Eptifibatide
2-[(3S,6S,12S,20R,23S)-20-carbamoyl-12-[4-(diaminomethylideneamino)butyl]-3-(1H-indol-3-ylmethyl)-2,5,8,11,14,22-hexaoxo-17,18-dithia-1,4,7,10,13,21-hexazabicyclo[21.3.0]hexacosan-6-yl]acetic acid
Molecular Identity
Eptifibatide
2-[(3S,6S,12S,20R,23S)-20-carbamoyl-12-[4-(diaminomethylideneamino)butyl]-3-(1H-indol-3-ylmethyl)-2,5,8,11,14,22-hexaoxo-17,18-dithia-1,4,7,10,13,21-hexazabicyclo[21.3.0]hexacosan-6-yl]acetic acid
PubChem CID: 448812
Eptifibatide is a synthetic homodetic cyclic peptide comprising Nalpha-(3-sulfanylpropanoyl)homoarginyl, glycyl, aspartyl, tryptophyl, prolyl and cysteinamide residues connected in sequence and cyclised via a disulfide bond. Derived from a protein found in the venom of the southeastern pygmy rattlesnake, Sistrurus miliarus barbouri, eptifibatide is an anti-coagulant that inhibits platelet aggregation by selectively blocking the platelet glycoprotein IIb/IIIa receptor, so preventing the binding of fibrinogen, von Willebrand factor, and other adhesive ligands. It is used in the management of unstable angina and in patients undergoing coronary angioplasty and stenting procedures. It has a role as an anticoagulant and a platelet aggregation inhibitor. It is a homodetic cyclic peptide, an organic disulfide and a macrocycle.
2D Structure
Properties
C35H49N11O9S2
Molecular Formula
832.00
Molecular Weight
g/mol
831.3156
Exact Mass
Da
-2.4
XLogP
Drug-like (Lipinski: < 5)
377
TPSA
May have limited oral absorption
10
H-Bond Donors
12
H-Bond Acceptors
1520
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
Eptifibatide188627-80-7IntegrilinIntegrelinEptifibatidaDTXSID7046673NA8320J834DTXCID5026673CHEBI:291902[(3R,11S,17S,20S,25aS)-11-(4-carbamimidamidobutyl)-3-carbamoyl-20-(1H-indol-3-ylmethyl)-1,9,12,15,18,21-hexaoxodocosahydro-7H-pyrrolo[2,1-g][1,2,5,8,11,14,17,20]dithiahexaazacyclotricosin-17-yl]acetic acidN(sup 6)-Amidino-N(sup 2)-(3-mercaptopropionyl)-L-lysylglycyl-L-alpha-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide, cyclic(1-6)-disulfideepifibatideepifibratideeptifibatidum((3R,11S,17S,20S,25aS)-11-(4-carbamimidamidobutyl)-3-carbamoyl-20-(1H-indol-3-ylmethyl)-1,9,12,15,18,21-hexaoxodocosahydro-7H-pyrrolo(2,1-g)(1,2,5,8,11,14,17,20)dithiahexaazacyclotricosin-17-yl)acetic acid
Data from PubChem (NCBI)
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