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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
Structure of PYRAZOFURIN

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

HIDE SMILES / InChI

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.

Approval Year

Doses

Doses

DosePopulationAdverse 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

PubMed

TitleDatePubMed
Design, synthesis, and broad spectrum antiviral activity of 1- -D-ribofuranosyl-1,2,4-triazole-3-carboxamide and related nucleosides.
1972 Nov
Rat hepatomas: chemotherapy with lycurim and pyrazofurin.
1982 Apr
Screening for new compounds with antiherpes activity.
1984 Oct
Synthesis and biological activity of certain nucleoside and nucleotide derivatives of pyrazofurin.
1986 Feb
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
Inhibitory effects of antiviral compounds on respiratory syncytial virus replication in vitro.
1987 Aug
Comparison of the anti-respiratory syncytial virus activity and toxicity of papaverine hydrochloride and pyrazofurin in vitro and in vivo.
1989 Feb
Inhibitory effect of selected antiviral compounds on measles (SSPE) virus replication in vitro.
1989 Sep
Antiviral and immunomodulating inhibitors of experimentally-induced Punta Toro virus infections.
1994 Oct
Identification of active antiviral compounds against a New York isolate of West Nile virus.
2002 Jul
Inhibition of severe acute respiratory syndrome-associated coronavirus (SARSCoV) by calpain inhibitors and beta-D-N4-hydroxycytidine.
2004 Jan
Patents

Sample Use Guides

In Vivo Use Guide
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
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 Fri Dec 15 15:16:45 UTC 2023
Edited
by admin
on Fri Dec 15 15:16:45 UTC 2023
Record UNII
4B15044GQZ
Record Status Validated (UNII)
Record Version
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Name Type Language
PYRAZOFURIN
USAN  
USAN  
Official Name English
PYRAZOFURIN [USAN]
Common Name English
NSC-143095
Code English
pirazofurin [INN]
Common Name English
PIRAZOFURIN
INN  
INN  
Official Name English
Classification Tree Code System Code
NCI_THESAURUS C1557
Created by admin on Fri Dec 15 15:16:45 UTC 2023 , Edited by admin on Fri Dec 15 15:16:45 UTC 2023
NCI_THESAURUS C2170
Created by admin on Fri Dec 15 15:16:45 UTC 2023 , Edited by admin on Fri Dec 15 15:16:45 UTC 2023
Code System Code Type Description
CAS
30868-30-5
Created by admin on Fri Dec 15 15:16:45 UTC 2023 , Edited by admin on Fri Dec 15 15:16:45 UTC 2023
PRIMARY
EVMPD
SUB09897MIG
Created by admin on Fri Dec 15 15:16:45 UTC 2023 , Edited by admin on Fri Dec 15 15:16:45 UTC 2023
PRIMARY
NSC
143095
Created by admin on Fri Dec 15 15:16:45 UTC 2023 , Edited by admin on Fri Dec 15 15:16:45 UTC 2023
PRIMARY
PUBCHEM
135413551
Created by admin on Fri Dec 15 15:16:45 UTC 2023 , Edited by admin on Fri Dec 15 15:16:45 UTC 2023
PRIMARY
CHEBI
90284
Created by admin on Fri Dec 15 15:16:45 UTC 2023 , Edited by admin on Fri Dec 15 15:16:45 UTC 2023
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SMS_ID
100000081640
Created by admin on Fri Dec 15 15:16:45 UTC 2023 , Edited by admin on Fri Dec 15 15:16:45 UTC 2023
PRIMARY
INN
3579
Created by admin on Fri Dec 15 15:16:45 UTC 2023 , Edited by admin on Fri Dec 15 15:16:45 UTC 2023
PRIMARY
ChEMBL
CHEMBL2105330
Created by admin on Fri Dec 15 15:16:45 UTC 2023 , Edited by admin on Fri Dec 15 15:16:45 UTC 2023
PRIMARY
EPA CompTox
DTXSID901028098
Created by admin on Fri Dec 15 15:16:45 UTC 2023 , Edited by admin on Fri Dec 15 15:16:45 UTC 2023
PRIMARY
FDA UNII
4B15044GQZ
Created by admin on Fri Dec 15 15:16:45 UTC 2023 , Edited by admin on Fri Dec 15 15:16:45 UTC 2023
PRIMARY
WIKIPEDIA
Pyrazofurin
Created by admin on Fri Dec 15 15:16:45 UTC 2023 , Edited by admin on Fri Dec 15 15:16:45 UTC 2023
PRIMARY
NCI_THESAURUS
C1208
Created by admin on Fri Dec 15 15:16:45 UTC 2023 , Edited by admin on Fri Dec 15 15:16:45 UTC 2023
PRIMARY
MESH
C002997
Created by admin on Fri Dec 15 15:16:45 UTC 2023 , Edited by admin on Fri Dec 15 15:16:45 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY