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Eptifibatide

CAT: 0013-GTR19236811-03Size: 1 gDry Ice: NoHazardous: No
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Description
Eptifibatide is a potent glycoprotein IIb/IIIa antagonist (GPIIb/IIIa; Kd = 120 nM) that inhibits platelet aggregation. Eptifibatide prevents binding of the adhesion proteins fibrinogen and von Willebrand factor to GPIIb/IIIa on the surface of activated platelets to prevent aggregation and thrombus formation. It inhibits ADP-induced citrated blood aggregation (IC50 = 0.11-0.22 μg/ml) in vitro and in vivo (IC50 = 52 μg/ml in porcine plasma) . Formulations containing eptifibatide have been used to reduce risk of thrombolysis in myocardial infarction in patients undergoing percutaneous coronary intervention.
CAS Number
188627-80-7
Field of Research
Pharmacology & Drug Discovery
Purity
>98%
Smiles
S1C ([H]) ([H]) [C@@] ([H]) (C (N ([H]) [H]) =O) N ([H]) C ([C@]2 ([H]) C ([H]) ([H]) C ([H]) ([H]) C ([H]) ([H]) N2C ([C@] ([H]) (C ([H]) ([H]) C2=C ([H]) N ([H]) C3=C ([H]) C ([H]) =C ([H]) C ([H]) =C23) N ([H]) C ([C@] ([H]) (C ([H]) ([H]) C (=O) O[H]) N ([H]) C (C ([H]) ([H]) N ([H]) C ([C@] ([H]) (C ([H]) ([H]) C ([H]) ([H]) C ([H]) ([H]) C ([H]) ([H]) /N=C (\N ([H]) [H]) /N ([H]) [H]) N ([H]) C (C ([H]) ([H]) C ([H]) ([H]) S1) =O) =O) =O) =O) =O) =O
Molecular Formula
C35H49N11O9S2
Molecular Weight
831.9619
Notes
For research use only.

Chemical Information

Eptifibatide

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.

CAS Number188627-80-7
PubChem CID448812
IUPAC Name2-[(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 FormulaC35H49N11O9S2
Molecular Weight832.0
XLogP-2.4
Topological Polar Surface Area377
Hydrogen Bond Donor Count10
Hydrogen Bond Acceptor Count12
Rotatable Bond Count10
Heavy Atom Count57
Formal Charge0
Complexity1520
SMILES
C1C[C@H]2C(=O)N[C@@H](CSSCCC(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N2C1)CC3=CNC4=CC=CC=C43)CC(=O)O)CCCCN=C(N)N)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
InChIKey
CZKPOZZJODAYPZ-LROMGURASA-N
Chemical Structure
2D Structure
2D structure of Eptifibatide
CAS: 188627-80-7
CID: 448812
Formula: C35H49N11O9S2
MW: 832.0
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight832.0
XLogP3-2.4
Hydrogen Bond Donor Count10
Hydrogen Bond Acceptor Count12
Rotatable Bond Count10
Exact Mass831.31561453
Monoisotopic Mass831.31561453
Topological Polar Surface Area377 Ų
Heavy Atom Count57
Formal Charge0
Complexity1520
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
PT_40510-01Eptifibatide Human (Eptifibatide Human)
H-6654.0005Eptifibatide

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