Eptifibatide

Eptifibatide
Clinical data
Trade names	Integrilin
AHFS/Drugs.com	Monograph
MedlinePlus	a601210
License data	EU EMA: by INN; US DailyMed: Eptifibatide; US FDA: Eptifibatide;
Routes of; administration	Intravenous
ATC code	B01AC16 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	n/a
Protein binding	~25%
Elimination half-life	~2.5 hours
Excretion	Kidney
Identifiers
	IUPAC name N6-(Aminoiminomethyl)-N2-(3-mercapto-1-oxopropyl)-L-lysylglycyl-L-α-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide, cyclic (1→6)disulfide;
CAS Number	188627-80-7 ;
PubChem CID	123610;
IUPHAR/BPS	6585;
DrugBank	DB00063 ;
ChemSpider	10482060 ;
UNII	NA8320J834;
KEGG	D06888 ;
ChEBI	CHEBI:291902 ;
ChEMBL	ChEMBL1174 ;
CompTox Dashboard (EPA)	DTXSID7046673 ;
ECHA InfoCard	100.169.160
Chemical and physical data
Formula	C35H49N11O9S2
Molar mass	831.97 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [H][C@@]14CCCN1C(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](CC(=O)O)NC(=O)CNC(=O)[C@H](CCCCNC(=N)N)NC(=O)CCSSC[C@@H](C(N)=O)NC4=O;
	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 ; Key:CZKPOZZJODAYPZ-LROMGURASA-N ;
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Eptifibatide (Integrilin, Millennium Pharmaceuticals, also co-promoted by Schering-Plough/Essex), is an antiplatelet drug of the glycoprotein IIb/IIIa inhibitor class. Eptifibatide is a cyclic heptapeptide derived from a disintegrin protein (P22827) found in the venom of the southeastern pygmy rattlesnake (Sistrurus miliarius barbouri). It belongs to the class of the 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.