ChemicalBook > CAS DataBase List > (S)-1-((S)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide

(S)-1-((S)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide

Product Name
(S)-1-((S)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide
CAS No.
273404-37-8
Chemical Name
(S)-1-((S)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide
Synonyms
Belnacasan;CS-387;VX-765，VX 765;Belnacasan (VX765);VX-765(Belnacasan);BELNACASAN;VX-765;VX 765;Belnacasan, 10 mM in DMSO;Caspase-1-4 Inhibitor VX-765;VX 765; VX-765; VX765. BELNACASAN;(S)-1-((S)-2-(4-Amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrah
CBNumber
CB72513725
Molecular Formula
C24H33ClN4O6
Formula Weight
508.99
MOL File
273404-37-8.mol
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(S)-1-((S)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide Property

Boiling point:
779.0±60.0 °C(Predicted)
Density 
1.32
storage temp. 
-20°C
solubility 
Soluble in DMSO (>25 mg/ml)
pka
12.60±0.40(Predicted)
form 
solid
color 
Off-white to white
Stability:
Stable for 1 year as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChIKey
SJDDOCKBXFJEJB-MOKWFATOSA-N
SMILES
C(N[C@H]1CC(=O)O[C@H]1OCC)(=O)[C@@H]1CCCN1C(=O)[C@H](C(C)(C)C)NC(=O)C1=CC=C(N)C(Cl)=C1
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
5.31372
Product name
Caspase-1/4 Inhibitor, VX-765 - CAS 273404-37-8 - Calbiochem
Purity
A cell-permeable prodrug that upon conversion to its active form inhibits caspase-1 and 4 activity (Ki = 800 pM and 600 pM, respectively).
Packaging
10MG
Price
$222
Updated
2025/07/31
TCI Chemical
Product number
V0176
Product name
VX-765
Packaging
10MG
Price
$108
Updated
2025/07/31
Cayman Chemical
Product number
28825
Product name
VX-765
Packaging
5mg
Price
$62
Updated
2024/03/01
Cayman Chemical
Product number
28825
Product name
VX-765
Packaging
10mg
Price
$104
Updated
2024/03/01
Cayman Chemical
Product number
28825
Product name
VX-765
Packaging
25mg
Price
$239
Updated
2024/03/01
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(S)-1-((S)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide Chemical Properties,Usage,Production

Description

Belnacasan (273404-37-8) is a prodrug of VRT-043198, a potent (Ki = 0.8 nM ICE/caspase-1; <0.6nM caspase-4) and selective inhibitor of interleukin-converting enzyme/caspase-1 subfamily caspases.1 VRT-043198 ICE/caspase-1 IC50 = 0.67 μM PBMCs, 1.0 μM whole blood.? It inhibited the release of IL-1b and IL-18 from human monocytes in vitro and their production in vivo in models of inflammation. Belnacasan inhibited the activation and expression of the NLRP3 Inflammasome leading to moderation of depressive-like behaviors induced by chronic mild stress2 and prevention of glial pyroptosis in multiple sclerosis models3. It inhibited pyroptosis in vascular smooth muscle cells during atherogenesis suggesting a possible therapeutic effect in treating atherosclerotic disease.4 Belnacasan reduced acute seizures and drug resistant chronic epileptic activity in mice5 and provided neuroprotection in two rat models of temporal lobe epilepsy6.? It also displays protective effects in models of stroke7and Alzheimer’s disease8.

Uses

VX-765 shows anti-convulsant activity by inhibiting interlukin-1β biosynthesis.

Definition

ChEBI: Belnacasan is a dipeptide.

General Description

The cell-permeable prodrug of the caspase-1/4-selective inhibitor VRT-43198 (Ki in nM = <0.6/Caspase-4, 0.8/Caspase-1, 100/Caspase-8, 560/Caspase-6, 1,030/Caspase-9, 9,000/Granzyme B, 16,000/Caspase-7, 21,500/Caspase-3; IC50 >100 μM against Cathepsin B & Trypsin). In addition to inhibiting LPS-induced IL-1β production in primary human PBMC cultures (IC50 ~1 μM), VX-765 is also effective in preventing HIV infection-induced IL-1β production and pyroptosis of CD4 T cells in human lymphoid aggregate cultures (HLAC; CD4 population = 29.2% in non-infected control cultures, 8.3% vs. 30.2% in infected cultures with or without 5 μM VX-765). VX-765 is orally available in mice (Blood Cmax = 0.78 μg/mL = 1.53 μM; Tmax = 1.0 h; AUClast = 2.06 μg · h/mL; 84 mg/kg, p.o.) and shown to display in vivo anti-inflammatory efficacy against LPS-induced plasma IL-1β production (EDmax = 100 mg/kg, p.o.), Oxazolone-induced delayed-type hypersensitivity (EDmax = 50 mg/kg, p.o.), collagen-induced arthritis (EDmax = 100 mg/kg, p.o.). When administered via intraperitoneal injection, VX-765 is also demonstrated to suppress the severity of seizure induction (EDmax = 50 mg/kg i.p.) among rats receiving kainic acid via intracerebroventricular injection.

