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MedKoo Cat#: 414961 | Name: Pimodivir tosylate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pimodivir, also known as VX-787, JNJ-872, is a novel inhibitor of influenza virus replication that blocks the PB2 cap-snatching activity of the influenza viral polymerase complex. VX-787 binds the cap-binding domain of the PB2 subunit with a KD (dissociation constant) of 24 nM as determined by isothermal titration calorimetry (ITC). The cell-based EC50 (the concentration of compound that ensures 50% cell viability of an uninfected control) for VX-787 is 1.6 nM in a cytopathic effect (CPE) assay, with a similar EC50 in a viral RNA replication assay. VX-787 is active against a diverse panel of influenza A virus strains, including H1N1pdm09 and H5N1 strains, as well as strains with reduced susceptibility to neuraminidase inhibitors (NAIs).

Chemical Structure

Pimodivir tosylate
Pimodivir tosylate
CAS#1777814-27-3 (tosylate)

Theoretical Analysis

MedKoo Cat#: 414961

Name: Pimodivir tosylate

CAS#: 1777814-27-3 (tosylate)

Chemical Formula: C27H27F2N5O5S

Exact Mass: 399.1507

Molecular Weight: 571.60

Elemental Analysis: C, 56.73; H, 4.76; F, 6.65; N, 12.25; O, 13.99; S, 5.61

Price and Availability

Size Price Availability Quantity
50mg USD 950.00 2 Weeks
100mg USD 1,650.00 2 Weeks
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Related CAS #
1777721-70-6 (HCl) 1629869-44-8 (free base) 1777814-27-3 (tosylate)
Synonym
Pimodivir tosylate; Pimodivir; VX787; VX 787; VX-787; JNJ 872; JNJ-872; JNJ872
IUPAC/Chemical Name
Bicyclo(2.2.2)octane-2-carboxylic acid, 3-((5-fluoro-2-(5-fluoro-1H-pyrrolo(2,3-b)pyridin-3-yl)-4-pyrimidinyl)amino)-, (2S,3S)-, tosylate
InChi Key
WUNFARYORPRLSH-PTZRGWEZSA-N
InChi Code
InChI=1S/C20H19F2N5O2.C7H8O3S/c21-11-5-12-13(7-24-17(12)23-6-11)18-25-8-14(22)19(27-18)26-16-10-3-1-9(2-4-10)15(16)20(28)29;1-6-2-4-7(5-3-6)11(8,9)10/h5-10,15-16H,1-4H2,(H,23,24)(H,28,29)(H,25,26,27);2-5H,1H3,(H,8,9,10)/t9?,10?,15-,16-;/m0./s1
SMILES Code
O=C([C@H]1C(CC2)CCC2[C@@H]1NC3=NC(C4=CNC5=NC=C(F)C=C54)=NC=C3F)O.OS(=O)(C6=CC=C(C)C=C6)=O
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 571.60 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
1: Ianevski A, Yao R, Zusinaite E, Lello LS, Wang S, Jo E, Yang J, Ravlo E, Wang W, Lysvand H, Løseth K, Oksenych V, Tenson T, Windisch MP, Poranen MM, Nieminen AI, Nordbø SA, Fenstad MH, Grødeland G, Aukrust P, Trøseid M, Kantele A, Lastauskienė E, Vitkauskienė A, Legrand N, Merits A, Bjørås M, Kainov DE. Synergistic Interferon-Alpha-Based Combinations for Treatment of SARS-CoV-2 and Other Viral Infections. Viruses. 2021 Dec 11;13(12):2489. doi: 10.3390/v13122489. PMID: 34960758; PMCID: PMC8705725. 2: Soh YQS, Malone KD, Eguia RT, Bloom JD. Comprehensive Profiling of Mutations to Influenza Virus PB2 That Confer Resistance to the Cap-Binding Inhibitor Pimodivir. Viruses. 