Nesbuvir
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MedKoo CAT#: 319894

CAS#: 691852-58-1

Description: Nesbuvir, also known as HCV-796 and VB-19796, is a potent and selective NS5B polymerase inhibitor with potent anti-hepatitis C virus activity in vitro, in mice with chimeric human livers, and in humans infected with hepatitis C virus. Enzyme assays yielded median inhibitory concentration (IC(50)) values of 0.01 to 0.14 microM for genotype 1, with half maximal effective concentration (EC(50)s) of 5 nM and 9 nM against genotype 1a and 1b replicons. HCV796 demonstrated potent anti-HCV activity consistently through enzyme inhibition assays, subgenomic replicon, and chimeric mouse studies.


Chemical Structure

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Nesbuvir
CAS# 691852-58-1

Theoretical Analysis

MedKoo Cat#: 319894
Name: Nesbuvir
CAS#: 691852-58-1
Chemical Formula: C22H23FN2O5S
Exact Mass: 446.13
Molecular Weight: 446.493
Elemental Analysis: C, 59.18; H, 5.19; F, 4.26; N, 6.27; O, 17.92; S, 7.18

Price and Availability

Size Price Availability Quantity
5mg USD 350 2 Weeks
10mg USD 625 2 Weeks
Bulk inquiry

Synonym: HCV-796; HCV 796; VB-19796 ; VB19796; HCV796; Nesbuvir.

IUPAC/Chemical Name: 5-Cyclopropyl-2-(4-fluorophenyl)-6-((2-hydroxyethyl)(methylsulfonyl)amino)-N-methyl-1-benzofuran-3-carboxamide

InChi Key: WTDWVLJJJOTABN-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H23FN2O5S/c1-24-22(27)20-17-11-16(13-3-4-13)18(25(9-10-26)31(2,28)29)12-19(17)30-21(20)14-5-7-15(23)8-6-14/h5-8,11-13,26H,3-4,9-10H2,1-2H3,(H,24,27)

SMILES Code: O=C(C1=C(C2=CC=C(F)C=C2)OC3=C1C=C(C4CC4)C(N(CCO)S(=O)(C)=O)=C3)NC

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Biological target: Nesbuvir is a nonnucleoside inhibitor of the hepatitis C virus (HCV) nonstructural protein 5B (NS5B) polymerase.
In vitro activity: TBD
In vivo activity: TBD

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.0 111.98

Preparing Stock Solutions

The following data is based on the product molecular weight 446.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: TBD
In vitro protocol: TBD
In vivo protocol: TBD

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1: Eltahla AA, Tay E, Douglas MW, White PA. Cross-genotypic examination of hepatitis C virus polymerase inhibitors reveals a novel mechanism of action for thumb binders. Antimicrob Agents Chemother. 2014 Dec;58(12):7215-24. doi: 10.1128/AAC.03699-14. Epub 2014 Sep 22. PubMed PMID: 25246395; PubMed Central PMCID: PMC4249545.

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3: Kalkeri G, Lin C, Gopilan J, Sloan K, Rijnbrand R, Kwong AD. Restoration of the activated Rig-I pathway in hepatitis C virus (HCV) replicon cells by HCV protease, polymerase, and NS5A inhibitors in vitro at clinically relevant concentrations. Antimicrob Agents Chemother. 2013 Sep;57(9):4417-26. doi: 10.1128/AAC.00399-13. Epub 2013 Jul 8. PubMed PMID: 23836176; PubMed Central PMCID: PMC3754339.

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6: Kim ND, Chun H, Park SJ, Yang JW, Kim JW, Ahn SK. Discovery of novel HCV polymerase inhibitors using pharmacophore-based virtual screening. Bioorg Med Chem Lett. 2011 Jun 1;21(11):3329-34. doi: 10.1016/j.bmcl.2011.04.010. Epub 2011 Apr 9. PubMed PMID: 21531135.

7: Zhu T, Fawzi MB, Flint M, Kong F, Szeliga J, Tsao R, Howe AY, Pan W. Design and synthesis of HCV agents with sequential triple inhibitory potentials. Bioorg Med Chem Lett. 2010 Sep 1;20(17):5212-6. doi: 10.1016/j.bmcl.2010.06.156. Epub 2010 Jul 23. PubMed PMID: 20655214.

8: Reich S, Golbik RP, Geissler R, Lilie H, Behrens SE. Mechanisms of activity and inhibition of the hepatitis C virus RNA-dependent RNA polymerase. J Biol Chem. 2010 Apr 30;285(18):13685-93. doi: 10.1074/jbc.M109.082206. Epub 2010 Mar 1. PubMed PMID: 20194503; PubMed Central PMCID: PMC2859531.

