Azvudine

• CAT Number: I003894
• CAS Number: 1011529-10-4
• Molecular Formula: C9H11FN6O4
• Molecular Weight: 286.22
• Purity: ≥95%
• Synonyms: 4-amino-1-[(2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• InChI: 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
• InChIKey: KTOLOIKYVCHRJW-XZMZPDFPSA-N
• SMILES: C1=CN(C(=O)N=C1N)C2C(C(C(O2)(CO)N=[N+]=[N-])O)F

Azvudine (RO-0622) is a potent nucleoside reverse transcriptase inhibitor (NRTI), with antiviral activity on HIV, HBV and HCV. Azvudine exerts highly potent inhibition on HIV-1 (EC50s ranging from 0.03 to 6.92 nM) and HIV-2 (EC50s ranging from 0.018 to 0.025 nM). Azvudine inhibits NRTI-resistant viral strains[1]. Azvudine is a click chemistry reagent, itcontains an Azide group and can undergo copper-catalyzed azide-alkyne cycloaddition reaction (CuAAc) with molecules containing Alkyne groups. Strain-promoted alkyne-azide cycloaddition (SPAAC) can also occur with molecules containing DBCO or BCN groups.
Azvudine (RO-0622) displays strong inhibition on wild-type HIV-1IIIB and HIV-1RF with an EC50 ranging from 30 to 110 pM. The EC50 values of Azvudine against HIV-1KM018, HIV-1TC-1 and HIV-1WAN T69N are 6.92, 0.34 and 0.45 nM, respectively. Azvudine is sensitive to NRTIs-resistant strain HIV-174V, PIs-resistant strains HIV-1L10R/M46I/L63P/V82T/I84V and HIV-1RF V82F/184V, and FIs-resistant strain pNL4-3 gp41 (36G) V38A/N42T. The EC50 values of Azvudine against these resistant strains are 0.11, 0.14, 0.37 and 0.36 nM respectively[1].

Reference

[1]. Wang RR, et al. 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.
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