pyrazofurin

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 3-[(2S,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1H-pyrazole-5-carboxamide

| image = Pyrazofurin.svg

| tradename = Pyrazofurin

| legal_US = Investigational New Drug

| legal_status =

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number = 30868-30-5

| PubChem = 135413551

| UNII = 4B15044GQZ

| ChemSpiderID = 10570780

| ChEBI = 90284

| ChEMBL = 2105330

| KEGG = D05658

| C=9 | H=13 | N=3 | O=6

| SMILES = C([C@@H]1[C@H]([C@H]([C@@H](O1)C2=NNC(=C2O)C(=O)N)O)O)O

| StdInChI=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

| StdInChIKey = 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.{{cite journal | vauthors = Canonico PG, Jahrling PB, Pannier WL | title = Antiviral efficacy of pyrazofurin against selected RNA viruses | journal = Antiviral Research | volume = 2 | issue = 6 | pages = 331–7 | date = December 1982 | pmid = 6299188 | doi = 10.1016/0166-3542(82)90002-x }}{{cite journal | vauthors = Buchanan JG | title = The C-nucleoside antibiotics | journal = Fortschritte der Chemie Organischer Naturstoffe | volume = 44 | pages = 243–99 | pmid = 6360831 | doi = 10.1007/978-3-7091-8714-2_4 | series = Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products | year = 1983 | isbn = 978-3-7091-8716-6 }}{{cite journal | vauthors = Hacksell U, Daves GD | title = The chemistry and biochemistry of C-nucleosides and C-arylglycosides | journal = Progress in Medicinal Chemistry | volume = 22 | pages = 1–65 | pmid = 3915364 | doi = 10.1016/s0079-6468(08)70228-5 | year = 1985 }}{{cite journal | vauthors = De Clercq E | title = Another ten stories in antiviral drug discovery (part C): "Old" and "new" antivirals, strategies, and perspectives | journal = Medicinal Research Reviews | volume = 29 | issue = 4 | pages = 611–45 | date = July 2009 | pmid = 19260077 | doi = 10.1002/med.20153 | s2cid = 140127449 }}{{cite journal | vauthors = De Clercq E | title = Curious (Old and New) Antiviral Nucleoside Analogues with Intriguing Therapeutic Potential | journal = Current Medicinal Chemistry | volume = 22 | issue = 34 | pages = 3866–80 | pmid = 26112146 | doi = 10.2174/0929867322666150625094705 | year = 2015 }}{{cite journal | vauthors = De Clercq E | title = C-Nucleosides To Be Revisited | journal = Journal of Medicinal Chemistry | volume = 59 | issue = 6 | pages = 2301–11 | date = March 2016 | pmid = 26513594 | doi = 10.1021/acs.jmedchem.5b01157 }}{{cite journal | vauthors = De Clercq E | title = New Nucleoside Analogues for the Treatment of Hemorrhagic Fever Virus Infections | journal = Chemistry: An Asian Journal | volume = 14 | issue = 22 | pages = 3962–3968 | date = November 2019 | pmid = 31389664 | doi = 10.1002/asia.201900841 | pmc = 7159701 }}{{cite journal | vauthors = Ren D, Wang SA, Ko Y, Geng Y, Ogasawara Y, Liu HW | title = Identification of the C-Glycoside Synthases during Biosynthesis of the Pyrazole-C-Nucleosides Formycin and Pyrazofurin | journal = Angewandte Chemie | volume = 58 | issue = 46 | pages = 16512–16516 | date = November 2019 | pmid = 31518483 | pmc = 6911263 | doi = 10.1002/anie.201910356 }}