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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

(S)-1-((S)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide Structure
(S)-1-((S)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide structure
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;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;N-(4-Amino-3-chlorobenzoyl)-3-methyl-L-valyl-N-[(2R,3S)-2-ethoxytetrahydro-5-oxo-3-furanyl]-L-prolinamide
CBNumber:
CB72513725
Molecular Formula:
C24H33ClN4O6
Molecular Weight:
508.99
MDL Number:
MFCD11100350
MOL File:
273404-37-8.mol
MSDS File:
SDS
Last updated:2023-06-30 15:45:59
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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 Properties

Boiling point 779.0±60.0 °C(Predicted)
Density 1.32
storage temp. -20°C
solubility Soluble in DMSO (>25 mg/ml)
form solid
pka 12.60±0.40(Predicted)
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.
FDA UNII 00OLE78529

(S)-1-((S)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide price More Price(33)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 5.31372 Caspase-1/4 Inhibitor, VX-765 - CAS 273404-37-8 - Calbiochem A cell-permeable prodrug that upon conversion to its active form inhibits caspase-1 and 4 activity (Ki = 800 pM and 600 pM, respectively). 273404-37-8 10MG $211 2023-06-20 Buy
Cayman Chemical 28825 VX-765 273404-37-8 5mg $62 2024-03-01 Buy
Cayman Chemical 28825 VX-765 273404-37-8 10mg $104 2024-03-01 Buy
Cayman Chemical 28825 VX-765 273404-37-8 25mg $239 2024-03-01 Buy
Cayman Chemical 28825 VX-765 273404-37-8 50mg $448 2024-03-01 Buy
Product number Packaging Price Buy
5.31372 10MG $211 Buy
28825 5mg $62 Buy
28825 10mg $104 Buy
28825 25mg $239 Buy
28825 50mg $448 Buy

(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,Uses,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

Wannamaker et al. (2007)(S)-1-((S)-2-{[1-(4-Amino-3-chlorophenyl)-methanoyl]-amino}-3,3-dimethylbutanoyl)-pyrrolidine-2-carboxylic acid ((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-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-1b and IL-18, J. Pharmacol. Exp. Ther.?321 509 Zhang et al. (2015) NLRP3 Inflammasome Mediates Chronic Mild Stress-Induced Depression in Mice via Neuroinflammation, J. Neuropsychopharmacol. 18 pyv006 McKenzie et al. (2018) Caspase-1 inhibition prevents glial inflammasome activation and pyroptosis in models of multiple sclerosis, Proc. Natl. Acad. Sci USA 115 E6065 Li et al. (2020) VX-765 attenuates atherosclerosis in ApoE deficient mice by modulating VSMCs pyroptosis, Exp. Cell Res. 389 111847 Maroso et al. (2011) Interleukin-1b biosynthesis inhibition reduces acute seizures and drug resistant chronic epileptic activity in mice, Neurotherapeutics 8 304 Noe et al. (2013) Pharmacological blockade of IL-1b/IL-1 receptor type 1 axis during epileptogenesis provides neuroprotection in two rat models of temporal lobe epilepsy, Neurobiol. Dis. 59 183 Li et al. (2019) Caspase-1 inhibition mediates neuroprotection in experimental stroke by polarizing M2 microglia/macrophage and suppressing NF-kB activation, Biochem. Biophys. Res. Commun. 513 479 Flores et al. (2018) Caspase-1 inhibition alleviates cognitive impairment in an Alzheimer’s disease mouse model, Nat. Commun. 9 3916

(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

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

Global( 127)Suppliers
Supplier Tel Email Country ProdList Advantage
Alpha Biopharmaceuticals Co., Ltd 		+86-411-39042497 +8613921981412 sales@alphabiopharm.com China 886 58
Hangzhou FandaChem Co.,Ltd. 		008657128800458; +8615858145714 fandachem@gmail.com China 9350 55
ATK CHEMICAL COMPANY LIMITED 		+undefined-21-51877795 ivan@atkchemical.com China 32480 60
Biochempartner 		0086-13720134139 candy@biochempartner.com CHINA 967 58
Hubei Jusheng Technology Co.,Ltd. 		18871490254 linda@hubeijusheng.com CHINA 28180 58
Changzhou PBpharmaceutical R&D Co.,Ltd 		0519-83990708 info@pbpharm.com CHINA 498 58
BOC Sciences 		+1-631-485-4226 inquiry@bocsci.com United States 19553 58
Hubei Ipure Biology Co., Ltd 		+8613367258412 ada@ipurechemical.com China 10326 58
HONG KONG IPURE BIOLOGY CO.,LIMITED 		86 18062405514 18062405514 ada@ipurechemical.com CHINA 3465 58
Dideu Industries Group Limited 		+86-29-89586680 +86-15129568250 1026@dideu.com China 29321 58
Supplier Advantage
Alpha Biopharmaceuticals Co., Ltd 		58
Hangzhou FandaChem Co.,Ltd. 		55
ATK CHEMICAL COMPANY LIMITED 		60
Biochempartner 		58
Hubei Jusheng Technology Co.,Ltd. 		58
Changzhou PBpharmaceutical R&D Co.,Ltd 		58
BOC Sciences 		58
Hubei Ipure Biology Co., Ltd 		58
HONG KONG IPURE BIOLOGY CO.,LIMITED 		58
Dideu Industries Group Limited 		58

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

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Belnacasan pictures 2022-10-14 Belnacasan
273404-37-8
 US $0.00-0.00 / KG 1KG 98% 1Ton Henan Aochuang Chemical Co.,Ltd.
  • Belnacasan pictures
  • Belnacasan
    273404-37-8
  • US $0.00-0.00 / KG
  • 98%
  • Henan Aochuang Chemical Co.,Ltd.

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

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

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-carboxamide)Related Search:

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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 Belnacasan (VX765) N-(4-Amino-3-chlorobenzoyl)-3-methyl-L-valyl-N-[(2R,3S)-2-ethoxytetrahydro-5-oxo-3-furanyl]-L-prolinamide 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) 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;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 Belnacasan Caspase-1-4 Inhibitor VX-765 273404-37-8 C24H33ClN4O6 Inhibitors API