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MedKoo Cat#: 317781 | Name: Eptifibatide acetate
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Description:

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

Eptifibatide, 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 protein 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.

Chemical Structure

Eptifibatide acetate
Eptifibatide acetate
CAS#148031-34-9 (acetate)

Theoretical Analysis

MedKoo Cat#: 317781

Name: Eptifibatide acetate

CAS#: 148031-34-9 (acetate)

Chemical Formula: C37H53N11O11S2

Exact Mass: 0.0000

Molecular Weight: 892.02

Elemental Analysis: C, 49.82; H, 5.99; N, 17.27; O, 19.73; S, 7.19

Price and Availability

Size Price Availability Quantity
1g USD 2,850.00 2 Weeks
2g USD 4,650.00 2 Weeks
5g USD 7,650.00 2 Weeks
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Related CAS #
188627-80-7 (free base) 148031-34-9 (acetate)
Synonym
Eptifibatide acetate; Integrilin; ptifibatide; Integrelin;
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 compound with acetic acid (1:1)
InChi Key
KWKBRYJYRIUYEI-QMYFOHRPSA-N
InChi Code
InChI=1S/C35H49N11O9S2.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t22-,23-,24-,25-,26-;/m0./s1
SMILES Code
NC(NCCCC[C@@H]1NC(CCSSC[C@@H](C(N)=O)NC([C@@H]2CCCN2C([C@@H](NC([C@@H](NC(CNC1=O)=O)CC(O)=O)=O)CC3=CNC4=C3C=CC=C4)=O)=O)=O)=N.CC(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, not in water
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 892.02 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: Pothineni NV, Watts TE, Ding Z, Dai Y, Deshmukh AJ. Eptifibatide-Induced Thrombocytopenia-When Inhibitor Turns Killer. Am J Ther. 2016 Jan-Feb;23(1):e298-9. doi: 10.1097/01.mjt.0000438283.01797.1a. PubMed PMID: 24368608. 2: Wilczynski M, Wybraniec MT, Milewski K, Sanak M, Wita K, Buldak Ł, Kondys M, Buszman P, Bochenek A. Eptifibatide infusion versus placebo in high risk patients with non-ST segment elevation acute coronary syndromes managed with urgent coronary artery bypass graft surgery. A prospective multicenter randomized placebo-controlled clinical trial. J Cardiovasc Surg (Torino). 2016 Feb;57(1):100-10. PubMed PMID: 26771733. 3: Esfandi A, Fotouhi M, Allami A, Ebrahimi M. Comparison between the Outcomes of Intracoronary and Intravenous Administration of Eptifibatide during Primary Percutaneous Coronary Intervention in Patients with Acute ST-Elevation Myocardial Infarction. J Atheroscler Thromb. 2015 Dec 2. [Epub ahead of print] PubMed PMID: 26632161. 4: Drijkoningen T, van Weel V, Eberlin KR, Cetrulo CL Jr. Eptifibatide Salvage of Arterial Anastomotic Thrombosis in Lower Extremity Free Flap Reconstruction: A Case Report. J Reconstr Microsurg. 2015 Sep;31(7):544-6. doi: 10.1055/s-0035-1555011. Epub 2015 Jun 26. PubMed PMID: 26115546. 5: Adeoye O, Sucharew H, Khoury J, Vagal A, Schmit PA, Ewing I, Levine SR, Demel S, Eckerle B, Katz B, Kleindorfer D, Stettler B, Woo D, Khatri P, Broderick JP, Pancioli AM. Combined Approach to Lysis Utilizing Eptifibatide and Recombinant Tissue-Type Plasminogen Activator in Acute Ischemic Stroke-Full Dose Regimen Stroke Trial. Stroke. 2015 Sep;46(9):2529-33. doi: 10.1161/STROKEAHA.115.010260. Epub 2015 Aug 4. PubMed PMID: 26243231; PubMed Central PMCID: PMC4550507. 6: Dézsi DA, Bokori G, Faluközy J, Bujáky C, Fogarassy G, Veress G, Aradi D. Eptifibatide-induced thrombocytopenia leading to acute stent thrombosis. J Thromb Thrombolysis. 2015 Aug 25. [Epub ahead of print] PubMed PMID: 26305043. 7: Wang XP, Zhou ZL, Yang M, Mai LP, Zheng ZJ, He GD, Wu YH, Lin QX, Shan ZX, Yu XY. Population pharmacokinetics and safety of eptifibatide in healthy Chinese volunteers and simulations on the dose regimens approved for a Western population. Int J Clin Pharmacol Ther. 2015 Aug;53(8):658-66. doi: 10.5414/CP202196. PubMed PMID: 26104033. 8: Gokhroo R, Kishor K, Ranwa B, Bisht DS, Gupta S, Anantharaj A. Eptifibatide in post-infarction angina patients who refused intervention: Ajmer postmyocardial infarction angina eptifibatide research (AJMER) study: a pilot study. Cardiovasc Ther. 2015 Aug;33(4):155-60. doi: 10.1111/1755-5922.12123. PubMed PMID: 25892271. 