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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
Molecular Formula C35H49N11O9S2
Molecular Weight 831.962
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
116
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 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
8429
INTEGRILIN

Approved Use

Eptifibatide

Launch Date

9.2871361E11
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
MolPort
MolPort-006-069-141
https://www.molport.com/shop/molecule-link/MolPort-006-069-141
ZINC
ZINC000085536935
http://zinc15.docking.org/substances/ZINC000085536935
eMolecules
10345050
https://www.emolecules.com/cgi-bin/more?vid=10345050
PubMed

PubMed

TitleDatePubMed
Platelet glycoprotein IIb-IIIa antagonists as prototypical integrin blockers: novel parenteral and potential oral antithrombotic agents.
2000 Sep 21
Binding of a fibrinogen mimetic stabilizes integrin alphaIIbbeta3's open conformation.
2001 Aug
Comparison of eptifibatide and abciximab with decision analysis.
2001 Aug 1
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
[Economic evaluation of eptifibatide].
2001 Feb
[Inhibitors of platelet glycoprotein IIb-IIIa in cardiology].
2001 Jan-Feb
Glycoprotein IIb/IIIa inhibitors: more different than alike?
2001 Jul
Mechanisms of thrombotic microangiopathy following xenogeneic hematopoietic progenitor cell transplantation.
2001 Jun 15
Comparative 30-day economic and clinical outcomes of platelet glycoprotein IIb/IIIa inhibitor use during elective percutaneous coronary intervention: Prairie ReoPro versus Integrilin Cost Evaluation (PRICE) Trial.
2001 Mar
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
Short-term comparative outcomes associated with the use of GP IIb/IIIa antagonists in patients undergoing coronary intervention.
2001 May
Glycoprotein IIb/IIIa antagonists and low-molecular weight heparin in acute coronary syndromes.
2001 May
Point-of-care measured platelet inhibition correlates with a reduced risk of an adverse cardiac event after percutaneous coronary intervention: results of the GOLD (AU-Assessing Ultegra) multicenter study.
2001 May 29
Drug-company sponsorship and the Declaration of Helsinki.
2001 May 5
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
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
Differential effects of citrate versus PPACK anticoagulation on measured platelet inhibition by abciximab, eptifibatide and tirofiban.
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
Severe thrombocytopenia possibly related to readministration of eptifibatide.
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
Minor myocardial damage and prognosis: are spontaneous and percutaneous coronary intervention-related events different?
2002 Feb 5
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
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
Patents

Patents

JP2011528275A
455

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 Sat Dec 16 15:52:31 UTC 2023
Edited
by admin
on Sat Dec 16 15:52:31 UTC 2023
Record UNII
NA8320J834
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
NDF-RT N0000008832
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
WHO-ATC B01AC16
Created by admin on Sat Dec 16 15:52:31 UTC 2023 , Edited by admin on Sat Dec 16 15:52:31 UTC 2023
NDF-RT N0000175578
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
EMA ASSESSMENT REPORTS INTEGRILIN (AUTHORIZED: ANGINA, UNSTABLE)
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
WHO-VATC QB01AC16
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
FDA ORPHAN DRUG 364012
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
EMA ASSESSMENT REPORTS INTEGRILIN (AUTHORIZED: MYOCARDIAL INFARCTION)
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
NDF-RT N0000008832
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
Code System Code Type Description
EVMPD
SUB12498MIG
Created by admin on Sat Dec 16 15:52:31 UTC 2023 , Edited by admin on Sat Dec 16 15:52:31 UTC 2023
PRIMARY
SMS_ID
100000089288
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
CAS
148031-34-9
Created by admin on Sat Dec 16 15:52:31 UTC 2023 , Edited by admin on Sat Dec 16 15:52:31 UTC 2023
SUPERSEDED
CHEBI
291902
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
MESH
C086648
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
EPA CompTox
DTXSID7046673
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
MERCK INDEX
m4968
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB00063
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
RXCUI
75635
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY RxNorm
LACTMED
Eptifibatide
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
RS_ITEM_NUM
1238501
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
CHEMBL
CHEMBL1174
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
IUPHAR
6585
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
CAS
188627-80-7
Created by admin on Sat Dec 16 15:52:31 UTC 2023 , Edited by admin on Sat Dec 16 15:52:31 UTC 2023
PRIMARY
HSDB
8313
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
DRUG CENTRAL
1040
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
WIKIPEDIA
EPTIFIBATIDE
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
PUBCHEM
448812
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
USAN
II-61
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
NCI_THESAURUS
C47516
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
FDA UNII
NA8320J834
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
INN
7717
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
DAILYMED
NA8320J834
Created by admin on Sat Dec 16 15:52:32 UTC 2023 , Edited by admin on Sat Dec 16 15:52:32 UTC 2023
PRIMARY
Related Record Type Details
ALPHA-IIB/BETA-3
TARGET -> INHIBITOR
Related Record Type Details
Structure of EPTIFIBATIDE
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