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Belnacasan

Belnacasan

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Also known as: Vx-765, 273404-37-8, Vx765, Belnacasan (vx-765), Belnacasan [usan], Belnacasan (vx765)

Molecular Formula

C₂₄H₃₃ClN₄O₆

Molecular Weight

509.0 g/mol

InChI Key

SJDDOCKBXFJEJB-MOKWFATOSA-N

FDA UNII

00OLE78529

VX-765 is the orally available prodrug of a potent and selective competitive inhibitor of ICE/caspase-1 (VRT-043198). VX-765 is currently under clinical development for the treatment of inflammatory and autoimmune conditions, as it blocks the hypersensitive response to an inflammatory stimulus.

1 2D Structure

Belnacasan

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-1-[(2S)-2-[(4-amino-3-chlorobenzoyl)amino]-3,3-dimethylbutanoyl]-N-[(2R,3S)-2-ethoxy-5-oxooxolan-3-yl]pyrrolidine-2-carboxamide

2.1.2 InChI

InChI=1S/C24H33ClN4O6/c1-5-34-23-16(12-18(30)35-23)27-21(32)17-7-6-10-29(17)22(33)19(24(2,3)4)28-20(31)13-8-9-15(26)14(25)11-13/h8-9,11,16-17,19,23H,5-7,10,12,26H2,1-4H3,(H,27,32)(H,28,31)/t16-,17-,19+,23+/m0/s1

2.1.3 InChI Key

SJDDOCKBXFJEJB-MOKWFATOSA-N

2.1.4 Canonical SMILES

CCOC1C(CC(=O)O1)NC(=O)C2CCCN2C(=O)C(C(C)(C)C)NC(=O)C3=CC(=C(C=C3)N)Cl

2.1.5 Isomeric SMILES

CCO[C@H]1[C@H](CC(=O)O1)NC(=O)[C@@H]2CCCN2C(=O)[C@H](C(C)(C)C)NC(=O)C3=CC(=C(C=C3)N)Cl

2.2 Other Identifiers

2.2.1 UNII

00OLE78529

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (s)-1-((s)-2-1((-(4-amino-3-chloro-phenyl)-methanoyl)-amino)-3,3-dimethyl-butanoyl)-pyrrolidine-2-carboxylic Acid ((2r,3s)-2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide

2. (s)-3-((1-((s)-1-((s)-2-((1-(4-amino-3-chlorophenyl)methanoyl)amino)-3,3-dimethyl-butanoyl)pyrrolidin-2yl)methanoyl)amino)-4-oxo-butyric Acid

3. 1-((2s)-2-((4-amino-3-chlorobenzoyl)amino)-3,3-dimethylbutanoyl)-n-((2r,3s)-2- Ethoxy-5-oxo-tetrahydrofuran-3-yl)-l-prolinamide

4. L-prolinamide, N-(4-amino-3-chlorobenzoyl)-3-methyl-l-valyl-n-((1s)-2-carboxy-1-formylethyl)-

5. N-(4-amino-3-chlorobenzoyl)-3-methyl-l-valyl-n-((1s)-2-carboxy-1-formylethyl)-l-prolinamide

6. O-desethyl-belnacasan

7. Vrt 043198

8. Vrt-043198

9. Vx 765

10. Vx-765

11. Vx-765 Hemiketal

12. Vx765

2.3.2 Depositor-Supplied Synonyms

1. Vx-765

2. 273404-37-8

3. Vx765

4. Belnacasan (vx-765)

5. Belnacasan [usan]

6. Belnacasan (vx765)

7. Belnacasan (usan)

8. (s)-1-((s)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-n-((2r,3s)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide

9. 851091-96-8

10. Unii-00ole78529

11. Belnacasan(vx-765)

12. Vx-765 (belnacasan)

13. (2s)-1-[(2s)-2-[(4-amino-3-chlorobenzoyl)amino]-3,3-dimethylbutanoyl]-n-[(2r,3s)-2-ethoxy-5-oxooxolan-3-yl]pyrrolidine-2-carboxamide

14. 00ole78529

15. (2s)-1-[(2s)-2-[(4-amino-3-chlorophenyl)formamido]-3,3-dimethylbutanoyl]-n-[(2r,3s)-2-ethoxy-5-oxooxolan-3-yl]pyrrolidine-2-carboxamide

16. 1-((2s)-2-((4-amino-3-chlorobenzoyl)amino)-3,3-dimethylbutanoyl)-n-((2r,3s)-2- Ethoxy-5-oxo-tetrahydrofuran-3-yl)-l-prolinamide

17. L-prolinamide, N-(4-amino-3-chlorobenzoyl)-3-methyl-l-valyl-n-((2r,3s)-2-ethoxytetrahydro-5-oxo-3-furanyl)-

18. N-(4-amino-3-chlorobenzoyl)-3-methyl-l-valyl-n-[(2r,3s)-2-ethoxytetrahydro-5-oxo-3-furanyl]-l-prolinamide

19. Vx 765

20. Belnacasan [usan:inn]

21. Belnacasan [inn]

22. Belnacasan [who-dd]

23. Gtpl9035

24. Schembl3393597

25. Chembl2107819

26. Chebi:188567

27. Dtxsid901017651

28. Hms3884b11

29. Amy24224

30. Zinc3963010

31. Mfcd11100350

32. S2228

33. Akos024464751

34. Ccg-269769

35. Ncgc00183682-09

36. Ncgc00183682-10

37. Ncgc00183682-13

38. (s)-1-((s)-2-{[1-(4-amino-3-chloro-phenyl)-methanoyl]-amino}-3,3-dimethyl-butanoyl)-pyrrolidine-2-carboxylic Acid ((2r,3s)-2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide

39. As-35159

40. Bcp0726000319

41. Ft-0774330

42. V0176

43. D10416

44. A857663

45. J-523035

46. Q27075000

47. (s)-1-((s)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-n-((2r,3s)-2-ethoxy-5-oxo-tetrahydrofuran-3-yl)pyrrolidine-2-carboxamide;vx-765

48. 1-((2s)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-n-((2r,3s)-2-ethoxy-5-oxooxolan-3-yl)-l-prolinamide

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₃₃ClN₄O₆
Molecular Weight	509.0 g/mol
XLogP3	2.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	8
Exact Mass	508.2088625 g/mol
Monoisotopic Mass	508.2088625 g/mol
Topological Polar Surface Area	140 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	818
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

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in inflammatory disorders (unspecified) and psoriasis and psoriatic disorders.

5 Pharmacology and Biochemistry

5.1 Pharmacology

VX-765 is an orally-absorbed pro-drug of VRT-043198, a potent and selective inhibitor of ICE/caspase-1 sub-family caspases. It has been shown to reduce disease severity and the expression of inflammatory mediators in models of rheumatoid arthritis and skin inflammation, suggesting that it may be useful for treatment of inflammatory diseases.

5.2 Mechanism of Action

VX-765 is a potent and selective inhibitor of ICE/caspase-1 sub-family caspases. In preclinical trials, VX-765 was efficiently converted to VRT-043198 when administered orally to mice and inhibited LPS-induced cytokine secretion. The result was a blocking of IL-1beta and IL-18 secretion, with out much effect on the release of several other cytokines, including IL-1{alpha}, tumor necrosis factor-{alpha}, IL-6 and IL-8. There was also no demonstrable activity in cellular models of apoptosis and it did not affect the proliferation of activated primary T-cells or T-cell lines.