Pyrazofurin

Pyrazofurin (pyrazomycin) is a natural product found in Streptomyces candidus, which is a nucleoside analogue related to ribavirin. It has antibiotic, antiviral and anti-cancer properties but was not successful in human clinical trials due to severe side effects. Nevertheless, it continues to be the subject of ongoing research as a potential drug of last resort, or a template for improved synthetic derivatives.[1][2][3][4][5][6][7][8]

Pyrazofurin
Clinical data
Trade namesPyrazofurin
Legal status
Legal status
Identifiers
  • 3-[(2S,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1H-pyrazole-5-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC9H13N3O6
Molar mass259.22 g·mol−1
3D model (JSmol)
  • C([C@@H]1[C@H]([C@H]([C@@H](O1)C2=NNC(=C2O)C(=O)N)O)O)O
  • InChI=1S/C9H13N3O6/c10-9(17)4-6(15)3(11-12-4)8-7(16)5(14)2(1-13)18-8/h2,5,7-8,13-16H,1H2,(H2,10,17)(H,11,12)/t2-,5-,7-,8+/m1/s1
  • Key:XESARGFCSKSFID-FLLFQEBCSA-N

See also

References
  1. Canonico PG, Jahrling PB, Pannier WL (December 1982). "Antiviral efficacy of pyrazofurin against selected RNA viruses". Antiviral Research. 2 (6): 331–7. doi:10.1016/0166-3542(82)90002-x. PMID 6299188.
  2. Buchanan JG (1983). "The C-nucleoside antibiotics". Fortschritte der Chemie Organischer Naturstoffe. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. 44: 243–99. doi:10.1007/978-3-7091-8714-2_4. ISBN 978-3-7091-8716-6. PMID 6360831.
  3. Hacksell U, Daves GD (1985). "The chemistry and biochemistry of C-nucleosides and C-arylglycosides". Progress in Medicinal Chemistry. 22: 1–65. doi:10.1016/s0079-6468(08)70228-5. PMID 3915364.
  4. De Clercq E (July 2009). "Another ten stories in antiviral drug discovery (part C): "Old" and "new" antivirals, strategies, and perspectives". Medicinal Research Reviews. 29 (4): 611–45. doi:10.1002/med.20153. PMID 19260077. S2CID 140127449.
  5. De Clercq E (2015). "Curious (Old and New) Antiviral Nucleoside Analogues with Intriguing Therapeutic Potential". Current Medicinal Chemistry. 22 (34): 3866–80. doi:10.2174/0929867322666150625094705. PMID 26112146.
  6. De Clercq E (March 2016). "C-Nucleosides To Be Revisited". Journal of Medicinal Chemistry. 59 (6): 2301–11. doi:10.1021/acs.jmedchem.5b01157. PMID 26513594.
  7. De Clercq E (November 2019). "New Nucleoside Analogues for the Treatment of Hemorrhagic Fever Virus Infections". Chemistry: An Asian Journal. 14 (22): 3962–3968. doi:10.1002/asia.201900841. PMC 7159701. PMID 31389664.
  8. Ren D, Wang SA, Ko Y, Geng Y, Ogasawara Y, Liu HW (November 2019). "Identification of the C-Glycoside Synthases during Biosynthesis of the Pyrazole-C-Nucleosides Formycin and Pyrazofurin". Angewandte Chemie. 58 (46): 16512–16516. doi:10.1002/anie.201910356. PMC 6911263. PMID 31518483.


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