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MedKoo Cat#: 596983 | Name: Eptifibatide (free base)
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Eptifibatide (free base)
Eptifibatide (free base)
CAS#188627-80-7 (free base)

Theoretical Analysis

MedKoo Cat#: 596983

Name: Eptifibatide (free base)

CAS#: 188627-80-7 (free base)

Chemical Formula: C35H49N11O9S2

Exact Mass: 831.3156

Molecular Weight: 831.96

Elemental Analysis: C, 50.53; H, 5.94; N, 18.52; O, 17.31; S, 7.71

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 650.00 2 Weeks
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Related CAS #
188627-80-7 (free base) 148031-34-9 (acetate)
Synonym
Eptifibatide; Integrilin; Integrelin; Intrifiban; Eptifibatida
IUPAC/Chemical Name
2-((3R,11S,17S,20S,25aS)-20-((1H-indol-3-yl)methyl)-3-carbamoyl-11-(4-guanidinobutyl)-1,9,12,15,18,21-hexaoxodocosahydro-7H-pyrrolo[2,1-g][1,2]dithia[5,8,11,14,17,20]hexaazacyclotricosin-17-yl)acetic acid
InChi Key
CZKPOZZJODAYPZ-LROMGURASA-N
InChi Code
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
SMILES Code
O=C(O)C[C@H](NC(CNC([C@H](CCCC/N=C(N)/N)NC(CCSSC[C@@H](C(N)=O)N1)=O)=O)=O)C(N[C@@H](CC2=CNC3=C2C=CC=C3)C(N4CCC[C@@]4([H])C1=O)=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 831.96 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Dillinger JG, Ducrocq G, Elbez Y, Cohen M, Bode C, Pollack C Jr, Nicolau JC, Henry P, Kedev S, Wiviott SD, Sabatine MS, Mehta SR, Steg PG. Activated Clotting Time to Guide Heparin Dosing in Non-ST-Segment-Elevation Acute Coronary Syndrome Patients Undergoing Percutaneous Coronary Intervention and Treated With IIb/IIIa Inhibitors: Impact on Ischemic and Bleeding Outcomes: Insights From the TAO Trial. Circ Cardiovasc Interv. 2018 Jun;11(6):e006084. doi: 10.1161/CIRCINTERVENTIONS.118.006084. PubMed PMID: 29895599. 2: Gurnani PK, Bohlmann A, March RJ. Prolonged use of eptifibatide as a bridge to maintain drug-eluting stent patency in a patient receiving extracorporeal membrane oxygenation. Perfusion. 2018 Jun 1:267659118780802. doi: 10.1177/0267659118780802. [Epub ahead of print] PubMed PMID: 29874954. 3: Budnik I, Shenkman B, Morozova O, Andreichyn J, Einav Y. Correction of coagulopathy in thrombocytopenia and Glanzmann thrombasthenia models by fibrinogen and factor XIII as assessed by thromboelastometry. Pathophysiology. 2018 May 24. pii: S0928-4680(18)30043-9. doi: 10.1016/j.pathophys.2018.05.005. [Epub ahead of print] PubMed PMID: 29805054. 4: Doustkami H, Sadeghieh Ahari S, Irani Jam E, Habibzadeh A. Eptifibatide Bolus Dose During Elective Percutaneous Coronary Intervention. Cardiol Res. 2018 Apr;9(2):107-110. doi: 10.14740/cr675w. Epub 2018 Apr 25. PubMed PMID: 29755628; PubMed Central PMCID: PMC5942240. 5: Bhatia N, Sawyer RD, Ikram S. Eptifibatide-Induced Profound Thrombocytopenia After Percutaneous Intervention for Acute Coronary Syndrome: A Challenging Clinical Scenario. Methodist Debakey Cardiovasc J. 2017 Oct-Dec;13(4):248-252. doi: 10.14797/mdcj-13-4-248. PubMed PMID: 29744018; PubMed Central PMCID: PMC5935285. 6: Sasikumar P, AlOuda KS, Kaiser WJ, Holbrook LM, Kriek N, Unsworth AJ, Bye AP, Sage T, Ushioda R, Nagata K, Farndale RW, Gibbins JM. The chaperone protein HSP47: a platelet collagen binding protein that contributes to thrombosis and hemostasis. J Thromb Haemost. 2018 May;16(5):946-959. doi: 10.1111/jth.13998. Epub 2018 Apr 15. PubMed PMID: 29512284. 7: Valerio L, Sheriff J, Tran PL, Brengle W, Redaelli A, Fiore GB, Pappalardo F, Bluestein D, Slepian MJ. Routine clinical anti-platelet agents have limited efficacy in modulating hypershear-mediated platelet activation associated with mechanical circulatory support. Thromb Res. 2018 Mar;163:162-171. doi: 10.1016/j.thromres.2017.12.001. Epub 2017 Dec 5. PubMed PMID: 29428715; PubMed Central PMCID: PMC5879002. 8: Ren T, Li R, Meng X, Fawcett JP, Sun D, Gu J. Differential mobility spectrometry followed by tandem mass spectrometry with multiple ion monitoring for bioanalysis of eptifibatide in rat plasma. J Pharm Biomed Anal. 2018 Mar 20;151:260-265. doi: 10.1016/j.jpba.2018.01.019. Epub 2018 Jan 11. PubMed PMID: 29358126. 