MK-608

MK-608
Clinical data
Trade names MK608
Legal status
Legal status
  • Investigational New Drug
Identifiers
CAS Number 443642-29-3 YesY
PubChem (CID) 3011893
ChemSpider 2280834
Chemical and physical data
Formula C12H16N4O4
Molar mass 280.279
3D model (Jmol) Interactive image

MK-608 (7-deaza-2’-C-methyladenosine, 7DMA) is an antiviral drug, an adenosine analog (a type of nucleoside analog). It was originally developed by Merck & Co. as a treatment for Hepatitis C, but despite promising results in animal studies,[1][2] it was ultimately unsuccessful in clinical trials.[3] Subsequently it has been widely used in antiviral research and has shown activity against a range of viruses, including Dengue fever,[4] Tick-borne encephalitis virus,[5] poliovirus,[6][7] and most recently Zika virus,[8][9] in both in vitro and animal models. Since it has already failed in human clinical trials previously, it is unlikely MK-608 itself will be developed as an antiviral medication, but the continuing lack of treatment options for these emerging viral diseases means that much research continues using MK-608 and related antiviral drugs.[10]

See also

References

  1. ↑ Carroll SS, Ludmerer S, Handt L, Koeplinger K, Zhang NR, Graham D, Davies ME, MacCoss M, Hazuda D, Olsen DB. Robust antiviral efficacy upon administration of a nucleoside analog to hepatitis C virus-infected chimpanzees. Antimicrob Agents Chemother. 2009 Mar;53(3):926-34. doi: 10.1128/AAC.01032-08. PMID 19075052
  2. ↑ Olsen DB, Davies ME, Handt L, Koeplinger K, Zhang NR, Ludmerer SW, Graham D, Liverton N, MacCoss M, Hazuda D, Carroll SS. Sustained viral response in a hepatitis C virus-infected chimpanzee via a combination of direct-acting antiviral agents. Antimicrob Agents Chemother. 2011 Feb;55(2):937-9. doi: 10.1128/AAC.00990-10. PMID 21115793
  3. ↑ Arnold JJ, Sharma SD, Feng JY, Ray AS, Smidansky ED, Kireeva ML, Cho A, Perry J, Vela JE, Park Y, Xu Y, Tian Y, Babusis D, Barauskus O, Peterson BR, Gnatt A, Kashlev M, Zhong W, Cameron CE. Sensitivity of mitochondrial transcription and resistance of RNA polymerase II dependent nuclear transcription to antiviral ribonucleosides. PLoS Pathog. 2012;8(11):e1003030. PMID 23166498 PMCID: PMC3499576 DOI: 10.1371/journal.ppat.1003030
  4. ↑ Schul W, Liu W, Xu HY, Flamand M, Vasudevan SG. A dengue fever viremia model in mice shows reduction in viral replication and suppression of the inflammatory response after treatment with antiviral drugs. J Infect Dis. 2007 Mar 1;195(5):665-74. PMID 17262707
  5. ↑ Eyer L, Valdés JJ, Gil VA, Nencka R, Hřebabecký H, Šála M, Salát J, Černý J, Palus M, De Clercq E, Růžek D. Nucleoside inhibitors of tick-borne encephalitis virus. Antimicrob Agents Chemother. 2015 Sep;59(9):5483-93. doi: 10.1128/AAC.00807-15. PMID 26124166
  6. ↑ Goris N, De Palma A, Toussaint JF, Musch I, Neyts J, De Clercq K. 2'-C-methylcytidine as a potent and selective inhibitor of the replication of foot-and-mouth disease virus. Antiviral Res. 2007 Mar;73(3):161-8. PMID 17055073
  7. ↑ Wu R, Smidansky ED, Oh HS, Takhampunya R, Padmanabhan R, Cameron CE, Peterson BR. Synthesis of a 6-methyl-7-deaza analogue of adenosine that potently inhibits replication of polio and dengue viruses. J Med Chem. 2010 Nov 25;53(22):7958-66. doi: 10.1021/jm100593s. PMID 20964406 PMCID: PMC2990348
  8. ↑ Eyer L, Nencka R, Huvarová I, Palus M, Joao Alves M, Gould EA, De Clercq E, Růžek D. Nucleoside inhibitors of Zika virus. J Infect Dis. 2016 Sep 1;214(5):707-11. PMID 27234417 DOI: 10.1093/infdis/jiw226
  9. ↑ Zmurko J, Marques RE, Schols D, Verbeken E, Kaptein SJ, Neyts J. The Viral Polymerase Inhibitor 7-Deaza-2'-C-Methyladenosine Is a Potent Inhibitor of In Vitro Zika Virus Replication and Delays Disease Progression in a Robust Mouse Infection Model. PLoS Negl Trop Dis. 2016 May 10;10(5):e0004695. doi: 10.1371/journal.pntd.0004695. PMID 27163257
  10. ↑ Vittori S, Dal Ben D, Lambertucci C, Marucci G, Volpini R, Cristalli G. Antiviral Properties of Deazaadenine Nucleoside Derivatives. Current Medicinal Chemistry December 2006, 13(29):3529-3552. doi: 10.2174/092986706779026228
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