Page last updated: 2024-10-15

pyrazofurin

Description

pirazofurin : A C-glycosyl compound that is 4-hydroxy-1H-pyrazole-5-carboxamide in which the hydrogen at position 3 has been replaced by a beta-D-ribofuranosyl group. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID135413551
CHEMBL ID2105330
CHEBI ID90284
SCHEMBL ID4860
SCHEMBL ID21379808
MeSH IDM0043899

Synonyms (51)

Synonym
4-hydroxy-3-beta-d-ribofuranosylpyrazole-5-carboxamide
pirazofurinum [inn-latin]
pirazofurina [inn-spanish]
compound 47599
4-hydroxy-3-beta-d-ribofuranosyl-1h-pyrazole-5-carboxamide
pirazofurine [inn-french]
3-beta-d-ribofuranosyl-4-hydroxypyrazole-5-carboxamide
nsc 143095
pirazofurin [inn]
antibiotic a 23813
1h-pyrazole-5-carboxamide, 4-hydroxy-3-beta-d-ribofuranosyl-
pyrazofurin [usan]
3-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-hydroxy-1h-pyrazole-5-carboxamide
4-hydroxy-3-.beta.-d-ribofuranosyl-1h-pyrazole-5-carboxamide
5-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-hydroxy-5h-pyrazole-3-carboxylic acid, amide
PZF ,
pyrazofurin (usan)
pirazofurin (inn)
D05658
nsc-143095
pirazofurin
pyrazofurin
pyrazomycin
30868-30-5
chebi:90284 ,
CHEMBL2105330
pirazofurine
pirazofurina
unii-4b15044gqz
pirazofurinum
4b15044gqz ,
SCHEMBL4860
4-hydroxy-3-beta-d-ribofuranosylpyrazole- 5-carboxamide
XESARGFCSKSFID-FLLFQEBCSA-N
3-(beta-d-ribofuranosyl)-4-hydroxypyrazole-5-carboxamide
(1s)-1,4-anhydro-1-(5-carbamoyl-4-hydroxy-1h-pyrazol-3-yl)-d-ribitol
beta-pyrazomycin
4-hydroxy-3-(beta-d-ribofuranosyl)-1h-pyrazole-5-carboxamide
AKOS027381076
Q6076735
5-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1h-pyrazole-3-carboxamide
4-hydroxy-3-beta-d-ribofuranosyl-1h-pyrazole-5-carboxamide monohydrate
3-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1h-pyrazole-5-carboxamide
HY-122502
CS-0085864
C22195
3-((2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-hydroxy-1h-pyrazole-5-carboxamide
MS-23649
SCHEMBL21379808
bdbm50459997
DTXSID901028098

Dosage Studied

Sixty-one patients with advanced disseminated cancer were given progressively increasing doses of pyrazofurin. The aim was to establish the dosage that produces maximum therapeutic effect with clinically tolerable toxicity.

ExcerptReference
"Sixty-one patients with advanced disseminated cancer were given progressively increasing doses of pyrazofurin to evaluate toxicity patterns and to establish the dosage that produces maximum therapeutic effect with clinically tolerable toxicity."( A phase I study of pyrazofurin.
Bodey, GP; Burgess, MA; Freireich, EJ; Murphy, WK; Salem, PA, 1977
)
" This technique has been used to generate dose-response curves describing the effects of mycophenolic acid and pyrazofurin on individual colonies of Chinese hamster ovary cells."( Ultrasensitive assay for ribonucleoside triphosphates in 50-1000 cells. Application to studies with pyrazofurin and mycophenolic acid.
Henderson, JF; Moyer, JD, 1983
)
" Treatment of cultures in each phase for 1 or 2 hrs resulted in threshold exponential type dose-response curves, yielding Do values of 3 and 1 microM, respectively."( Action of lycurim and pyrazofurin on hepatoma 3924A cells in culture.
Ban, J; Olah, E; Werber, G, 1982
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
antimetaboliteA substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
EC 4.1.1.23 (orotidine-5'-phosphate decarboxylase) inhibitorAny EC 4.1.1.* (carboxy-lyase) inhibitor that interferes with the action of orotidine-5'-phosphate decarboxylase (EC 4.1.1.23).
antimicrobial agentA substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
C-glycosyl compoundA glycosyl compound arising formally from the elimination of water from a glycosidic hydroxy group and an H atom bound to a carbon atom, thus creating a C-C bond.
pyrazoles
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Orotidine 5'-phosphate decarboxylaseMethanothermobacter thermautotrophicus str. Delta HKi6.20001.10003.65006.2000AID1388713
Uridine 5'-monophosphate synthaseHomo sapiens (human)Ki0.01700.01700.01700.0170AID1388714
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
'de novo' pyrimidine nucleobase biosynthetic processUridine 5'-monophosphate synthaseHomo sapiens (human)
UMP biosynthetic processUridine 5'-monophosphate synthaseHomo sapiens (human)
UDP biosynthetic processUridine 5'-monophosphate synthaseHomo sapiens (human)
female pregnancyUridine 5'-monophosphate synthaseHomo sapiens (human)
lactationUridine 5'-monophosphate synthaseHomo sapiens (human)
'de novo' UMP biosynthetic processUridine 5'-monophosphate synthaseHomo sapiens (human)
cellular response to xenobiotic stimulusUridine 5'-monophosphate synthaseHomo sapiens (human)
pyrimidine nucleobase biosynthetic processUridine 5'-monophosphate synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
orotate phosphoribosyltransferase activityUridine 5'-monophosphate synthaseHomo sapiens (human)
orotidine-5'-phosphate decarboxylase activityUridine 5'-monophosphate synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
nucleusUridine 5'-monophosphate synthaseHomo sapiens (human)
cytoplasmUridine 5'-monophosphate synthaseHomo sapiens (human)
cytosolUridine 5'-monophosphate synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID1388713Inhibition of Methanobacterium thermoautotrophicum ODCase2018Bioorganic & medicinal chemistry, 02-01, Volume: 26, Issue:3
Synthesis and biological evaluation of 6-substituted-5-fluorouridine ProTides.
AID409954Inhibition of mouse brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID1388714Inhibition of human ODCase2018Bioorganic & medicinal chemistry, 02-01, Volume: 26, Issue:3
Synthesis and biological evaluation of 6-substituted-5-fluorouridine ProTides.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (99)

TimeframeStudies, This Drug (%)All Drugs %
pre-199069 (69.70)18.7374
1990's15 (15.15)18.2507
2000's7 (7.07)29.6817
2010's6 (6.06)24.3611
2020's2 (2.02)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials7 (6.60%)5.53%
Reviews5 (4.72%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other94 (88.68%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]