Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H12FN6O4 |
| Molecular Weight | 287.2278 |
| 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]2F
InChI
InChIKey=YGDJSOUUXVJBBP-XZMZPDFPSA-N
InChI=1S/C9H12FN6O4/c10-5-6(18)9(3-17,14-15-12)20-7(5)16-2-1-4(11)13-8(16)19/h1-2,5-7,12,17-18H,3H2,(H2,11,13,19)/t5-,6-,7+,9+/m0/s1
| Molecular Formula | C9H11FN6O4 |
| Molecular Weight | 286.2198 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
Approval Year
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:36:22 UTC 2023
by
admin
on
Sat Dec 16 10:36:22 UTC 2023
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| Record UNII |
IJ2XP0ID0K
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| Record Status |
Validated (UNII)
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| Record Version |
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IJ2XP0ID0K
Created by
admin on Sat Dec 16 10:36:22 UTC 2023 , Edited by admin on Sat Dec 16 10:36:22 UTC 2023
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1011529-10-4
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Azvudine
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admin on Sat Dec 16 10:36:22 UTC 2023 , Edited by admin on Sat Dec 16 10:36:22 UTC 2023
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DTXSID901027757
Created by
admin on Sat Dec 16 10:36:22 UTC 2023 , Edited by admin on Sat Dec 16 10:36:22 UTC 2023
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ACTIVE MOIETY |
2'-deoxy-2'-beta-fluoro-4'-azidocytidine (RO-0622) and 2'-deoxy-2'-beta-hydroxy-4'-azidocytidine (RO-9187) were excellent substrates for deoxycytidine kinase and were phosphorylated with efficiencies up to 3-fold higher than deoxycytidine. As compared with previous reports on ribonucleosides, higher levels of triphosphate were formed from RO-9187 in primary human hepatocytes, and both compounds were potent inhibitors of HCV virus replication in the replicon system (IC(50) = 171 +/- 12 nM and 24 +/- 3 nM for RO-9187 and RO-0622, respectively CC(50) >1 mM for both). Both compounds inhibited RNA synthesis by HCV polymerases from either HCV genotypes 1a and 1b or containing S96T or S282T point mutations with similar potencies, suggesting no cross-resistance with either R1479 (4'-azidocytidine) or 2'-C-methyl nucleosides.
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ACTIVE MOIETY |
The most potent compound, designated RO-0622, inhibited replication in the HCV replicon model with an IC50 of 24 nM, and thus was about 50-fold more potent than R1479 (the active version of R1626 in the body). RO-0622 inhibited HIV-1 replication in MT-4 cells with an antiviral IC50 of 0.4 nM, and was therefore more than 6000-fold more potent than lamivudine.
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ACTIVE MOIETY |
Originator: Roche; Class: Deoxyribonucleoside; Mechanism of Action: Hepatitis C virus NS 5 protein inhibitor, Nucleoside reverse transcriptase inhibitor, RNA-directed DNA polymerase inhibitor; Highest Development Phases: Preclinical for Hepatitis C, HIV-1 infection; Most Recent Events: 26 Apr 2009 Preclinical trials in HIV-1 infections in Europe (unspecified route), 26 Apr 2009 Antimicrobial data from a preclinical study presented at the 44th Annual Meeting of the European Association for the study of the Liver (EASL-2009), 20 Feb 2006 This programme is still in active development
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