BalapiravirPolymerase inhibitor,anti-HCV CAS# 690270-29-2 |
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Quality Control & MSDS
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| Cas No. | 690270-29-2 | SDF | Download SDF |
| PubChem ID | 11691726 | Appearance | Powder |
| Formula | C21H30N6O8 | M.Wt | 494.5 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | Ro 4588161; R1626 | ||
| Solubility | DMSO : ≥ 100 mg/mL (202.22 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-azido-3,4-bis(2-methylpropanoyloxy)oxolan-2-yl]methyl 2-methylpropanoate | ||
| SMILES | CC(C)C(=O)OCC1(C(C(C(O1)N2C=CC(=NC2=O)N)OC(=O)C(C)C)OC(=O)C(C)C)N=[N+]=[N-] | ||
| Standard InChIKey | VKXWOLCNTHXCLF-DXEZIKHYSA-N | ||
| Standard InChI | InChI=1S/C21H30N6O8/c1-10(2)17(28)32-9-21(25-26-23)15(34-19(30)12(5)6)14(33-18(29)11(3)4)16(35-21)27-8-7-13(22)24-20(27)31/h7-8,10-12,14-16H,9H2,1-6H3,(H2,22,24,31)/t14-,15+,16-,21-/m1/s1 | ||
| General tips | For 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. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Balapiravir (R1626, Ro 4588161) is the prodrug of a nucleoside analogue inhibitor of the hepatitis C virus (HCV) RNA-dependent RNA polymerase (R1479, RG1479).
IC50 Value:
Target: HCV
Balapiravir(R-1626; R 1626; Ro 4588161) is useful for Anti HCV. Balapiravir (R1626) is the tri-isobutyrate ester prodrug of R1479 under clinical development to improve exposure of R1479 upon oral administration. Balapiravir was discontinued for safety reasons in 28-36% of patients (most often for lymphopenia) and the percentage of patients with serious adverse events (especially hematological, infection, ocular events) was dose related. Serious hematological adverse events (particularly neutropenia, lymphopenia) were more common in balapiravir recipients. Two deaths in the balapiravir/peginterferon alfa-2a/ribavirin combination groups were considered possibly related to study medication. References: | |||||
Balapiravir Dilution Calculator
Balapiravir Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.0222 mL | 10.1112 mL | 20.2224 mL | 40.4449 mL | 50.5561 mL |
| 5 mM | 0.4044 mL | 2.0222 mL | 4.0445 mL | 8.089 mL | 10.1112 mL |
| 10 mM | 0.2022 mL | 1.0111 mL | 2.0222 mL | 4.0445 mL | 5.0556 mL |
| 50 mM | 0.0404 mL | 0.2022 mL | 0.4044 mL | 0.8089 mL | 1.0111 mL |
| 100 mM | 0.0202 mL | 0.1011 mL | 0.2022 mL | 0.4044 mL | 0.5056 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Balapiravir(R-1626; R 1626; Ro 4588161) is useful for Anti HCV.
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Chemical stability of 4'-azidocytidine and its prodrug balapiravir.[Pubmed:19778160]
Drug Dev Ind Pharm. 2010 Apr;36(4):413-20.
BACKGROUND: R1479, a 4'-azidocytidine nucleoside analog, was developed for the treatment of Hepatitis C virus infection. Balapiravir (R1626) is the tri-isobutyrate ester prodrug of R1479 under clinical development to improve exposure of R1479 upon oral administration. OBJECTIVE: The chemical stability and the rate of azide release of R1479 and Balapiravir were studied. METHODS: R1479 and Balapiravir solutions were prepared at different pH values and stored at various temperatures. An ion pair high-performance liquid chromatography (HPLC) method with gradient elution was employed to analyze the prodrug, parent, and degradation products. Azide was measured using a reversed phase HPLC method with UV detection after formation of the 3,5-dinitrobenzoyl azide derivative with 3,5-dinitrobenzoyl chloride. The data were analyzed using initial rate and conventional first-order kinetic methods. RESULTS: R1479 degrades to cytosine and azide in aqueous solutions, whereas Balapiravir mainly degrades to R1479 and mono- and diesters of R1479. The rates of azide release from R1479 and Balapiravir were generally comparable with the corresponding amount formed of cytosine. CONCLUSION: Azide release is pH dependent and is faster in acidic solutions than in neutral solutions. The amount of azide released is significantly less from Balapiravir than that from R1479, suggesting a potential advantage of the prodrug over the parent drug.
A randomized, double-blind placebo controlled trial of balapiravir, a polymerase inhibitor, in adult dengue patients.[Pubmed:22807519]
J Infect Dis. 2013 May 1;207(9):1442-50.
