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Telaprevir (VX-950)

In stock
Catalog No.
A4031
HCV NS3-4A protease inhibitor
Grouped product items
SizePriceStock Qty
10mM (in 1mL DMSO)
$180.00
In stock
2mg
$80.00
In stock
5mg
$110.00
In stock
10mg
$165.00
In stock
25mg
$320.00
In stock

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Background

Telaprevir (also known as VX-950), derived from the viral NS5A/5B substrate of the protease through structure-based techniques, is a novel and potent inhibitor of hepatitis C virus (HCV) NS3-4A protease, which covalently and reversibly inhibit the NS3-4A protease via a slow-binding and slow-dissociation mechanism. Results of multiple studies show that telaprevir potently inhibits a genotype 1 (H strain) NS3 protease domain plus a NS4A cofactor peptide with the inhibitory constant (Ki) of 7 nM, exhibits strong anti-HCV in HCV replicon cells in vitro, and suppresses HCV replication as well as the emergence of resistance in HCV replicon cells with a synergistic effect with IFN-α.

Reference

Kai Lin, Robert B. Perni, Ann D. Kwong, and Chao Lin. VX-950, a novel hepatitis C virus (HCV) NS3-4A protease inhibitor, exhibits potent antiviral activities in HCV replicon cells. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY 2006; 50(5): 1813-1822

Chemical Properties

Physical AppearanceA solid
StorageStore at -20°C
M.Wt679.9
Cas No.402957-28-2
FormulaC36H53N7O6
SynonymsVX950, VX 950, MP-424,Telaprevir
Solubility≥32.95 mg/mL in DMSO, <2.46 mg/mL in EtOH, <2.5 mg/mL in H2O
Chemical Name(3S,3aS,6aR)-2-[(2S)-2-[[(2S)-2-cyclohexyl-2-(pyrazine-2-carbonylamino)acetyl]amino]-3,3-dimethylbutanoyl]-N-[(3S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-3-carboxamide
SDFDownload SDF
Canonical SMILESCCCC(C(=O)C(=O)NC1CC1)NC(=O)C2C3CCCC3CN2C(=O)C(C(C)(C)C)NC(=O)C(C4CCCCC4)NC(=O)C5=NC=CN=C5
Shipping ConditionEvaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tipsFor obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Protocol

Cell experiment [1]:

Cell lines

Con1 (genotype 1b) subgenomic HCV replicon cells, Primary human fetal liver cells

Preparation method

The solubility of this compound in DMSO is >33 mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months.

Reacting condition

5 or 50 μM, 48 h

Applications

VX-950 reduced HCV RNA levels in a time- and dose-dependent manner. The IC50s following a 24-, 48-, 72-, and 120-h incubation with VX-950 were 0.574, 0.488, 0.210, and 0.139 μM, respectively. VX-950 (30 μM) showed no significant cytotoxicity in both parental Huh-7 and HepG2 cell lines. VX-950 reduced HCV proteins in the replicon cells. VX-950 showed no cytotoxicity in proliferating PBMC. VX-950 induced a multilog reduction of HCV RNA levels in replicon cells. VX-950 inhibited HCV replication in primary human fetal liver cells.

Animal experiment [2]:

Animal models

HCV NS3-4A protease mouse model

Dosage form

Oral administration, 10-300 mg/kg

Application

Oral administration of VX-950 in a PVP polymer matrix resulted in good exposure in rats and dogs. VX-950 inhibited HCV NS3-4A serine protease and reduced SEAP levels in the NS3-4A protease mouse model. Oral administration of VX-950 reduced HCV protease-dependent cleavage and subsequent secretion of SEAP from the liver into the blood in the mice model to 18.7% and 18.4% at dosage of 10 and 25 mg/kg, respectively.

Other notes

Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.

References:

[1]. Lin K, Perni R B, Kwong A D, et al. VX-950, a novel hepatitis C virus (HCV) NS3-4A protease inhibitor, exhibits potent antiviral activities in HCV replicon cells[J]. Antimicrobial agents and chemotherapy, 2006, 50(5): 1813-1822.

[2]. Perni R B, Almquist S J, Byrn R A, et al. Preclinical profile of VX-950, a potent, selective, and orally bioavailable inhibitor of hepatitis C virus NS3-4A serine protease[J]. Antimicrobial agents and chemotherapy, 2006, 50(3): 899-909.

Quality Control

Quality Control & MSDS

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Chemical structure

Telaprevir (VX-950)