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
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 |
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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: |
PubMed
Title | Date | PubMed |
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Screening for new compounds with antiherpes activity. | 1984 Oct |
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Comparative inhibitory effects of suramin and other selected compounds on the infectivity and replication of human T-cell lymphotropic virus (HTLV-III)/lymphadenopathy-associated virus (LAV). | 1986 Mar 15 |
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Comparison of the anti-respiratory syncytial virus activity and toxicity of papaverine hydrochloride and pyrazofurin in vitro and in vivo. | 1989 Feb |
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Comparative activities of several nucleoside analogs against duck hepatitis B virus in vitro. | 1990 Jul |
Patents
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.
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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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90284
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CHEMBL2105330
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4B15044GQZ
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Pyrazofurin
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C1208
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C002997
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ACTIVE MOIETY