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SML1051

Sigma-Aldrich

Bivalirudin trifluoroacetate salt

≥97% (HPLC)

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Synonym(s):
D-Phenylalanyl-L-prolyl-L-arginyl-L-prolylglycylglycylglycylglycyl-L-aspariginylglycyl-L-α-aspartyl-L-phenylalanyl-L-α-glutamyl-L-α-glutamyl-L-isoleucyl-L-prolyl-L-α-glutamyl-L-α-glutamyl-L-tyrosyl-L-leucine trifluoroacetate, Hirulog trifluoroacetate salt
Empirical Formula (Hill Notation):
C98H138N24O33 · xC2HF3O2
CAS Number:
128270-60-0
Molecular Weight:
2180.29 (free base basis)

Quality Level

100

Assay

≥97% (HPLC)

form

powder

color

white to off-white

shipped in

wet ice

storage temp.

−20°C

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

InChI key

OIRCOABEOLEUMC-GEJPAHFPSA-N

Biochem/physiol Actions

Bivalirudin is a specific and reversible bivalent direct thrombin inhibitor. Bivalirudin specifically binds to both the catalytic site and to the anion-binding exosite of circulating and clot-bound thrombin.
Bivalirudin trifluoroacetate salt is a synthetic peptide composed of 20 amino acids. It serves as an anticoagulant for patients with unstable angina undergoing coronary angioplasty.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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John C Rohloff et al.
Molecular therapy. Nucleic acids, 3, e201-e201 (2014-10-08)
Limited chemical diversity of nucleic acid libraries has long been suspected to be a major constraining factor in the overall success of SELEX (Systematic Evolution of Ligands by EXponential enrichment). Despite this constraint, SELEX has enjoyed considerable success over the
Matthew A Cavender et al.
Lancet (London, England), 384(9943), 599-606 (2014-08-19)
Bivalirudin is an alternative to heparin in patients undergoing percutaneous coronary intervention (PCI). We aimed to define the effects of a bivalirudin-based anticoagulation regimen compared with a heparin-based anticoagulation regimen on ischaemic and bleeding outcomes. We searched Medline, the Cochrane
Uzoma N Ibebuogu et al.
American journal of cardiovascular drugs : drugs, devices, and other interventions, 15(4), 275-285 (2015-03-19)
Diabetes mellitus (DM) is a pro-thrombotic state with enhanced thrombin generation and platelet reactivity. For most patients undergoing percutaneous coronary intervention (PCI), bivalirudin demonstrates efficacy comparable with that of heparin and glycoprotein IIb/IIIa inhibitors (GPIs). Yet, because of their pro-thrombotic
Anthony A Bavry et al.
PloS one, 10(5), e0127832-e0127832 (2015-05-27)
Percutaneous coronary intervention with bivalirudin plus bail-out glycoprotein IIb/IIIa inhibitors has been shown to be as effective as unfractionated heparin plus routine glycoprotein IIb/IIIa inhibitors in preventing cardiac ischemic events, but with a lower bleeding risk. It is unknown whether
Gregg W Stone et al.
Journal of the American College of Cardiology, 65(1), 27-38 (2015-01-13)
In the HORIZONS-AMI (Harmonizing Outcomes with RevasculariZatiON and Stents in Acute Myocardial Infarction) trial, 3,602 patients undergoing primary percutaneous coronary intervention (PCI) for ST-segment elevation myocardial infarction (STEMI) treated with bivalirudin had lower bleeding and mortality rates, but higher acute
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