Biochem/physiol Actions

Cell permeable: yes

target

Caspase-1

storage

Store at -20°C

References

[1] WOODS WANNAMAKER. (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.[J]. Journal of Pharmacology and Experimental Therapeutics, 2007, 321 2: 509-516. DOI:10.1124/jpet.106.111344
[2] YI ZHANG. NLRP3 Inflammasome Mediates Chronic Mild Stress-Induced Depression in Mice via Neuroinflammation.[J]. International Journal of Neuropsychopharmacology, 2015, 18 8. DOI:10.1093/ijnp/pyv006
[3] BRIENNE A MCKENZIE. Caspase-1 inhibition prevents glial inflammasome activation and pyroptosis in models of multiple sclerosis.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2018: E6065-E6074. DOI:10.1073/pnas.1722041115
[4] YIYI LI . VX-765 attenuates atherosclerosis in ApoE deficient mice by modulating VSMCs pyroptosis[J]. Experimental cell research, 2020, 389 1: Article 111847. DOI:10.1016/j.yexcr.2020.111847
[5] MATTIA MAROSO . Interleukin-1β Biosynthesis Inhibition Reduces Acute Seizures and Drug Resistant Chronic Epileptic Activity in Mice[J]. Neurotherapeutics, 2011, 8 2: Pages 304-315. DOI:10.1007/s13311-011-0039-z
[6] F.M. NOE . Pharmacological blockade of IL-1β/IL-1 receptor type 1 axis during epileptogenesis provides neuroprotection in two rat models of temporal lobe epilepsy[J]. Neurobiology of Disease, 2013, 59: Pages 183-193. DOI:10.1016/j.nbd.2013.07.015
[7] QIAN LI . Caspase-1 inhibition mediates neuroprotection in experimental stroke by polarizing M2 microglia/macrophage and suppressing NF-κB activation[J]. Biochemical and biophysical research communications, 2019, 513 2: Pages 479-485. DOI:10.1016/j.bbrc.2019.03.202
[8] JOSEPH FLORES. Caspase-1 inhibition alleviates cognitive impairment and neuropathology in an Alzheimer’s disease mouse model.[J]. Nature Communications, 2018: 3916. DOI:10.1038/s41467-018-06449-x

(S)-1-((S)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide Preparation Products And Raw materials

Raw materials

Preparation Products

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(S)-1-((S)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide Suppliers

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View Lastest Price from (S)-1-((S)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide manufacturers

Henan Aochuang Chemical Co.,Ltd.
Product
Belnacasan 273404-37-8
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1Ton
Release date
2022-10-13

273404-37-8, (S)-1-((S)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamideRelated Search:

Lumacaftor (VX-809) VX-661 1H-Pyrrole-2-carboxaMide, 4-[2-[(2-chloro-4-fluorophenyl)aMino]-5-Methyl-4-pyriMidinyl]-N-[(1S)-1-(3-chlorophenyl)-2-hydroxyethyl]- VX 702 VX-745 AVN-944 VE 822 Telaprevir VX-770 Pimodivir 2-AMINOBENZHYDRAZIDE Sulfanilamide MK-2206 2HCl PLX-4720 1,9-Pyrazoloanthrone KU-60019 Trametinib PLX4032

  • (S)-1-((S)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide
  • Belnacasan (VX765)
  • N-(4-Amino-3-chlorobenzoyl)-3-methyl-L-valyl-N-[(2R,3S)-2-ethoxytetrahydro-5-oxo-3-furanyl]-L-prolinamide
  • CS-387
  • VX 765; VX-765; VX765. BELNACASAN
  • (2S)-1-[(2S)-2-[(4-amino-3-chlorophenyl)formamido]-3,3-dimethylbutanoyl]-N-[(2R,3S)-2-ethoxy-5-oxooxolan-3-yl]pyrrolidine-2-carboxamide
  • Belnacasan
  • L-Prolinamide, N-(4-amino-3-chlorobenzoyl)-3-methyl-L-valyl-N-[(2R,3S)-2-ethoxytetrahydro-5-oxo-3-furanyl]-
  • (S)-1-((S)-2-(4-Amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrah
  • N-(4-Amino-3-chlorobenzoyl)-3-methyl-L-valyl-N-[(2R,3S)-2-ethoxytetrahydro-5-oxo-3-furanyl]-L-prolinamide VX 765
  • VX-765(Belnacasan)
  • BELNACASAN;VX-765;VX 765
  • (S)-1-((S)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide USP/EP/BP
  • VX-765，VX 765
  • Caspase-1-4 Inhibitor VX-765
  • Belnacasan, 10 mM in DMSO
  • 273404-37-8
  • C24H33ClN4O6
  • Inhibitors
  • API