setrobuvir
{{Short description|Chemical compound}}
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 461749550
| Reference =
| ImageFile = Setrobuvir.svg
| ImageSize =200px
| ImageAlt =
| PIN = 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{{cite web|title=International Nonproprietary Names for Pharmaceutical Substances (INN). RECOMMENDED International Nonproprietary Names: List 68|url=https://www.who.int/medicines/publications/druginformation/innlists/RL68.pdf|publisher=World Health Organization|page=322}}
| OtherNames = ANA-598; ANA598
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|changed|CAS}}
| CASNo = 1071517-39-9
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = T5B2GI8F84
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1076263
| PubChem = 45136829
| 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
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 24680206
| KEGG = D10165
| KEGG_Ref = {{keggcite|changed|kegg}}
| 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
| InChIKey = DEKOYVOWOVJMPM-RLHIPHHXBY
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DEKOYVOWOVJMPM-RLHIPHHXSA-N
}}
|Section2={{Chembox Properties
| C=25 | H=25 | F=1 | N=4 | O=6 | S=2
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
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.{{cite web|title=Setrobuvir|url=http://adisinsight.springer.com/drugs/800014226|publisher=AdisInsight|accessdate=28 August 2017|language=en}}{{cite web | url = http://cenblog.org/the-haystack/2011/10/anadys-acquired/ | title = HCV Followup: Anadys Acquired for Active Antiviral | date = October 24, 2011 | publisher = Chemical & Engineering News}} It was in Phase IIb clinical trials, used in combination with interferon and ribavirin, targeting hepatitis C patients with genotype 1.
Setrobuvir works by inhibiting the hepatitis C enzyme NS5B, an RNA polymerase.{{cite journal | pmid = 19818610 | year = 2009 | last1 = Ruebsam | first1 = F | last2 = Murphy | first2 = DE | last3 = Tran | first3 = CV | last4 = Li | first4 = LS | last5 = Zhao | first5 = J | last6 = Dragovich | first6 = PS | last7 = McGuire | first7 = HM | last8 = Xiang | first8 = AX | last9 = Sun | first9 = Z | last10 = Ayida | first10 = Benjamin K. | last11 = Blazel | first11 = Julie K. | last12 = Kim | first12 = Sun Hee | last13 = Zhou | first13 = Yuefen | last14 = Han | first14 = Qing | last15 = Kissinger | first15 = Charles R. | last16 = Webber | first16 = Stephen E. | last17 = Showalter | first17 = Richard E. | last18 = Shah | first18 = Amit M. | last19 = Tsan | first19 = Mei | last20 = Patel | first20 = Rupal A. | last21 = Thompson | first21 = Peggy A. | last22 = Lebrun | first22 = Laurie A. | last23 = Hou | first23 = Huiying J. | last24 = Kamran | first24 = Ruhi | last25 = Sergeeva | first25 = Maria V. | last26 = Bartkowski | first26 = Darian M. | last27 = Nolan | first27 = Thomas G. | last28 = Norris | first28 = Daniel A. | last29 = Khandurina | first29 = Julia | last30 = Brooks | first30 = Jennifer | title = Discovery of tricyclic 5,6-dihydro-1H-pyridin-2-ones as novel, potent, and orally bioavailable inhibitors of HCV NS5B polymerase | volume = 19 | issue = 22 | pages = 6404–12 | doi = 10.1016/j.bmcl.2009.09.045 | journal = Bioorganic & Medicinal Chemistry Letters| s2cid = 5870912 | display-authors = 8 }}