Azvudine

Azvudine
Clinical data
Trade names	Azvudine
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	1011529-10-4 ;
PubChem CID	24769759;
ChemSpider	24717759;
UNII	IJ2XP0ID0K;
ChEMBL	ChEMBL519846;
Chemical and physical data
Formula	C9H11FN6O4
Molar mass	286.22 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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]

References

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.
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.
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.
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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