Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C24H33ClN4O6 |
Molecular Weight | 508.995 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCO[C@@H]1OC(=O)C[C@@H]1NC(=O)[C@@H]2CCCN2C(=O)[C@@H](NC(=O)C3=CC=C(N)C(Cl)=C3)C(C)(C)C
InChI
InChIKey=SJDDOCKBXFJEJB-MOKWFATOSA-N
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
Molecular Formula | C24H33ClN4O6 |
Molecular Weight | 508.995 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/23176519Curator's Comment: Description was created based on several sources, including
http://www.selleckchem.com/products/vx-765.html
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23176519
Curator's Comment: Description was created based on several sources, including
http://www.selleckchem.com/products/vx-765.html
Belnacasan (VX-765), and its active metabolite VRT- 043198, is a novel and irreversible IL-converting enzyme/ caspase-1 inhibitor. VRT-043198 exhibits 100- to 10,000-fold selectivity against other caspase-3, -6 and -9. It exhibited potent inhibition against ICE/caspase-1 and caspase-4 with Ki of 0.8 nM and less than 0.6 nM, respectively. And VRT-043198 also inhibits IL-1β release from both PBMCs and whole blood with IC50 of 0.67 uM and 1.9 uM, respectively. Belnacasan inhibits the release of IL-1, IL-18 and IL-33. Belnacasan has shown to inhibit acute partial seizures in preclinical models and has shown activity in preclinical models of chronic partial epilepsy that do not respond to currently available compounds for epilepsy. In addition, it seems to reduce disease severity and the expression of inflammatory mediators in models of rheumatoid arthritis and skin inflammation. Belnacasan had been in phase II clinical trials by Vertex for the treatment of epilepsy. However, this study has been terminated later.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4801 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17289835 |
0.8 nM [Ki] | ||
Target ID: CHEMBL2226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17289835 |
|||
Target ID: CHEMBL1909490 |
0.67 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
(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 (VX-765), an orally available selective interleukin (IL)-converting enzyme/caspase-1 inhibitor, exhibits potent anti-inflammatory activities by inhibiting the release of IL-1beta and IL-18. | 2007 May |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01048255
300mg Oral Tablet, 900mg TID
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17289835
VRT-043198, active moiety of BELNACASAN, inhibited IL-1beta release from both human PBMCs and whole blood with IC50 values of 0.67 and 1.9 uM, respectively.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 18:03:09 GMT 2023
by
admin
on
Sat Dec 16 18:03:09 GMT 2023
|
Record UNII |
00OLE78529
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
DB05507
Created by
admin on Sat Dec 16 18:03:09 GMT 2023 , Edited by admin on Sat Dec 16 18:03:09 GMT 2023
|
PRIMARY | |||
|
Belnacasan
Created by
admin on Sat Dec 16 18:03:09 GMT 2023 , Edited by admin on Sat Dec 16 18:03:09 GMT 2023
|
PRIMARY | |||
|
300000034117
Created by
admin on Sat Dec 16 18:03:09 GMT 2023 , Edited by admin on Sat Dec 16 18:03:09 GMT 2023
|
PRIMARY | |||
|
CHEMBL2107819
Created by
admin on Sat Dec 16 18:03:09 GMT 2023 , Edited by admin on Sat Dec 16 18:03:09 GMT 2023
|
PRIMARY | |||
|
11398092
Created by
admin on Sat Dec 16 18:03:09 GMT 2023 , Edited by admin on Sat Dec 16 18:03:09 GMT 2023
|
PRIMARY | |||
|
DTXSID901017651
Created by
admin on Sat Dec 16 18:03:09 GMT 2023 , Edited by admin on Sat Dec 16 18:03:09 GMT 2023
|
PRIMARY | |||
|
C171755
Created by
admin on Sat Dec 16 18:03:09 GMT 2023 , Edited by admin on Sat Dec 16 18:03:09 GMT 2023
|
PRIMARY | |||
|
273404-37-8
Created by
admin on Sat Dec 16 18:03:09 GMT 2023 , Edited by admin on Sat Dec 16 18:03:09 GMT 2023
|
PRIMARY | |||
|
00OLE78529
Created by
admin on Sat Dec 16 18:03:09 GMT 2023 , Edited by admin on Sat Dec 16 18:03:09 GMT 2023
|
PRIMARY | |||
|
9658
Created by
admin on Sat Dec 16 18:03:09 GMT 2023 , Edited by admin on Sat Dec 16 18:03:09 GMT 2023
|
PRIMARY | |||
|
ZZ-06
Created by
admin on Sat Dec 16 18:03:09 GMT 2023 , Edited by admin on Sat Dec 16 18:03:09 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE ACTIVE -> PRODRUG |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|