Bivalirudin

Base Information

• Chemical Name: Bivalirudin
• CAS No.: 128270-60-0
• Molecular Formula: C98H138N24O33
• Molecular Weight: 2180.31
• Hs Code.: 2942000000
• Mol file: 128270-60-0.mol

Synonyms:L-Leucine,D-phenylalanyl-L-prolyl-L-arginyl-L-prolylglycylglycylglycylglycyl-L-asparaginylglycyl-L-a-aspartyl-L-phenylalanyl-L-a-glutamyl-L-a-glutamyl-L-isoleucyl-L-prolyl-L-a-glutamyl-L-a-glutamyl-L-tyrosyl-;126:PN: WO2004076484 PAGE: 31 claimed protein;Angiomax;BG 8967;Hirulog;Hirulog 1;Bivalirudin Trifluoroacetate;

Chemical Property of Bivalirudin

Chemical Property:

• Appearance/Colour: White powder
• Refractive Index: 1.675
• PSA: 901.57000
• Density: 1.52 g/cm³
• LogP: 0.54320
• Storage Temp.: ?20°C
• Solubility.: ≥54.5 mg/mL in DMSO with gentle warming; ≥10.18 mg/mL in EtOH with gentle warming and ultrasonic; ≥43.5 mg/mL in H2O with gentle warming

Purity/Quality:

99% ^*data from raw suppliers

Bivalirudin trifluoroacetate salt ≥97% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Alternative medicine as ordinary heparin and platelet glycoprotein IIb/IIIa antagonists. Anticoagulant; antithrombotic.
• Description: Bivalirudin is an inhibitor of α- and ζ-thrombin (Kis = 2.56 and 1.84 nM, respectively), enzymes that exhibit high fibrinogen-clotting activities. It is selective for α- and ζ-thrombin, lacking activity at trypsin and γ-thrombin, which lacks clotting activity, at a >1,000-fold excess of bivalirudin. Bivalirudin inhibits α-thrombin-stimulated activation of the clotting factors Factor X, Factor V, and prothrombin in contact-activated plasma at a concentration of 0.1 μM. Administration of bivalirudin (0.5-1.5 mg/kg, i.v.) reduces platelet deposition in a rat carotid endarterectomy model in a dose-dependent manner. Formulations containing bivalirudin have been used to prevent ischemic events during angioplasty for thrombus-containing lesions. Bivalirudin was launched in New Zealand as an anticoagulant for i.v. treatment of patients with unstable angina undergoing percutaneous transluminal coronary angioplasty. Bivalirubin is a synthetic 20 amino acid peptide rationally modeled on hirudin (residues 53- 64), the most potent and specific naturally-occuring known inhibitor of thrombin, the enzyme that plays a key role in hemostasis and blood clot formation. This peptide is a direct thrombin inhibitor that maintains the unique bivalent binding properties of hirudin to the catalytic site and to the fibrin-recognition exosite of the enzyme, so acting directly on thrombin with high affinity and specificity. In vitro studies demonstrated that alpha- and zeta-thrombins, both with the higher fibrinogen-procoagulant activities, were inhibited. In rats receiving high doses of bivalirudin, the platelet deposition in carotide was reduced by 63% compared to controls. The results of clinical studies, conducted only in patients receiving concomitant aspirin, suggested that the use of bivalirudin was more efficacious and more predictable than unfractionated heparin, with fewer bleeding complications. Despite some unresolved developmental issues, the attractive properties of this novel agent could make it a useful alternative to heparin in a variety of coagulation disorders.
• Therapeutic Function: Anticoagulant
• Clinical Use: Bivalirudin, a 20-amino-acid peptide, has been approved for use in patients with unstable angina undergoing percutaneous coronary intervention.
• Drug interactions: Potentially hazardous interactions with other drugs Analgesics: increased risk of haemorrhage with IV diclofenac and ketorolac. Antiplatelets and anticoagulants: increased risk of bleeding. Thrombolytics: may increase risk of bleeding complications; enhance effect of bivalirudin.

Technology Process of Bivalirudin

There total 11 articles about Bivalirudin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 14.0%

→ bivalirudin (128270-60-0)

Guidance literature:

Reference yield:

HCl*H-D-Phe-Pro-Arg(Pbf)-Pro-Gly-Gly-Gly-Gly-Asn(Trt)-Gly-Asp(OtBu)-Phe-Glu(OtBu)-Glu(OtBu)-Ile-Pro-Glu(OtBu)-Glu(OtBu)-Tyr(tBu)-Leu-OKb, Kb=2,4-didocosyloxybenzyl → bivalirudin (128270-60-0)

Guidance literature:

With chlorotriisopropylsilane; water; trifluoroacetic acid; at 20 ℃; for 3h;

Reference yield:

Boc-D-Phe-Pro-Arg(Pbf)-Pro-Gly-Gly-Gly-Gly-Asn(Trt)-Gly-Asp(tBu)-Phe-Glu(tBu)-Glu(tBu)-Ile-Pro-Glu(tBu)-Glu(tBu)-Tyr(tBu)-Leu-OtBu → bivalirudin (128270-60-0)

Guidance literature:

With water; trifluoroacetic acid; 1-dodecylthiol; at 20 ℃; for 1h; Reagent/catalyst;

upstream raw materials:

L-leucine tert-butyl ester

N-(fluoren-9-ylmethoxycarbonyl)glycine

N-Fmoc-Tyr-OH

Boc-D-Phe-OH

Refernces

• 1、 Albericio, Fernando,Dettner, Frank,Egelund, Peter H. G.,Haselmann, Kim F.,Jadhav, Sandip,Johansson Castro, Henrik,Krüger, Tobias,Lechner, Carolin,Liffert, Raphael,Martin, Vincent,Pedersen, Daniel Sejer,Sch?nleber, Ralph,Thordal Le Quement, Sebastian. "Harnessing polarity and viscosity to identify green binary solvent mixtures as viable alternatives to DMF in solid-phase peptide synthesis". . p. 3295 - 3311. Retrieved 2021.
• 2、 -. "SYNTHETIC METHOD OF BIVALIRUNDIN". Page/Page column 13; 14. . Retrieved 2020/01/24.