Eptifibatide

Title: Eptifibatide
CAS Registry Number: 188627-80-7
CAS Name: N6-(Aminoiminomethyl)-N2-(3-mercapto-1-oxopropyl)-L-lysylglycyl-L-a-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide, cyclic (1®6)-disulfide
Trademarks: Integrilin (COR)
Molecular Formula: C35H49N11O9S2
Molecular Weight: 831.96
Percent Composition: C 50.53%, H 5.94%, N 18.52%, O 17.31%, S 7.71%
Literature References: Fibrinogen receptor antagonist. Specifically inhibits fibrinogen binding to the platelet integrin GPIIb-IIIa which prevents platelet aggregation and subsequent clot formation. Synthetic, disulfide-linked cyclic heptapeptide based on barbourin, a specific GPIIb-IIIa antagonist isolated from venom of the southeastern pigmy rattlesnake, Sistrurus m. barbouri. Contains the Lys-Gly-Asp (KGD) amino acid sequence, a modification of the Arg-Gly-Asp (RGD) recognition site which appears to confer specificity: R. M. Scarborough et al., J. Biol. Chem. 266, 9359 (1991). Design and structure-activity study of integrin antagonists: eidem, ibid. 268, 1066 (1993). Prepn: R. M. Scarborough et al., US 5686570 (1997 to COR Therapeutics). Pharmacology: F. A. Nicolini et al., Circulation 89, 1802 (1994); K. Uthoff et al., ibid. 90, pt 2, II-269 (1994). Clinical trial in patients undergoing percutaneous cardiovascular intervention: IMPACT-II Investigators, Lancet 349, 1422 (1997). Clinical trial in acute coronary syndromes: PURSUIT Trial Investigators, N. Engl. J. Med. 339, 436 (1998).
Therap-Cat: Antithrombotic.
Keywords: Antithrombotic.
Equilenin Erabutoxins Erbium Sulfate Erdin Erdosteine

Eptifibatide
Eptifibatide structure.svg
Eptifibatide ball-and-stick.png
Systematic (IUPAC) name
N6-(aminoiminomethyl)-N2-(3-mercapto-1-oxopropyl)-L-lysylglycyl-L-α-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide, cyclic (1→6)disulfide
Clinical data
Trade names Integrilin
AHFS/Drugs.com monograph
MedlinePlus a601210
Licence data EMA:Link, US FDA:link
Pregnancy cat. B (US)
Legal status POM (UK) -only (US)
Routes IV only
Pharmacokinetic data
Bioavailability n/a
Protein binding ~25%
Half-life ~2.5 hours
Excretion Renal
Identifiers
CAS number 188627-80-7 YesY
ATC code B01AC16
PubChem CID 123610
DrugBank DB00063
ChemSpider 10482060 YesY
UNII NA8320J834 YesY
KEGG D06888 YesY
ChEBI CHEBI:291902 YesY
ChEMBL CHEMBL1174 YesY
Chemical data
Formula C35H49N11O9S2 
Mol. mass 831.96 g/mol
 YesY (what is this?)  (verify)

Eptifibatide (Integrilin, Millennium Pharmaceuticals, also co-promoted by Schering-Plough/Essex), is an antiplatelet drug of the glycoprotein IIb/IIIa inhibitor class.[1] Eptifibatide is a cyclic heptapeptide derived from a protein found in the venom of the southeastern pygmy rattlesnake (Sistrurus miliarius barbouri). It belongs to the class of the so-called arginin-glycin-aspartat-mimetics and reversibly binds to platelets. Eptifibatide has a short half-life. The drug is the third inhibitor of GPIIb/IIIa that has found broad acceptance after the specific antibody abciximab and the non-peptide tirofiban entered the global market.

Integrilin is sold in two strengths, globally: vials containing 2 mg/ml (20 mg totally) and 0.75 mg/ml (75 mg totally). A third size is sold in the US: 100 ml vials containing 2 mg/ml (200 mg totally).