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Chemistry

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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

Belnacasan
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 Weight 509.0 g/mol
Molecular Formula C24H33ClN4O6
XLogP32.3
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count7
Rotatable Bond Count8
Exact Mass508.2088625 g/mol
Monoisotopic Mass508.2088625 g/mol
Topological Polar Surface Area140 Ų
Heavy Atom Count35
Formal Charge0
Complexity818
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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.


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API | Excipient name

Belnacasan

Synonyms

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

Cas Number

273404-37-8

Unique Ingredient Identifier (UNII)

00OLE78529

About Belnacasan

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.

Belnacasan Manufacturers

A Belnacasan manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Belnacasan, including repackagers and relabelers. The FDA regulates Belnacasan manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Belnacasan API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Belnacasan Suppliers

A Belnacasan supplier is an individual or a company that provides Belnacasan active pharmaceutical ingredient (API) or Belnacasan finished formulations upon request. The Belnacasan suppliers may include Belnacasan API manufacturers, exporters, distributors and traders.

Belnacasan GMP

Belnacasan Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Belnacasan GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Belnacasan GMP manufacturer or Belnacasan GMP API supplier for your needs.

Belnacasan CoA

A Belnacasan CoA (Certificate of Analysis) is a formal document that attests to Belnacasan's compliance with Belnacasan specifications and serves as a tool for batch-level quality control.

Belnacasan CoA mostly includes findings from lab analyses of a specific batch. For each Belnacasan CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Belnacasan may be tested according to a variety of international standards, such as European Pharmacopoeia (Belnacasan EP), Belnacasan JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Belnacasan USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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