Bivalirudin Trifluoroacetate

Bivalirudin is a DTI that overcomes many limitations seen with indirect thrombin inhibitors. It is a short, synthetic peptide that is potent, highly specific, and a reversible inhibitor of thrombin. Bivalirudin inhibits both circulating and clot-bound thrombin, while also inhibiting thrombin-mediated platelet activation and aggregation. It has a quick onset of action and a short half-life, without binding to plasma proteins (other than thrombin) or red blood cells. Therefore it has a predictable antithrombotic response.

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CAT No: 10-101-06

CAS No: 128270-60-0 (net)

Synonyms/Alias: BG 8967; Hirulog; Hirulog I; Bivalirudin; Angiomax; Hirulog-1; Hirulog1; Hirulog 1; BG8967; BG 8967; BG-8967; LS-172701; LS172701; LS 172701

Chemical Name: 2-[[2-[[2-[[2-[[1-[(2S)-2-[[2-[[2-[[2-[[2-[[2-[[4-amino-2-[[2-[[2-[[2-[[2-[[1-[2-[[1-(2-amino-3-phenylpropanoyl)pyrrolidine-2-carbonyl]amino]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]acetyl]amino]acetyl]amino]acetyl]amino]-4-oxobutanoyl]amino]acetyl]amino]-3-carboxypropanoyl]amino]-3-phenylpropanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoic acid

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M.F/FormulaC98H138N24O33
M.W/Mr.2180.32
SequenceOne Letter Code: FPRPGGGGNGDFEEXPEEYL
Three Letter Code: H-DL-Phe-DL-Pro-DL-Arg-DL-Pro-Gly-Gly-Gly-Gly-DL-Asn-Gly-DL-Asp-DL-Phe-DL-Glu-DL-Glu-xiIle-DL-Pro-DL-Glu-DL-Glu-DL-Tyr-DL-Leu-OH
Labeling TargetProthrombin
ApplicationModerate to high risk acute coronary syndromes;
Percutaneous coronary intervention
AppearanceSolid powder
Purity>98% (or refer to the Certificate of Analysis)
ActivityInhibitor
Areas of InterestCardiovascular System & Diseases
Pituitary & Hypothalamic Hormones
FunctionsThrombospondin receptor activity
TargetThrombin
Source#Synthetic
Long-term Storage ConditionsSoluble in DMSO, not in water
Shipping ConditionShipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Short-term Storage ConditionsDry, dark and at 0 - 4 °C
Solubility-20 °C
OrganismHuman
InChIInChI=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
InChI KeyOIRCOABEOLEUMC-ONGBENNUSA-N
Canonical SMILESCCC(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
Isomeric SMILESCCC(C)[C@@H](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
BoilingPointN/A
ShelfLife>2 years if stored properly
References

Growing data demonstrate procedural success with bivalirudin in patients with HIT undergoing cardiovascular surgery. However, bivalirudin dosing and goal-activated clotting times varied between the studies and case reports. Bivalirudin represents a viable alternative to heparin in patients with HIT undergoing cardiovascular surgery; however, further trials are warranted to identify optimal dosing and monitoring parameters.

Czosnowski Q A, Finks S W, Rogers K C. Bivalirudin for patients with heparin-induced thrombocytopenia undergoing cardiovascular surgery[J]. Annals of Pharmacotherapy, 2008, 42(9): 1304-1309.

Among the current agents in the class of direct thrombin inhibitors, bivalirudin has seen increased use in cardiovascular medicine over the past decade through its primary indication as an anticoagulant used during percutaneous coronary interventions. Bivalirudin has been further investigated and used as the anticoagulation strategy in the setting of cardiac and endovascular surgical procedures and is frequently utilized in the management of patients with heparin-induced thrombocytopenia. In comparison with heparin, bivalirudin exhibits a low immunogenic profile and provides similar or reduced major bleeding rates as well as a predictable degree of anticoagulation that is dose related. Bivalirudin primarily undergoes dual elimination via proteolytic cleavage and renal elimination, and requires dose adjustment in the setting of severe renal dysfunction. Given the body of supportive data, bivalirudin is likely to continue to figure prominently as a reliable and efficient anticoagulation strategy. Additional agents in the class of direct thrombin inhibitors are under investigation and may find increasing clinical use.

Van De Car D A, Rao S V, Ohman E M. Bivalirudin: a review of the pharmacology and clinical application[J]. Expert review of cardiovascular therapy, 2010, 8(12): 1673-1681.

Melting PointN/A
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