1. Anti-infection
    Metabolic Enzyme/Protease
  2. HCV Protease
    HCV
  3. Telaprevir

Telaprevir (Synonyms: VX-950)

Cat. No.: HY-10235 Purity: 99.07%
Handling Instructions

Telaprevir is a highly selective, reversible, and potent peptidomimetic inhibitor of the HCV NS3-4A protease, the steady-state inhibitory constant (Ki) of Telaprevir is 7 nM against a genotype 1 (H strain) NS3 protease domain plus a NS4A cofactor peptide.

For research use only. We do not sell to patients.

Telaprevir Chemical Structure

Telaprevir Chemical Structure

CAS No. : 402957-28-2

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10 mM * 1 mL in DMSO USD 218 In-stock
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Customer Review

Based on 41 publication(s) in Google Scholar

Top Publications Citing Use of Products

Publications Citing Use of MCE Telaprevir

    Telaprevir purchased from MCE. Usage Cited in: Open Virol J. 2014 Mar 7;8:1-8.

    The PKR activation block is not unique to CypI, DAAs also prevent the IFN-induced PKR activation in HCV-infected cells. JFH-1-infected Huh7.5.1 cells are treated with or without CypI (cyclosporine A and alisporivir), DAAs (the HCV NS5A inhibitor daclatasvir and the HCV protease inhibitor telaprevir) and an HIV-1 inhibitor (reverse transcriptase inhibitor emtricitabine). Results are representative of 4 independent experiments.

    Telaprevir purchased from MCE. Usage Cited in: Virology. 2014 May;456-457:300-9.

    Jurkat cells are transfected with plasmids expressing (A) HCV NS3/4A or (B) HPgV NS3/4AB-HA. Telaprevir, Boceprevir, and Danoprevir are added at concentrations of 100 µM, 16.6 µM, 2.7 µM, or 0 µM in 0.1% DMSO. Lysates are harvested after 24 h and resolved by immunoblots probed with anti-HCV NS3 (A) or anti-HA (B). The position of HCV NS3/4A (~75kDa), HCV NS3 (~73kDa), NS3/4AB-HA, and NS4B-HA (~30kDa) are indicated. Molecular markers are on the right.

    Telaprevir purchased from MCE. Usage Cited in: Antiviral Res. 2015 Dec;124:54-60.

    Cell lysates at 52 h.p.e are analysed by western blot for NS5A and GAPDH. Both 160 and Telaprevir cause a comparable reduction in NS5A relative to DMSO control.

    Telaprevir purchased from MCE. Usage Cited in: Sci Rep. 2016 Feb 22;6:21808.

    While compounds SSO and VX-950 show HCV inhibitory activity in the Group 1 (P < 0.01), SSO-treated viruses display infectivity equal to that of untreated control and negative reference VX-950 in Group 2 (P > 0.05).

    Telaprevir purchased from MCE. Usage Cited in: Biomed Res Int. 2017;2017:1236801.

    Naïve Huh7.5 cells are infected with wild and mutant type HCV and simultaneously treated with drugs. Intracellular proteins were extracted and detected with WB in 72 hours. Telaprevir (VX-950) against WT and A156T mutant HCV.

    Telaprevir purchased from MCE. Usage Cited in: Eur J Med Chem. 2018 Jan 1;143:1053-1065.

    GS4.3 cells are treated with 7f (20 μM), or Telaprevir (0.5μM), Sofosbuvir (0.8 μM), Daclatasvir (0.15 μM) or solvent control for 6 days.

    Telaprevir purchased from MCE. Usage Cited in: Antimicrob Agents Chemother. 2015 Dec;59(12):7666-7670.

    Effects of antiviral drugs on cellular uptake of fluorescein by BeWo cells. The cells are incubated with 1 μM fluorescein in the presence of 100 μM compounds for 10 min at 37°C.
    • Biological Activity

    • Protocol

    • Purity & Documentation

    • References

    • Customer Review

    Description

    Telaprevir is a highly selective, reversible, and potent peptidomimetic inhibitor of the HCV NS3-4A protease, the steady-state inhibitory constant (Ki) of Telaprevir is 7 nM against a genotype 1 (H strain) NS3 protease domain plus a NS4A cofactor peptide.