BACKGROUND: Dengue is the most common arboviral infection of humans. There are currently no specific treatments for dengue. Balapiravir is a prodrug of a nucleoside analogue (called R1479) and an inhibitor of hepatitis C virus replication in vivo. METHODS: We conducted in vitro experiments to determine the potency of Balapiravir against dengue viruses and then an exploratory, dose-escalating, randomized placebo-controlled trial in adult male patients with dengue with <48 hours of fever. RESULTS: The clinical and laboratory adverse event profile in patients receiving Balapiravir at doses of 1500 mg (n = 10) or 3000 mg (n = 22) orally for 5 days was similar to that of patients receiving placebo (n = 32), indicating Balapiravir was well tolerated. However, twice daily assessment of viremia and daily assessment of NS1 antigenemia indicated Balapiravir did not measurably alter the kinetics of these virological markers, nor did it reduce the fever clearance time. The kinetics of plasma cytokine concentrations and the whole blood transcriptional profile were also not attenuated by Balapiravir treatment. CONCLUSIONS: Although this trial, the first of its kind in dengue, does not support Balapiravir as a candidate drug, it does establish a framework for antiviral treatment trials in dengue and provides the field with a clinically evaluated benchmark molecule. CLINICAL TRIALS REGISTRATION: NCT01096576.
Balapiravir plus peginterferon alfa-2a (40KD)/ribavirin in a randomized trial of hepatitis C genotype 1 patients.[Pubmed:22166557]
Ann Hepatol. 2012 Jan-Feb;11(1):15-31.
INTRODUCTION: Balapiravir (R1626, RG1626) is the prodrug of a nucleoside analogue inhibitor of the hepatitis C virus (HCV) RNA-dependent RNA polymerase (R1479, RG1479). This phase 2, double-blind international trial evaluated the optimal treatment regimen of Balapiravir plus peginterferon alfa-2a (40KD)/ribavirin. MATERIAL AND METHODS: Treatment-naive genotype 1 patients (N = 516) were randomized to one of seven treatment groups in which they received Balapiravir 500, 1,000, or 1,500 mg twice daily, peginterferon alfa-2a (40KD) 180 or 90 microg/week and ribavirin 1,000/1,200 mg/day or peginterferon alfa-2a (40KD)/ribavirin. The planned treatment duration with Balapiravir was reduced from 24 to 12 weeks due to safety concerns. RESULTS: The percentage of patients with undetectable HCV RNA was consistently higher in all Balapiravir groups from week 2 to 12. However, high rates of dose modifications and discontinuations of one/all study drugs compromised the efficacy assessment and resulted in similar sustained virological response rates in the Balapiravir groups (range 32-50%) and the peginterferon alfa-2a (40KD)/ribavirin group (43%). Balapiravir was discontinued for safety reasons in 28-36% of patients (most often for lymphopenia) and the percentage of patients with serious adverse events (especially hematological, infection, ocular events) was dose related. Serious hematological adverse events (particularly neutropenia, lymphopenia) were more common in Balapiravir recipients. Two deaths in the Balapiravir/peginterferon alfa-2a/ribavirin combination groups were considered possibly related to study medication. CONCLUSION: Further development of Balapiravir for the treatment of chronic hepatitis C has been halted because of the unacceptable benefit to risk ratio revealed in this study (www.ClinicalTrials.gov NCT 00517439).
Activation of peripheral blood mononuclear cells by dengue virus infection depotentiates balapiravir.[Pubmed:24257621]
J Virol. 2014 Feb;88(3):1740-7.
In a recent clinical trial, Balapiravir, a prodrug of a cytidine analog (R1479), failed to achieve efficacy (reducing viremia after treatment) in dengue patients, although the plasma trough concentration of R1479 remained above the 50% effective concentration (EC(50)). Here, we report experimental evidence to explain the discrepancy between the in vitro and in vivo results and its implication for drug development. R1479 lost its potency by 125-fold when Balapiravir was used to treat primary human peripheral blood mononuclear cells (PBMCs; one of the major cells targeted for viral replication) that were preinfected with dengue virus. The elevated EC(50) was greater than the plasma trough concentration of R1479 observed in dengue patients treated with Balapiravir and could possibly explain the efficacy failure. Mechanistically, dengue virus infection triggered PBMCs to generate cytokines, which decreased their efficiency of conversion of R1479 to its triphosphate form (the active antiviral ingredient), resulting in decreased antiviral potency. In contrast to the cytidine-based compound R1479, the potency of an adenosine-based inhibitor of dengue virus (NITD008) was much less affected. Taken together, our results demonstrate that viral infection in patients before treatment could significantly affect the conversion of the prodrug to its active form; such an effect should be calculated when estimating the dose efficacious for humans.
