Setrobuvir

Setrobuvir (also known as ANA-598) was an experimental drug candidate for the treatment of hepatitis C that was discovered at Anadys Pharmaceuticals, which was acquired by Roche in 2011; Roche terminated development in July 2015.[2][3] It was in Phase IIb clinical trials, used in combination with interferon and ribavirin, targeting hepatitis C patients with genotype 1.[3]

Setrobuvir
Names
Preferred IUPAC name
N-(3-{(4aR,5S,8R,8aS)-1-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,8a-octahydro-5,8-methanoquinolin-3-yl}-1,1-dioxo-1,4-dihydro-1λ6,2,4-benzothiadiazin-7-yl)methanesulfonamide[1]
Other names
ANA-598; ANA598
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
InChI
  • InChI=1S/C25H25FN4O6S2/c1-37(33,34)28-17-8-9-18-19(11-17)38(35,36)29-24(27-18)21-23(31)20-14-4-5-15(10-14)22(20)30(25(21)32)12-13-2-6-16(26)7-3-13/h2-3,6-9,11,14-15,20,22,28,31H,4-5,10,12H2,1H3,(H,27,29)/t14-,15+,20+,22-/m0/s1 Y
    Key: DEKOYVOWOVJMPM-RLHIPHHXSA-N Y
  • InChI=1/C25H25FN4O6S2/c1-37(33,34)28-17-8-9-18-19(11-17)38(35,36)29-24(27-18)21-23(31)20-14-4-5-15(10-14)22(20)30(25(21)32)12-13-2-6-16(26)7-3-13/h2-3,6-9,11,14-15,20,22,28,31H,4-5,10,12H2,1H3,(H,27,29)/t14-,15+,20+,22-/m0/s1
    Key: DEKOYVOWOVJMPM-RLHIPHHXBY
SMILES
  • CS(NC(C=C1)=CC2=C1NC(C3=C(O)[C@@]4([H])[C@@]([C@@H]5CC[C@H]4C5)([H])N(CC6=CC=C(F)C=C6)C3=O)=NS2(=O)=O)(=O)=O
Properties
Chemical formula
 C25H25FN4O6S2
Molar mass 560.62 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Setrobuvir works by inhibiting the hepatitis C enzyme NS5B, an RNA polymerase.[4]

References
  1. "International Nonproprietary Names for Pharmaceutical Substances (INN). RECOMMENDED International Nonproprietary Names: List 68" (PDF). World Health Organization. p. 322.
  2. "Setrobuvir". AdisInsight. Retrieved 28 August 2017.
  3. "HCV Followup: Anadys Acquired for Active Antiviral". Chemical & Engineering News. October 24, 2011.
  4. Ruebsam, F; Murphy, DE; Tran, CV; Li, LS; Zhao, J; Dragovich, PS; McGuire, HM; Xiang, AX; et al. (2009). "Discovery of tricyclic 5,6-dihydro-1H-pyridin-2-ones as novel, potent, and orally bioavailable inhibitors of HCV NS5B polymerase". Bioorganic & Medicinal Chemistry Letters. 19 (22): 6404–12. doi:10.1016/j.bmcl.2009.09.045. PMID 19818610. S2CID 5870912.


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