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Chemistry

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Also known as: 1071992-99-8, At-406, Debio-1143, N65wc8pxdd, Sm-406, Unii-n65wc8pxdd

Molecular Formula

C₃₂H₄₃N₅O₄

Molecular Weight

561.7 g/mol

InChI Key

LSXUTRRVVSPWDZ-MKKUMYSQSA-N

FDA UNII

N65WC8PXDD

Xevinapant is an orally available mimetic of the natural second mitochondrial-derived activator of caspases (Smac) and inhibitor of Inhibitor of Apoptosis Proteins (IAPs), with potential immunomodulating, apoptotic-inducing, chemo-radio-sensitizing and antineoplastic activities. Upon oral administration,xevinapant targets and binds to the Smac binding groove on IAPs, including the direct caspase inhibitor X chromosome-linked IAP (XIAP), and the cellular IAPs 1 (c-IAP1) and 2 (c-IAP2). This inhibits the activities of these IAPs and promotes the induction of apoptosis. Additionally, as xevinapant inhibits the activity of IAPs, it may work synergistically with cytotoxic drugs and/or radiation to overcome tumor cell resistance to apoptosis. As IAPs regulate nuclear factor-kappa B (NFkB) signaling pathways, which drives the expression of genes involved in immune and inflammatory responses, xevinapant may enhance anti-tumor immune responses when administered with certain immunomodulating agents, such as immune checkpoint inhibitors. IAPs are overexpressed by many cancer cell types and suppress both intrinsic and extrinsic apoptosis by binding to and inhibiting active caspases via their baculoviral lAP repeat (BIR) domains. They contribute to chemo-radio-resistance of cancer cells to certain cytotoxic agents and radiation, promote tumor cell survival and are associated with poor prognosis in certain types of cancer. SMAC, a pro-apoptotic mitochondrial protein, is an endogenous inhibitor of the IAPs family of cellular proteins.

1 2D Structure

Xevinapant

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5S,8S,10aR)-N-benzhydryl-5-[[(2S)-2-(methylamino)propanoyl]amino]-3-(3-methylbutanoyl)-6-oxo-1,2,4,5,8,9,10,10a-octahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide

2.1.2 InChI

InChI=1S/C32H43N5O4/c1-21(2)19-28(38)36-18-17-25-15-16-27(37(25)32(41)26(20-36)34-30(39)22(3)33-4)31(40)35-29(23-11-7-5-8-12-23)24-13-9-6-10-14-24/h5-14,21-22,25-27,29,33H,15-20H2,1-4H3,(H,34,39)(H,35,40)/t22-,25+,26-,27-/m0/s1

2.1.3 InChI Key

LSXUTRRVVSPWDZ-MKKUMYSQSA-N

2.1.4 Canonical SMILES

CC(C)CC(=O)N1CCC2CCC(N2C(=O)C(C1)NC(=O)C(C)NC)C(=O)NC(C3=CC=CC=C3)C4=CC=CC=C4

2.1.5 Isomeric SMILES

C[C@@H](C(=O)N[C@H]1CN(CC[C@H]2CC[C@H](N2C1=O)C(=O)NC(C3=CC=CC=C3)C4=CC=CC=C4)C(=O)CC(C)C)NC

2.2 Other Identifiers

2.2.1 UNII

N65WC8PXDD

2.3 Synonyms

2.3.1 MeSH Synonyms

1. At 406

2. At-406

3. At406 Cpd

4. Debio1143

5. N-benzhydryl-5-(2-(methylamino)propanamido)-3-(3-methylbutanoyl)-6-oxodecahydropyrrolo(1,2-a)(1,5)diazocine-8-carboxamide

6. Sm 406

7. Sm-406

8. Sm406 Cpd

2.3.2 Depositor-Supplied Synonyms

1. 1071992-99-8

2. At-406

3. Debio-1143

4. N65wc8pxdd

5. Sm-406

6. Unii-n65wc8pxdd

7. At406

8. (5s,8s,10ar)-n-benzhydryl-5-((s)-2-(methylamino)propanamido)-3-(3-methylbutanoyl)-6-oxodecahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide

9. At 406

10. Debio 1143

11. Sm 406

12. Xevinapant [inn]

13. Chembl2158051

14. Iap Inhibitor At-406

15. Debio-1143 (at-406)

16. At-406 (sm-406)

17. 1071992-99-8 (free Base)

18. At-406(at406)

19. D-1143

20. (5s,8s,10ar)-n-benzhydryl-5-[[(2s)-2-(methylamino)propanoyl]amino]-3-(3-methylbutanoyl)-6-oxo-1,2,4,5,8,9,10,10a-octahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide

21. Qcr-136

22. (5s,8s,10ar)-n-(diphenylmethyl)-5-[(n-methyl-l-alanyl)amino]-3-(3-methylbutanoyl)-6-oxodecahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide

23. At406 (sm-406)

24. Debio1143

25. Xevinapant [who-dd]

26. Gtpl7729

27. Schembl2724374

28. Dtxsid50648496

29. Ex-a104

30. Bcp04668

31. Bdbm50393505

32. Mfcd22124467

33. Nsc764757

34. S2754

35. Zinc43208643

36. Ccg-270056

37. Cs-0962

38. Nsc-764757

39. Ncgc00346675-01

40. Ncgc00346675-03

41. Ac-30282

42. As-56453

43. Hy-15454

44. D 1143

45. At406 (sm-406, Arry-334543)

46. J-501625

47. Q27074566

48. 1071992-99-8, 1071992-57-8 (hcl)

49. (5s,8s,10ar)-n-(diphenylmethyl)decahydro-5-(((2s)-2-(methylamino)-1-oxopropyl)amino)-3-(3-methyl-1-oxobutyl)-6-oxopyrrolo(1,2-a)(1,5)diazocine-8-carboxamide

50. (5s,8s,10ar)-n-(diphenylmethyl)decahydro-5-[[(2s)-2-(methylamino)-1-oxopropyl]amino]-3-(3-methyl-1-oxobutyl)-6-oxopyrrolo[1,2-a][1,5 ]diazocine-8-carboxamide

51. Pyrrolo(1,2-a)(1,5)diazocine-8-carboxamide, N-(diphenylmethyl)decahydro-5-(((2s)-2-(methylamino)-1-oxopropyl)amino)-3-(3-methyl-1-oxobutyl)-6-oxo-, (5s,8s,10ar)-

2.4 Create Date

2008-11-10

3 Chemical and Physical Properties

Molecular Formula	C₃₂H₄₃N₅O₄
Molecular Weight	561.7 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	9
Exact Mass	561.33150487 g/mol
Monoisotopic Mass	561.33150487 g/mol
Topological Polar Surface Area	111 Å²
Heavy Atom Count	41
Formal Charge	0
Complexity	896
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1