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Uprifosbuvir

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Chemical compound Pharmaceutical compound
Uprifosbuvir
Clinical data
Trade namesUprifosbuvir
Legal status
Legal status
Identifiers
IUPAC name
  • propan-2-yl (2R)-2-methoxy-phenoxyphosphoryl]amino]propanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC22H29ClN3O9P
Molar mass545.91 g·mol
3D model (JSmol)
SMILES
  • C(C(=O)OC(C)C)N(=O)(OC1(((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

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.

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.

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.
RNA virus antivirals (primarily J05, also S01AD and D06BB)
Hepatitis C
NS3/4A protease inhibitors (–previr)
NS5A inhibitors (–asvir)
NS5B RNA polymerase inhibitors (–buvir)
Combination drugs
Hepatitis D
Picornavirus
Anti-influenza agents
Multiple/general
Interferon
3CL protease inhibitors (–trelvir)
RNA pol inhibitors
Multiple/Unknown/Other
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