Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H13N3O6 |
Molecular Weight | 259.216 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)C1=C(O)C(=NN1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O
InChI
InChIKey=XESARGFCSKSFID-FLLFQEBCSA-N
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
Molecular Formula | C9H13N3O6 |
Molecular Weight | 259.216 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Pyrazofurin (PF) (3,β-D-ribofuranosyl, 4-hydroxyprazole-5-carboxamide) is a C-nucleoside antibiotic, one in which the ribose joins the base-ring carbon instead of a base-ring nitrogen. Pyrazofurin potently inhibits orotidine 5'-monophosphate (OMP) decarboxylase, thereby interfering with de novo synthesis of uridine nucleotides and resulting in cytotoxicity. This agent also causes a rapid depletion of the pyrimidine deoxynucleotide pool, thereby inhibiting DNA synthesis and cell replication. PF was isolated from fermentation filtrate of Strepomyces candidus. This compound was initially found to have inhibitory activity against the vaccinia, herpes simplex, rhino and measles viruses in vitro and the vaccinia virus in vivo. More recently the antiviral spectrum has been extended to include the polio, Coxsackie, Sindbis and vesicular stomatitis viruses.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
5.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Doses
Dose | Population | Adverse events |
---|---|---|
200 mg/m2 1 times / week multiple, intravenous Studied dose Dose: 200 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 200 mg/m2, 1 times / week Sources: |
unhealthy n = 21 Health Status: unhealthy Condition: cancer Sex: unknown Food Status: UNKNOWN Population Size: 21 Sources: |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/157807
Pyrazofurin was administered to 21 patients with solid tumors at a dose of 200 mg/m2 iv weekly, because this dose had been shown to be well-tolerated and pharmacologic effects of a single dose at this level persisted for up to 7 days.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2713848
Measurement of levels of pyrimidine and purine intermediates in cultured mouse L1210 leukemia cells has shown that 25 uM pyrazofurin induces an 8-fold accumulation of OMP and large accumulations of intermediates proximal to the blockade with abrupt decreases in uridine and cytidine nucleotides.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:16:45 GMT 2023
by
admin
on
Fri Dec 15 15:16:45 GMT 2023
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Record UNII |
4B15044GQZ
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C1557
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NCI_THESAURUS |
C2170
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30868-30-5
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SUB09897MIG
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143095
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135413551
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90284
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100000081640
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3579
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CHEMBL2105330
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DTXSID901028098
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4B15044GQZ
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Pyrazofurin
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C1208
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C002997
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Related Record | Type | Details | ||
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ACTIVE MOIETY |