Azvudine

Azvudine (RO-0622) is an antiviral drug which acts as a reverse transcriptase inhibitor.[1][2] It was developed for the treatment of Hepatitis C and has since been investigated for use against other viral diseases such as AIDS and COVID-19.[3][4]

Azvudine
Clinical data
Trade namesAzvudine
Legal status
Legal status
  • US: Investigational drug
Identifiers
IUPAC name
  • 4-amino-1-[(2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC9H11FN6O4
Molar mass286.22 g·mol−1
3D model (JSmol)
SMILES
  • C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@](O2)(CO)N=[N+]=[N-])O)F
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
  • Key:KTOLOIKYVCHRJW-XZMZPDFPSA-N

References

  1. Smith DB, Kalayanov G, Sund C, Winqvist A, Maltseva T, Leveque VJ, et al. (May 2009). "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". Journal of Medicinal Chemistry. 52 (9): 2971–8. doi:10.1021/jm801595c. PMID 19341305.
  2. Wang RR, Yang QH, Luo RH, Peng YM, Dai SX, Zhang XJ, et al. (2014). "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. 9 (8): e105617. doi:10.1371/journal.pone.0105617. PMC 4140803. PMID 25144636.
  3. Liu Y, Liu B, Zhang Y, Peng Y, Huang C, Wang N, et al. (July 2017). "Intestinal absorption mechanisms of 2'-deoxy-2'-β-fluoro-4'-azidocytidine, a cytidine analog for AIDS treatment, and its interaction with P-glycoprotein, multidrug resistance-associated protein 2 and breast cancer resistance protein". European Journal of Pharmaceutical Sciences. 105: 150–158. doi:10.1016/j.ejps.2017.05.009. PMID 28487144. S2CID 4252337.
  4. Harrison C (27 February 2020). "Coronavirus puts drug repurposing on the fast track". Nature Biotechnology. 38 (4): 379–381. doi:10.1038/d41587-020-00003-1. PMID 32205870.


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