Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H30N6O8.ClH |
Molecular Weight | 530.959 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(C)C(=O)OC[C@]1(O[C@H]([C@H](OC(=O)C(C)C)[C@@H]1OC(=O)C(C)C)N2C=CC(N)=NC2=O)N=[N+]=[N-]
InChI
InChIKey=RAJFQMDUVDHLII-PYZPAVLJSA-N
InChI=1S/C21H30N6O8.ClH/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);1H/t14-,15+,16-,21-;/m1./s1
Molecular Formula | C21H30N6O8 |
Molecular Weight | 494.4983 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL5375 |
40.0 nM [Ki] | ||
Target ID: CHEMBL5375 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16316989 |
40.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/18553458/ |
no | |||
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
yes [Km 23 uM] | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides. | 1992 Apr 17 |
|
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 |
|
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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Robust antiviral activity of R1626, a novel nucleoside analog: a randomized, placebo-controlled study in patients with chronic hepatitis C. | 2008 Aug |
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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 |
|
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 |
|
Substituted imidazopyridines as potent inhibitors of HCV replication. | 2009 May |
|
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 |
|
PSI-7851, a pronucleotide of beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine monophosphate, is a potent and pan-genotype inhibitor of hepatitis C virus replication. | 2010 Aug |
|
Balapiravir plus peginterferon alfa-2a (40KD)/ribavirin in a randomized trial of hepatitis C genotype 1 patients. | 2012 Jan-Feb |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22166557
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16316989
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
by
admin
on
Edited
Fri Dec 15 16:16:54 GMT 2023
by
admin
on
Fri Dec 15 16:16:54 GMT 2023
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Record UNII |
C860V13650
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Record Status |
Validated (UNII)
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Record Version |
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-
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NCI_THESAURUS |
C25995
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NCI_THESAURUS |
C281
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300000044591
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C860V13650
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16126873
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690270-65-6
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WW-124
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CHEMBL550936
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DBSALT002171
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C87440
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |