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Uprifosbuvir

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Chemical compound

Pharmaceutical compound

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
PubChemCID	90055716
DrugBank	DB15206
ChemSpider	57427403
UNII	JW31KPS26S
KEGG	D10996
ChEMBL	ChEMBL3833371
Chemical and physical data
Formula	C₂₂H₂₉ClN₃O₉P
Molar mass	545.91 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

Uprifosbuvir (MK-3682) is anantiviral drug developed for the treatment ofhepatitis C. It is anucleotide analogue which acts as anNS5B RNA polymerase inhibitor. As of 2019^[update] it was in Phase III humanclinical trials.^[1]^[2]^[3]

In 2017 owner Merck wrote down the value of uprifosbuvir toUS$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 ofsofosbuvir and the combinationledipasvir/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

[edit]

^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.
^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.
^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.
^Weintraub, Arlene (24 February 2017)."Merck swallows $2.9B write-down of experimental hep C drug as market plummets".Fierce Pharma.

RNA virus antivirals (primarilyJ05, alsoS01AD andD06BB)

Hepatitis C

NS3/4A protease inhibitors (–previr)	Asunaprevir Boceprevir^‡ Ciluprevir^§ Danoprevir^† Faldaprevir^‡ Glecaprevir Grazoprevir Narlaprevir Paritaprevir Simeprevir Sovaprevir^† Telaprevir^‡ Vaniprevir Vedroprevir^§ Voxilaprevir
NS5A inhibitors (–asvir)	Coblopasvir Daclatasvir^# Elbasvir Ledipasvir Odalasvir^† Ombitasvir Pibrentasvir Ravidasvir^† Ruzasvir^† Samatasvir^† Velpatasvir
NS5B RNA polymerase inhibitors (–buvir)	Beclabuvir^† Bemnifosbuvir^† Dasabuvir^# Deleobuvir^§ Filibuvir^§ GS-6620^§ IDX-184^§ Setrobuvir^§ Sofosbuvir^# Tegobuvir^§ TMC-647055^§ Radalbuvir^† Uprifosbuvir^†
Combination drugs	Elbasvir/grazoprevir Glecaprevir/pibrentasvir Ledipasvir/sofosbuvir^# Ombitasvir/paritaprevir/ritonavir^# Sofosbuvir/daclatasvir Sofosbuvir/velpatasvir^# Sofosbuvir/velpatasvir/voxilaprevir

Hepatitis D

Bulevirtide

Picornavirus

viral entry:Pleconaril^†

Anti-influenza agents

neuraminidase inhibitors/release phase (Oseltamivir^#
Zanamivir
Peramivir,Laninamivir^†)

Multiple/general

Interferon	Interferon alfa 2b Peginterferon alfa-2a^# Peginterferon alfa-2b^#
3CL protease inhibitors (–trelvir)	Atilotrelvir Ensitrelvir^† Ibuzatrelvir Leritrelvir Lufotrelvir Nirmatrelvir^† (+ritonavir)^† Rupintrivir Simnotrelvir (+ritonavir^†)
RNA pol inhibitors	CMX521^§ Deuremidevir^† Favipiravir Galidesivir^† GS-441524^§ Remdesivir MK-608^§ Mericitabine^† Molnupiravir NITD008^§ Ribavirin^# Taribavirin^† Triazavirin Valopicitabine^†
Multiple/Unknown/Other	EICAR^§ Merimepodib^§ Moroxydine Presatovir^†

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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