2021 Jun 22;13(7):1196. doi: 10.3390/v13071196. PMID: 34206520; PMCID: PMC8310130. 3: Mengual-Chuliá B, Alonso-Cordero A, Cano L, Mosquera MDM, de Molina P, Vendrell R, Reyes-Prieto M, Jané M, Torner N, Martínez AI, Vila J, Díez-Domingo J, Marcos MÁ, López-Labrador FX. Whole-Genome Analysis Surveillance of Influenza A Virus Resistance to Polymerase Complex Inhibitors in Eastern Spain from 2016 to 2019. Antimicrob Agents Chemother. 2021 May 18;65(6):e02718-20. doi: 10.1128/AAC.02718-20. PMID: 33782005; PMCID: PMC8315920. 4: Gregor J, Radilová K, Brynda J, Fanfrlík J, Konvalinka J, Kožíšek M. Structural and Thermodynamic Analysis of the Resistance Development to Pimodivir (VX-787), the Clinical Inhibitor of Cap Binding to PB2 Subunit of Influenza A Polymerase. Molecules. 2021 Feb 14;26(4):1007. doi: 10.3390/molecules26041007. PMID: 33673017; PMCID: PMC7917969. 5: Patel MC, Chesnokov A, Jones J, Mishin VP, De La Cruz JA, Nguyen HT, Zanders N, Wentworth DE, Davis TC, Gubareva LV. Susceptibility of widely diverse influenza a viruses to PB2 polymerase inhibitor pimodivir. Antiviral Res. 2021 Apr;188:105035. doi: 10.1016/j.antiviral.2021.105035. Epub 2021 Feb 10. PMID: 33581212. 6: O'Neil B, Ison MG, Hallouin-Bernard MC, Nilsson AC, Torres A, Wilburn JM, van Duijnhoven W, Van Dromme I, Anderson D, Deleu S, Kosoglou T, Vingerhoets J, Rossenu S, Leopold L. A Phase 2 Study of Pimodivir (JNJ-63623872) in Combination with Oseltamivir in Elderly and NonElderly Adults Hospitalized with Influenza A Infection: OPAL study. J Infect Dis. 2020 Jun 30:jiaa376. doi: 10.1093/infdis/jiaa376. Epub ahead of print. PMID: 32604406. 7: Takashita E. Influenza Polymerase Inhibitors: Mechanisms of Action and Resistance. Cold Spring Harb Perspect Med. 2021 May 3;11(5):a038687. doi: 10.1101/cshperspect.a038687. PMID: 32122918; PMCID: PMC8091960. 8: O'Sullivan S, Torres A, Rodriguez A, Martin-Loeches I. Influenza management with new therapies. Curr Opin Pulm Med. 2020 May;26(3):215-221. doi: 10.1097/MCP.0000000000000667. PMID: 32068576. 9: McGowan DC, Balemans W, Embrechts W, Motte M, Keown JR, Buyck C, Corbera J, Funes M, Moreno L, Cooymans L, Tahri A, Eymard J, Stoops B, Strijbos R, Van den Berg J, Fodor E, Grimes JM, Koul A, Jonckers THM, Raboisson P, Guillemont J. Design, Synthesis, and Biological Evaluation of Novel Indoles Targeting the Influenza PB2 Cap Binding Region. J Med Chem. 2019 Nov 14;62(21):9680-9690. doi: 10.1021/acs.jmedchem.9b01091. Epub 2019 Oct 30. PMID: 31647875; PMCID: PMC7611167. 10: Zhang H, Zhou L, Amichai S, Zandi K, Cox B, Schinazi R, Amblard F. Novel influenza polymerase PB2 inhibitors for the treatment of influenza A infection. Bioorg Med Chem Lett. 2019 Oct 15;29(20):126639. doi: 10.1016/j.bmcl.2019.126639. Epub 2019 Aug 24. PMID: 31493987; PMCID: PMC7732027. 11: Mifsud EJ, Hayden FG, Hurt AC. Antivirals targeting the polymerase complex of influenza viruses. Antiviral Res. 2019 Sep;169:104545. doi: 10.1016/j.antiviral.2019.104545. Epub 2019 Jun 25. PMID: 31247246. 