Bivalirudin TFA salt
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MedKoo CAT#: 326640

CAS#: 128270-60-0 (free base)

Description: Bivalirudin, also known as BG-8967, is a specific and reversible direct thrombin inhibitor (DTI). Chemically, it is a synthetic congener of the naturally occurring drug hirudin (found in the saliva of the medicinal leech Hirudo medicinalis). Bivalirudin overcomes many limitations seen with indirect thrombin inhibitors, such as heparin. Bivalirudin is a short, synthetic peptide that is potent, highly specific, and a reversible inhibitor of thrombin. It inhibits both circulating and clot-bound thrombin.

Chemical Structure

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Bivalirudin TFA salt
CAS# 128270-60-0 (free base)
Instruction

Theoretical Analysis

MedKoo Cat#: 326640
Name: Bivalirudin TFA salt
CAS#: 128270-60-0 (free base)
Chemical Formula: C100H139F3N24O35
Exact Mass: 0.00
Molecular Weight: 2,294.340
Elemental Analysis: C, 52.35; H, 6.11; F, 2.48; N, 14.65; O, 24.41

Price and Availability

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10mg USD 350 2 weeks
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Synonym: BG-8967; BG 8967; BG8967; Bivalirudin Trifluoroacetate; Brand name: Angiomax Angiox.

IUPAC/Chemical Name: H-D-Phe-Pro-Arg-Pro-Gly-Gly-Gly-Gly-Asn-Gly-Asp-Phe-Glu-Glu-Ile-Pro-Glu-Glu-Tyr-Leu-OH

InChi Key: ZXZYMGVTLNJMKP-GRDNZSJBSA-N

InChi Code: InChI=1S/C98H138N24O33.C2HF3O2/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;3-2(4,5)1(6)7/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);(H,6,7)/t52-,57+,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,82-;/m0./s1

SMILES Code: O=C(N1[C@@H](CCC1)C(N[C@@H](CCCNC(N)=N)C(N2[C@@H](CCC2)C(NCC(NCC(NCC(NCC(N[C@@H](CC(N)=O)C(NCC(N[C@@H](CC(O)=O)C(N[C@@H](CC3=CC=CC=C3)C(N[C@@H](CCC(O)=O)C(N[C@@H](CCC(O)=O)C(N[C@@H]([C@@H](C)CC)C(N4[C@@H](CCC4)C(N[C@@H](CCC(O)=O)C(N[C@@H](CCC(O)=O)C(N[C@@H](CC5=CC=C(C=C5)O)C(N[C@@H](CC(C)C)C(O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)[C@@H](CC6=CC=CC=C6)N.O=C(O)C(F)(F)F

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 2,294.34 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Esteve-Pastor MA, Hernández-Romero D, Valdés M, Marín F. New Approaches to the Role of Thrombin in Acute Coronary Syndromes: Quo Vadis Bivalirudin, a Direct Thrombin Inhibitor? Molecules. 2016 Feb 27;21(3). pii: E284. doi: 10.3390/molecules21030284. Review. PubMed PMID: 26927051.

2: Zhang S, Gao W, Li H, Zou M, Sun S, Ba Y, Liu Y, Cheng G. Efficacy and safety of bivalirudin versus heparin in patients undergoing percutaneous coronary intervention: A meta-analysis of randomized controlled trials. Int J Cardiol. 2016 Apr 15;209:87-95. doi: 10.1016/j.ijcard.2016.01.206. Epub 2016 Jan 26. Review. PubMed PMID: 26882192.

3: Buck ML. Bivalirudin as an Alternative to Heparin for Anticoagulation in Infants and Children. J Pediatr Pharmacol Ther. 2015 Nov-Dec;20(6):408-17. doi: 10.5863/1551-6776-20.6.408. Review. PubMed PMID: 26766931; PubMed Central PMCID: PMC4708951.

4: Shah R, Rogers KC, Matin K, Askari R, Rao SV. An updated comprehensive meta-analysis of bivalirudin vs heparin use in primary percutaneous coronary intervention. Am Heart J. 2016 Jan;171(1):14-24. doi: 10.1016/j.ahj.2015.10.006. Epub 2015 Oct 20. Review. PubMed PMID: 26699596.

5: Faulkenberg KD, Beavers JC, Finks SW. Heparin Versus Bivalirudin Monotherapy in the Setting of Primary Percutaneous Coronary Intervention for Patients With ST-Segment Elevation Myocardial Infarction. Ann Pharmacother. 2016 Feb;50(2):141-51. doi: 10.1177/1060028015618206. Epub 2015 Dec 17. Review. PubMed PMID: 26681442.

6: Li J, Yu S, Qian D, He Y, Jin J. Bivalirudin Anticoagulant Therapy With or Without Platelet Glycoprotein IIb/IIIa Inhibitors During Transcatheter Coronary Interventional Procedures: A Meta-Analysis. Medicine (Baltimore). 2015 Aug;94(32):e1067. doi: 10.1097/MD.0000000000001067. Review. PubMed PMID: 26266343; PubMed Central PMCID: PMC4616679.

7: McNair E, Marcoux JA, Bally C, Gamble J, Thomson D. Bivalirudin as an adjunctive anticoagulant to heparin in the treatment of heparin resistance during cardiopulmonary bypass-assisted cardiac surgery. Perfusion. 2016 Apr;31(3):189-99. doi: 10.1177/0267659115583525. Epub 2015 May 1. Review. PubMed PMID: 25934498.

