Birinapant

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Also known as: 1260251-31-7, Birinapant (tl32711), Tl-32711, Tl32711, Tl 32711, (2s)-n-[(2s)-1-[(2r,4s)-2-[[6-fluoro-2-[6-fluoro-3-[[(2r,4s)-4-hydroxy-1-[(2s)-2-[[(2s)-2-(methylamino)propanoyl]amino]butanoyl]pyrrolidin-2-yl]methyl]-1h-indol-2-yl]-1h-indol-3-yl]methyl]-4-hydroxypyrrolidin-1-yl]-1-oxobutan-2-yl]-2-(methylamino)propanamide

Molecular Formula

C₄₂H₅₆F₂N₈O₆

Molecular Weight

806.9 g/mol

InChI Key

PKWRMUKBEYJEIX-DXXQBUJASA-N

FDA UNII

6O4Z07B57R

Birinapant is a synthetic small molecule that is both a peptidomimetic of second mitochondrial-derived activator of caspases (SMAC) and inhibitor of IAP (Inhibitor of Apoptosis Protein) family proteins, with potential antineoplastic activity. As a SMAC mimetic and IAP antagonist, birinapant selectively binds to and inhibits the activity of IAPs, such as X chromosome-linked IAP (XIAP) and cellular IAPs 1 (cIAP1) and 2 (cIAP2), with a greater effect on cIAP1 than cIAP2. Since IAPs shield cancer cells from the apoptosis process, this agent may restore and promote the induction of apoptosis through apoptotic signaling pathways in cancer cells and inactivate the nuclear factor-kappa B (NF-kB)-mediated survival pathway. IAPs are overexpressed by many cancer cell types. They are able to suppress apoptosis by binding to, via their baculoviral lAP repeat (BIR) domains, and inhibiting active caspases-3, -7 and -9. IAP overexpression promotes both cancer cell survival and chemotherapy resistance.

1 2D Structure

Birinapant

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-N-[(2S)-1-[(2R,4S)-2-[[6-fluoro-2-[6-fluoro-3-[[(2R,4S)-4-hydroxy-1-[(2S)-2-[[(2S)-2-(methylamino)propanoyl]amino]butanoyl]pyrrolidin-2-yl]methyl]-1H-indol-2-yl]-1H-indol-3-yl]methyl]-4-hydroxypyrrolidin-1-yl]-1-oxobutan-2-yl]-2-(methylamino)propanamide

2.1.2 InChI

InChI=1S/C42H56F2N8O6/c1-7-33(49-39(55)21(3)45-5)41(57)51-19-27(53)15-25(51)17-31-29-11-9-23(43)13-35(29)47-37(31)38-32(30-12-10-24(44)14-36(30)48-38)18-26-16-28(54)20-52(26)42(58)34(8-2)50-40(56)22(4)46-6/h9-14,21-22,25-28,33-34,45-48,53-54H,7-8,15-20H2,1-6H3,(H,49,55)(H,50,56)/t21-,22-,25-,26-,27-,28-,33-,34-/m0/s1

2.1.3 InChI Key

PKWRMUKBEYJEIX-DXXQBUJASA-N

2.1.4 Canonical SMILES

CCC(C(=O)N1CC(CC1CC2=C(NC3=C2C=CC(=C3)F)C4=C(C5=C(N4)C=C(C=C5)F)CC6CC(CN6C(=O)C(CC)NC(=O)C(C)NC)O)O)NC(=O)C(C)NC

2.1.5 Isomeric SMILES

CC[C@@H](C(=O)N1C[C@H](C[C@H]1CC2=C(NC3=C2C=CC(=C3)F)C4=C(C5=C(N4)C=C(C=C5)F)C[C@@H]6C[C@@H](CN6C(=O)[C@H](CC)NC(=O)[C@H](C)NC)O)O)NC(=O)[C@H](C)NC

2.2 Other Identifiers

2.2.1 UNII

6O4Z07B57R

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Tl32711

2.3.2 Depositor-Supplied Synonyms

1. 1260251-31-7

2. Birinapant (tl32711)

3. Tl-32711

4. Tl32711

5. Tl 32711

6. (2s)-n-[(2s)-1-[(2r,4s)-2-[[6-fluoro-2-[6-fluoro-3-[[(2r,4s)-4-hydroxy-1-[(2s)-2-[[(2s)-2-(methylamino)propanoyl]amino]butanoyl]pyrrolidin-2-yl]methyl]-1h-indol-2-yl]-1h-indol-3-yl]methyl]-4-hydroxypyrrolidin-1-yl]-1-oxobutan-2-yl]-2-(methylamino)propanamide

