Uprifosbuvir

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	545.91 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;

Trade namesUprifosbuvir

Legal status

US: Investigational New Drug

CAS Number

1496551-77-9

PubChem CID

90055716

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^[update] 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]

[1]

[2]

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