Eptifibatide Acetate

Base Information

• Chemical Name: Eptifibatide Acetate
• CAS No.: 188627-80-7
• Molecular Formula: C₃₅H₄₉N₁₁O₉S₂
• Molecular Weight: 831.974
• Hs Code.: 2933299090
• European Community (EC) Number: 641-366-7
• DSSTox Substance ID: DTXSID60861477
• Wikipedia: Eptifibatide
• ChEMBL ID: CHEMBL4303580
• Mol file: 188627-80-7.mol

Synonyms:7H-Pyrrolo(2,1-g)(1,2,5,8,11,14,17,20)dithiahexaazacyclotricosine-17-acetic acid, 3-(aminocarbonyl)-11-(4-((aminoiminomethyl)amino)butyl)docosahydro-20-(1H-indol-3-ylmethyl)-1,9,12,15,18,21-hexaoxo-, (3R,11S,17S,20S,25aS)-;epifibatide;epifibratide;eptifibatide;Integrelin;Integrilin

Chemical Property of Eptifibatide Acetate

Chemical Property:

• Appearance/Colour: White powder
• Refractive Index: 1.742
• PKA: 4.01±0.10(Predicted)
• PSA: 374.49000
• Density: 1.605 g/cm³
• LogP: 1.62840
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 10
• Exact Mass: 831.31561453
• Heavy Atom Count: 57
• Complexity: 1520

Purity/Quality:

98% ^*data from raw suppliers

Eptifibatide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C(=O)NC(CSSCCC(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)N2C1)CC3=CNC4=CC=CC=C43)CC(=O)O)CCCCN=C(N)N)C(=O)N
• Description: Eptifibatide is a kind of synthetic cyclic hexapeptide consisting of 6 amino acids and 1 mercaptopropionyl residue. It is capable of binding to the platelet receptor glycoprotein (GP) IIb/IIIa of human platelets and inhibiting the platelet aggregation, thus blocking the binding of the fibrinogen, von Willebrand factor and other adhesive ligands. It is indicated for the treatment of acute coronary syndrome (ACS) and Percutaneous coronary intervention (PCI). It is able to reduce the risk of acute cardiac ischemic events in patients with unstable angina or non-ST segment-elevation myocardial infection. It is often used in combination with aspirin or clopidogrel and heparin. It can be manufactured through solution-phase peptide synthesis, and can be purified by preparative reverse-phase liquid chromatography and lyophilization. Eptifibatide is a reversible antagonist of the glycoprotein llb/llla complex, a specific platelet adhesion receptor that plays a central role in the cascade of thrombus formation by allowing mediators such as fibrinogen or von Willbrand factor to cross-link adjacent platelets and to give rise to aggregation. In diverse animal experimental models of arterial thrombosis, treatment with Eptifibatide resulted in an enhanced lysis of occlusive thrombus and a restoration of arterial blood flow. In clinical trials involving patients with acute coronary syndromes, Eptifibatide demonstrated a significant decrease in the incidence of death or nonfatal myocardial infarction at 30 days. In other trials in patients undergoing percutaneous coronary intervention (PCI), it showed a positive trend. Eptifibatide has the advantage of being short acting, its antiplatelet effect being rapidly reversible.
• Uses: Eptifibatide is a cyclical heptapeptide with anticoagulant activity. Eptifibatide selectively and reversibly binds to and blocks the platelet glycoprotein IIb/IIIa receptor. This prevents the binding of fibrinogen, von Willebrand factor, and other adhesive ligands and leads to an inhibition of platelet aggregation and prevents thrombus development. It is an efficient peptide drug to reduce the risk of cardiac ischemic events, however has a short half-life. Therefore, antithrombotic agents like eptifibatide are required to become improved with a protected and targeted delivery system such as using nano-liposomes to the site of thrombus.
• Clinical Use: Eptifibatide is a cyclic heptapeptide composed of six amino acids and one mercaptopropionyl residue. The cyclization is completed via a disulfide linkage between the cysteine and the mercaptopropionyl moieties. The lysine-glycine-aspartate component of eptifibatide is highly specific for the GPIIb/IIIa receptor, with low binding affinity, as indicated by the rapid dissociation constant. Because of this, eptifibatide is a reversible, parenterally administered antagonist of platelet aggregation.
• Drug interactions: Potentially hazardous interactions with other drugs Iloprost: increased risk of bleeding.

Technology Process of Eptifibatide Acetate

There total 3 articles about Eptifibatide Acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

Mpa-Har-Gly-Asp-Trp-Pro-Cys-NH2 (135900-78-6) → integrilin (157630-07-4,188627-80-7)

Guidance literature:

With ammonium hydroxide; In water; acetonitrile; at 23 ℃; for 2h; pH=9;

DOI:10.1021/ol302002g

Reference yield:

di-isopropyl ether (108-20-3) + chlorotriisopropylsilane (6485-79-6) → integrilin (157630-07-4,188627-80-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; water; ethyl acetate;

Reference yield:

→ integrilin (157630-07-4,188627-80-7)

Guidance literature:

With ammonium hydroxide; acetic acid; In water; acetonitrile;

upstream raw materials:

Mpa-Har-Gly-Asp-Trp-Pro-Cys-NH₂

di-isopropyl ether

chlorotriisopropylsilane

Downstream raw materials:

eptifibatide acetate

Refernces

• 1、 Takahashi, Daisuke,Yano, Tatsuya,Fukui, Tatsuya. "Novel diphenylmethyl-derived amide protecting group for efficient liquid-phase peptide synthesis: AJIPHASE". supporting information. p. 4514 - 4517. Retrieved 2012/10/29.