the ESPRIT trial.
2001 Sep
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
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
Long-term efficacy of platelet glycoprotein IIb/IIIa integrin blockade with eptifibatide in coronary stent intervention.
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
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
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
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  
USAN   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 [USAN]
Common Name English
EPTIFIBATIDE [VANDF]
Common Name English
L-Cysteinamide, N6-(aminoiminomethyl)-N2-(3-mercapto-1-oxopropyl)-L-lysylglycyl-L-α-aspartyl-L-tryptophyl-L-prolyl-, cyclic (1→6)-disulfide
Systematic 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 Dec 16 15:52:32 GMT 2023 , Edited by admin on Sat Dec 16 15:52:32 GMT 2023
NDF-RT N0000008832
Created by admin on Sat Dec 16 15:52:32 GMT 2023 , Edited by admin on Sat Dec 16 15:52:32 GMT 2023
WHO-ATC B01AC16
Created by admin on Sat Dec 16 15:52:31 GMT 2023 , Edited by admin on Sat Dec 16 15:52:31 GMT 2023
NDF-RT N0000175578
Created by admin on Sat Dec 16 15:52:32 GMT 2023 , Edited by admin on Sat Dec 16 15:52:32 GMT 2023
EMA ASSESSMENT REPORTS INTEGRILIN (AUTHORIZED: ANGINA, UNSTABLE)
Created by admin on Sat Dec 16 15:52:32 GMT 2023 , Edited by admin on Sat Dec 16 15:52:32 GMT 2023
WHO-VATC QB01AC16
Created by admin on Sat Dec 16 15:52:32 GMT 2023 , Edited by admin on Sat Dec 16 15:52:32 GMT 2023
FDA ORPHAN DRUG 364012
Created by admin on Sat Dec 16 15:52:32 GMT 2023 , Edited by admin on Sat Dec 16 15:52:32 GMT 2023
EMA ASSESSMENT REPORTS INTEGRILIN (AUTHORIZED: MYOCARDIAL INFARCTION)
Created by admin on Sat Dec 16 15:52:32 GMT 2023 , Edited by admin on Sat Dec 16 15:52:32 GMT 2023
NDF-RT N0000008832
Created by admin on Sat Dec 16 15:52:32 GMT 2023 , Edited by admin on Sat Dec 16 15:52:32 GMT 2023
Code System Code Type Description
EVMPD
SUB12498MIG
Created by admin on Sat Dec 16 15:52:31 GMT 2023 , Edited by admin on Sat Dec 16 15:52:31 GMT 2023
PRIMARY
SMS_ID
100000089288
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PRIMARY
CAS
148031-34-9
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SUPERSEDED
CHEBI
291902
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PRIMARY
MESH
C086648
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PRIMARY
EPA CompTox
DTXSID7046673
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PRIMARY
MERCK INDEX
m4968
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PRIMARY Merck Index
DRUG BANK
DB00063
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PRIMARY
RXCUI
75635
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PRIMARY RxNorm
LACTMED
Eptifibatide
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PRIMARY
RS_ITEM_NUM
1238501
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PRIMARY
CHEMBL
CHEMBL1174
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PRIMARY
IUPHAR
6585
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PRIMARY
CAS
188627-80-7
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PRIMARY
HSDB
8313
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PRIMARY
DRUG CENTRAL
1040
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PRIMARY
WIKIPEDIA
EPTIFIBATIDE
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PRIMARY
PUBCHEM
448812
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PRIMARY
USAN
II-61
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PRIMARY
NCI_THESAURUS
C47516
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PRIMARY
FDA UNII
NA8320J834
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PRIMARY
INN
7717
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PRIMARY
DAILYMED
NA8320J834
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PRIMARY