7. 6o4z07b57r

8. Birinapant [usan]

9. (2s,2's)-n,n'-((2s,2's)-((3s,3's,5r,5'r)-5,5'-((6,6'-difluoro-1h,1'h-[2,2'-biindole]-3,3'-diyl)bis(methylene))bis(3-hydroxypyrrolidine-5,1-diyl))bis(1-oxobutane-2,1-diyl))bis(2-(methylamino)propanamide)

10. (2s,2's)-n,n'-[(6,6'-difluoro-1h,1'h-2,2'-biindole-3,3'-diyl)bis{methanediyl[(2r,4s)-4-hydroxypyrrolidine-2,1-diyl][(2s)-1-oxobutane-1,2-diyl]}]bis[2-(methylamino)propanamide]

11. Birinapant [usan:inn]

12. Unii-6o4z07b57r

13. Birinapant Di-hcl

14. Propanamide, N,n'-((6,6'-difluoro(2,2'-bi-1h-indole)-3,3'-diyl)bis(methylene((2r,4s)-4-hydroxy-2,1-pyrrolidinediyl)((1s)-1-ethyl-2-oxo-2,1-ethanediyl)))bis(2-(methylamino)-, (2s,2's)-

15. Propanamide, N,n'-[(6,6'-difluoro[2,2'-bi-1h-indole]-3,3'-diyl)bis[methylene[(2r,4s)-4-hydroxy-2,1-pyrrolidinediyl][(1s)-1-ethyl-2-oxo-2,1-ethanediyl]]]bis[2-(methylamino)-, (2s,2's)-

16. Birinapant [inn]

17. Birinapant (usan/inn)

18. Birinapant [who-dd]

19. Mls006011237

20. Gtpl7432

21. Tl32711 2hcl

22. Chembl3039522

23. Schembl10049847

24. Dtxsid30155057

25. Ex-a258

26. Tl-32711 2hcl

27. Chebi:177705

28. Bdbm50071920

29. Mfcd25976869

30. Nsc767128

31. Nsc816007

32. S7015

33. Zinc96941868

34. Akos030526366

35. Ccg-270498

36. Cs-1719

37. Db11782

38. Nsc-767128

39. Nsc-816007

40. Ac-32868

41. As-17035

42. Hy-16591

43. Smr004702997

44. Sw220103-1

45. D10417

46. A852939

47. Q27075298

48. (2s)-n-[(2s)-1-[(2r,4s)-2-[[6-luoro-2-[6-luoro-3-[[(2r,4s)-4-hydroxy-1-[(2s)-2-[[(2s)-2-(methylamino)propanoyl]amino]butanoyl]pyrrolidin-2-yl]methyl]-1h-indol-2-yl]-1h-indol-3-yl]methyl]-4-hydroxypyrrolidin-1-yl]-1-oxobutan-2-yl]-2-(methylamino)propanamide

49. (2s,2's)-n,n'-((2s,2's)-1,1'-((3s,3's,5r,5'r)-5,5'-(6,6'-difluoro-1h,1'h-2,2'-biindole-3,3'-diyl)bis(methylene)bis(3-hydroxypyrrolidine-5,1-diyl))bis(1-oxobutane-2,1-diyl))bis(2-(methylamino)propanamide)

50. (2s,2's)-n,n'-[(6,6'-difluoro-1h,1'h-2,2'-biindole-3,3'-diyl)bis{methanediyl[(2r,4s)-4-hydroxypyrrolidine-2,1-diyl][(2s)-1-oxobutane-1,2-diyl]}]bis[2-(methylamino)propanamide] (non-preferred Name)

51. Gt6

52. N,n'-((6,6'-difluoro(1h,1'h-2,2'-biindole)- 3,3'-diyl)bis(methylene((2r,4s)-4-hydroxypyrrolidine-2,1-diyl)((2s)-1- Oxobutane-1,2-diyl) Bis((2s)-2-(methylamino)propanamide)

2.4 Create Date

2011-01-17

3 Chemical and Physical Properties

Molecular Formula	C₄₂H₅₆F₂N₈O₆
Molecular Weight	806.9 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	15
Exact Mass	806.42908786 g/mol
Monoisotopic Mass	806.42908786 g/mol
Topological Polar Surface Area	195 Å²
Heavy Atom Count	58
Formal Charge	0
Complexity	1350
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1