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

[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
Molecular Formula C35H49N11O9S2
Molecular Weight 831.9654
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

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

COR Therapeutics
1
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

1998
123
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 8.7 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Acute coronary syndrome
33
Sources: www.accessdata.fda.gov/drugsatfda_docs/label/2011/020718s034lbl.pdf
 Primary
Approved
8583
INTEGRILIN

Approved Use

Eptifibatide

Launch Date

1999
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.59 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15110131/
2880 μg/kg bw other, intravenous
dose: 2880 μg/kg bw
route of administration: Intravenous
experiment type: OTHER
co-administered:
EPTIFIBATIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
43.08 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15110131/
2880 μg/kg bw other, intravenous
dose: 2880 μg/kg bw
route of administration: Intravenous
experiment type: OTHER
co-administered:
EPTIFIBATIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.18 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15110131/
2880 μg/kg bw other, intravenous
dose: 2880 μg/kg bw
route of administration: Intravenous
experiment type: OTHER
co-administered:
EPTIFIBATIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:291902
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:291902
ChemicalBook
CB0416566
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0416566
ChemicalBook
CB7416565
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7416565
eMolecules
10345050
https://www.emolecules.com/cgi-bin/more?vid=10345050
MolPort
MolPort-006-069-141
https://www.molport.com/shop/molecule-link/MolPort-006-069-141
ZINC
ZINC000085536935
http://zinc15.docking.org/substances/ZINC000085536935
PubMed

PubMed

TitleDatePubMed
Pharmacodynamic profile of the direct thrombin antagonist bivalirudin given in combination with the glycoprotein IIb/IIIa antagonist eptifibatide.
2002-04
Indications for appropriate platelet glycoprotein IIb/IIIa inhibitor therapy.
2002-04
Reversible thrombocytopenia associated with eptifibatide.
2002-04
A structural and dynamic investigation of the facilitating effect of glycoprotein IIb/IIIa inhibitors in dissolving platelet-rich clots.
2002-03-08
Platelet aggregation inhibitors for use in peripheral vascular interventions: what can we learn from the experience in the coronary arteries?
2002-03
Using a peptide inhibitor of the glycoprotein IIb/IIIa platelet receptor: initial experience in patients with acute peripheral arterial occlusions.
2002-03
Eptifibatide and 7E3, but not tirofiban, inhibit alpha(v)beta3 integrin-mediated binding of smooth muscle cells to thrombospondin and prothrombin.
2002-02-12
Long-term efficacy of platelet glycoprotein IIb/IIIa integrin blockade with eptifibatide in coronary stent intervention.
2002-02-06
Eptifibatide and low-dose tissue plasminogen activator in acute myocardial infarction: the integrilin and low-dose thrombolysis in acute myocardial infarction (INTRO AMI) trial.
2002-02-06
Minor myocardial damage and prognosis: are spontaneous and percutaneous coronary intervention-related events different?
2002-02-05
The role of alpha(v)beta3 integrins in vascular healing.
2002-02
[Eptifibatide blocks the increase in C-reactive protein concentration after coronary angioplasty].
2002-02
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.
2002-02
Platelet glycoprotein IIb/IIIa inhibitor effect examined in 2 studies.
2002-01-22
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.
2002-01-22
A synthetic polymer matrix for the delayed or pulsatile release of water-soluble peptides.
2002-01-17
Activated monocytes induce smooth muscle cell death: role of macrophage colony-stimulating factor and cell contact.
2002-01-15
In-hospital costs of coronary stent implantation with and without eptifibatide (the ESPRIT Trial). Enhanced Suppression of the Platelet IIb/IIIa Receptor with Integrilin.
2002-01-01
Relationship of creatine kinase-myocardial band release to Thrombolysis in Myocardial Infarction perfusion grade after intracoronary stent placement: an ESPRIT substudy.
2002-01
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.
2002-01
Platelet inhibition after glycoprotein IIb/IIIa inhibitor therapy.
2001-12-18
Glycoprotein IIb/IIIa receptor blockers in acute coronary syndromes.
2001-12-08
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.
2001-12-04
A risk stratification scheme for selection of a glycoprotein IIb/IIIa inhibitor during percutaneous coronary intervention based on clinical and angiographic criteria.
2001-12-01
Intravenous glycoprotein IIb/IIIa inhibition in non-ST segment elevation acute coronary syndromes.
2001-12-01
GP IIb/IIIa inhibitors in coronary artery disease management: what the latest trials tell us.
2001-12
Clinical pharmacology of higher dose eptifibatide in percutaneous coronary intervention (the PRIDE study).
2001-11-15
Effect of eptifibatide on angiographic complications during percutaneous coronary intervention in the IMPACT--(Integrilin to Minimize Platelet Aggregation and Coronary Thrombosis) II Trial.
2001-11-01
[Indications for intravenous GPIIb/IIIa receptor inhibitors in acute coronary syndrome without prolonged ST syndrome].
2001-11
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.
2001-11
ESPRIT in context: pharmacology matters!
2001-11
The role of glycoprotein IIb/IIIa inhibition in the management of acute coronary syndromes.
2001-10-18
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.
2001-10-15
Comparison of GP IIB/IIIA inhibitors and their activity as measured by aggregometry, flow cytometry, single platelet counting, and the rapid platelet function analyzer.
2001-10
Differential effects of citrate versus PPACK anticoagulation on measured platelet inhibition by abciximab, eptifibatide and tirofiban.
2001-10
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.
2001-10
Eptifibatide and abciximab exhibit equivalent antiplatelet efficacy in an experimental model of stenting in both healthy volunteers and patients with coronary artery disease.
2001-10
Bleeding in a patient receiving platelet aggregation inhibitors.
2001-10
Oral glycoprotein IIb/IIa antagonists for unstable angina--is there still a chance for the oral substances?
2001-09-30
Dissociation of glycoprotein IIb/IIIa antagonists from platelets does not result in fibrinogen binding or platelet aggregation.
2001-09-18
Differential inhibition of adenosine diphosphate- versus thrombin receptor-activating peptide-stimulated platelet fibrinogen binding by abciximab due to different glycoprotein IIb/IIIa activation kinetics.
2001-09-01
[Platelet glycoprotein IIb/IIIa blockade with eptifibatide in angioplasty followed by stent implantation at 6 month in the ESPRIT study].
2001-09
Severe thrombocytopenia possibly related to readministration of eptifibatide.
2001-09
Effect of glycoprotein IIb/IIIa receptor inhibition on angiographic complications during percutaneous coronary intervention in the ESPRIT trial.
2001-09
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.
2001-08-15
Association of eptifibatide and acute profound thrombocytopenia.
2001-08-15
[Optimal thrombolysis].
2001-08
Platelet glycoprotein IIb/IIIa-receptor inhibitors in patients with acute coronary syndromes or undergoing percutaneous coronary interventions: a review.
2001-08
Short-term comparative outcomes associated with the use of GP IIb/IIIa antagonists in patients undergoing coronary intervention.
2001-05
Administration of abciximab to patients receiving tirofiban or eptifibatide: effect on platelet function.
2001-03-01
Patents