9: Rubboli A, Patti G. What is the role for Glycoprotein IIb/IIIa inhibitor use in the catheterisation laboratory in the current era? Curr Vasc Pharmacol. 2018 Jan 16. doi: 10.2174/1570161116666180117102422. [Epub ahead of print] PubMed PMID: 29345590. 10: Brittain JE, Anea C, Desai P, Delaney J, McDonald A, Looney SW, Key NS, Parise LV, Ataga KI. Effect of eptifibatide on inflammation during acute pain episodes in sickle cell disease. Am J Hematol. 2018 Aug;93(4):E99-E101. doi: 10.1002/ajh.25032. Epub 2018 Jan 30. PubMed PMID: 29322543; PubMed Central PMCID: PMC5926197. 11: Induruwa I, Moroi M, Bonna A, Malcor JD, Howes JM, Warburton EA, Farndale RW, Jung SM. Platelet collagen receptor Glycoprotein VI-dimer recognizes fibrinogen and fibrin through their D-domains, contributing to platelet adhesion and activation during thrombus formation. J Thromb Haemost. 2018 Feb;16(2):389-404. doi: 10.1111/jth.13919. Epub 2018 Jan 15. PubMed PMID: 29210180; PubMed Central PMCID: PMC5838801. 12: Rathod KS, Antoniou S, Avari P, Ding N, Wright P, Knight C, Jain AK, Mathur A, Smith EJ, Weerackody R, Wragg A, Jones DA. Eptifibatide is associated with significant cost savings and similar clinical outcomes to abciximab when used during primary percutaneous coronary intervention for ST-elevation myocardial infarction: An observational cohort study of 3863 patients. JRSM Cardiovasc Dis. 2017 Oct 5;6:2048004017734431. doi: 10.1177/2048004017734431. eCollection 2017 Jan-Dec. PubMed PMID: 29051816; PubMed Central PMCID: PMC5637964. 13: Bavand Savadkouhi M, Vahidi H, Ayatollahi AM, Hooshfar S, Kobarfard F. RP-HPLC Method Development and Validation for Determination of Eptifibatide Acetate in Bulk Drug Substance and Pharmaceutical Dosage Forms. Iran J Pharm Res. 2017 Spring;16(2):490-497. PubMed PMID: 28979304; PubMed Central PMCID: PMC5603858. 14: Deharo P, Ducrocq G, Bode C, Cohen M, Cuisset T, Mehta SR, Pollack C Jr, Wiviott SD, Elbez Y, Sabatine MS, Steg PG. Timing of Angiography and Outcomes in High-Risk Patients With Non-ST-Segment-Elevation Myocardial Infarction Managed Invasively: Insights From the TAO Trial (Treatment of Acute Coronary Syndrome With Otamixaban). Circulation. 2017 Nov 14;136(20):1895-1907. doi: 10.1161/CIRCULATIONAHA.117.029779. Epub 2017 Sep 11. PubMed PMID: 28893843. 15: Kuo YJ, Chen YR, Hsu CC, Peng HC, Huang TF. An α(II)(b) β(3) antagonist prevents thrombosis without causing Fc receptor γ-chain IIa-mediated thrombocytopenia. J Thromb Haemost. 2017 Nov;15(11):2230-2244. doi: 10.1111/jth.13803. Epub 2017 Oct 9. PubMed PMID: 28815933. 16: Golden T, Ghazala S, Wadeea R, Junna S. Abciximab-induced acute profound thrombocytopenia postpercutaneous coronary intervention. BMJ Case Rep. 2017 Jul 14;2017. pii: bcr-2017-221182. doi: 10.1136/bcr-2017-221182. PubMed PMID: 28710245. 17: Christen JR, Soubrier C, Martinez E, Roumieu V, Darmon O, Scandaliaris S, Picou L, Cuisset T, Grados A, Bernit E, Ebbo M, Harlé JR, Schleinitz N. [Long-lasting thrombocytopenia induced by glycoprotein IIb/IIIa inhibitor]. Rev Med Interne. 2017 Nov;38(11):769-773. doi: 10.1016/j.revmed.2017.05.013. Epub 2017 Jul 6. French. PubMed PMID: 28690092. 18: Bitar A, Vijayakrishnan R, Lenneman A, Birks E, Massey T, Slaughter M, Abramov D. The Use of Eptifibatide Alone or in Combination With Heparin or Argatroban for Suspected Thrombosis in Patients With Left Ventricular Assist Devices. Artif Organs. 2017 Dec;41(12):1092-1098. doi: 10.1111/aor.12910. Epub 2017 Jun 16. PubMed PMID: 28621461. 19: Marian MJ, Alli O, Al Solaiman F, Brott BC, Sasse M, Leesar T, Prabhu SD, Leesar MA. Ticagrelor and Eptifibatide Bolus Versus Ticagrelor and Eptifibatide Bolus With 2-Hour Infusion in High-Risk Acute Coronary Syndromes Patients Undergoing Early Percutaneous Coronary Intervention. J Am Heart Assoc. 2017 Jun 13;6(6). pii: e005562. doi: 10.1161/JAHA.117.005562. PubMed PMID: 28611098; PubMed Central PMCID: PMC5669172. 20: Ahsan SA, Haque KS, Arzu J, Mahmood M, Fatema N, Hasan MN. Immediate & Short Term Outcome of Using Single Bolus Eptifibatide in Percutaneous Coronary Intervention: A Randomized Control Study. Mymensingh Med J. 2017 Apr;26(2):300-305. PubMed PMID: 28588165.