Uprifosbuvir

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Uprifosbuvir
Clinical data
Trade namesUprifosbuvir
Legal status
Legal status
Identifiers
  • 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 mass545.91 g·mol−1
3D model (JSmol)
  • 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=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

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. As of 2019 it was in Phase III human clinical trials.[1][2][3]

In 2017 owner Merck wrote down the value of uprifosbuvir to US$240 million, for a write-down of $2.9 billion, reducing its earnings per share from 42¢ to a loss of 22¢ for the fourth quarter of 2016. This was attributed to the hepatitis C drug market rather than uprifosbuvir itself; the population of treatable patients diminished rapidly after the introduction in 2014 of sofosbuvir and the combination ledipasvir/sofosbuvir, drugs that cured hepatitis C, and whose market was also diminishing following their success in curing patients. Clinical testing of uprifosbuvir continued.[4]

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. hdl:11343/286144. PMID 31108015. S2CID 160014275.
  4. ^ Weintraub, Arlene (24 February 2017). "Merck swallows $2.9B write-down of experimental hep C drug as market plummets". Fierce Pharma.
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