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

NC(=N)NCCCC[C@@H]1NC(=O)CCSSC[C@H](NC(=O)[C@@H]2CCCN2C(=O)[C@H](CC3=CNC4=C3C=CC=C4)NC(=O)[C@H](CC(O)=O)NC(=O)CNC1=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

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.7 nM [IC50]
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
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
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
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
180 ug/kg
Route of Administration: Intravenous
In Vitro Use Guide
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
NDF-RT N0000008832
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
WHO-ATC B01AC16
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
NDF-RT N0000175578
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
EMA ASSESSMENT REPORTS INTEGRILIN (AUTHORIZED: ANGINA, UNSTABLE)
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
WHO-VATC QB01AC16
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
EMA ASSESSMENT REPORTS INTEGRILIN (AUTHORIZED: MYOCARDIAL INFARCTION)
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
NDF-RT N0000008832
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
Code System Code Type Description
EVMPD
SUB12498MIG
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
PRIMARY
MESH
C086648
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
PRIMARY
EPA CompTox
188627-80-7
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
PRIMARY
MERCK INDEX
M4968
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
PRIMARY Merck Index
DRUG BANK
DB00063
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
PRIMARY
RXCUI
75635
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
PRIMARY RxNorm
ChEMBL
CHEMBL1174
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
PRIMARY
IUPHAR
6585
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
PRIMARY
CAS
188627-80-7
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
PRIMARY
HSDB
188627-80-7
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
PRIMARY
WIKIPEDIA
EPTIFIBATIDE
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
PRIMARY
PUBCHEM
448812
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
PRIMARY SWITZERF
NCI_THESAURUS
C47516
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
PRIMARY
INN
7717
Created by admin on Tue Mar 06 11:19:16 UTC 2018 , Edited by admin on Tue Mar 06 11:19:16 UTC 2018
PRIMARY