eptifibatide   Click here for help

GtoPdb Ligand ID: 6585

Synonyms: C68-22 | Eptifibatide Accord (generic) | Integrelin®
Approved drug
eptifibatide is an approved drug (FDA (1998), EMA (1999))
Compound class: Synthetic organic
Comment: Eptifibatide is a synthetic cyclic hexapeptide inhibitor of the integrin αIIbβ3 protein complex.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 19
Hydrogen bond donors 11
Rotatable bonds 11
Topological polar surface area 374.49
Molecular weight 831.32
XLogP 0.57
No. Lipinski's rules broken 3
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Canonical SMILES OC(=O)CC1NC(=O)CNC(=O)C(CCCCNC(=N)N)NC(=O)CCSSCC(NC(=O)C2N(C(=O)C(NC1=O)Cc1c[nH]c3c1cccc3)CCC2)C(=O)N
Isomeric SMILES OC(=O)C[C@@H]1NC(=O)CNC(=O)[C@H](CCCCNC(=N)N)NC(=O)CCSSC[C@H](NC(=O)[C@H]2N(C(=O)[C@@H](NC1=O)Cc1c[nH]c3c1cccc3)CCC2)C(=O)N
InChI 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
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Summary of Clinical Use Click here for help
Eptifibatide is administered with aspirin and unfractionated heparin (other anti-thrombotic drugs) to prevent myocardial infarction in high risk patients, such as those experiencing acute angina.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Eptifibatide inhibits platelet aggregation by binding to platelet receptor glycoprotein (integrin αIIb/β3 complex), thus preventing the binding of clot forming components such as fibrinogen, von Willebrand factor, and other adhesive ligands.
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