Bivalirudin Trifluoroacetate

• CAT Number: I001113
• CAS Number: 128270-60-0
• Molecular Formula: C98H138N24O33
• Molecular Weight: 2180.317
• Purity: ≥95%
• Target: Thrombin
• Solubility: DMSO：≥ 31 mg/mL
• Storage: Store at -20°C
• InChI: InChI=1S/C98H138N24O33/c1-5-52(4)82(96(153)122-39-15-23-70(122)92(149)114-60(30-34-79(134)135)85(142)111-59(29-33-78(132)133)86(143)116-64(43-55-24-26-56(123)27-25-55)89(146)118-67(97(154)155)40-51(2)3)119-87(144)61(31-35-80(136)137)112-84(141)58(28-32-77(130)131)113-88(145)63(42-54-18-10-7-11-19-54)117-90(147)66(45-81(138)139)110-76(129)50-107-83(140)65(44-71(100)124)109-75(128)49-106-73(126)47-104-72(125)46-105-74(127)48-108-91(148)68-21-13-38-121(68)95(152)62(20-12-36-103-98(101)102)115-93(150)69-22-14-37-120(69)94(151)57(99)41-53-16-8-6-9-17-53/h6-11,16-19,24-27,51-52,57-70,82,123H,5,12-15,20-23,28-50,99H2,1-4H3,(H2,100,124)(H,104,125)(H,105,127)(H,106,126)(H,107,140)(H,108,148)(H,109,128)(H,110,129)(H,111,142)(H,112,141)(H,113,145)(H,114,149)(H,115,150)(H,116,143)(H,117,147)(H,118,146)(H,119,144)(H,130,131)(H,132,133)(H,134,135)(H,136,137)(H,138,139)(H,154,155)(H4,101,102,103)/t52-,57+,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,82-/m0/s1
• InChIKey: OIRCOABEOLEUMC-GEJPAHFPSA-N
• SMILES: CCC(C)C(C(=O)N1CCCC1C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)O)C(=O)NC(CC2=CC=C(C=C2)O)C(=O)NC(CC(C)C)C(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(CC3=CC=CC=C3)NC(=O)C(CC(=O)O)NC(=O)CNC(=O)C(CC(=O)N)NC(=O)CNC(=O)CNC(=O)CNC(=O)CNC(=O)C4CCCN4C(=O)C(CCCNC(=N)N)NC(=O)C5CCCN5C(=O)C(CC6=CC=CC=C6)N

Bivalirudin Trifluoroacetate is a synthetic 20 residue peptide which reversibly inhibits thrombin.
IC50 Value:
Target: thrombin
in vitro: Eptifibatide (8 mg/mL) added together with a low (70 ng/mL) concentration of bivalirudin (a direct thrombin inhibitor) effectively (approximately 90%) reduced platelet aggregation induced by thrombin (0.2 U/mL) [1]. In thrombin generation assay (TGA), bivalirudin had no effect on these parameters up to 10 μmol/l [2]. Bivalirudin-facilitated binding of MPO to BAEC resulted also in functional changes in terms of increased NO consumption as well as enhanced MPO-mediated redox modifications [3].
in vivo: The use of bivalirudinprevented further increase in antiheparin/PF4 antibody IgG levels in rats [4]. Three animals in the 500-mg/kg/24 h group, and 7 animals in the 2000-mg/kg/24 h group in the toxicokinetic assessment phase of the study were found dead or euthanized in extremis (following blood sampling). Plasma concentrations of bivalirudin appeared to be linear and dose independent [5].
Clinical trial: Antithrombotic Effects of Ticagrelor Versus Clopidogrel . Phase 4

Reference

[1]. Ciborowski M, Tomasiak M. The in vitro effect of eptifibatide, a glycoprotein IIb/IIIa antagonist, on various responses of porcine blood platelets. Acta Pol Pharm. 2009 May-Jun;66(3):235-42.
[2]. Xu Y, Wu W, Wang L, Differential profiles of thrombin inhibitors (heparin, hirudin, bivalirudin, and dabigatran) in the thrombin generation assay and thromboelastography in vitro. Blood Coagul Fibrinolysis. 2013 Apr;24(3):332-8.
[3]. Rudolph V, Rudolph TK, Schopfer FJ, Bivalirudin decreases NO bioavailability by vascular immobilization of myeloperoxidase. J Pharmacol Exp Ther. 2008 Nov;327(2):324-31.
[4]. Zhang R, Huang Y, Zhang M, Bivalirudin Utilization in Rats Undergoing Cardiopulmonary Bypass: Preventing the Increase of Antiheparin/Platelet Factor 4 Antibody in Perioperative Period. Clin Appl Thromb Hemost. 2012 Aug 21. [Epub ahead of print]
[5]. Gleason TG, Chengelis CP, Jackson CB, A 24-hour continuous infusion study of bivalirudin in the rat. Int J Toxicol. 2003 May-Jun;22(3):195-206.