Patents

JP2011528275A
456

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
Substance Class Chemical
Created
by admin
on Wed Apr 02 06:53:10 GMT 2025
Edited
by admin
on Wed Apr 02 06:53:10 GMT 2025
Record UNII
NA8320J834
Record Status FAILED
Record Version
  • Download
Name Type Language
EPTIFIBATIDE
EMA EPAR   INN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
USAN   INN  
Official Name English
INTEGRILIN
Preferred 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-?-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
Classification Tree Code System Code
NCI_THESAURUS C1327
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
NDF-RT N0000008832
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
WHO-ATC B01AC16
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
NDF-RT N0000175578
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
EMA ASSESSMENT REPORTS INTEGRILIN (AUTHORIZED: ANGINA, UNSTABLE)
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
WHO-VATC QB01AC16
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
FDA ORPHAN DRUG 364012
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
EMA ASSESSMENT REPORTS INTEGRILIN (AUTHORIZED: MYOCARDIAL INFARCTION)
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
NDF-RT N0000008832
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
Code System Code Type Description
EVMPD
SUB12498MIG
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
SMS_ID
100000089288
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
CAS
148031-34-9
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
SUPERSEDED
CHEBI
291902
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
MESH
C086648
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
EPA CompTox
DTXSID7046673
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
MERCK INDEX
m4968
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB00063
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
RXCUI
75635
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY RxNorm
LACTMED
Eptifibatide
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
RS_ITEM_NUM
1238501
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
CHEMBL
CHEMBL1174
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
IUPHAR
6585
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
CAS
188627-80-7
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
HSDB
8313
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
DRUG CENTRAL
1040
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
WIKIPEDIA
EPTIFIBATIDE
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
PUBCHEM
448812
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
USAN
II-61
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
NCI_THESAURUS
C47516
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
FDA UNII
NA8320J834
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
INN
7717
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
DAILYMED
NA8320J834
Created by admin on Wed Apr 02 06:53:10 GMT 2025 , Edited by admin on Wed Apr 02 06:53:10 GMT 2025
PRIMARY
Related Record Type Details
Glycoprotein IIb/IIIa
TARGET -> INHIBITOR
Related Record Type Details
Structure of EPTIFIBATIDE
ACTIVE MOIETY
NIH
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