8: Mahmoud A, Saad M, Elgendy AY, Abuzaid A, Elgendy IY. Bivalirudin in percutaneous coronary intervention, is it the anticoagulant of choice? Cardiovasc Ther. 2015 Aug;33(4):227-35. doi: 10.1111/1755-5922.12124. Review. PubMed PMID: 25879426.

9: Mavrakanas TA, Chatzizisis YS. Bivalirudin in stable angina and acute coronary syndromes. Pharmacol Ther. 2015 Aug;152:1-10. doi: 10.1016/j.pharmthera.2015.04.003. Epub 2015 Apr 7. Review. PubMed PMID: 25857452.

10: Huang FY, Huang BT, Peng Y, Liu W, Zhao ZG, Wang PJ, Zuo ZL, Zhang C, Liao YB, Luo XL, Meng QT, Chen C, Huang KS, Chai H, Li Q, Chen M, Zhu Y. Heparin is Not Inferior to Bivalirudin in Percutaneous Coronary Intervention-Focusing on the Effect of Glycoprotein IIb/IIIa Inhibitor Use: A Meta-Analysis. Angiology. 2015 Oct;66(9):845-55. doi: 10.1177/0003319715568972. Epub 2015 Jan 29. Review. PubMed PMID: 25635117.

11: Capodanno D, De Caterina R. Bivalirudin for acute coronary syndromes: premises, promises and doubts. Thromb Haemost. 2015 Apr;113(4):698-707. doi: 10.1160/TH14-09-0765. Epub 2014 Dec 18. Review. PubMed PMID: 25519159.

12: Efeovbokhan N, Khouzam RN, Al-Fakhouri A, Salama L. An objective comparison between bivalirudin and heparin during peripheral vascular interventions. Future Cardiol. 2014 Nov;10(6):717-24. doi: 10.2217/fca.14.50. Review. PubMed PMID: 25495814.

13: Nairooz R, Sardar P, Amin H, Swaminathan RV, Kim LK, Chatterjee S, Feldman DN. Meta-analysis of randomized clinical trials comparing bivalirudin versus heparin plus glycoprotein IIb/IIIa inhibitors in patients undergoing percutaneous coronary intervention and in patients with ST-segment elevation myocardial infarction. Am J Cardiol. 2014 Jul 15;114(2):250-9. doi: 10.1016/j.amjcard.2014.04.033. Epub 2014 May 2. Review. PubMed PMID: 24890986.

14: Malik N, Gershlick AH. The clinical and economic impact of bivalirudin for percutaneous coronary intervention. Expert Rev Pharmacoecon Outcomes Res. 2013 Dec;13(6):699-706. doi: 10.1586/14737167.2013.844650. Review. PubMed PMID: 24219045.

15: Kinnaird T, Medic G, Casella G, Schiele F, Kaul U, Radke PW, Eijgelshoven I, Bergman G, Chew DP. Relative efficacy of bivalirudin versus heparin monotherapy in patients with ST-segment elevation myocardial infarction treated with primary percutaneous coronary intervention: a network meta-analysis. J Blood Med. 2013 Oct 2;4:129-40. doi: 10.2147/JBM.S50595. Review. PubMed PMID: 24124401; PubMed Central PMCID: PMC3794970.

16: Ten Y, Devlin G. Bivalirudin in acute coronary syndromes and percutaneous coronary intervention: should we use it? Heart Lung Circ. 2013 Oct;22(10):793-800. doi: 10.1016/j.hlc.2013.05.636. Epub 2013 Jul 31. Review. PubMed PMID: 23916503.

17: Sergie Z, Lefèvre T, Van Belle E, Kakoulides S, Baber U, Deliargyris EN, Mehran R, Grube E, Reinöhl J, Dangas GD. Current periprocedural anticoagulation in transcatheter aortic valve replacement: could bivalirudin be an option? Rationale and design of the BRAVO 2/3 studies. J Thromb Thrombolysis. 2013 May;35(4):483-93. doi: 10.1007/s11239-013-0890-3. Review. PubMed PMID: 23553245.

18: Simpson EL, Fitzgerald P, Evans P, Tappenden P, Kalita N, Reckless JP, Bakhai A. Bivalirudin for the treatment of ST-segment elevation myocardial infarction: a NICE single technology appraisal. Pharmacoeconomics. 2013 Apr;31(4):269-75. doi: 10.1007/s40273-013-0036-7. Review. PubMed PMID: 23512147.

19: De Servi S, Mariani G, Mariani M, D'Urbano M. The bivalirudin paradox: high evidence, low use. J Cardiovasc Med (Hagerstown). 2013 May;14(5):334-41. doi: 10.2459/JCM.0b013e32835f1915. Review. PubMed PMID: 23442811.

20: Lupi A, Rognoni A, Cavallino C, Secco GG, Prando MD, Santagostino M, Lazzero M, Cassetti E, Bongo AS. Pharmacological adjuvant therapies in primary coronary interventions: bivalirudin. Cardiovasc Hematol Agents Med Chem. 2013 Jun;11(2):106-14. Review. PubMed PMID: 22963495.