EPTIFIBATIDE

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 Search

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Integrin alpha-IIb/beta-3 14 Target ID: CHEMBL2093869 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10577440	Inhibitor 8146		8.7 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute coronary syndrome 32 Sources: www.accessdata.fda.gov/drugsatfda_docs/label/2011/020718s034lbl.pdf	Primary		Approved 8307	INTEGRILIN Approved Use Eptifibatide Launch Date 9.2871361E11

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Platelet aggregation inhibition with glycoprotein IIb--IIIa inhibitors.	2001 Apr	11406724
[GPIIb-IIIa inhibitors].	2001 Apr	11386043
[Pathophysiology of platelet activation and pharmacology of GPIIb/IIIa inhibitors].	2001 Apr	11349624
Greater inhibition of platelet procoagulant activity by antibody-derived glycoprotein IIb--IIIa inhibitors than by peptide and peptidomimetic inhibitors.	2001 Apr	11328283
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	11285593
In vitro dose response to different GPIIb/IIIa-antagonists: inter-laboratory comparison of various platelet function tests.	2001 Apr 1	11323013
Platelet glycoprotein IIb/IIIa-receptor inhibitors in patients with acute coronary syndromes or undergoing percutaneous coronary interventions: a review.	2001 Aug	11558855
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	11479455
Binding of a fibrinogen mimetic stabilizes integrin alphaIIbbeta3's open conformation.	2001 Aug	11468358
Association of eptifibatide and acute profound thrombocytopenia.	2001 Aug 15	11545770
GP IIb/IIIa inhibitors in coronary artery disease management: what the latest trials tell us.	2001 Dec	11765119
Platelet inhibition after glycoprotein IIb/IIIa inhibitor therapy.	2001 Dec 18	11748127
[Integrin-ligands binding reaction upregulates the antioxidant activity of rabbit bronchial epithelial cells].	2001 Feb	11354796
Glycoprotein IIb/IIIa inhibitors: more different than alike?	2001 Jul	11458404
Atrial fibrillation and mortality among patients with acute coronary syndromes without ST-segment elevation: results from the PURSUIT trial.	2001 Jul 1	11423065
AlphaIIb's cytoplasmic domain is not required for ligand-induced clustering of integrin alphaIIbbeta3.	2001 Jul 25	11476897
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	11479257
Randomized comparison of ticlopidine and clopidogrel after intracoronary stent implantation in a broad patient population.	2001 Jul 31	11479250
Successful use of eptifibatide as an adjunct to coronary stenting in a patient with abciximab-associated acute profound thrombocytopenia.	2001 Jun	11385174
Effect of eptifibatide on coronary flow reserve following coronary stent implantation (an ESPRIT substudy). Enhanced Suppression of the Platelet IIb/IIIa Receptor with Integrilin Therapy.	2001 Jun 1	11377359
Mechanisms of thrombotic microangiopathy following xenogeneic hematopoietic progenitor cell transplantation.	2001 Jun 15	11435972
Unexpected flow cytometric results with two small GPIIb/IIIa blockers: eptifibatide and tirofiban.	2001 Mar	11307832
Effect of Ca2+ chelation on the platelet inhibitory ability of the GPIIb/IIIa antagonists abciximab, eptifibatide and tirofiban.	2001 Mar	11307828
Initial experience with a newer generation coronary stent.	2001 Mar	11231647
New approaches to diagnosis and management of unstable angina and non-ST-segment elevation myocardial infarction.	2001 Mar 12	11231699
Short-term comparative outcomes associated with the use of GP IIb/IIIa antagonists in patients undergoing coronary intervention.	2001 May	11577258
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	11334301
Platelet glycoprotein IIb/IIIa integrin blockade with eptifibatide in coronary stent intervention: the ESPRIT trial: a randomized controlled trial.	2001 May 16	11368699
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	11382726
Monitoring platelet function in glycoprotein IIB/IIIA inhibitor therapy.	2001 May 29	11382717
Drug-company sponsorship and the Declaration of Helsinki.	2001 May 5	11360954
Stabilization of eptifibatide by cosolvents.	2001 May 7	11337148
Novel dosing regimen of eptifibatide in planned coronary stent implantation (ESPRIT): a randomized placebo-controlled study.	2001 May-Jun	11516048
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	11704707
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	11703991
Intravenous glycoprotein IIb/IIIa inhibition in non-ST segment elevation acute coronary syndromes.	2001 Nov-Dec	11727277
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	11729364
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	11602859
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	11520817
Oral glycoprotein IIb/IIa antagonists for unstable angina--is there still a chance for the oral substances?	2001 Sep 30	11567679
Indications for appropriate platelet glycoprotein IIb/IIIa inhibitor therapy.	2002 Apr	11919540
Eptifibatide and 7E3, but not tirofiban, inhibit alpha(v)beta3 integrin-mediated binding of smooth muscle cells to thrombospondin and prothrombin.	2002 Feb 12	11839641
Long-term efficacy of platelet glycoprotein IIb/IIIa integrin blockade with eptifibatide in coronary stent intervention.	2002 Feb 6	11829701
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 Feb 6	11823073
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	11741362
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	11779525
A synthetic polymer matrix for the delayed or pulsatile release of water-soluble peptides.	2002 Jan 17	11772456
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	11804987
Platelet aggregation inhibitors for use in peripheral vascular interventions: what can we learn from the experience in the coronary arteries?	2002 Mar	11875083
Using a peptide inhibitor of the glycoprotein IIb/IIIa platelet receptor: initial experience in patients with acute peripheral arterial occlusions.	2002 Mar	11856686

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

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-?-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