    IC50 & Target

    Ki: 7 nM (genotype 1 HCV NS3-4A protease)[1]

    In Vitro

    Telaprevir (VX-950) is a covalent, reversible inhibitor of the NS3-4A protease with a slow-binding and slow-dissociation mechanism. Telaprevir exhibits significantly different kinetics in enzyme inhibition, which is most clearly exemplified by a very long half-life (58 min) of the bound enzyme-inhibitor complex. Telaprevir is additive to moderately synergistic with IFN-α in inhibiting HCV replication and in suppressing the emergence of resistance in replicon cells. Telaprevir reduces HCV RNA levels in a time- and dose-dependent manner. The IC50s following a 24, 48, 72, and 120 h incubation with Telaprevir are determined to be 0.574, 0.488, 0.21, and 0.139 μM, respectively, indicating an increase in inhibitory effects with time. Following three independent experiments using the 48 h incubation in the presence of 2% FBS, the average IC50 of Telaprevir is determined to be 0.354 ± 0.035 μM, and the average IC90 is 0.830 ± 0.190 μM[1]. Telaprevir (VX-950) is a potent, selective, peptidomimetic inhibitor of the hepatitis C virus (HCV) NS3-4A serine protease, and Telaprevir demonstrates excellent antiviral activity both in genotype 1b HCV replicon cells (IC50=354 nM) and in human fetal hepatocytes infected with genotype 1a HCV-positive patient sera (IC50=280 nM)[2].

    In Vivo

    There is an ~5-fold reduction of serum SEAP activity in mice dosed with Telaprevir (VX-950) at either 10 or 25 mg/kg, which has an average value (±SEM) of 18.7±8.3% or 18.4±5.4%, respectively, compare to those administered vehicle (100±28%). These data demonstrates that Telaprevir is able to inhibit the HCV NS3-4A serine protease activity in mouse liver and block cleavage and subsequent secretion of SEAP into blood circulation in these mice[2].

    Clinical Trial
    Molecular Weight

    679.85

    Formula

    C₃₆H₅₃N₇O₆

    CAS No.

    402957-28-2

    SMILES

    O=C(N([[email protected]@H]1C(N[[email protected]](C(C(NC2CC2)=O)=O)CCC)=O)C[[email protected]@]3(CCC[[email protected]@]31[H])[H])[[email protected]@H](NC([[email protected]@H](NC(C4=NC=CN=C4)=O)C5CCCCC5)=O)C(C)(C)C

    Shipping

    Room temperature in continental US; may vary elsewhere.

    Storage
    Powder -20°C 3 years
    4°C 2 years
    In solvent -80°C 6 months
    -20°C 1 month
    Solvent & Solubility
    In Vitro: 

    DMSO : ≥ 50 mg/mL (73.55 mM)

    H2O : < 0.1 mg/mL (insoluble)

    *"≥" means soluble, but saturation unknown.

    Preparing
    Stock Solutions
    Concentration Solvent Mass 1 mg 5 mg 10 mg
    1 mM 1.4709 mL 7.3546 mL 14.7091 mL
    5 mM 0.2942 mL 1.4709 mL 2.9418 mL
    10 mM 0.1471 mL 0.7355 mL 1.4709 mL
    *Please refer to the solubility information to select the appropriate solvent.
    In Vivo:
    • 1.

