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Also known as: 128270-60-0, Angiomax, Bivalirudin trifluoroacetate, Bg-8967, Bg8967, Hirulog

Molecular Formula

C₉₈H₁₃₈N₂₄O₃₃

Molecular Weight

2180.3 g/mol

InChI Key

OIRCOABEOLEUMC-GEJPAHFPSA-N

Bivalirudin is a 20 amino acid long synthetic peptide with thrombin-specific anticoagulant properties. Bivalirudin reversibly binds thrombin, free as well as clot bound, at the catalytic site and the anion-binding exosite, thereby preventing the formation and activation of fibrin, factor XIIIa, and other coagulation factors. This drug is primarily used during coronary angioplasty procedures, in combination with aspirin, in patients with unstable angina.

1 2D Structure

CAS 128270-60-0

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-4-amino-2-[[2-[[2-[[2-[[2-[[(2S)-1-[(2S)-2-[[(2S)-1-[(2R)-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

2.1.2 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

2.1.3 InChI Key

OIRCOABEOLEUMC-GEJPAHFPSA-N

2.1.4 Canonical 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

2.1.5 Isomeric SMILES

CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC2=CC=C(C=C2)O)C(=O)N[C@@H](CC(C)C)C(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC3=CC=CC=C3)NC(=O)[C@H](CC(=O)O)NC(=O)CNC(=O)[C@H](CC(=O)N)NC(=O)CNC(=O)CNC(=O)CNC(=O)CNC(=O)[C@@H]4CCCN4C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]5CCCN5C(=O)[C@@H](CC6=CC=CC=C6)N

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Angiomax

2. Angiomax Rtu

3. Bg 8967

4. Bg-8967

5. Bg8967

6. Bivalirudin Trifluoroacetate

7. Ctb-001

8. Hirulog

9. Hirulog-1

10. L-leucine, D-phenylalanyl-l-prolyl-l-arginyl-l-prolylglycylglycylglycylglycyl-l-asparaginylglycyl-l-alpha-aspartyl-l-phenylalanyl-l-alpha-glutamyl-l-alpha-glutamyl-l-isoleucyl-l-prolyl-l-alpha-glutamyl-l-alpha-glutamyl-l-tyrosyl-

11. Phe-pro-arg-pro-(gly)4 Desulfato-tyr63'-hirugen

12. Phe-pro-arg-pro-(gly)4-asn-gly-asp-phe-glu-glu-ile-pro-glu-glu-tyr-leu

13. Phe-pro-arg-pro-(gly)4-desulfohirudin-(53-64)

2.2.2 Depositor-Supplied Synonyms

1. 128270-60-0

2. Angiomax

3. Bivalirudin Trifluoroacetate

4. Bg-8967

5. Bg8967

6. Hirulog

7. Chebi:59173

8. Hirulog-1

9. D-phenylalanyl-l-prolyl-l-arginyl-l-prolylglycylglycylglycylglycyl-l-asparaginylglycyl-l-alpha-aspartyl-l-phenylalanyl-l-alpha-glutamyl-l-alpha-glutamyl-l-isoleucyl-l-prolyl-l-alpha-glutamyl-l-alpha-glutamyl-l-tyrosyl-l-leucine

11. Angiox

12. Bivalirudina

13. Bivalirudine

14. Bivalirudinum

15. Bg 8967

16. Unii-tn9bex005g

17. Bivalirudin [usan:inn:ban]

18. Bivalirudin Tfa

19. 1191386-55-6

20. Hs-2004

21. Tn9bex005g

22. Schembl25739

23. Gtpl6470

24. Bivalirudin Trifluoroacetate Salt

25. Chembl2103749

26. Dtxsid00155847

27. Bivalirudin;0.9% Sodium Chloride

28. Ex-a5843

29. Bdbm50248103

30. Mfcd08692016

31. Akos015994644

32. Db00006

33. 70b600

34. 270b600

35. J-005587

36. Q4919218

37. Bivalirudin Trifluoroacetate (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.tfa)

2.3 Create Date

2007-07-03

3 Chemical and Physical Properties

Molecular Formula	C₉₈H₁₃₈N₂₄O₃₃
Molecular Weight	2180.3 g/mol
XLogP3	-7.1
Hydrogen Bond Donor Count	28
Hydrogen Bond Acceptor Count	35
Rotatable Bond Count	67
Exact Mass	2179.9891678 g/mol
Monoisotopic Mass	2178.9858129 g/mol
Topological Polar Surface Area	902 Å²
Heavy Atom Count	155
Formal Charge	0
Complexity	4950
Isotope Atom Count	0
Defined Atom Stereocenter Count	16
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 3
Drug Name	ANGIOMAX
Active Ingredient	BIVALIRUDIN
Company	THE MEDICINES CO (Application Number: N020873. Patents: 7582727, 7582727PED, 7598343, 7598343PED)

