Pyrazofurin

Pyrazofurin
Clinical data
Trade names	Pyrazofurin
Legal status
Legal status	US: Investigational New Drug;
Identifiers
	IUPAC name 3-[(2S,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1H-pyrazole-5-carboxamide;
CAS Number	30868-30-5;
PubChem CID	135413551;
ChemSpider	10570780;
UNII	4B15044GQZ;
KEGG	D05658;
ChEBI	CHEBI:90284;
ChEMBL	ChEMBL2105330;
Chemical and physical data
Formula	C9H13N3O6
Molar mass	259.218 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C([C@@H]1[C@H]([C@H]([C@@H](O1)C2=NNC(=C2O)C(=O)N)O)O)O;
	InChI 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;

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]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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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[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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Pyrazofurin

See also

References