R-1479HCV replication inhibitor CAS# 478182-28-4 |
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Quality Control & MSDS
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Chemical structure
3D structure
| Cas No. | 478182-28-4 | SDF | Download SDF |
| PubChem ID | 457388 | Appearance | Powder |
| Formula | C9H12N6O5 | M.Wt | 284.23 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | 4'-Azidocytidine | ||
| Solubility | DMSO : ≥ 50 mg/mL (175.91 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | 4-amino-1-[(2R,3R,4S,5R)-5-azido-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one | ||
| SMILES | C1=CN(C(=O)N=C1N)C2C(C(C(O2)(CO)N=[N+]=[N-])O)O | ||
| Standard InChIKey | ODLGMSQBFONGNG-JVZYCSMKSA-N | ||
| Standard InChI | InChI=1S/C9H12N6O5/c10-4-1-2-15(8(19)12-4)7-5(17)6(18)9(3-16,20-7)13-14-11/h1-2,5-7,16-18H,3H2,(H2,10,12,19)/t5-,6+,7-,9-/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 | R1479 (4'-azidocytidine) is a potent and highly specific inhibitor of HCV replication with an IC50 value of 1.28 μM in the HCV subgenomic replicon system. | |||||
| Targets | HCV | |||||
| IC50 | 1.28 μM | |||||
R-1479 Dilution Calculator
R-1479 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.5183 mL | 17.5914 mL | 35.1828 mL | 70.3655 mL | 87.9569 mL |
| 5 mM | 0.7037 mL | 3.5183 mL | 7.0366 mL | 14.0731 mL | 17.5914 mL |
| 10 mM | 0.3518 mL | 1.7591 mL | 3.5183 mL | 7.0366 mL | 8.7957 mL |
| 50 mM | 0.0704 mL | 0.3518 mL | 0.7037 mL | 1.4073 mL | 1.7591 mL |
| 100 mM | 0.0352 mL | 0.1759 mL | 0.3518 mL | 0.7037 mL | 0.8796 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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R1479 is a specific inhibitor of HCV replication in cell culture with IC50 value of 1.28 μM [1].
Hepatitis C virus (HCV) is an enveloped (+)-single stranded RNA virus, and the viral RNA is replicated in host cell via RNA-dependent RNA polymerase of HIV, which is the cause of hepatitis C and some cancer lymphomas [2].
R1479 is a potent and specific inhibitor of HCV NS5B RNA polymerase to inhibit HCV replication in the HCV subgenomic replicon system. In proliferating replicon cells of 2209-23 cell line, 72 h incubation of R1479 showed inhibition of HCV RNA replication (IC 50 = 1.28 μM), which had the similar potency with 2_-C-methylcytidine (IC 50 = 1.13 μM). R1479 had no influence on cell proliferation and viability of Huh-7 cells at concentration up to 2 mM, which suggested the inhibition by R1479 was a direct antiviral mechanism [2]. Furthermore, prolong incubation of R1479 for HCV replicon cells led to a continuous reduction of HCV RNA to an undetectable level within 15 days of incubation [2].Finally, R1479 showed no cytotoxicity in replicon cells [1].
References:
[1] Smith D B, et al. Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: the discovery of R1479. Bioorg Med Chem Lett., 2007, 17(9): 2570-6.
[2] Klumpp K, et al. The novel nucleoside analog R1479 (4'-azidocytidine) is a potent inhibitor of NS5B-dependent RNA synthesis and hepatitis C virus replication in cell culture. J Biol Chem., 2006, 281(7): 3793-9.
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R-1626, a specific oral NS5B polymerase inhibitor of hepatitis C virus.[Pubmed:18828074]
IDrugs. 2008 Oct;11(10):738-49.
Roche Holding AG is developing R-1626, an oral nucleoside inhibitor of HCV RNA polymerase. R-1626 has been demonstrated to be well absorbed and rapidly converted to the active component R-1479. The compound has demonstrated a strong capacity to inhibit HCV replication in vitro and in vivo, without the rapid development of viral resistance. After 4 weeks of treatment with R-1626 in combination with PEG-IFN plus ribavirin in treatment-naive patients with genotype 1 HCV infection, HCV RNA could no longer be detected in approximately 74% of patients, compared with 5% of patients treated with PEG-IFN plus ribavirin alone, indicating the high potency of R-1626 to induce HCV RNA viral load reductions. R-1626 was generally well tolerated, although severe side effects of neutropenia were observed at high doses. A phase IIb clinical trial was ongoing at the time of publication to test the efficacy of R-1626 in combination with a standard or lower dose of PEG-IFN and ribavirin in HCV genotype 1-infected patients. Given its potent antiviral effect with an apparent high genetic barrier, R-1626 represents an important advancement in improving the outcome of patients with chronic HCV infection.