2 of 3
Drug Name	BIVALIRUDIN IN 0.9% SODIUM CHLORIDE
Active Ingredient	BIVALIRUDIN
Company	BAXTER HLTHCARE CORP (Application Number: N208374)

3 of 3
Drug Name	BIVALIRUDIN
Active Ingredient	BIVALIRUDIN
Company	ACCORD HLTHCARE (Application Number: A206551); APOTEX INC (Application Number: A204876); DR REDDYS LABS LTD (Application Number: A201577); FRESENIUS KABI USA (Application Number: A090189); HOSPIRA INC (Application Number: A090811); HOSPIRA INC (Application Number: A090816)

4.2 Drug Indication

For treatment of heparin-induced thrombocytopenia and for the prevention of thrombosis. Bivalirudin is indicated for use in patients undergoing percutaneous coronary intervention (PCI), in patients at moderate to high risk acute coronary syndromes due to unstable angina or non-ST segment elevation in whom a PCI is planned.

FDA Label

Angiox is indicated as an anticoagulant in adult patients undergoing percutaneous coronary intervention (PCI), including patients with ST-segment-elevation myocardial infarction (STEMI) undergoing primary PCI.

Angiox is also indicated for the treatment of adult patients with unstable angina / non-ST-segment-elevation myocardial infarction (UA / NSTEMI) planned for urgent or early intervention.

Angiox should be administered with aspirin and clopidogrel.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Bivalirudin mediates an inhibitory action on thrombin by directly and specifically binding to both the catalytic site and anion-binding exosite of circulating and clot-bound thrombin. The action of bivalirudin is reversible because thrombin will slowly cleave the thrombin-bivalirudin bond which recovers the active site of thrombin.

5.2 MeSH Pharmacological Classification

Antithrombins

Endogenous factors and drugs that directly inhibit the action of THROMBIN, usually by blocking its enzymatic activity. They are distinguished from INDIRECT THROMBIN INHIBITORS, such as HEPARIN, which act by enhancing the inhibitory effects of antithrombins. (See all compounds classified as Antithrombins.)

5.3 FDA Pharmacological Classification

5.3.1 Pharmacological Classes

Direct Thrombin Inhibitor [EPC]; Thrombin Inhibitors [MoA]; Anti-coagulant [EPC]

5.4 ATC Code

B01AE06

B - Blood and blood forming organs

B01 - Antithrombotic agents

B01A - Antithrombotic agents

B01AE - Direct thrombin inhibitors

B01AE06 - Bivalirudin

5.5 Absorption, Distribution and Excretion

Absorption

Following intravenous administration, bivalirudin exhibits linear pharmacokinetics. The mean steady state concentration is 12.3 +/- 1.7mcg/mL after administration of an intravenous bolus of 1mg/kg followd by a 2.5mg/kg/hr intravenous infusion given over 4 hours.

Route of Elimination

Bivalirudin is cleared from plasma by a combination of renal mechanisms (20%) and proteolytic cleavage.

Volume of Distribution

0.2L/kg

Clearance

3.4 mL/min/kg [Normal renal function]

3.4 mL/min/kg [mild renal function]

2.7 mL/min/kg [moderate renal function]

2.8 mL/min/kg [severe renal function]

1 mL/min/kg [Dialysis-dependent patients]

5.6 Metabolism/Metabolites

80% proteolytic cleavage

5.7 Biological Half-Life

Normal renal function: 25 min (in normal conditions)

Creatinine clearance 10-29mL/min: 57min

Dialysis-dependant patients: 3.5h

5.8 Mechanism of Action

Inhibits the action of thrombin by binding both to its catalytic site and to its anion-binding exosite. Thrombin is a serine proteinase that plays a central role in the thrombotic process, acting to cleave fibrinogen into fibrin monomers and to activate Factor XIII to Factor XIIIa, allowing fibrin to develop a covalently cross-linked framework which stabilizes the thrombus; thrombin also activates Factors V and VIII, promoting further thrombin generation, and activates platelets, stimulating aggregation and granule release.

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