CHEBI:291902 - eptifibatide

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ChEBI Name eptifibatide
ChEBI ID CHEBI:291902
Definition A synthetic homodetic cyclic peptide comprising Nα-(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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C35H49N11O9S2
Net Charge 0
Average Mass 831.96200
Monoisotopic Mass 831.31561
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
SMILES [H][C@@]1(Cc2c[nH]c3ccccc23)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)CCSSC[C@H](NC(=O)[C@@H]2CCCN2C1=O)C(N)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Application(s): platelet aggregation inhibitor
A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
anticoagulant
An agent that prevents blood clotting.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing eptifibatide (CHEBI:291902) has role anticoagulant (CHEBI:50249)
eptifibatide (CHEBI:291902) has role platelet aggregation inhibitor (CHEBI:50427)
eptifibatide (CHEBI:291902) is a homodetic cyclic peptide (CHEBI:24613)
eptifibatide (CHEBI:291902) is a macrocycle (CHEBI:51026)
eptifibatide (CHEBI:291902) is a organic disulfide (CHEBI:35489)
IUPAC Name
[(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
Synonyms Sources
EPTIFIBATIDE ChEMBL
N6-amidino-N2-(3-mercaptopropionyl)-L-lysylglycyl-L-α-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide, cyclic(1-6)-disulfide ChemIDplus
S1,S6-cyclo[N6-carbamimidoyl-N2-(3-sulfanylpropanoyl)-L-lysylglycyl-L-α-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide] ChEBI
Manual Xrefs Databases
1040 DrugCentral
D06888 KEGG DRUG
DB00063 DrugBank
Eptifibatide Wikipedia
US5686570 Patent
View more database links
Registry Numbers Types Sources
188627-80-7 CAS Registry Number ChemIDplus
9608167 Beilstein Registry Number Beilstein
Last Modified
22 February 2017