2'-Deoxy-2'-fluorocytidine

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2'-Deoxy-2'-fluorocytidine
2'-Deoxy-2'-fluorocytidine.svg
Legal status
Legal status
Identifiers
  • 4-amino-1-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C9H12FN3O4
Molar mass 245.210 g·mol−1
3D model (JSmol)
  • C1=CN(C(=O)N=C1N)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)F
  • InChI=1S/C9H12FN3O4/c10-6-7(15)4(3-14)17-8(6)13-2-1-5(11)12-9(13)16/h1-2,4,6-8,14-15H,3H2,(H2,11,12,16)/t4-,6-,7-,8-/m1/s1
  • Key:NVZFZMCNALTPBY-XVFCMESISA-N

2'-Deoxy-2'-fluorocytidine is a nucleoside derivative developed in the 1960s, which has antiviral properties against many different kinds of viral diseases. It is closely related to several other antiviral drugs such as azvudine and lumicitabine, as well as the anti-cancer drug gemcitabine. 2'-Deoxy-2'-fluorocytidine has never been developed for medical use due to its comparatively harsh side effect profile, despite its broad spectrum antiviral properties, but has attracted renewed attention in recent years as a potential treatment for Crimean–Congo hemorrhagic fever (CCHF), a tick-borne hemorrhagic fever from the bunyavirus family. CCHF is highly lethal with a case fatality rate upwards of 30%, and no vaccine is currently available though some are in development. Some existing drugs such as ribavirin and favipiravir show activity against CCHF, but neither is very effective and there are no approved treatments for human use. There is therefore a pressing need for improved treatments for CCHF, and 2'-deoxy-2'-fluorocytidine was one of the most effective agents identified in vitro and in animal studies. It is currently in pre-clinical development with a view to potential human clinical trials. [1] [2] [3] [4] [5] [6] [7] [8] [9] [10]

References

  1. ↑ Doerr IL, Fox JJ (May 1967). "Nucleosides. XXXIX. 2'-deoxy-2'-fluorocytidine, 1-beta-D-arabinofuranosyl-2-amino-1,4(2H)-4-iminopyrimidine, and related derivatives". The Journal of Organic Chemistry. 32 (5): 1462–1471. doi:10.1021/jo01280a035. PMID   6041430.
  2. ↑ Wohlrab F, Jamieson AT, Hay J, Mengel R, Guschlbauer W (March 1985). "The effect of 2'-fluoro-2'-deoxycytidine on herpes virus growth". Biochimica et Biophysica Acta. 824 (3): 233–242. doi:10.1016/0167-4781(85)90053-3. PMID   2982405.
  3. ↑ Bajramovic JJ, Volmer R, Syan S, Pochet S, Gonzalez-Dunia D (April 2004). "2'-fluoro-2'-deoxycytidine inhibits Borna disease virus replication and spread". Antimicrobial Agents and Chemotherapy. 48 (4): 1422–1425. doi:10.1128/AAC.48.4.1422-1425.2004. PMC   375289 . PMID   15047559.
  4. ↑ Kumaki Y, Day CW, Smee DF, Morrey JD, Barnard DL (November 2011). "In vitro and in vivo efficacy of fluorodeoxycytidine analogs against highly pathogenic avian influenza H5N1, seasonal, and pandemic H1N1 virus infections". Antiviral Research. 92 (2): 329–340. doi:10.1016/j.antiviral.2011.09.001. PMC   3216401 . PMID   21925541.
  5. ↑ Welch SR, Guerrero LW, Chakrabarti AK, McMullan LK, Flint M, Bluemling GR, et al. (December 2016). "Lassa and Ebola virus inhibitors identified using minigenome and recombinant virus reporter systems". Antiviral Research. 136: 9–18. doi:10.1016/j.antiviral.2016.10.007. PMID   27771389.
  6. ↑ Welch SR, Scholte FE, Flint M, Chatterjee P, Nichol ST, Bergeron É, et al. (November 2017). "Identification of 2'-deoxy-2'-fluorocytidine as a potent inhibitor of Crimean-Congo hemorrhagic fever virus replication using a recombinant fluorescent reporter virus". Antiviral Research. 147: 91–99. doi:10.1016/j.antiviral.2017.10.008. PMC   8191813 . PMID   29024765.
  7. ↑ Smee DF, Jung KH, Westover J, Gowen BB (December 2018). "2'-Fluoro-2'-deoxycytidine is a broad-spectrum inhibitor of bunyaviruses in vitro and in phleboviral disease mouse models". Antiviral Research. 160: 48–54. doi:10.1016/j.antiviral.2018.10.013. PMID   30339848.
  8. ↑ Yu P, Wang Y, Li Y, Li Y, Miao Z, Peppelenbosch MP, et al. (November 2020). "2'-Fluoro-2'-deoxycytidine inhibits murine norovirus replication and synergizes MPA, ribavirin and T705". Archives of Virology. 165 (11): 2605–2613. doi:10.1007/s00705-020-04759-4. PMC   7414258 . PMID   32770483.
  9. ↑ Dai S, Deng F, Wang H, Ning Y (June 2021). "Crimean-Congo Hemorrhagic Fever Virus: Current Advances and Future Prospects of Antiviral Strategies". Viruses. 13 (7): 1195. doi: 10.3390/v13071195 . PMC   8310003 . PMID   34206476.
  10. ↑ Hawman DW, Feldmann H (July 2023). "Crimean-Congo haemorrhagic fever virus". Nature Reviews. Microbiology. 21 (7): 463–477. doi:10.1038/s41579-023-00871-9. PMC   10013989 . PMID   36918725.
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