9: Sorkin GC, Dumont TM, Mokin M, Eller JL, Natarajan SK, Levy EI, Siddiqui AH. Hyperacute Carotid Stent Thrombosis During Emergent Revascularization Treated with Intraarterial Eptifibatide After Systemic Administration of Recombinant Tissue Plasminogen Activator. J Vasc Interv Neurol. 2015 Jul;8(3):50-5. PubMed PMID: 26301032; PubMed Central PMCID: PMC4535607. 10: Nei SD, Armon JJ, Dierkhising RA, Bell MR, Mathew V, Barsness GW, Ou NN. Effect of a shortened-duration Eptifibatide infusion (75 mg) as adjunctive therapy for percutaneous coronary intervention on in-hospital cardiovascular outcomes and bleeding. Am J Cardiol. 2015 Mar 15;115(6):707-10. doi: 10.1016/j.amjcard.2014.12.031. Epub 2015 Jan 6. PubMed PMID: 25604931. 11: Sherwood MW, Tcheng JE. Eptifibatide in coronary intervention: past time for the next chapter. Circ Cardiovasc Interv. 2015 Feb;8(2):e002340. doi: 10.1161/CIRCINTERVENTIONS.115.002340. PubMed PMID: 25657317. 12: Sedat J, Chau Y, Gaudard J, Suissa L, Lachaud S, Lonjon M. Administration of eptifibatide during endovascular treatment of ruptured cerebral aneurysms reduces the rate of thromboembolic events. Neuroradiology. 2015 Feb;57(2):197-203. doi: 10.1007/s00234-014-1452-x. Epub 2014 Oct 18. PubMed PMID: 25326169. 13: Gurm HS, Hosman C, Bates ER, Share D, Hansen BB; Blue Cross Blue Shield of Michigan Cardiovascular Consortium. Comparative effectiveness and safety of a catheterization laboratory-only eptifibatide dosing strategy in patients undergoing percutaneous coronary intervention. Circ Cardiovasc Interv. 2015 Feb;8(2):e001880. doi: 10.1161/CIRCINTERVENTIONS.114.001880. PubMed PMID: 25657314. 14: Adeoye O, Sucharew H, Khoury J, Tomsick T, Khatri P, Palesch Y, Schmit PA, Pancioli AM, Broderick JP; CLEAR-ER, IMS III, and ALIAS Part 2 Investigators. Recombinant tissue-type plasminogen activator plus eptifibatide versus recombinant tissue-type plasminogen activator alone in acute ischemic stroke: propensity score-matched post hoc analysis. Stroke. 2015 Feb;46(2):461-4. doi: 10.1161/STROKEAHA.114.006743. Epub 2014 Dec 18. PubMed PMID: 25523054; PubMed Central PMCID: PMC4308493. 15: Kononczuk J, Surazynski A, Czyzewska U, Prokop I, Tomczyk M, Palka J, Miltyk W. αIIbβ3-integrin Ligands: Abciximab and Eptifibatide as Proapoptotic Factors in MCF-7 Human Breast Cancer Cells. Curr Drug Targets. 2015;16(13):1429-37. PubMed PMID: 25090985. 16: Heath M, Barbeito A, Welsby I, Maxwell C, Iribarne A, Raghunathan K. Using Zero-Balance Ultrafiltration With Dialysate as a Replacement Solution for Toxin and Eptifibatide Removal on a Dialysis-Dependent Patient During Cardiopulmonary Bypass. J Cardiothorac Vasc Anesth. 2014 Dec 8. pii: S1053-0770(14)00607-7. doi: 10.1053/j.jvca.2014.12.007. [Epub ahead of print] PubMed PMID: 25857672. 17: Wilczynski M, Wybraniec MT, Milewski K, Sanak M, Wita K, Buldak L, Kondys M, Buszman P, Bochenek A. Eptifibatide infusion versus placebo in high risk patients with non-st segment elevation acute coronary syndromes managed with urgent coronary artery bypass graft surgery. a prospective multicenter randomized placebo-controlled clinical trial. J Cardiovasc Surg (Torino). 2014 Nov 14. [Epub ahead of print] PubMed PMID: 25394877. 18: Dharma S, Firdaus I, Danny SS, Juzar DA, Wardeh AJ, Jukema JW, van der Laarse A. Impact of Timing of Eptifibatide Administration on Preprocedural Infarct-Related Artery Patency in Acute STEMI Patients Undergoing Primary PCI. Int J Angiol. 2014 Sep;23(3):207-14. doi: 10.1055/s-0034-1382158. PubMed PMID: 25317034; PubMed Central PMCID: PMC4169102. 19: Dababneh H, Guerrero W, Mehta S, Moussavi M, Kirmani JF. Possible role of Eptifibatide drip in-patient with aneurysmal subarachnoid hemorrhage in vasospasm prevention. J Vasc Interv Neurol. 2014 Sep;7(3):8-13. PubMed PMID: 25298852; PubMed Central PMCID: PMC4188253. 20: Swoboda S, Walter T, Lang S, Wendel HP, Beyer ME, Griesel E, Hoffmeister HM, Gruettner J. Effect of GPIIb/IIIa inhibition with eptifibatide or tirofiban on the expression of cellular adhesion molecules on monocytes. In Vivo. 2014 Sep-Oct;28(5):691-7. PubMed PMID: 25189879.