MedKoo Cat#: 526812 | Name: R1479

Description:

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

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.

Chemical Structure

R1479
R1479
CAS#478182-28-4

Theoretical Analysis

MedKoo Cat#: 526812

Name: R1479

CAS#: 478182-28-4

Chemical Formula: C9H12N6O5

Exact Mass: 284.0869

Molecular Weight: 284.23

Elemental Analysis: C, 38.03; H, 4.26; N, 29.57; O, 28.14

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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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
InChi Key
ODLGMSQBFONGNG-JVZYCSMKSA-N
InChi Code
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
SMILES Code
NC1=NC(N([C@@H]2O[C@@](N=[N+]=[N-])([C@H]([C@H]2O)O)CO)C=C1)=O
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 284.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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.