QuickView for Eptifibatide (compound)

Summary
General Info

PubChem

PubChem Compound 123610

Name:	eptifibatide
PubChem Compound ID:	123610
Molecular formula:	C₃₅H₄₉N₁₁O₉S₂
Molecular weight:	831.964 g/mol
Synonyms:	188627-80-7; Integrelin; Integrilin; 148031-34-9; 157630-07-4; Eptifibatide; L-Cysteinamide, N6-(aminoiminomethyl)-N2-(3-mercapto-1-oxopropyl)-L-lysylglycyl-L-alpha-aspartyl-L-tryptophy-L-prolyl-, cyclic (1-6)-disulfide

DrugBank

Identification

Name:	eptifibatide
Name (isomeric):	DB00063
Drug Type:	biotech
Synonyms:	Integrelin; Intrifiban
Brand:	Integrilin
Category:	Anticoagulants, Platelet Aggregation Inhibitors, Antiplatelet Agents
CAS number:	188627-80-7

Pharmacology

Indication:	For treatment of myocardial infarction and acute coronary syndrome.
Pharmacology:	Eptifibatide is an anti-coagulant that selectively blocks the platelet glycoprotein IIb/IIIa receptor. Eptifibatide is a cyclic heptapeptide derived from a protein found in the venom of the southeastern pygmy rattlesnake (Sistrurus miliarus barbouri). It belongs to the class of the so called arginin-glycin-aspartat-mimetics and reversibly binds to ... show more » Eptifibatide is an anti-coagulant that selectively blocks the platelet glycoprotein IIb/IIIa receptor. Eptifibatide is a cyclic heptapeptide derived from a protein found in the venom of the southeastern pygmy rattlesnake (Sistrurus miliarus barbouri). It belongs to the class of the so called arginin-glycin-aspartat-mimetics and reversibly binds to platelets. show less «
Mechanism of Action:	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.
Protein binding:	Approximately 25%
Biotransformation:	No major metabolites have been detected in human plasma. Deamidated eptifibatide and other, more polar metabolites have been detected in urine.
Half Life:	Approximately 2.5 hours
Clearance:	55 mL/kg/h [patients with coronary artery disease]
Toxicity:	Eptifibatide was not lethal to rats, rabbits, or monkeys when administered by continuous intravenous infusion for 90 minutes at a total dose of 45 mg/kg (about 2 to 5 times the recommended maximum daily human dose on a body surface area basis)
Affected organisms:	Humans and other mammals

Interactions

Drug interaction:

Tirofiban	Additive effects. Concomitant use is contraindicated.
Ginkgo biloba	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Treprostinil	The prostacyclin analogue, Treprostinil, increases the risk of bleeding when combined with the antiplatelet agent, Eptifibatide. Monitor for increased bleeding during concomitant thearpy.

Targets

Integrin beta-3

Integrin alpha-V/beta-3 is a receptor for cytotactin, fibronectin, laminin, matrix metalloproteinase-2, osteopontin, osteomodulin, prothrombin, thrombospondin, vitronectin and von Willebrand factor. Integrin alpha-IIb/beta-3 is a receptor for fibronectin, fibrinogen, plasminogen, prothrombin, thrombospondin and vitronectin. Integrins alpha-IIb/beta-3 and alpha-V/beta-3 recognize the sequence R-G-D in a wide array of ligands. Integrin alpha-IIb/beta-3 recognizes the sequence H-H-L-G-G-G-A-K-Q-A-G-D-V in fibrinogen gamma chain. Following activation integrin alpha- IIb/beta-3 brings about platelet/platelet interaction through binding of soluble fibrinogen. This step leads to rapid platelet aggregation which physically plugs ruptured endothelial surface. In case of HIV-1 infection, the interaction with extracellular viral Tat protein seems to enhance angiogenesis in Kaposi's sarcoma lesions

UniProt ID:

P05106

Gene:

ITGB3

Actions:

yes

References:

Amoroso G, van Boven AJ, van Veldhuisen DJ, Tio RA, Balje-Volkers CP, Petronio AS, van Oeveren W: Eptifibatide and abciximab exhibit equivalent antiplatelet efficacy in an experimental model of stenting in both healthy volunteers and patients with coronary artery disease. J Cardiovasc Pharmacol. 2001 Oct;38(4):633-41.
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Schror K, Weber AA: Comparative pharmacology of GP IIb/IIIa antagonists. J Thromb Thrombolysis. 2003 Apr;15(2):71-80.
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Fischer TH, Thatte HS, Nichols TC, Bender-Neal DE, Bellinger AD, Vournakis JN: Synergistic platelet integrin signaling and factor XII activation in poly-N-acetyl glucosamine fiber-mediated hemostasis. Biomaterials. 2005 Sep;26(27):5433-43.
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Weber AA, Jacobs C, Meila D, Weber S, Zotz RB, Scharf RE, Kelm M, Strauer BE, Schror K: No evidence for an influence of the human platelet antigen-1 polymorphism on the antiplatelet effects of glycoprotein IIb/IIIa inhibitors. Pharmacogenetics. 2002 Oct;12(7):581-3.
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Schwarz M, Katagiri Y, Kotani M, Bassler N, Loeffler C, Bode C, Peter K: Reversibility versus persistence of GPIIb/IIIa blocker-induced conformational change of GPIIb/IIIa (alphaIIbbeta3, CD41/CD61). J Pharmacol Exp Ther. 2004 Mar;308(3):1002-11. Epub 2003 Nov 14.
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Auer J, Berent R, Lassnig E, Weber T, Maurer E, Eber B: [Platelet glycoprotein IIb/IIIa inhibitors in coronary artery disease] Herz. 2003 Aug;28(5):393-403.
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Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
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