12: Pavia A. One hundred years after the 1918 pandemic: new concepts for preparing for influenza pandemics. Curr Opin Infect Dis. 2019 Aug;32(4):365-371. doi: 10.1097/QCO.0000000000000564. PMID: 31116135. 13: Beigel JH, Nam HH, Adams PL, Krafft A, Ince WL, El-Kamary SS, Sims AC. Advances in respiratory virus therapeutics - A meeting report from the 6th isirv Antiviral Group conference. Antiviral Res. 2019 Jul;167:45-67. doi: 10.1016/j.antiviral.2019.04.006. Epub 2019 Apr 8. PMID: 30974127; PMCID: PMC7132446. 14: Hayden FG, Shindo N. Influenza virus polymerase inhibitors in clinical development. Curr Opin Infect Dis. 2019 Apr;32(2):176-186. doi: 10.1097/QCO.0000000000000532. PMID: 30724789; PMCID: PMC6416007. 15: Finberg RW, Lanno R, Anderson D, Fleischhackl R, van Duijnhoven W, Kauffman RS, Kosoglou T, Vingerhoets J, Leopold L. Phase 2b Study of Pimodivir (JNJ-63623872) as Monotherapy or in Combination With Oseltamivir for Treatment of Acute Uncomplicated Seasonal Influenza A: TOPAZ Trial. J Infect Dis. 2019 Mar 15;219(7):1026-1034. doi: 10.1093/infdis/jiy547. PMID: 30428049. 16: Deleu S, Kakuda TN, Spittaels K, Vercauteren JJ, Hillewaert V, Lwin A, Leopold L, Hoetelmans RMW. Single- and multiple-dose pharmacokinetics and safety of pimodivir, a novel, non-nucleoside polymerase basic protein 2 subunit inhibitor of the influenza A virus polymerase complex, and interaction with oseltamivir: a Phase 1 open-label study in healthy volunteers. Br J Clin Pharmacol. 2018 Nov;84(11):2663-2672. doi: 10.1111/bcp.13733. Epub 2018 Sep 14. PMID: 30098042; PMCID: PMC6177716. 17: Trevejo JM, Asmal M, Vingerhoets J, Polo R, Robertson S, Jiang Y, Kieffer TL, Leopold L. Pimodivir treatment in adult volunteers experimentally inoculated with live influenza virus: a Phase IIa, randomized, double-blind, placebo- controlled study. Antivir Ther. 2018;23(4):335-344. doi: 10.3851/IMP3212. PMID: 29244026. 18: Pflug A, Gaudon S, Resa-Infante P, Lethier M, Reich S, Schulze WM, Cusack S. Capped RNA primer binding to influenza polymerase and implications for the mechanism of cap-binding inhibitors. Nucleic Acids Res. 2018 Jan 25;46(2):956-971. doi: 10.1093/nar/gkx1210. PMID: 29202182; PMCID: PMC5778463. 19: McKimm-Breschkin JL, Jiang S, Hui DS, Beigel JH, Govorkova EA, Lee N. Prevention and treatment of respiratory viral infections: Presentations on antivirals, traditional therapies and host-directed interventions at the 5th ISIRV Antiviral Group conference. Antiviral Res. 2018 Jan;149:118-142. doi: 10.1016/j.antiviral.2017.11.013. Epub 2017 Nov 21. PMID: 29162476; PMCID: PMC7133686. 20: Smee DF, Barnard DL, Jones SM. Activities of JNJ63623872 and oseltamivir against influenza A H1N1pdm and H3N2 virus infections in mice. Antiviral Res. 2016 Dec;136:45-50. doi: 10.1016/j.antiviral.2016.10.009. Epub 2016 Oct 19. PMID: 27771390.

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