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CAS 128270-60-0
PharmaCompass
  • Chemistry
CAS 128270-60-0
Also known as: Angiomax, 128270-60-0, Hirulog, Hirulog-1, Bivalirudina, Bivalirudinum
Molecular Formula
C98H138N24O33
Molecular Weight
2180.317  g/mol
InChI Key
OIRCOABEOLEUMC-GEJPAHFPSA-N
FDA UNII
TN9BEX005G

Bivalirudin is a synthetic 20 residue peptide (thrombin inhibitor) which reversibly inhibits thrombin. Once bound to the active site, thrombin cannot activate fibrinogen into fibrin, the crucial step in the formation of thrombus. It is administered intravenously. Because it can cause blood stagnation, it is important to monitor changes in hematocrit, activated partial thromboplastin time, international normalized ratio and blood pressure.
1 2D Structure

CAS 128270-60-0

2 Identification
2.1 Computed Descriptors
2.1.1 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
2.1.2 InChI Key
OIRCOABEOLEUMC-GEJPAHFPSA-N
2.1.3 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
2.1.4 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 Other Identifiers
2.2.1 UNII
TN9BEX005G
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. Angiomax

2. 128270-60-0

3. Hirulog

4. Hirulog-1

5. Bivalirudina

6. Bivalirudinum

7. Angiox

8. Bg-8967

9. Bivalirudine

10. Bivalirudin Trifluoroacetate

11. Bg8967

12. Bg 8967

13. Bivalirudin [usan:ban:inn]

14. Hs-2004

15. 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

16. Chebi:59173

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

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

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

20. 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-

21. Unii-tn9bex005g

22. Bivalirudin [usan:inn:ban]

23. Angiomax (tn)

24. C98h138n24o33

25. Bivalirudin Trifluoacetate

26. D03zvy

27. D09fgs

28. D09hvl

29. D0f4ho

30. Tn9bex005g

31. Schembl25739

32. Gtpl6470

33. C9h11no.c2h6.ch4

34. Chembl2103749

35. Ks-00002wun

36. Molport-006-167-455

37. Ebd32115

38. Akos015994644

39. An-7543

40. Db00006

41. Am006888

42. Bc657176

43. The Medicines Company Brand Of Bivalirudin

44. Ls-172701

45. 70b600

46. 8-methoxy-naphtho[2,3-b]thiophen-4,9-quinone

47. 270b600

48. J-005587

49. (r,r)-2,6-bis(4,5-dihydro-4-phenyl-2-oxazolyl)pyridine; (r,r)-2,6-bis(4-phenyl-2-oxazolinyl)pyridine; (+)-2,6-bis[(4r)-4-phenyl-2-oxazolin-2-yl]pyridine

2.4 Create Date
2007-07-03
3 Chemical and Physical Properties
Molecular Weight 2180.317 g/mol
Molecular Formula C98H138N24O33
Hydrogen Bond Donor Count28
Hydrogen Bond Acceptor Count35
Rotatable Bond Count67
Exact Mass2179.989 g/mol
Monoisotopic Mass2178.986 g/mol
Topological Polar Surface Area902 A^2
Heavy Atom Count155
Formal Charge0
Complexity4950
Isotope Atom Count0
Defined Atom Stereocenter Count16
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 3  
Drug NameANGIOMAX
Active IngredientBIVALIRUDIN
CompanyTHE MEDICINES CO (Application Number: N020873. Patents: 7582727, 7582727*PED, 7598343, 7598343*PED)

2 of 3  
Drug NameBIVALIRUDIN IN 0.9% SODIUM CHLORIDE
Active IngredientBIVALIRUDIN
CompanyBAXTER HLTHCARE CORP (Application Number: N208374)

3 of 3  
Drug NameBIVALIRUDIN
Active IngredientBIVALIRUDIN
CompanyACCORD 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 directly and reversibly inhibits thrombin by specifically binding both to the catalytic site and to the 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.


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.


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.


5.3 ATC Code

Anatomical main group: B - Blood and blood forming organs
Therapeutic subgroup: B01 - Antithrombotic agents
Pharmacological subgroup: B01A - Antithrombotic agents
Chemical subgroup: B01AE - Direct thrombin inhibitors
Chemical substance: B01AE06 - bivalirudin


B - Blood and blood forming organs
B01 - Antithrombotic agents
B01A - Antithrombotic agents
B01AE - Direct thrombin inhibitors
B01AE06 - Bivalirudin


5.4 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


5.5 Metabolism/Metabolites

Metabolism

80% proteolytic cleavage


5.6 Biological Half-Life

5.7 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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