      Add each solvent one by one:  10% DMSO    90% corn oil

      Solubility: ≥ 2.5 mg/mL (3.68 mM); Clear solution

    *All of the co-solvents are provided by MCE.
    References
    Cell Assay
    [1]

    Determination of IC50, IC90, CC50 of Telaprevir (VX-950) or IFN-α in HCV replicon cells is performed. Briefly, 1×104 replicon cells per well are plated in 96-well plates. On the following day, replicon cells is incubated at 37°C for the indicated period of time with antiviral agents serially diluted in DMEM plus 2% FBS and 0.5% DMSO. Total cellular RNA is extracted using an RNeasy-96 kit, and the copy number of HCV RNA is determined using a quantitative RT-PCR (QRT-PCR) assay. Each datum point represents the average of five replicates in cell culture. The cytotoxicity of Telaprevir is measured under the same experimental settings using a tetrazolium (MTS)-based cell viability assay. For the cytotoxicity assay with human hepatocyte cell lines, 1×104 parental Huh-7 cells per well or 4×104 HepG2 cells per well are used. To determine cytotoxicity of Telaprevir against resting PBMC, 1×105 cells per well are incubated with Telaprevir in RPMI-1640 medium (no serum) for 48 h, and the cell viability is determined by the MTS-based assay. To determine cytotoxicity of VX-950 against proliferating PBMC, 1×105 cells per well in RPMI-1640 medium are added to a 96-well plate, which is precoated with anti-human CD3 antibody. The cells are incubated with Telaprevir and anti-human CD28 antibody for 72 h at 37°C, and the cell growth is determined by [3H]thymidine update between the 48th and 72nd h[1].

    MCE has not independently confirmed the accuracy of these methods. They are for reference only.

    Animal Administration
    [2]

    Mice[2]
    Five groups of 6-week-old SCID mice (6 animals per group) are injected with 109 IFU per mouse of recombinant adenovirus Ad-WT-HCVpro-SEAP through the tail vein. Each group of mice is given two oral administrations of Telaprevir (VX-950) at one of the following doses: 10, 25, 75, 150, or 300 mg/kg. The first Telaprevir dose is given 2 h before the adenovirus injection, and the second dose is given 10 h after injection. An additional group of 10 mice is given vehicle alone. Serum samples are collected 24 h postinjection, and the SEAP activity in each Telaprevir-dosed group is compared to that of the vehicle group. Rat and Dog[2] The intravenous and oral pharmacokinetics of Telaprevir (VX-950) are evaluated in rats and dogs. A group of 3 male Sprague-Dawley rats weighing 250 to 300 g is administered an intravenous bolus dose of 0.95 mg/kg Telaprevir. Serial blood samples are collected in heparinized tubes before dosing and at 0.083, 0.167, 0.25, 0.5, 1, 1.5, 2, 3, 4, 6, and 8 h after dose administration. A group of 3 male beagle dogs (8 to 12 kg) is administered an intravenous bolus dose of 3.5 mg/kg Telaprevir in 10% ethanol, 40% polyethylene glycol 400, and 50% D5W. Serial blood samples are collected in heparinized tubes before dosing and at 0.083, 0.167, 0.25, 0.5, 1, 1.5, 2, 4, 6, 8, 12, and 24 h after dose administration. For oral studies in rats and dogs, Telaprevir is formulated in polyvinylpyrrolidone (PVP) K-30 plus 2% sodium lauryl sulfate and then dosed as an oral gavage. A group of 3 male Sprague-Dawley rats (250 to 300 g) is dosed orally with 40 mg/kg VX-950, and a group of 4 male beagle dogs (10.9 to 12.0 kg) is administered an oral dose of 9.6 mg/kg VX-950. In both oral studies, blood samples are taken before dosing and at 0.25, 0.5, 1, 1.5, 2, 3, 4, 6, 8, 12, and 24 h after dose administration. In both intravenous and oral studies, plasma samples are obtained by centrifugation and stored at −70°C until analysis. Samples from the intravenous studies are analyzed by a chiral liquid chromatography followed by tandem mass spectrometry (LC/MS/MS) method, and samples from the oral studies are analyzed using an achiral LC/MS/MS method.

    MCE has not independently confirmed the accuracy of these methods. They are for reference only.

    References

    Purity: 99.07%

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    Keywords:

    TelaprevirVX-950VX950VX 950HCV ProteaseHCVHepatitis C virusInhibitorinhibitorinhibit

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