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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
113
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8228
 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
8360
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 aggregation inhibition with glycoprotein IIb--IIIa inhibitors.
2001 Apr
[GPIIb-IIIa inhibitors].
2001 Apr
Antiplatelet agents in tissue factor-induced blood coagulation.
2001 Apr 15
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
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
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
[Integrin-ligands binding reaction upregulates the antioxidant activity of rabbit bronchial epithelial cells].
2001 Feb
Therapeutic value of eptifibatide at community hospitals transferring patients to tertiary referral centers early after admission for acute coronary syndromes. PURSUIT Investigators.
2001 Feb
Anti-GPIIb/IIIa drugs: current strategies and future directions.
2001 Jul
Atrial fibrillation and mortality among patients with acute coronary syndromes without ST-segment elevation: results from the PURSUIT trial.
2001 Jul 1
Emergency room administration of eptifibatide before primary angioplasty for ST elevation acute myocardial infarction and its effect on baseline coronary flow and procedure outcomes.
2001 Jul 1
Pharmacodynamics and pharmacokinetics of higher-dose, double-bolus eptifibatide in percutaneous coronary intervention.
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
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
Comparative specificity of platelet alpha(IIb)beta(3) integrin antagonists.
2001 Mar
Glycoprotein IIb/IIIa antagonists and low-molecular weight heparin in acute coronary syndromes.
2001 May
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
Intravenous glycoprotein IIb/IIIa inhibition in non-ST segment elevation acute coronary syndromes.
2001 Nov-Dec
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
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
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
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
A structural and dynamic investigation of the facilitating effect of glycoprotein IIb/IIIa inhibitors in dissolving platelet-rich clots.
2002 Mar 8
Patents

Patents

JP2011528275A
453

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 Thu Jul 06 21:24:48 UTC 2023
Edited
by admin
on Thu Jul 06 21:24:48 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 Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
NDF-RT N0000008832
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
WHO-ATC B01AC16
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
NDF-RT N0000175578
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
EMA ASSESSMENT REPORTS INTEGRILIN (AUTHORIZED: ANGINA, UNSTABLE)
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
WHO-VATC QB01AC16
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
FDA ORPHAN DRUG 364012
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
EMA ASSESSMENT REPORTS INTEGRILIN (AUTHORIZED: MYOCARDIAL INFARCTION)
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
NDF-RT N0000008832
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
Code System Code Type Description
EVMPD
SUB12498MIG
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
SMS_ID
100000089288
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
CAS
148031-34-9
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
SUPERSEDED
CHEBI
291902
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
MESH
C086648
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
EPA CompTox
DTXSID7046673
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
MERCK INDEX
M4968
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB00063
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
RXCUI
75635
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY RxNorm
LACTMED
Eptifibatide
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
RS_ITEM_NUM
1238501
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
CHEMBL
CHEMBL1174
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
IUPHAR
6585
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
CAS
188627-80-7
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
HSDB
8313
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
DRUG CENTRAL
1040
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
WIKIPEDIA
EPTIFIBATIDE
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
PUBCHEM
448812
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
USAN
II-61
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
NCI_THESAURUS
C47516
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
FDA UNII
NA8320J834
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
INN
7717
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
DAILYMED
NA8320J834
Created by admin on Thu Jul 06 21:24:48 UTC 2023 , Edited by admin on Thu Jul 06 21:24:48 UTC 2023
PRIMARY
Related Record Type Details
ALPHA-IIB/BETA-3
TARGET -> INHIBITOR
Related Record Type Details
Structure of EPTIFIBATIDE
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