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.


Chemical Structure

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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: 284.232
Elemental Analysis: C, 38.03; H, 4.26; N, 29.57; O, 28.14

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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

Preparing Stock Solutions

The following data is based on the product molecular weight 284.232 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

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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.