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 namesUprifosbuvir
Legal status
Legal status
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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC22H29ClN3O9P
Molar mass545.9 g·mol−1
3D model (JSmol)
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. S2CID 205819421.
  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. S2CID 3672885.
  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. S2CID 160014275.
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