Uprifosbuvir

Uprifosbuvir (MK-3682) is an antiviral drug developed for the treatment of Hepatitis C. It is a nucleotide analogue which acts as an NS5B RNA polymerase inhibitor. It is currently in Phase III human clinical trials.[1][2][3]

Uprifosbuvir

Clinical data
Trade names	Uprifosbuvir
Legal status
Legal status	US: Investigational New Drug
Identifiers
IUPAC name propan-2-yl (2R)-2-[[[(2R,3R,4R,5R)-4-chloro-5-(2,4-dioxopyrimidin-1-yl)-3-hydroxy-4-methyloxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
CAS Number	1496551-77-9
PubChem CID	90055716
DrugBank	DB15206
ChemSpider	57427403
UNII	JW31KPS26S
KEGG	D10996
ChEMBL	ChEMBL3833371
Chemical and physical data
Formula	C22H29ClN3O9P
Molar mass	545.9 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C[C@H](C(=O)OC(C)C)N[P@@](=O)(OC[C@@H]1[C@H]([C@@]([C@@H](O1)N2C=CC(=O)NC2=O)(C)Cl)O)OC3=CC=CC=C3
InChI InChI=1S/C22H29ClN3O9P/c1-13(2)33-19(29)14(3)25-36(31,35-15-8-6-5-7-9-15)32-12-16-18(28)22(4,23)20(34-16)26-11-10-17(27)24-21(26)30/h5-11,13-14,16,18,20,28H,12H2,1-4H3,(H,25,31)(H,24,27,30)/t14-,16-,18-,20-,22-,36-/m1/s1 Key:SFPFZQKYPOWCSI-KHFYHRBSSA-N

References

1. Soriano V, Fernandez-Montero JV, de Mendoza C, Benitez-Gutierrez L, Peña JM, Arias A, Barreiro P (August 2017). "Treatment of hepatitis C with new fixed dose combinations". Expert Opinion on Pharmacotherapy. 18 (12): 1235–1242. doi:10.1080/14656566.2017.1346609. PMID 28644739.
2. Borgia G, Maraolo AE, Nappa S, Gentile I, Buonomo AR (March 2018). "NS5B polymerase inhibitors in phase II clinical trials for HCV infection". Expert Opinion on Investigational Drugs. 27 (3): 243–250. doi:10.1080/13543784.2018.1420780. PMID 29271672.
3. Lawitz E, Gane E, Feld JJ, Buti M, Foster GR, Rabinovitz M, et al. (September 2019). "Efficacy and safety of a two-drug direct-acting antiviral agent regimen ruzasvir 180 mg and uprifosbuvir 450 mg for 12 weeks in adults with chronic hepatitis C virus genotype 1, 2, 3, 4, 5 or 6". Journal of Viral Hepatitis. 26 (9): 1127–1138. doi:10.1111/jvh.13132. PMID 31108015.