Azvudine

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

MedKoo CAT#: 528502

CAS#: 1011529-10-4

Description: Azvudine, also known as FNC and RO-0622, is a reverse transcriptase inhibitor potentially for the treatment of HIV infection. Azvudine showed synergism in combination with six approved anti-HIV drugs on both C8166 and PBMC. Azvudine also showed potent inhibition on NRTI-resistant strains (L74V and T69N). Treatment with Azudine and the protein biosynthesis inhibitor, cycloheximide (CHX), accelerated the inhibition of viral protein synthesis in the HTLV‑1‑infected cells.


Price and Availability

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Azvudine (FNC, RO-0622) 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#: 528502
Name: Azvudine
CAS#: 1011529-10-4
Chemical Formula: C9H11FN6O4
Exact Mass: 286.0826
Molecular Weight: 286.2234
Elemental Analysis: C, 37.77; H, 3.87; F, 6.64; N, 29.36; O, 22.36


Synonym: Azvudine; FNC; RO-0622; RO 0622; RO0622

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

InChi Key: KTOLOIKYVCHRJW-XZMZPDFPSA-N

InChi Code: InChI=1S/C9H11FN6O4/c10-5-6(18)9(3-17,14-15-12)20-7(5)16-2-1-4(11)13-8(16)19/h1-2,5-7,17-18H,3H2,(H2,11,13,19)/t5-,6-,7+,9+/m0/s1

SMILES Code: O=C1N=C(N)C=CN1[C@H]2[C@@H](F)[C@@H]([C@](CO)(N=[N+]=[N-])O2)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: Li Z, Li Z, Yang L, Xie Y, Shi J, Wang R, Chang J. Investigation of the binding between pepsin and nucleoside analogs by spectroscopy and molecular simulation. J Fluoresc. 2015 Mar;25(2):451-63. doi: 10.1007/s10895-015-1532-2. Epub 2015 Feb 27. PubMed PMID: 25721993.

2: Zhang Y, Wang CP, Ding XX, Wang N, Ma F, Jiang JH, Wang QD, Chang JB. FNC, a novel nucleoside analogue, blocks invasion of aggressive non-Hodgkin lymphoma cell lines via inhibition of the Wnt/β-catenin signaling pathway. Asian Pac J Cancer Prev. 2014;15(16):6829-35. PubMed PMID: 25169533.

3: Wang RR, Yang QH, Luo RH, Peng YM, Dai SX, Zhang XJ, Chen H, Cui XQ, Liu YJ, Huang JF, Chang JB, Zheng YT. Azvudine, a novel nucleoside reverse transcriptase inhibitor showed good drug combination features and better inhibition on drug-resistant strains than lamivudine in vitro. PLoS One. 2014 Aug 21;9(8):e105617. doi: 10.1371/journal.pone.0105617. eCollection 2014 Aug 21. PubMed PMID: 25144636; PubMed Central PMCID: PMC4140803.

4: Wang J, Wang X, Gao C, Song X, Niu Z, Gao Z, Qin Z, Chang J, Wang H. The pyrimidine analog FNC inhibits cell proliferation and viral protein synthesis in HTLV 1 infected cells. Mol Med Rep. 2013 May;7(5):1656-60. doi: 10.3892/mmr.2013.1358. Epub 2013 Mar 5. PubMed PMID: 23467991.

5: Zhou Y, Zhang Y, Yang X, Zhao J, Zheng L, Sun C, Jiang J, Yang Q, Wang Q, Chang J. Novel nucleoside analogue FNC is effective against both wild-type and lamivudine-resistant HBV clinical isolates. Antivir Ther. 2012;17(8):1593-9. doi: 10.3851/IMP2292. Epub 2012 Aug 9. PubMed PMID: 22910281.

6: Zheng L, Wang Q, Yang X, Guo X, Chen L, Tao L, Dong L, Li Y, An H, Yu X, Wang Q, Chang J. Antiviral activity of FNC, 2'-deoxy-2'-β-fluoro-4'-azidocytidine, against human and duck HBV replication. Antivir Ther. 2012;17(4):679-87. doi: 10.3851/IMP2094. Epub 2012 Mar 27. PubMed PMID: 22452880.

7: Wang Q, Liu X, Wang Q, Zhang Y, Jiang J, Guo X, Fan Q, Zheng L, Yu X, Wang N, Pan Z, Song C, Qi W, Chang J. FNC, a novel nucleoside analogue inhibits cell proliferation and tumor growth in a variety of human cancer cells. Biochem Pharmacol. 2011 Apr 1;81(7):848-55. doi: 10.1016/j.bcp.2011.01.001. Epub 2011 Jan 8. PubMed PMID: 21219886.

8: Smith DB, Kalayanov G, Sund C, Winqvist A, Maltseva T, Leveque VJ, Rajyaguru S, Le Pogam S, Najera I, Benkestock K, Zhou XX, Kaiser AC, Maag H, Cammack N, Martin JA, Swallow S, Johansson NG, Klumpp K, Smith M. 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. J Med Chem. 2009 May 14;52(9):2971-8. doi: 10.1021/jm801595c. PubMed PMID: 19341305.