Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H12N6O5 |
| Molecular Weight | 284.2288 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(=O)N(C=C1)[C@@H]2O[C@@](CO)(N=[N+]=[N-])[C@@H](O)[C@H]2O
InChI
InChIKey=ODLGMSQBFONGNG-JVZYCSMKSA-N
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
| Molecular Formula | C9H12N6O5 |
| Molecular Weight | 284.2288 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/18828074 | https://www.ncbi.nlm.nih.gov/pubmed/16316989 | https://www.ncbi.nlm.nih.gov/pubmed/22166557 | https://www.ncbi.nlm.nih.gov/pubmed/22807519 | https://www.ncbi.nlm.nih.gov/pubmed/26596942 | https://www.ncbi.nlm.nih.gov/pubmed/22166557https://www.ncbi.nlm.nih.gov/pubmed/16316989 | https://www.ncbi.nlm.nih.gov/pubmed/19778160
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18828074 | https://www.ncbi.nlm.nih.gov/pubmed/16316989 | https://www.ncbi.nlm.nih.gov/pubmed/22166557 | https://www.ncbi.nlm.nih.gov/pubmed/22807519 | https://www.ncbi.nlm.nih.gov/pubmed/26596942 | https://www.ncbi.nlm.nih.gov/pubmed/22166557https://www.ncbi.nlm.nih.gov/pubmed/16316989 | https://www.ncbi.nlm.nih.gov/pubmed/19778160
R1479 (4′-azidocytidine) is a specific inhibitor of hepatitis C virus (HCV) replication. 4′-azidocytidine triphosphate is an inhibitor of native HCV replicase and recombinant HCV polymerase (NS5B). Balapiravir (R1626) is the tri-isobutyrate ester prodrug of R1479 under clinical development to improve exposure of R1479 upon oral administration.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides. | 1992 Apr 17 |
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| The novel nucleoside analog R1479 (4'-azidocytidine) is a potent inhibitor of NS5B-dependent RNA synthesis and hepatitis C virus replication in cell culture. | 2006 Feb 17 |
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| Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: the discovery of R1479. | 2007 May 1 |
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| 2'-deoxy-4'-azido nucleoside analogs are highly potent inhibitors of hepatitis C virus replication despite the lack of 2'-alpha-hydroxyl groups. | 2008 Jan 25 |
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| Existence of hepatitis C virus NS5B variants naturally resistant to non-nucleoside, but not to nucleoside, polymerase inhibitors among untreated patients. | 2008 Jun |
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| The hepatitis C virus replicon presents a higher barrier to resistance to nucleoside analogs than to nonnucleoside polymerase or protease inhibitors. | 2008 May |
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| R-1626, a specific oral NS5B polymerase inhibitor of hepatitis C virus. | 2008 Oct |
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| Amidinoanthracyclines - a new group of potential anti-hepatitis C virus compounds. | 2009 Apr |
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| The design, synthesis, and antiviral activity of 4'-azidocytidine analogues against hepatitis C virus replication: the discovery of 4'-azidoarabinocytidine. | 2009 Jan 8 |
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| Substituted imidazopyridines as potent inhibitors of HCV replication. | 2009 May |
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| The design, synthesis, and antiviral activity of monofluoro and difluoro analogues of 4'-azidocytidine against hepatitis C virus replication: the discovery of 4'-azido-2'-deoxy-2'-fluorocytidine and 4'-azido-2'-dideoxy-2',2'-difluorocytidine. | 2009 May 14 |
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| Synthesis of new acridone derivatives, inhibitors of NS3 helicase, which efficiently and specifically inhibit subgenomic HCV replication. | 2010 Apr 22 |
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| Activation of peripheral blood mononuclear cells by dengue virus infection depotentiates balapiravir. | 2014 Feb |
Sample Use Guides
The phase 2, double-blind international trial evaluated the optimal treatment regimen of balapiravir plus peginterferon alfa-2a (40KD)/ribavirin in hepatitis C genotype 1 patients. Treatment-naive genotype 1 patients 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 µg/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.
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: Activity is given for R1479. Balapiravir (R-1626) is the tri-isobutyl ester prodrug of a nucleoside analogue inhibitor of the hepatitis C virus (HCV) RNA-dependent RNA polymerase (R1479).
R1479 (4'-azidocytidine) is a specific inhibitor of HCV replication in the HCV subgenomic replicon system (IC(50) = 1.28 microM). R1479 showed no effect on cell viability or proliferation of HCV replicon or Huh-7 cells at concentrations up to 2 mM.
| Substance Class |
Chemical
Created
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| Record UNII |
M71RA9DMGJ
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| Record Status |
Validated (UNII)
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R-1479
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PRIMARY | Target: HCV; In vitro: R1479 (4'-azidocytidine) is a specific inhibitor of HCV replication in the HCV subgenomic replicon system (IC(50) = 1.28 microM) with similar potency compared with 2'-C-methylcytidine (IC(50) = 1.13 microM). R1479 showed no effect on cell viability or proliferation of HCV replicon or Huh-7 cells at concentrations up to 2 mM. HCV replicon RNA could be fully cleared from replicon cells after prolonged incubation with R1479.; In vivo:Toxicity: R1479 displayed good activity in the replicon assay with no measurable cytotoxic or cytostatic effect.; Clinical trial: A Study of Balapiravir in Patients With Dengue Virus Infection. Phase 1 | ||
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457388
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M71RA9DMGJ
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DTXSID80332457
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PRODRUG -> METABOLITE ACTIVE |
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ACTIVE MOIETY |
Hepatitis C virus (HCV) polymerase activity is essential for HCV replication. Targeted screening of nucleoside analogs identified R1479 (4-azidocytidine) as a specific inhibitor of HCV replication in the HCV subgenomic replicon system (IC50 = 1.28 .MU.m) with similar potency compared with 2-C-methylcytidine (IC50 = 1.13 .MU.m). R1479 showed no effect on cell viability or proliferation of HCV replicon or Huh-7 cells at concentrations up to 2 mm.
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