R1479

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 526812

CAS#: 478182-28-4

Description: R-1479, also known as 4'-azidocytidine, is a potent inhibitor of NS5B-dependent RNA synthesis and hepatitis C virus replication in cell culture. R-1479 is a specific inhibitor of HCV replication in the HCV subgenomic replicon system (IC(50) = 1.28 microM). The corresponding 5'-triphosphate derivative (R1479-TP) is a potent inhibitor of native HCV replicase isolated from replicon cells and of recombinant HCV polymerase (NS5B)-mediated RNA synthesis activity. R1479-TP inhibited RNA synthesis as a CTP-competitive inhibitor with a K(i) of 40 nM.


Price and Availability

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R-1479 is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526812
Name: R1479
CAS#: 478182-28-4
Chemical Formula: C9H12N6O5
Exact Mass: 284.0869
Molecular Weight: 284.232
Elemental Analysis: C, 38.03; H, 4.26; N, 29.57; O, 28.14


Synonym: R-1479; R 1479; R1479; 4'-azidocytidine; 4'-c-Azidocytidine.

IUPAC/Chemical Name: 4-amino-1-((2R,3R,4S,5R)-5-azido-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one

SMILES Code: NC1=NC(N([C@@H]2O[C@@](N=[N+]=[N-])([C@H]([C@H]2O)O)CO)C=C1)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: McGuigan C, Kelleher MR, Perrone P, Mulready S, Luoni G, Daverio F, Rajyaguru S, Le Pogam S, Najera I, Martin JA, Klumpp K, Smith DB. The application of phosphoramidate ProTide technology to the potent anti-HCV compound 4'-azidocytidine (R1479). Bioorg Med Chem Lett. 2009 Aug 1;19(15):4250-4. doi: 10.1016/j.bmcl.2009.05.099. Epub 2009 May 29. PubMed PMID: 19505826.

2: Ali S, Leveque V, Le Pogam S, Ma H, Philipp F, Inocencio N, Smith M, Alker A, Kang H, Najera I, Klumpp K, Symons J, Cammack N, Jiang WR. Selected replicon variants with low-level in vitro resistance to the hepatitis C virus NS5B polymerase inhibitor PSI-6130 lack cross-resistance with R1479. Antimicrob Agents Chemother. 2008 Dec;52(12):4356-69. doi: 10.1128/AAC.00444-08. Epub 2008 Oct 6. PubMed PMID: 18838588; PubMed Central PMCID: PMC2592884.

3: Smith DB, Martin JA, Klumpp K, Baker SJ, Blomgren PA, Devos R, Granycome C, Hang J, Hobbs CJ, Jiang WR, Laxton C, Le Pogam S, Leveque V, Ma H, Maile G, Merrett JH, Pichota A, Sarma K, Smith M, Swallow S, Symons J, Vesey D, Najera I, Cammack N. 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 May 1;17(9):2570-6. Epub 2007 Feb 4. PubMed PMID: 17317178.

4: Le Pogam S, Jiang WR, Leveque V, Rajyaguru S, Ma H, Kang H, Jiang S, Singer M, Ali S, Klumpp K, Smith D, Symons J, Cammack N, Nájera I. In vitro selected Con1 subgenomic replicons resistant to 2'-C-methyl-cytidine or to R1479 show lack of cross resistance. Virology. 2006 Aug 1;351(2):349-59. Epub 2006 May 19. PubMed PMID: 16713611.

5: Klumpp K, Lévêque V, Le Pogam S, Ma H, Jiang WR, Kang H, Granycome C, Singer M, Laxton C, Hang JQ, Sarma K, Smith DB, Heindl D, Hobbs CJ, Merrett JH, Symons J, Cammack N, Martin JA, Devos R, Nájera I. 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 Feb 17;281(7):3793-9. Epub 2005 Nov 29. PubMed PMID: 16316989.