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CHEBI:291902 - eptifibatide

Default Structure
ChEBI IDCHEBI:291902
ChEBI Nameeptifibatide
Stars
DefinitionA 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.
Last Modified22 February 2017
DownloadsMolfile
FormulaC35H49N11O9S2
Net Charge0
Average Mass831.979
Monoisotopic Mass831.31561
SMILES[H][C@@]1(Cc2cnc3ccccc23)NC(=O)[C@H](CC(=O)O)NC(=O)CNC(=O)[C@H](CCCCNC(=N)N)NC(=O)CCSSC[C@@H](C(N)=O)NC(=O)[C@@H]2CCCN2C1=O
InChIInChI=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
InChIKeyCZKPOZZJODAYPZ-LROMGURASA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
N6-amidino-N2-(3-mercaptopropionyl)-L-lysylglycyl-L-α-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide, cyclic(1-6)-disulfideChemIDplus
S1,S6-cyclo[N6-carbamimidoyl-N2-(3-sulfanylpropanoyl)-L-lysylglycyl-L-α-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide]ChEBI
EPTIFIBATIDEChEMBL
Manual XrefsDatabases
1040DrugCentral
D06888KEGG DRUG
DB00063DrugBank
EptifibatideWikipedia
US5686570Patent
Registry NumbersSources
Beilstein:9608167Beilstein
CAS:188627-80-7KEGG COMPOUND
CAS:188627-80-7ChemIDplus