9: Delang L, Paeshuyse J, Vliegen I, Leyssen P, Obeid S, Durantel D, Zoulim F, Op de Beeck A, Neyts J. Statins potentiate the in vitro anti-hepatitis C virus activity of selective hepatitis C virus inhibitors and delay or prevent resistance development. Hepatology. 2009 Jul;50(1):6-16. doi: 10.1002/hep.22916. PubMed PMID: 19437494.

10: McCown MF, Rajyaguru S, Kular S, Cammack N, Nájera I. GT-1a or GT-1b subtype-specific resistance profiles for hepatitis C virus inhibitors telaprevir and HCV-796. Antimicrob Agents Chemother. 2009 May;53(5):2129-32. doi: 10.1128/AAC.01598-08. Epub 2009 Mar 9. PubMed PMID: 19273674; PubMed Central PMCID: PMC2681573.

11: Hang JQ, Yang Y, Harris SF, Leveque V, Whittington HJ, Rajyaguru S, Ao-Ieong G, McCown MF, Wong A, Giannetti AM, Le Pogam S, Talamás F, Cammack N, Nájera I, Klumpp K. Slow binding inhibition and mechanism of resistance of non-nucleoside polymerase inhibitors of hepatitis C virus. J Biol Chem. 2009 Jun 5;284(23):15517-29. doi: 10.1074/jbc.M808889200. Epub 2009 Feb 26. PubMed PMID: 19246450; PubMed Central PMCID: PMC2708848.

12: Feldstein A, Kleiner D, Kravetz D, Buck M. Severe hepatocellular injury with apoptosis induced by a hepatitis C polymerase inhibitor. J Clin Gastroenterol. 2009 Apr;43(4):374-81. doi: 10.1097/MCG.0b013e318178d91f. PubMed PMID: 19098685.

13: Kneteman NM, Howe AY, Gao T, Lewis J, Pevear D, Lund G, Douglas D, Mercer DF, Tyrrell DL, Immermann F, Chaudhary I, Speth J, Villano SA, O'Connell J, Collett M. HCV796: A selective nonstructural protein 5B polymerase inhibitor with potent anti-hepatitis C virus activity in vitro, in mice with chimeric human livers, and in humans infected with hepatitis C virus. Hepatology. 2009 Mar;49(3):745-52. doi: 10.1002/hep.22717. PubMed PMID: 19072827.

14: Flint M, Mullen S, Deatly AM, Chen W, Miller LZ, Ralston R, Broom C, Emini EA, Howe AY. Selection and characterization of hepatitis C virus replicons dually resistant to the polymerase and protease inhibitors HCV-796 and boceprevir (SCH 503034). Antimicrob Agents Chemother. 2009 Feb;53(2):401-11. doi: 10.1128/AAC.01081-08. Epub 2008 Oct 20. PubMed PMID: 18936191; PubMed Central PMCID: PMC2630598.

15: Howe AY, Cheng H, Johann S, Mullen S, Chunduru SK, Young DC, Bard J, Chopra R, Krishnamurthy G, Mansour T, O'Connell J. Molecular mechanism of hepatitis C virus replicon variants with reduced susceptibility to a benzofuran inhibitor, HCV-796. Antimicrob Agents Chemother. 2008 Sep;52(9):3327-38. doi: 10.1128/AAC.00238-08. Epub 2008 Jun 16. PubMed PMID: 18559648; PubMed Central PMCID: PMC2533464.

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17: Le Pogam S, Seshaadri A, Kosaka A, Chiu S, Kang H, Hu S, Rajyaguru S, Symons J, Cammack N, Nájera I. Existence of hepatitis C virus NS5B variants naturally resistant to non-nucleoside, but not to nucleoside, polymerase inhibitors among untreated patients. J Antimicrob Chemother. 2008 Jun;61(6):1205-16. doi: 10.1093/jac/dkn085. Epub 2008 Mar 13. PubMed PMID: 18343801.

18: McCown MF, Rajyaguru S, Le Pogam S, Ali S, Jiang WR, Kang H, Symons J, Cammack N, Najera I. The hepatitis C virus replicon presents a higher barrier to resistance to nucleoside analogs than to nonnucleoside polymerase or protease inhibitors. Antimicrob Agents Chemother. 2008 May;52(5):1604-12. doi: 10.1128/AAC.01317-07. Epub 2008 Feb 19. PubMed PMID: 18285474; PubMed Central PMCID: PMC2346640.